The Genus Terminalia (Combretaceae): An Ethnopharmacological, Phytochemical and Pharmacological Review
Identifieur interne : 000249 ( Pmc/Corpus ); précédent : 000248; suivant : 000250The Genus Terminalia (Combretaceae): An Ethnopharmacological, Phytochemical and Pharmacological Review
Auteurs : Xiao-Rui Zhang ; Joseph Sakah Kaunda ; Hong-Tao Zhu ; Dong Wang ; Chong-Ren Yang ; Ying-Jun ZhangSource :
- Natural Products and Bioprospecting [ 2192-2195 ] ; 2019.
Abstract
Url:
DOI: 10.1007/s13659-019-00222-3
PubMed: 31696441
PubMed Central: 6872704
Links to Exploration step
PMC:6872704Le document en format XML
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<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">The Genus <italic>Terminalia</italic>
(Combretaceae): An Ethnopharmacological, Phytochemical and Pharmacological Review</title>
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<front><div type="abstract" xml:lang="en"><p id="Par1"><italic>Terminalia</italic>
Linn, a genus of mostly medium or large trees in the family Combretaceae with about 250 species in the world, is distributed mainly in southern Asia, Himalayas, Madagascar, Australia, and the tropical and subtropical regions of Africa. Many species are used widely in many traditional medicinal systems, e.g., traditional Chinese medicine, Tibetan medicine, and Indian Ayurvedic medicine practices. So far, about 39 species have been phytochemically studied, which led to the identification of 368 compounds, including terpenoids, tannins, flavonoids, phenylpropanoids, simple phenolics and so on. Some of the isolates showed various bioactivities, in vitro or in vivo, such as antitumor, anti HIV-1, antifungal, antimicrobial, antimalarial, antioxidant, diarrhea and analgesic. This review covers research articles from 1934 to 2018, retrieved from SciFinder, Wikipedia, Google Scholar, Chinese Knowledge Network and Baidu Scholar by using “<italic>Terminalia</italic>
” as the search term (“all fields”) with no specific time frame setting for the search. Thirty-nine important medicinal and edible <italic>Terminalia</italic>
species were selected and summarized on their geographical distribution, traditional uses, phytochemistry and related pharmacological activities.</p>
</div>
</front>
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<biblStruct><analytic><author><name sortKey="Sekhar, Yc" uniqKey="Sekhar Y">YC Sekhar</name>
</author>
<author><name sortKey="Kumar, Gp" uniqKey="Kumar G">GP Kumar</name>
</author>
<author><name sortKey="Anilakumar, Kr" uniqKey="Anilakumar K">KR Anilakumar</name>
</author>
</analytic>
</biblStruct>
</listBibl>
</div1>
</back>
</TEI>
<pmc article-type="review-article"><pmc-dir>properties open_access</pmc-dir>
<front><journal-meta><journal-id journal-id-type="nlm-ta">Nat Prod Bioprospect</journal-id>
<journal-id journal-id-type="iso-abbrev">Nat Prod Bioprospect</journal-id>
<journal-title-group><journal-title>Natural Products and Bioprospecting</journal-title>
</journal-title-group>
<issn pub-type="ppub">2192-2195</issn>
<issn pub-type="epub">2192-2209</issn>
<publisher><publisher-name>Springer Singapore</publisher-name>
<publisher-loc>Singapore</publisher-loc>
</publisher>
</journal-meta>
<article-meta><article-id pub-id-type="pmid">31696441</article-id>
<article-id pub-id-type="pmc">6872704</article-id>
<article-id pub-id-type="publisher-id">222</article-id>
<article-id pub-id-type="doi">10.1007/s13659-019-00222-3</article-id>
<article-categories><subj-group subj-group-type="heading"><subject>Review</subject>
</subj-group>
</article-categories>
<title-group><article-title>The Genus <italic>Terminalia</italic>
(Combretaceae): An Ethnopharmacological, Phytochemical and Pharmacological Review</article-title>
</title-group>
<contrib-group><contrib contrib-type="author"><name><surname>Zhang</surname>
<given-names>Xiao-Rui</given-names>
</name>
<xref ref-type="aff" rid="Aff1">1</xref>
<xref ref-type="aff" rid="Aff2">2</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Kaunda</surname>
<given-names>Joseph Sakah</given-names>
</name>
<xref ref-type="aff" rid="Aff1">1</xref>
<xref ref-type="aff" rid="Aff2">2</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Zhu</surname>
<given-names>Hong-Tao</given-names>
</name>
<xref ref-type="aff" rid="Aff1">1</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Wang</surname>
<given-names>Dong</given-names>
</name>
<xref ref-type="aff" rid="Aff1">1</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Yang</surname>
<given-names>Chong-Ren</given-names>
</name>
<xref ref-type="aff" rid="Aff1">1</xref>
</contrib>
<contrib contrib-type="author" corresp="yes"><contrib-id contrib-id-type="orcid">http://orcid.org/0000-0002-0295-337X</contrib-id>
<name><surname>Zhang</surname>
<given-names>Ying-Jun</given-names>
</name>
<address><phone>+86 871 65223235</phone>
<email>zhangyj@mail.kib.ac.cn</email>
</address>
<xref ref-type="aff" rid="Aff1">1</xref>
<xref ref-type="aff" rid="Aff3">3</xref>
</contrib>
<aff id="Aff1"><label>1</label>
<institution-wrap><institution-id institution-id-type="GRID">grid.9227.e</institution-id>
<institution-id institution-id-type="ISNI">0000000119573309</institution-id>
<institution>State Key Laboratory of Phytochemistry and Plant Resources in West China. Kunming Institute of Botany,</institution>
<institution>Chinese Academy of Sciences,</institution>
</institution-wrap>
Kunming, 650204 People’s Republic of China</aff>
<aff id="Aff2"><label>2</label>
<institution-wrap><institution-id institution-id-type="GRID">grid.410726.6</institution-id>
<institution-id institution-id-type="ISNI">0000 0004 1797 8419</institution-id>
<institution>University of Chinese Academy of Sciences,</institution>
</institution-wrap>
Beijing, 100049 People’s Republic of China</aff>
<aff id="Aff3"><label>3</label>
<institution-wrap><institution-id institution-id-type="GRID">grid.9227.e</institution-id>
<institution-id institution-id-type="ISNI">0000000119573309</institution-id>
<institution>Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany,</institution>
<institution>Chinese Academy of Sciences,</institution>
</institution-wrap>
Kunming, 650201 People’s Republic of China</aff>
</contrib-group>
<pub-date pub-type="epub"><day>6</day>
<month>11</month>
<year>2019</year>
</pub-date>
<pub-date pub-type="pmc-release"><day>6</day>
<month>11</month>
<year>2019</year>
</pub-date>
<pub-date pub-type="collection"><month>12</month>
<year>2019</year>
</pub-date>
<volume>9</volume>
<issue>6</issue>
<fpage>357</fpage>
<lpage>392</lpage>
<history><date date-type="received"><day>31</day>
<month>7</month>
<year>2019</year>
</date>
<date date-type="accepted"><day>15</day>
<month>10</month>
<year>2019</year>
</date>
</history>
<permissions><copyright-statement>© The Author(s) 2019</copyright-statement>
<license license-type="OpenAccess"><license-p><bold>Open Access</bold>
This article is distributed under the terms of the Creative Commons Attribution 4.0 International License (<ext-link ext-link-type="uri" xlink:href="http://creativecommons.org/licenses/by/4.0/">http://creativecommons.org/licenses/by/4.0/</ext-link>
), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made.</license-p>
</license>
</permissions>
<abstract id="Abs1"><p id="Par1"><italic>Terminalia</italic>
Linn, a genus of mostly medium or large trees in the family Combretaceae with about 250 species in the world, is distributed mainly in southern Asia, Himalayas, Madagascar, Australia, and the tropical and subtropical regions of Africa. Many species are used widely in many traditional medicinal systems, e.g., traditional Chinese medicine, Tibetan medicine, and Indian Ayurvedic medicine practices. So far, about 39 species have been phytochemically studied, which led to the identification of 368 compounds, including terpenoids, tannins, flavonoids, phenylpropanoids, simple phenolics and so on. Some of the isolates showed various bioactivities, in vitro or in vivo, such as antitumor, anti HIV-1, antifungal, antimicrobial, antimalarial, antioxidant, diarrhea and analgesic. This review covers research articles from 1934 to 2018, retrieved from SciFinder, Wikipedia, Google Scholar, Chinese Knowledge Network and Baidu Scholar by using “<italic>Terminalia</italic>
” as the search term (“all fields”) with no specific time frame setting for the search. Thirty-nine important medicinal and edible <italic>Terminalia</italic>
species were selected and summarized on their geographical distribution, traditional uses, phytochemistry and related pharmacological activities.</p>
</abstract>
<kwd-group xml:lang="en"><title>Keywords</title>
<kwd><italic>Terminalia</italic>
</kwd>
<kwd>Combretaceae</kwd>
<kwd>Ethnomedicine</kwd>
<kwd>Traditional uses</kwd>
<kwd>Phytochemistry</kwd>
<kwd>Hydrolyzable tannins</kwd>
<kwd>Pharmacology</kwd>
</kwd-group>
<funding-group><award-group><funding-source><institution>Yunnan Key Laboratory of Natural Medicinal Chemistry</institution>
</funding-source>
<award-id>S2017-ZZ14</award-id>
<principal-award-recipient><name><surname>Zhang</surname>
<given-names>Ying-Jun</given-names>
</name>
</principal-award-recipient>
</award-group>
</funding-group>
<custom-meta-group><custom-meta><meta-name>issue-copyright-statement</meta-name>
<meta-value>© The Author(s) 2019</meta-value>
</custom-meta>
</custom-meta-group>
</article-meta>
</front>
<body><sec id="Sec1" sec-type="introduction"><title>Introduction</title>
<p id="Par21"><italic>Terminalia</italic>
Linn, comprising about 250 species in the world mostly as medium or large trees, is the second largest genus in the family Combretaceae. The name “<italic>Terminalia</italic>
” is derived from Latin word “terminus”, which means the leaves are located at the tip of the branch. The bark of <italic>Terminalia</italic>
plants usually has cracks and branches tucked into layers. Most of the <italic>Terminalia</italic>
plants’ leaves are large, leathery with solitary or clustered small green white flowers. Their fruits are yellow, dark red or black; drupe, usually angular or winged. Some fruits are edible, highly nutritious and possess medicinal values.</p>
<p id="Par22"><italic>Terminalia</italic>
species are widely distributed in the southern Asia, Himalayas, Madagascar, Australia, and the tropical and subtropical regions of Africa. <italic>Terminalia</italic>
plants in southern Asia have been intensively studied phytochemically due to their wide usage in Asian (India, Tibetan, and Chinese) traditional medicine systems [<xref ref-type="bibr" rid="CR1">1</xref>
]. For example, the fruits of <italic>Terminalia bellirica</italic>
and <italic>Terminalia chebula</italic>
, together with <italic>Phyllanthus emblica</italic>
(Euphorbiaceae) which form the herbal remedy, Triphala, in Tibetan medicine, have received much attention because of its extensive and remarkable effectiveness in the treatment of anticancer, antifungal, antimicrobial, antimalarial, antioxidant.</p>
<p id="Par23">So far, 39 <italic>Terminalia</italic>
species have been investigated for their phytochemical constituents, which resulted in the identification of terpenes, tannins, flavonoids, lignans and simple phenols, amongst others. Pharmacological studies suggest that they have exhibited activity on liver and kidney protection, antibacterial, antiinflammatory, anticancer, and have displayed a positive effect on immune regulation, cardiovascular disease and diabetes, and acceleration of wound healing.</p>
<p id="Par24">This paper features 39 important medicinal and edible <italic>Terminalia</italic>
species and summarizes their traditional usage, geographical distribution, structures of isolated chemical constituents and pharmacological activities.</p>
</sec>
<sec id="Sec2"><title>Species’ Description, Distribution and Traditional Uses</title>
<p id="Par25">So far, 50 <italic>Terminalia</italic>
species have been documented, 39 of which have been reported to possess medicinal properties and/or being edible. Among them, eight species and four varieties including <italic>T. argyrophylla</italic>
, <italic>T. bellirica</italic>
, <italic>T. catappa</italic>
, <italic>T. chebula</italic>
, <italic>T. franchetii</italic>
, <italic>T. hainanensis</italic>
, <italic>T. myriocarpa</italic>
, <italic>T. intricate</italic>
, <italic>T. chebula</italic>
var. <italic>tomentella</italic>
, <italic>T. franchetii</italic>
var. <italic>membranifolia</italic>
, <italic>T. franchetii</italic>
var. <italic>glabra</italic>
, and <italic>T. myriocarpa</italic>
var. <italic>hirsuta</italic>
are distributed in China (Yunnan, southeast Tibet, Taiwan, Guangdong, south Guangxi and southwest Sichuan). Their distribution and traditional applications are shown in Table <xref rid="Tab1" ref-type="table">1</xref>
.<table-wrap id="Tab1"><label>Table 1</label>
<caption><p>Local names, distributions and traditional uses of <italic>Terminalia</italic>
plants</p>
</caption>
<table frame="hsides" rules="groups"><thead><tr><th align="left">No.</th>
<th align="left">Plants</th>
<th align="left">Local names</th>
<th align="left">Distributions</th>
<th align="left">Traditional uses</th>
</tr>
</thead>
<tbody><tr><td align="left">T1</td>
<td align="left"><italic>T. alata</italic>
</td>
<td align="left">Unknown</td>
<td align="left">Southern Vietnam [<xref ref-type="bibr" rid="CR2">2</xref>
, <xref ref-type="bibr" rid="CR3">3</xref>
]</td>
<td align="left">Anti-diarrhea, ulcer, diuretics, supplements [<xref ref-type="bibr" rid="CR3">3</xref>
]</td>
</tr>
<tr><td align="left">T2</td>
<td align="left"><italic>T. amazonia</italic>
</td>
<td align="left">White olive</td>
<td align="left">Southern Costa Rica [<xref ref-type="bibr" rid="CR4">4</xref>
]</td>
<td align="left">Wood</td>
</tr>
<tr><td align="left">T3</td>
<td align="left"><italic>T. arborea</italic>
</td>
<td align="left">Jaha Kling</td>
<td align="left">Indonesia </td>
<td align="left">Cardiovascular disease, myocardial infarction, atherosclerosis, diabetes, cancer, stroke, cataract, shoulder stiffness, cold allergy, hypertension, senile dementia, inflammation, gum disease (e.g. gingivitis, pneumonia), Alzheimer’s, skin conditions [<xref ref-type="bibr" rid="CR5">5</xref>
]</td>
</tr>
<tr><td align="left">T4</td>
<td align="left"><italic>T. arjuna</italic>
</td>
<td align="left">Arjuna, White Marudah, Koha</td>
<td align="left">India, South Asia, Sri Lanka [<xref ref-type="bibr" rid="CR6">6</xref>
]</td>
<td align="left"><p>Cardiotonic, sores, bile infection, poison antidote [<xref ref-type="bibr" rid="CR6">6</xref>
]</p>
<p>Coughs, dysentery, fractures, contusions, ulcers, hypertension ischaemic heart diseases [<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
</td>
</tr>
<tr><td align="left">T5</td>
<td align="left"><italic>T. argyrophylla</italic>
</td>
<td align="left">Silver leaves Chebula, Xiao Chebula (Yunnan), Manna (Yunnan Dai language)</td>
<td align="left">China (Yunnan) [<xref ref-type="bibr" rid="CR7">7</xref>
]</td>
<td align="left">Autoimmune diseases [<xref ref-type="bibr" rid="CR7">7</xref>
]</td>
</tr>
<tr><td align="left">T6</td>
<td align="left"><italic>T. australis</italic>
</td>
<td align="left">Tanimbu, palo amarillo</td>
<td align="left">Punta Lara, Argentina (Buenos Aires) [<xref ref-type="bibr" rid="CR8">8</xref>
]</td>
<td align="left">Hemostasis</td>
</tr>
<tr><td align="left">T7</td>
<td align="left"><italic>T. avicennioides</italic>
</td>
<td align="left">kpayi, Kpace, baushe</td>
<td align="left">Nigeria [<xref ref-type="bibr" rid="CR9">9</xref>
, <xref ref-type="bibr" rid="CR10">10</xref>
]</td>
<td align="left">Malaria, worms, gastric peptic ulcer [<xref ref-type="bibr" rid="CR9">9</xref>
], scorpion bites [<xref ref-type="bibr" rid="CR10">10</xref>
], tuberculosis, cough [<xref ref-type="bibr" rid="CR90">90</xref>
]</td>
</tr>
<tr><td align="left">T8</td>
<td align="left"><italic>T. bellirica</italic>
</td>
<td align="left">Beleric</td>
<td align="left">China (southern Yunnan), Vietnam, Laos, Thailand, Cambodia, Myanmar, India (except West), Malaysia, Indonesia</td>
<td align="left"><p>Laxative, edible</p>
<p>Edema, diarrhea, leprosy, bile congestion, indigestion, headache [<xref ref-type="bibr" rid="CR11">11</xref>
]</p>
<p>Fever, diarrhea, cough, dysentery, skin diseases [<xref ref-type="bibr" rid="CR12">12</xref>
]</p>
<p>Wine, palm sugar [<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>Diarrhea [<xref ref-type="bibr" rid="CR94">94</xref>
]</p>
</td>
</tr>
<tr><td align="left">T9</td>
<td align="left"><italic>T. bentzoe</italic>
</td>
<td align="left">Unknown</td>
<td align="left">Rodrigues [<xref ref-type="bibr" rid="CR13">13</xref>
]</td>
<td align="left">Essential oil [<xref ref-type="bibr" rid="CR13">13</xref>
]</td>
</tr>
<tr><td align="left">T10</td>
<td align="left"><italic>T. bialata</italic>
</td>
<td align="left">Indian silver greywood</td>
<td align="left">India, South Asia</td>
<td align="left">Wood [<xref ref-type="bibr" rid="CR14">14</xref>
]</td>
</tr>
<tr><td align="left">T11</td>
<td align="left"><italic>T. brachystemma</italic>
</td>
<td align="left">Kalahari cluster leaf</td>
<td align="left">Southern Africa</td>
<td align="left">Shistosomiasis, gastrointestinal disorders [<xref ref-type="bibr" rid="CR15">15</xref>
]</td>
</tr>
<tr><td align="left">T12</td>
<td align="left"><italic>T. brownii</italic>
</td>
<td align="left">kuuku, muvuku (Kamba, Kenya), koloswa (northern region, Kenya), weba (Ethiopia), lbukoi (Samburu, Kenya), orbukoi (Maasai, Tanzania), and mbarao or mwalambe, in Kiswahili</td>
<td align="left">Southern and central Africa</td>
<td align="left"><p>Diarrhea, stomach pain, gastric ulcer, colic, heartburn</p>
<p>Genitourinary infection, urethral pain, endometritis, cystitis, leucorrhea, syphilis, gonorrhea, malaria, dysmenorrhea, nervousness, hysteria, epilepsy, athlete’s foot, indigestion, stomach pain, gastric ulcer, colitis, cough, vomiting, hepatitis, jaundice, cirrhosis, yellow fever [<xref ref-type="bibr" rid="CR16">16</xref>
]</p>
</td>
</tr>
<tr><td align="left">T13</td>
<td align="left"><italic>T. bursarina</italic>
</td>
<td align="left">Yellow wood</td>
<td align="left">Australia, South Asia [<xref ref-type="bibr" rid="CR17">17</xref>
]</td>
<td align="left">Unknown</td>
</tr>
<tr><td align="left">T14</td>
<td align="left"><italic>T. calamansanai</italic>
</td>
<td align="left">Phillipine almond, Anarep</td>
<td align="left">Philippines, Southeast Asia</td>
<td align="left">Lithontriptic [<xref ref-type="bibr" rid="CR18">18</xref>
], horticultural plant [<xref ref-type="bibr" rid="CR102">102</xref>
]</td>
</tr>
<tr><td align="left">T15</td>
<td align="left"><italic>T. calcicola</italic>
</td>
<td align="left">Unknown</td>
<td align="left">Madagascar Rain Forest [<xref ref-type="bibr" rid="CR19">19</xref>
]</td>
<td align="left">Unknown</td>
</tr>
<tr><td align="left">T16</td>
<td align="left"><italic>T. catappa</italic>
</td>
<td align="left">Indian almond, umbrella tree, tropical almond</td>
<td align="left">China (Guangdong, Taiwan, SE Yunnan), Australia and SE Asia, Africa, South America Tropical Coast</td>
<td align="left"><p>Blood stasis, liver injury [<xref ref-type="bibr" rid="CR20">20</xref>
]</p>
<p>Diarrhea, dysentery, biliary inflammation [<xref ref-type="bibr" rid="CR23">23</xref>
], dermatitis, hepatitis [<xref ref-type="bibr" rid="CR106">106</xref>
]</p>
</td>
</tr>
<tr><td align="left">T17</td>
<td align="left"><italic>T. chebula</italic>
</td>
<td align="left">Black Mytrobalan, Inknut, Chebulic Myrobalan</td>
<td align="left">Nepal, northern India, Myanmar, Sri Lanka, Thailand, Bangladesh, China (Yunnan), Himalayan</td>
<td align="left">Digestion appetizers, vomiting, infertility, asthma, sore throat, vomiting, urticaria, diarrhea, dysentery, bleeding, ulcers, gout, bladder disease [<xref ref-type="bibr" rid="CR21">21</xref>
]</td>
</tr>
<tr><td align="left">T18</td>
<td align="left"><italic>T. chebula</italic>
var. <italic>tomentella</italic>
</td>
<td align="left">Weimaohezi (variant)</td>
<td align="left">China (western Yunnan), Myanmar</td>
<td align="left">Unknown</td>
</tr>
<tr><td align="left">T19</td>
<td align="left"><italic>T. citrina</italic>
</td>
<td align="left">Manahei, Yellow myrobalan</td>
<td align="left">India, Bangladesh [<xref ref-type="bibr" rid="CR22">22</xref>
]</td>
<td align="left">Dysmenorrhea, bleeding, heart disease, dysentery, constipation [<xref ref-type="bibr" rid="CR22">22</xref>
]</td>
</tr>
<tr><td align="left">T20</td>
<td align="left"><italic>T. elliptica</italic>
</td>
<td align="left">Indian laurel</td>
<td align="left">SE Asia, India, Bangladesh, Laos, Myanmar, Nepal, Thailand, Cambodia, Vietnam</td>
<td align="left"><p>Wine, palm sugar</p>
<p>Ulcers, fractures, bleeding, bronchitis, diarrhea [<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
</td>
</tr>
<tr><td align="left">T21</td>
<td align="left"><italic>T. franchetii</italic>
</td>
<td align="left">Dianlanren</td>
<td align="left">SW China [<xref ref-type="bibr" rid="CR24">24</xref>
]</td>
<td align="left">Unknown</td>
</tr>
<tr><td align="left">T22</td>
<td align="left"><italic>T. franchetii</italic>
var. <italic>membranifolia</italic>
</td>
<td align="left">Baoyedianlanren (variant)</td>
<td align="left">China [western Guangxi (Longlin), central to SE Yunnan]</td>
<td align="left">Unknown</td>
</tr>
<tr><td align="left">T23</td>
<td align="left"><italic>T. franchetii</italic>
var. <italic>glabra</italic>
</td>
<td align="left">Guang yedianlanren (variant)</td>
<td align="left">China (Sichuan and Yunnan Jinsha River Basin)</td>
<td align="left">Unknown</td>
</tr>
<tr><td align="left">T24</td>
<td align="left"><italic>T. ferdinandiana</italic>
</td>
<td align="left">Gubinge, Bbillygoat plum, Kakadu plum, green plum, salty plum, murunga, mador</td>
<td align="left">Australia [<xref ref-type="bibr" rid="CR25">25</xref>
]</td>
<td align="left">Dietary supplements, skin care [<xref ref-type="bibr" rid="CR25">25</xref>
]</td>
</tr>
<tr><td align="left">T25</td>
<td align="left"><italic>T. glaucescens</italic>
</td>
<td align="left">Unknown</td>
<td align="left">Nigeria [<xref ref-type="bibr" rid="CR26">26</xref>
]</td>
<td align="left"><p>Amenorrhea, vaginal infections, syphilis, sores, neurological disorders</p>
<p>Anti-plasma, antiparasitic, antiviral, antimicrobial [<xref ref-type="bibr" rid="CR26">26</xref>
, <xref ref-type="bibr" rid="CR27">27</xref>
]</p>
</td>
</tr>
<tr><td align="left">T26</td>
<td align="left"><italic>T. hainanensis</italic>
</td>
<td align="left">Ji zhenmu, Hainan lanren</td>
<td align="left">China (Hainan)</td>
<td align="left">Antioxidant [<xref ref-type="bibr" rid="CR28">28</xref>
]</td>
</tr>
<tr><td align="left">T27</td>
<td align="left"><italic>T. intricate</italic>
</td>
<td align="left">Cuozhilanren</td>
<td align="left">China (NW Yunnan and SW Sichuan)</td>
<td align="left">Unknown</td>
</tr>
<tr><td align="left">T28</td>
<td align="left"><italic>T. ivorensis</italic>
</td>
<td align="left">Idigbo, Black Afara, Shingle Wood, Brimstone Wood, Blackbark</td>
<td align="left">Cameroon, West Africa, Ivory Coast, Liberia, Nigeria, Sierra Leone, Ghana</td>
<td align="left"><p>Rheumatism, gastroenteritis, psychotic analgesics [<xref ref-type="bibr" rid="CR29">29</xref>
]</p>
<p>Syphilis, burns and bruises [<xref ref-type="bibr" rid="CR30">30</xref>
]</p>
</td>
</tr>
<tr><td align="left">T29</td>
<td align="left"><italic>T. kaernbachii</italic>
</td>
<td align="left">Okari Nut</td>
<td align="left">Solomon Islands, Papua New Guinea</td>
<td align="left"><italic>α</italic>
-Glucosidase inhibitor activity [<xref ref-type="bibr" rid="CR31">31</xref>
]</td>
</tr>
<tr><td align="left">T30</td>
<td align="left"><italic>T. kaiserana</italic>
</td>
<td align="left">Unknown</td>
<td align="left">Tanzania</td>
<td align="left">Diarrhea, gonorrhea vomiting [<xref ref-type="bibr" rid="CR44">44</xref>
]</td>
</tr>
<tr><td align="left">T31</td>
<td align="left"><italic>T. laxiflora</italic>
</td>
<td align="left">Unknown</td>
<td align="left">West Africa, Sudan Savannah</td>
<td align="left"><p>Malaria, cough [<xref ref-type="bibr" rid="CR32">32</xref>
]</p>
<p>Fumigant, rheumatic pain, smoothen skin, body relaxation [<xref ref-type="bibr" rid="CR33">33</xref>
]</p>
</td>
</tr>
<tr><td align="left">T32</td>
<td align="left"><italic>T. macroptera</italic>
</td>
<td align="left">Bayankada</td>
<td align="left">Tropical (West Africa)</td>
<td align="left">Wound, hepatitis, malaria, fever, cough, diarrhea, tuberculosis, skin diseases [<xref ref-type="bibr" rid="CR34">34</xref>
]</td>
</tr>
<tr><td align="left">T33</td>
<td align="left"><italic>T. mantaly</italic>
</td>
<td align="left">Unknown</td>
<td align="left">Africa, Madagascar</td>
<td align="left">Dysentery</td>
</tr>
<tr><td align="left">T34</td>
<td align="left"><italic>T. mollis</italic>
</td>
<td align="left">Bush willow</td>
<td align="left">Africa</td>
<td align="left">Diarrhea, gonorrhea, malaria, AIDS adjuvant therapy [<xref ref-type="bibr" rid="CR35">35</xref>
]</td>
</tr>
<tr><td align="left">T35</td>
<td align="left"><italic>T. muelleri</italic>
</td>
<td align="left">Ketapang kencana</td>
<td align="left">Indonesia, SE Asia, South Asia</td>
<td align="left">Antibacterial [<xref ref-type="bibr" rid="CR36">36</xref>
], antioxidants [<xref ref-type="bibr" rid="CR37">37</xref>
]</td>
</tr>
<tr><td align="left">T36</td>
<td align="left"><italic>T. myriocarpa</italic>
</td>
<td align="left">Qianguolanren</td>
<td align="left">China [Guangxi (Longjin), Yunnan (central to the south), and Tibet (Medog)], northern Vietnam, Thailand, Laos, northern Myanmar, Malaysia, NE India, Sikkim</td>
<td align="left">Antioxidant, liver protection [<xref ref-type="bibr" rid="CR38">38</xref>
]</td>
</tr>
<tr><td align="left">T37</td>
<td align="left"><italic>T. myriocarpa</italic>
var. <italic>hirsuta</italic>
</td>
<td align="left">Yingmaoqianguolanren (variant)</td>
<td align="left">Yunnan, China; Thailand</td>
<td align="left">Unknown</td>
</tr>
<tr><td align="left">T38</td>
<td align="left"><italic>T. oblongata</italic>
</td>
<td align="left">Rose wood, yellow wood</td>
<td align="left">Central Queensland [<xref ref-type="bibr" rid="CR39">39</xref>
]</td>
<td align="left">Unknown [<xref ref-type="bibr" rid="CR39">39</xref>
]</td>
</tr>
<tr><td align="left">T39</td>
<td align="left"><italic>T. paniculata</italic>
</td>
<td align="left">Vellamaruth</td>
<td align="left">India</td>
<td align="left">Cholera, mumps, menstrual disorders, cough, bronchitis, heart failure, hepatitis, diabetes, obesity [<xref ref-type="bibr" rid="CR40">40</xref>
]</td>
</tr>
<tr><td align="left">T40</td>
<td align="left"><italic>T. parviflora</italic>
</td>
<td align="left">Tropical almond, umbrella tree, Indian almond</td>
<td align="left">Sri Lanka and India [<xref ref-type="bibr" rid="CR41">41</xref>
]</td>
<td align="left">Diarrhea [<xref ref-type="bibr" rid="CR41">41</xref>
]</td>
</tr>
<tr><td align="left">T41</td>
<td align="left"><italic>T. prunioides</italic>
</td>
<td align="left">Hareri, Sterkbos, Purple pod Terminalia, Mwangati</td>
<td align="left">Southern Africa</td>
<td align="left">Postnatal abdominal pain</td>
</tr>
<tr><td align="left">T42</td>
<td align="left"><italic>T. sambesiaca</italic>
</td>
<td align="left">Unknown</td>
<td align="left">Southern Africa</td>
<td align="left"><p>Cancer, gastric ulcer, appendicitis</p>
<p>Bloody diarrhea [<xref ref-type="bibr" rid="CR45">45</xref>
]</p>
</td>
</tr>
<tr><td align="left">T43</td>
<td align="left"><italic>T. schimperiana</italic>
</td>
<td align="left">Idi odan</td>
<td align="left">Africa, Sierra Leone, Guinea, Uganda, Ethiopia</td>
<td align="left">Local burns, bronchitis, dysentery [<xref ref-type="bibr" rid="CR42">42</xref>
]</td>
</tr>
<tr><td align="left">T44</td>
<td align="left"><italic>T. sericea</italic>
</td>
<td align="left">Monakanakane, Mososo, Mogonono, Amangwe, Vaalboom, Mangwe, Silver clutter-leaf</td>
<td align="left">Northern South Africa, Botswana (except central Kalahari), southern Mozambique, Tanzania, Namibia, Zimbabwe, Northern Democratic Republic of Congo, tropical Africa [<xref ref-type="bibr" rid="CR43">43</xref>
]</td>
<td align="left"><p>Diarrhea, sexually transmitted infections, rash, tuberculosis [<xref ref-type="bibr" rid="CR43">43</xref>
]</p>
<p>Fever, high blood pressure [<xref ref-type="bibr" rid="CR44">44</xref>
]</p>
</td>
</tr>
<tr><td align="left">T45</td>
<td align="left"><italic>T. spinosa</italic>
</td>
<td align="left">Musosahwai, spiny cluster leaf, Kasansa</td>
<td align="left">Southern Africa</td>
<td align="left"><p>Malaria, fever [<xref ref-type="bibr" rid="CR46">46</xref>
]</p>
<p>Epilepsy, poisoning [<xref ref-type="bibr" rid="CR47">47</xref>
]</p>
</td>
</tr>
<tr><td align="left">T46</td>
<td align="left"><italic>T. stenostachya</italic>
</td>
<td align="left">Rosette leaf Terminalia</td>
<td align="left">Southern Africa</td>
<td align="left">Epilepsy, poisoning [<xref ref-type="bibr" rid="CR47">47</xref>
]</td>
</tr>
<tr><td align="left">T47</td>
<td align="left"><italic>T. stuhlmannii</italic>
</td>
<td align="left">Unknown</td>
<td align="left">Acacia [<xref ref-type="bibr" rid="CR48">48</xref>
]</td>
<td align="left">Unknown</td>
</tr>
<tr><td align="left">T48</td>
<td align="left"><italic>T. superba</italic>
</td>
<td align="left">Limba</td>
<td align="left">Tropical Western Africa</td>
<td align="left">Gastroenteritis, diabetes, female infertility, abdominal pain, bacteria/fungi/viral infections [<xref ref-type="bibr" rid="CR49">49</xref>
], diabetes remedies, anesthetic, hepatitis [<xref ref-type="bibr" rid="CR50">50</xref>
]</td>
</tr>
<tr><td align="left">T49</td>
<td align="left"><italic>T. triflora</italic>
</td>
<td align="left">Lanza, lanza amarilla, amarillo derío, paloamarillo</td>
<td align="left"><p>Tropical (South America)</p>
<p>Northern and Northwest Argentina [<xref ref-type="bibr" rid="CR149">149</xref>
]</p>
</td>
<td align="left">Making posts, furniture, weapons, fuel [<xref ref-type="bibr" rid="CR149">149</xref>
]</td>
</tr>
<tr><td align="left">T50</td>
<td align="left"><italic>T. tropophylla</italic>
</td>
<td align="left">Unknown</td>
<td align="left">Madagascan [<xref ref-type="bibr" rid="CR51">51</xref>
]</td>
<td align="left">Unknown</td>
</tr>
</tbody>
</table>
<table-wrap-foot><p><italic>SE</italic>
southeastern, <italic>NE</italic>
northeastern, <italic>SW</italic>
southwestern, <italic>NW</italic>
northwestern</p>
</table-wrap-foot>
</table-wrap>
</p>
<p id="Par26"><italic>Terminalia</italic>
species are broadly used in many aspects. Some are employed as drugs, while others can provide high quality wood, tannin or dyes. For example, fruits of <italic>T. ferdinandiana</italic>
, a species largely distributed in Australia, are rich in vitamin C, and possess strong antioxidant activity [<xref ref-type="bibr" rid="CR25">25</xref>
]. <italic>T. bellirica</italic>
and <italic>T. chebula</italic>
are not only recorded in every version of Chinese pharmacopoeia, but are also the important and most commonly applied drugs in Han, Tibetan, Mongolian and many other folk medicinal systems in India, Burma, Thailand, Malaysia, Vietnam and other southeast asian countries. <italic>T. catappa</italic>
is a commonly used medicinal plant for liver protection in China [<xref ref-type="bibr" rid="CR20">20</xref>
].</p>
</sec>
<sec id="Sec3"><title>Chemical Composition</title>
<p id="Par27">Since 1930s, the chemical compositions of the genus <italic>Terminalia</italic>
have been vastly studied. <italic>T. arjuna</italic>
, <italic>T. bellirica</italic>
, <italic>T. catappa</italic>
and <italic>T. chebula</italic>
, having been frequently used in the Ayurvedic, Chinese and Tibetan medicines, attracted scholars’ attention. To date, 368 compounds, largely terpenoids (<bold>1–104</bold>
), tannins (<bold>105–196</bold>
), flavonoids (<bold>197–241</bold>
), lignans (<bold>242–265</bold>
), phenols and glycosides (<bold>268–318</bold>
) were reported from the genus (Tables <xref rid="Tab2" ref-type="table">2</xref>
, <xref rid="Tab3" ref-type="table">3</xref>
).<table-wrap id="Tab2"><label>Table 2</label>
<caption><p>Chemical constituents isolated from the genus <italic>Terminalia</italic>
and the studied plant organs</p>
</caption>
<table frame="hsides" rules="groups"><thead><tr><th align="left">No.</th>
<th align="left">Compounds</th>
<th align="left">Plants</th>
<th align="left">Organs</th>
<th align="left">References</th>
</tr>
</thead>
<tbody><tr><td align="left" colspan="5">Triterpenes (86)</td>
</tr>
<tr><td align="left"> <bold>1</bold>
</td>
<td align="left">2α,3β,19α-Trihydroxyolean-12-en-20-oic acid 3-<italic>O</italic>
-β-<sc>d</sc>
-galactosyl-(1 → 3)-β-<sc>d</sc>
-glucoside</td>
<td align="left">T1</td>
<td align="left">R</td>
<td align="left">[<xref ref-type="bibr" rid="CR3">3</xref>
]</td>
</tr>
<tr><td align="left"> <bold>2</bold>
</td>
<td align="left">2α,3β,19α-Trihydroxyolean-12-en-28-oic acid methylester 3β-<italic>O</italic>
-rutinoside</td>
<td align="left">T1</td>
<td align="left">R</td>
<td align="left">[<xref ref-type="bibr" rid="CR53">53</xref>
]</td>
</tr>
<tr><td align="left"> <bold>3</bold>
</td>
<td align="left">2α,3β,19β,23-Tetrahydroxyolean-12-en-28-oic acid 3β-<italic>O</italic>
-β-<sc>d</sc>
-galactosyl-(1 → 3)-β-<sc>d</sc>
-glucoside-28-<italic>O</italic>
-β-<sc>d</sc>
-glucoside</td>
<td align="left">T1</td>
<td align="left">R</td>
<td align="left">[<xref ref-type="bibr" rid="CR52">52</xref>
]</td>
</tr>
<tr><td align="left"> <bold>4</bold>
</td>
<td align="left">3-Acetylmaslinic acid</td>
<td align="left">T1</td>
<td align="left">RB</td>
<td align="left">[<xref ref-type="bibr" rid="CR54">54</xref>
]</td>
</tr>
<tr><td align="left"> <bold>5</bold>
</td>
<td align="left">Arjunic acid</td>
<td align="left"><p>T1</p>
<p>T4</p>
<p>T17</p>
<p>T25</p>
<p>T28</p>
<p>T32</p>
<p>T44</p>
</td>
<td align="left"><p>B</p>
<p>SB, F</p>
<p>F</p>
<p>SB</p>
<p>B</p>
<p>B</p>
<p>R</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR55">55</xref>
, <xref ref-type="bibr" rid="CR74">74</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR60">60</xref>
, <xref ref-type="bibr" rid="CR79">79</xref>
, <xref ref-type="bibr" rid="CR124">124</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR146">146</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR130">130</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR132">132</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR145">145</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR133">133</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>6</bold>
</td>
<td align="left">Arjunoside I</td>
<td align="left">T4</td>
<td align="left">SB</td>
<td align="left">[<xref ref-type="bibr" rid="CR61">61</xref>
]</td>
</tr>
<tr><td align="left"> <bold>7</bold>
</td>
<td align="left">Arjunoside II</td>
<td align="left">T4</td>
<td align="left">SB</td>
<td align="left">[<xref ref-type="bibr" rid="CR61">61</xref>
]</td>
</tr>
<tr><td align="left"> <bold>8</bold>
</td>
<td align="left">Arjunoside III</td>
<td align="left">T4</td>
<td align="left">R</td>
<td align="left">[<xref ref-type="bibr" rid="CR62">62</xref>
, <xref ref-type="bibr" rid="CR63">63</xref>
]</td>
</tr>
<tr><td align="left"> <bold>9</bold>
</td>
<td align="left">Arjunoside IV</td>
<td align="left">T4</td>
<td align="left">R</td>
<td align="left">[<xref ref-type="bibr" rid="CR62">62</xref>
, <xref ref-type="bibr" rid="CR63">63</xref>
]</td>
</tr>
<tr><td align="left"> <bold>10</bold>
</td>
<td align="left">Arjunetin</td>
<td align="left"><p>T1</p>
<p>T4</p>
<p>T8, T16, T17, T20, T39</p>
</td>
<td align="left"><p>B</p>
<p>B, L, S, R, F</p>
<p>B, L, S, R, F</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR55">55</xref>
, <xref ref-type="bibr" rid="CR74">74</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
, <xref ref-type="bibr" rid="CR67">67</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>11</bold>
</td>
<td align="left">Oleanolic acid</td>
<td align="left"><p>T1</p>
<p>T9</p>
<p>T4, T16, T20</p>
<p>T8, T17</p>
<p>T39</p>
<p>T28</p>
<p>T36</p>
</td>
<td align="left"><p>H</p>
<p>L</p>
<p>B, L, S, R, F</p>
<p>B, L, S, R</p>
<p>L, S, R, F</p>
<p>B</p>
<p>B</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR56">56</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR97">97</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR132">132</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR140">140</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>12</bold>
</td>
<td align="left">Ursolic Acid</td>
<td align="left"><p>T4, T16, T20</p>
<p>T8, T17</p>
<p>T39</p>
</td>
<td align="left"><p>B, L, S, R, F</p>
<p>L, S, R</p>
<p>B, L, S, F</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>13</bold>
</td>
<td align="left">Maslinic acid</td>
<td align="left"><p>T1</p>
<p>T9</p>
<p>T17</p>
<p>T36</p>
</td>
<td align="left"><p>H</p>
<p>L</p>
<p>F</p>
<p>B</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR56">56</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR97">97</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR21">21</xref>
, <xref ref-type="bibr" rid="CR116">116</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR140">140</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>14</bold>
</td>
<td align="left">2α,3α,24-Trihydroxyolean-11,13(18)-dien-28-oic acid</td>
<td align="left">T33</td>
<td align="left">SB</td>
<td align="left">[<xref ref-type="bibr" rid="CR158">158</xref>
]</td>
</tr>
<tr><td align="left"> <bold>15</bold>
</td>
<td align="left">Terminoside A</td>
<td align="left">T4</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR58">58</xref>
]</td>
</tr>
<tr><td align="left"> <bold>16</bold>
</td>
<td align="left">Arjungenin</td>
<td align="left"><p>T4</p>
<p>T25</p>
<p>T12</p>
<p>T8, T16, T20, T39</p>
<p>T17</p>
<p>T25</p>
<p>T28</p>
<p>T32</p>
<p>T33</p>
<p>T44</p>
</td>
<td align="left"><p>SB,L,R,F</p>
<p>R</p>
<p>B</p>
<p>B, L, S, R, F</p>
<p>B, L, S, R, F</p>
<p>R, SB</p>
<p>B</p>
<p>B</p>
<p>SB</p>
<p>RB</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR23">23</xref>
, <xref ref-type="bibr" rid="CR60">60</xref>
, <xref ref-type="bibr" rid="CR70">70</xref>
, <xref ref-type="bibr" rid="CR74">74</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR60">60</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR99">99</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
, <xref ref-type="bibr" rid="CR146">146</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR69">69</xref>
, <xref ref-type="bibr" rid="CR130">130</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR132">132</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR145">145</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR158">158</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR133">133</xref>
, <xref ref-type="bibr" rid="CR152">152</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>17</bold>
</td>
<td align="left">Hypatic acid</td>
<td align="left">T25</td>
<td align="left">R</td>
<td align="left">[<xref ref-type="bibr" rid="CR69">69</xref>
]</td>
</tr>
<tr><td align="left"> <bold>18</bold>
</td>
<td align="left">Arjunglucoside I</td>
<td align="left"><p>T4</p>
<p>T17</p>
<p>T50</p>
<p>T32</p>
</td>
<td align="left"><p>B, R</p>
<p>F</p>
<p>R</p>
<p>B</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR70">70</xref>
, <xref ref-type="bibr" rid="CR74">74</xref>
, <xref ref-type="bibr" rid="CR78">78</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR146">146</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR72">72</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR145">145</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>19</bold>
</td>
<td align="left">Sericoside</td>
<td align="left"><p>T4</p>
<p>T25</p>
<p>T28</p>
<p>T44</p>
<p>T32</p>
<p>T50</p>
</td>
<td align="left"><p>B</p>
<p>SB</p>
<p>B</p>
<p>R, L, SB</p>
<p>B</p>
<p>R</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR71">71</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR130">130</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR76">76</xref>
, <xref ref-type="bibr" rid="CR131">131</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR43">43</xref>
, <xref ref-type="bibr" rid="CR133">133</xref>
, <xref ref-type="bibr" rid="CR149">149</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR145">145</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR72">72</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>20</bold>
</td>
<td align="left">Crataegioside</td>
<td align="left"><p>T4</p>
<p>T17</p>
</td>
<td align="left"><p>B</p>
<p>F</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR75">75</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR146">146</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>21</bold>
</td>
<td align="left">23-<italic>O</italic>
-neochebuloylarjungenin 28-<italic>O</italic>
-β-<sc>d</sc>
-glycosyl ester</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR146">146</xref>
]</td>
</tr>
<tr><td align="left"> <bold>22</bold>
</td>
<td align="left">23-<italic>O</italic>
-4′-<italic>epi</italic>
-neochebuloylarjungenin</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR146">146</xref>
]</td>
</tr>
<tr><td align="left" rowspan="2"> <bold>23</bold>
</td>
<td align="left" rowspan="2">23-<italic>O</italic>
-galloylarjunic acid</td>
<td align="left"><p>T39</p>
<p>T32</p>
</td>
<td align="left"><p>B</p>
<p>B</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR144">144</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR145">145</xref>
]</p>
</td>
</tr>
<tr><td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR146">146</xref>
]</td>
</tr>
<tr><td align="left" rowspan="2"> <bold>24</bold>
</td>
<td align="left" rowspan="2">Quercotriterpenoside I</td>
<td align="left">T32</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR145">145</xref>
]</td>
</tr>
<tr><td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR146">146</xref>
]</td>
</tr>
<tr><td align="left"> <bold>25</bold>
</td>
<td align="left">Sericic acid</td>
<td align="left"><p>T28</p>
<p>T32</p>
<p>T44</p>
</td>
<td align="left"><p>B</p>
<p>B</p>
<p>R</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR132">132</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR145">145</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR150">150</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>26</bold>
</td>
<td align="left">24-Deoxy-sericoside</td>
<td align="left">T32</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR138">138</xref>
]</td>
</tr>
<tr><td align="left"> <bold>27</bold>
</td>
<td align="left">Arjunolic acid</td>
<td align="left"><p>T1</p>
<p>T4</p>
<p>T7</p>
<p>T9</p>
<p>T8</p>
<p>T16, T17, T20, T39</p>
<p>T34</p>
<p>T36</p>
</td>
<td align="left"><p>B, H</p>
<p>B, H, L, S, R, F</p>
<p>RB</p>
<p>L</p>
<p>B, L, S, R</p>
<p>B, L, S, R, F</p>
<p>L</p>
<p>B</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR55">55</xref>
, <xref ref-type="bibr" rid="CR56">56</xref>
, <xref ref-type="bibr" rid="CR74">74</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
, <xref ref-type="bibr" rid="CR77">77</xref>
, <xref ref-type="bibr" rid="CR78">78</xref>
, <xref ref-type="bibr" rid="CR91">91</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR97">97</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
, <xref ref-type="bibr" rid="CR144">144</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR35">35</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR140">140</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>28</bold>
</td>
<td align="left">Terminolic acid</td>
<td align="left"><p>T1</p>
<p>T17</p>
<p>T7, T16, T31</p>
<p>T25</p>
<p>T32</p>
</td>
<td align="left"><p>H</p>
<p>F</p>
<p>H</p>
<p>H, Rl</p>
<p>H, B</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR56">56</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR146">146</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR128">128</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR128">128</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR128">128</xref>
, <xref ref-type="bibr" rid="CR145">145</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>29</bold>
</td>
<td align="left">Arjunglucoside II</td>
<td align="left"><p>T4</p>
<p>T17</p>
</td>
<td align="left"><p>B</p>
<p>F</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR70">70</xref>
, <xref ref-type="bibr" rid="CR74">74</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR146">146</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>30</bold>
</td>
<td align="left">23-<italic>O</italic>
-galloylarjunolic acid</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR146">146</xref>
]</td>
</tr>
<tr><td align="left"> <bold>31</bold>
</td>
<td align="left">23-<italic>O</italic>
-galloylarjunolic acid 28-<italic>O</italic>
-β-<sc>d</sc>
-glucosyl ester</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR146">146</xref>
]</td>
</tr>
<tr><td align="left"> <bold>32</bold>
</td>
<td align="left">23-<italic>O</italic>
-galloylterminolic acid 28-<italic>O</italic>
-β-<sc>d</sc>
-glucosyl ester</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR146">146</xref>
]</td>
</tr>
<tr><td align="left"> <bold>33</bold>
</td>
<td align="left">Arjunolitin</td>
<td align="left">T4</td>
<td align="left">SB</td>
<td align="left">[<xref ref-type="bibr" rid="CR80">80</xref>
]</td>
</tr>
<tr><td align="left"> <bold>34</bold>
</td>
<td align="left">Terminolitin</td>
<td align="left">T4</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR80">80</xref>
]</td>
</tr>
<tr><td align="left"> <bold>35</bold>
</td>
<td align="left">Arjunglucoside III</td>
<td align="left">T4</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR74">74</xref>
]</td>
</tr>
<tr><td align="left"> <bold>36</bold>
</td>
<td align="left">Methyl oleanate</td>
<td align="left">T4</td>
<td align="left">R, F</td>
<td align="left">[<xref ref-type="bibr" rid="CR80">80</xref>
, <xref ref-type="bibr" rid="CR124">124</xref>
]</td>
</tr>
<tr><td align="left"> <bold>37</bold>
</td>
<td align="left">Olean-3α,22β-diol-12 en-28-oic acid 3-<italic>O</italic>
-β-<sc>d</sc>
-glucosyl-(1 → 4)-β-<sc>d</sc>
-glucoside</td>
<td align="left">T4</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR81">81</xref>
, <xref ref-type="bibr" rid="CR84">84</xref>
]</td>
</tr>
<tr><td align="left"> <bold>38</bold>
</td>
<td align="left">Arjunetoside</td>
<td align="left">T4</td>
<td align="left">R, SB</td>
<td align="left">[<xref ref-type="bibr" rid="CR82">82</xref>
]</td>
</tr>
<tr><td align="left"> <bold>39</bold>
</td>
<td align="left">Olean 3β,6β,22α-triol-12en-28-oic acid-3-<italic>O</italic>
-β-<sc>d</sc>
-glucosyl-(1 → 4)-β-<sc>d</sc>
-glucoside</td>
<td align="left">T4</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR84">84</xref>
]</td>
</tr>
<tr><td align="left"> <bold>40</bold>
</td>
<td align="left">2α,19α,Dihydroxy-3-oxo-olean-12-en-28-oic acid-28-<italic>O</italic>
-β-<sc>d</sc>
-glucoside</td>
<td align="left">T4</td>
<td align="left">R</td>
<td align="left">[<xref ref-type="bibr" rid="CR85">85</xref>
]</td>
</tr>
<tr><td align="left"> <bold>41</bold>
</td>
<td align="left">Ivorengenin A (2α,19α,24-trihydroxy-3-oxoolean-12-en-28-oic acid)</td>
<td align="left">T28</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR132">132</xref>
]</td>
</tr>
<tr><td align="left"> <bold>42</bold>
</td>
<td align="left">Chebuloside I</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR115">115</xref>
]</td>
</tr>
<tr><td align="left"> <bold>43</bold>
</td>
<td align="left">Chebuloside II</td>
<td align="left"><p>T17</p>
<p>T32</p>
</td>
<td align="left"><p>F</p>
<p>B</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR115">115</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR138">138</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>44</bold>
</td>
<td align="left">Arjunglucoside</td>
<td align="left"><p>T17</p>
<p>T44</p>
<p>T33</p>
</td>
<td align="left"><p>F</p>
<p>R, SB</p>
<p>SB</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR115">115</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR133">133</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR158">158</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>45</bold>
</td>
<td align="left">Glaucescic acid (2α,3α,6α,23-tetrahydroxyolean-2-en-28-oic acid)</td>
<td align="left">T25</td>
<td align="left">R</td>
<td align="left">[<xref ref-type="bibr" rid="CR69">69</xref>
]</td>
</tr>
<tr><td align="left"> <bold>46</bold>
</td>
<td align="left">Glaucinoic acid (2α,3β,19α,24-tetrahydroxyolean-12-en-30-oic acid)</td>
<td align="left">T25</td>
<td align="left">SB</td>
<td align="left">[<xref ref-type="bibr" rid="CR130">130</xref>
]</td>
</tr>
<tr><td align="left"> <bold>47</bold>
</td>
<td align="left">Termiarjunoside I (olean-1α,3β,9α,22α-tetraol-12-en-28-oic acid-3-β-<sc>d</sc>
-glucoside)</td>
<td align="left">T4</td>
<td align="left">SB</td>
<td align="left">[<xref ref-type="bibr" rid="CR156">156</xref>
]</td>
</tr>
<tr><td align="left"> <bold>48</bold>
</td>
<td align="left">Termiarjunoside II (olean-3α,5α,25-triol-12-en-23,28-dioic acid-3α-<sc>d</sc>
-glucoside)</td>
<td align="left">T4</td>
<td align="left">SB</td>
<td align="left">[<xref ref-type="bibr" rid="CR156">156</xref>
]</td>
</tr>
<tr><td align="left"> <bold>49</bold>
</td>
<td align="left">β-Amyrin</td>
<td align="left"><p>T25</p>
<p>T36</p>
</td>
<td align="left"><p>SB</p>
<p>B</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR129">129</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR140">140</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>50</bold>
</td>
<td align="left">Ivorenoside A</td>
<td align="left">T28</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR131">131</xref>
]</td>
</tr>
<tr><td align="left"> <bold>51</bold>
</td>
<td align="left">Ivorenoside B</td>
<td align="left">T28</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR131">131</xref>
]</td>
</tr>
<tr><td align="left"> <bold>52</bold>
</td>
<td align="left">Ivorenoside C</td>
<td align="left">T28</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR131">131</xref>
]</td>
</tr>
<tr><td align="left"> <bold>53</bold>
</td>
<td align="left">Ivorengenin B (4-oxo-19α-hydroxy-3,24-dinor-2,4-secoolean-12-ene-2,28-dioic acid)</td>
<td align="left">T28</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR132">132</xref>
]</td>
</tr>
<tr><td align="left"> <bold>54</bold>
</td>
<td align="left">1α,3β-Hydroxyimberbic acid 23-<italic>O</italic>
-α-<sc>l</sc>
-4-acetylrhamnoside</td>
<td align="left">T47</td>
<td align="left">SB</td>
<td align="left">[<xref ref-type="bibr" rid="CR48">48</xref>
]</td>
</tr>
<tr><td align="left"> <bold>55</bold>
</td>
<td align="left">1α,3β,3,23-Trihydroxy-olean-12-en-29-oate-23-<italic>O</italic>
-α-[4-acetoxyrhamnosyl]-29-α-rhamnoside</td>
<td align="left">T47</td>
<td align="left">SB</td>
<td align="left">[<xref ref-type="bibr" rid="CR48">48</xref>
]</td>
</tr>
<tr><td align="left"> <bold>56</bold>
</td>
<td align="left">2α,3β-Dihydroxyolean-12-en-28-oic acid 28-<italic>O</italic>
-β-<sc>d</sc>
-glucoside</td>
<td align="left">T48</td>
<td align="left">SB</td>
<td align="left">[<xref ref-type="bibr" rid="CR49">49</xref>
]</td>
</tr>
<tr><td align="left"> <bold>57</bold>
</td>
<td align="left">2α,3β,21β-Trihydroxyolean-12-en-28-oic acid 28-<italic>O</italic>
-β-<sc>d</sc>
-glucoside</td>
<td align="left">T48</td>
<td align="left">SB</td>
<td align="left">[<xref ref-type="bibr" rid="CR49">49</xref>
]</td>
</tr>
<tr><td align="left"> <bold>58</bold>
</td>
<td align="left">2α,3β,29-Trihydroxyolean-12-en-28-oic acid 28-<italic>O</italic>
-β-<sc>d</sc>
-glucoside</td>
<td align="left">T48</td>
<td align="left">SB</td>
<td align="left">[<xref ref-type="bibr" rid="CR49">49</xref>
]</td>
</tr>
<tr><td align="left"> <bold>59</bold>
</td>
<td align="left">2α,3β,23,27-Tetrahydroxyolean-12-en-28-oic acid 28-<italic>O</italic>
-β-<sc>d</sc>
-glucoside</td>
<td align="left">T48</td>
<td align="left">SB</td>
<td align="left">[<xref ref-type="bibr" rid="CR49">49</xref>
]</td>
</tr>
<tr><td align="left"> <bold>60</bold>
</td>
<td align="left">Terminaliaside A ((3β,21β,22α)-3-<italic>O</italic>
-(3′-<italic>O</italic>
-angeloylglucosyl)-21,22-dihydroxy-28-<italic>O</italic>
-sophorosyl-16-oxoolean-12-ene)</td>
<td align="left">T50</td>
<td align="left">R</td>
<td align="left">[<xref ref-type="bibr" rid="CR72">72</xref>
]</td>
</tr>
<tr><td align="left"> <bold>61</bold>
</td>
<td align="left">2, 3, 23-Trihydroxylolean-12-ene</td>
<td align="left">T7</td>
<td align="left">RB</td>
<td align="left">[<xref ref-type="bibr" rid="CR91">91</xref>
]</td>
</tr>
<tr><td align="left"> <bold>62</bold>
</td>
<td align="left">2α,3β,23-Trihydroxylolean-12-en-28-oic acid</td>
<td align="left">T48</td>
<td align="left">SB</td>
<td align="left">[<xref ref-type="bibr" rid="CR49">49</xref>
]</td>
</tr>
<tr><td align="left"> <bold>63</bold>
</td>
<td align="left">23-<italic>O</italic>
-galloylpinfaenoic acid 28-<italic>O</italic>
-β-<sc>d</sc>
-glucosyl ester</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR146">146</xref>
]</td>
</tr>
<tr><td align="left"> <bold>64</bold>
</td>
<td align="left">Pinfaenoic acid 28-<italic>O</italic>
-β-<sc>d</sc>
-glucosyl ester</td>
<td align="left"><p>T4</p>
<p>T17</p>
</td>
<td align="left"><p>B</p>
<p>F</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR76">76</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR146">146</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>65</bold>
</td>
<td align="left">2α,3β-Dihydroxyurs-12,18-dien-28-oic acid 28-<italic>O</italic>
-β-<sc>d</sc>
-glucosyl ester</td>
<td align="left">T4</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR76">76</xref>
]</td>
</tr>
<tr><td align="left"> <bold>66</bold>
</td>
<td align="left">Quadranoside VIII</td>
<td align="left">T4</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR76">76</xref>
]</td>
</tr>
<tr><td align="left"> <bold>67</bold>
</td>
<td align="left">Kajiichigoside F1</td>
<td align="left">T4</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR76">76</xref>
]</td>
</tr>
<tr><td align="left"> <bold>68</bold>
</td>
<td align="left">2α,3β,23Trihydroxyurs-12,19-dien-28-oic acid 28-<italic>O</italic>
-β-<sc>d</sc>
-glucosyl ester</td>
<td align="left">T4</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR76">76</xref>
]</td>
</tr>
<tr><td align="left"> <bold>69</bold>
</td>
<td align="left">α-Amyrin</td>
<td align="left">T7</td>
<td align="left">RB</td>
<td align="left">[<xref ref-type="bibr" rid="CR91">91</xref>
]</td>
</tr>
<tr><td align="left"> <bold>70</bold>
</td>
<td align="left">2α,3β,23-Trihydroxy-urs-12-en-28-oic acid</td>
<td align="left">T34</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR35">35</xref>
]</td>
</tr>
<tr><td align="left"> <bold>71</bold>
</td>
<td align="left">2α-Hydroxyursolic acid</td>
<td align="left"><p>T34</p>
<p>T17</p>
</td>
<td align="left"><p>L</p>
<p>F</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR35">35</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR115">115</xref>
, <xref ref-type="bibr" rid="CR116">116</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>72</bold>
</td>
<td align="left">Ursolic acid</td>
<td align="left">T11</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR35">35</xref>
]</td>
</tr>
<tr><td align="left"> <bold>73</bold>
</td>
<td align="left">2α-Hydroxymicromeric acid</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR115">115</xref>
, <xref ref-type="bibr" rid="CR116">116</xref>
]</td>
</tr>
<tr><td align="left"> <bold>74</bold>
</td>
<td align="left">Betulinic acid</td>
<td align="left"><p>T1</p>
<p>T11</p>
<p>T12</p>
<p>T4, T16, T17, T20, T39</p>
<p>T8</p>
<p>T25</p>
<p>T28</p>
<p>T36</p>
</td>
<td align="left"><p>B</p>
<p>L</p>
<p>B</p>
<p>B, L, S, R, F</p>
<p>B, L, S, R</p>
<p>SB</p>
<p>B</p>
<p>B</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR55">55</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR35">35</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR99">99</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR129">129</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR132">132</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR140">140</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>75</bold>
</td>
<td align="left">Terminic acid</td>
<td align="left">T4</td>
<td align="left">R, H</td>
<td align="left">[<xref ref-type="bibr" rid="CR57">57</xref>
, <xref ref-type="bibr" rid="CR62">62</xref>
]</td>
</tr>
<tr><td align="left"> <bold>76</bold>
</td>
<td align="left">Lupeol</td>
<td align="left"><p>T4</p>
<p>T25</p>
<p>T44</p>
</td>
<td align="left"><p>SB</p>
<p>SB</p>
<p>SB, R</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR80">80</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR129">129</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR43">43</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>77</bold>
</td>
<td align="left">Monogynol A</td>
<td align="left">T12</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR99">99</xref>
]</td>
</tr>
<tr><td align="left"> <bold>78</bold>
</td>
<td align="left">Triterpenes</td>
<td align="left"><p>T25</p>
<p>T44</p>
</td>
<td align="left"><p>SB</p>
<p>R, SB</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR129">129</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR133">133</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>79</bold>
</td>
<td align="left">Friedelin</td>
<td align="left"><p>T4</p>
<p>T7</p>
<p>T25</p>
<p>T34</p>
</td>
<td align="left"><p>F</p>
<p>RB</p>
<p>SB</p>
<p>SB</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR83">83</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR93">93</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR129">129</xref>
, <xref ref-type="bibr" rid="CR130">130</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR35">35</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>80</bold>
</td>
<td align="left">Maslinic lactone</td>
<td align="left">T1</td>
<td align="left">H</td>
<td align="left">[<xref ref-type="bibr" rid="CR56">56</xref>
]</td>
</tr>
<tr><td align="left"> <bold>81</bold>
</td>
<td align="left">Terminalin A</td>
<td align="left">T25</td>
<td align="left">SB</td>
<td align="left">[<xref ref-type="bibr" rid="CR129">129</xref>
]</td>
</tr>
<tr><td align="left"> <bold>82</bold>
</td>
<td align="left">Arjunaside A</td>
<td align="left">T4</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR68">68</xref>
]</td>
</tr>
<tr><td align="left"> <bold>83</bold>
</td>
<td align="left">Arjunaside B</td>
<td align="left">T4</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR68">68</xref>
]</td>
</tr>
<tr><td align="left"> <bold>84</bold>
</td>
<td align="left">Arjunaside C</td>
<td align="left">T4</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR68">68</xref>
]</td>
</tr>
<tr><td align="left"> <bold>85</bold>
</td>
<td align="left">Arjunaside D</td>
<td align="left">T4</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR68">68</xref>
]</td>
</tr>
<tr><td align="left"><bold>86</bold>
</td>
<td align="left">Arjunaside E</td>
<td align="left">T4</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR68">68</xref>
]</td>
</tr>
<tr><td align="left" colspan="5">Mono- (14) and sesqui- (4) terpendoids</td>
</tr>
<tr><td align="left"> <bold>87</bold>
</td>
<td align="left">α-Pinene</td>
<td align="left">T9</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR13">13</xref>
]</td>
</tr>
<tr><td align="left"> <bold>88</bold>
</td>
<td align="left">Sabinene</td>
<td align="left">T9</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR13">13</xref>
]</td>
</tr>
<tr><td align="left"> <bold>89</bold>
</td>
<td align="left">Myrcene</td>
<td align="left">T9</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR13">13</xref>
]</td>
</tr>
<tr><td align="left"> <bold>90</bold>
</td>
<td align="left">β-Pinene</td>
<td align="left">T9</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR13">13</xref>
]</td>
</tr>
<tr><td align="left"> <bold>91</bold>
</td>
<td align="left">1,8-Cineole</td>
<td align="left">T9</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR13">13</xref>
]</td>
</tr>
<tr><td align="left"> <bold>92</bold>
</td>
<td align="left">Linalool</td>
<td align="left">T9</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR13">13</xref>
]</td>
</tr>
<tr><td align="left"> <bold>93</bold>
</td>
<td align="left">Menthone</td>
<td align="left">T9</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR13">13</xref>
]</td>
</tr>
<tr><td align="left"> <bold>94</bold>
</td>
<td align="left">γ-Terpineol</td>
<td align="left">T9</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR13">13</xref>
]</td>
</tr>
<tr><td align="left"> <bold>95</bold>
</td>
<td align="left">α-Terpineol</td>
<td align="left">T9</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR13">13</xref>
]</td>
</tr>
<tr><td align="left"> <bold>96</bold>
</td>
<td align="left">Limonene</td>
<td align="left">T9</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR13">13</xref>
]</td>
</tr>
<tr><td align="left"> <bold>97</bold>
</td>
<td align="left">Neral</td>
<td align="left">T9</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR13">13</xref>
]</td>
</tr>
<tr><td align="left"> <bold>98</bold>
</td>
<td align="left">Geraniol</td>
<td align="left">T9</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR13">13</xref>
]</td>
</tr>
<tr><td align="left"> <bold>99</bold>
</td>
<td align="left">Thymol</td>
<td align="left">T9</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR13">13</xref>
]</td>
</tr>
<tr><td align="left"> <bold>100</bold>
</td>
<td align="left">Isomenthone</td>
<td align="left">T9</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR13">13</xref>
]</td>
</tr>
<tr><td align="left"> <bold>101</bold>
</td>
<td align="left">β-Copaene</td>
<td align="left">T9</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR13">13</xref>
]</td>
</tr>
<tr><td align="left"> <bold>102</bold>
</td>
<td align="left">β-Caryophyllene</td>
<td align="left">T9</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR13">13</xref>
]</td>
</tr>
<tr><td align="left"> <bold>103</bold>
</td>
<td align="left">Caryophyllene</td>
<td align="left">T9</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR13">13</xref>
]</td>
</tr>
<tr><td align="left"> <bold>104</bold>
</td>
<td align="left">α-Humulene</td>
<td align="left">T9</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR13">13</xref>
]</td>
</tr>
<tr><td align="left" colspan="5">Hydrolysable (89) and condensed tannins (2)</td>
</tr>
<tr><td align="left"> <bold>105</bold>
</td>
<td align="left">1,2,3,6-Tetra-<italic>O</italic>
-galloyl-β-<sc>d</sc>
-glucose</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR159">159</xref>
]</td>
</tr>
<tr><td align="left"> <bold>106</bold>
</td>
<td align="left">Gallotannin (1,2,3,4,6 penta galloyl glucose)</td>
<td align="left"><p>T4</p>
<p>T17</p>
<p>T19</p>
<p>T30</p>
<p>T45, T46</p>
</td>
<td align="left"><p>SB, L</p>
<p>F</p>
<p>F</p>
<p>R</p>
<p>L</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR86">86</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR21">21</xref>
, <xref ref-type="bibr" rid="CR118">118</xref>
, <xref ref-type="bibr" rid="CR119">119</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR120">120</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR133">133</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR133">133</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>107</bold>
</td>
<td align="left">1,3,4,6-Tetra-<italic>O</italic>
-galloyl-β-<sc>d</sc>
-glucose</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR159">159</xref>
]</td>
</tr>
<tr><td align="left"> <bold>108</bold>
</td>
<td align="left">2,3,4,6-Tetra-<italic>O</italic>
-galloyl-<sc>d</sc>
-glucose</td>
<td align="left"><p>T3</p>
<p>T4</p>
</td>
<td align="left"><p>F</p>
<p>SB, L</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR154">154</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR86">86</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>109</bold>
</td>
<td align="left">1,2,6-Tri-<italic>O</italic>
-galloyl-β-<sc>d</sc>
-glucose</td>
<td align="left">T31</td>
<td align="left">R</td>
<td align="left">[<xref ref-type="bibr" rid="CR101">101</xref>
]</td>
</tr>
<tr><td align="left"> <bold>110</bold>
</td>
<td align="left">Sanguiin H-1</td>
<td align="left">T14</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR102">102</xref>
]</td>
</tr>
<tr><td align="left"> <bold>111</bold>
</td>
<td align="left">1,6-Di-<italic>O</italic>
-galloyl-β-<sc>d</sc>
-glucose</td>
<td align="left"><p>T3</p>
<p>T17</p>
<p>T40</p>
</td>
<td align="left"><p>F</p>
<p>F</p>
<p>B</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR154">154</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR21">21</xref>
, <xref ref-type="bibr" rid="CR119">119</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR41">41</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>112</bold>
</td>
<td align="left">1,3,6-Tri-<italic>O</italic>
-galloyl-β-<sc>d</sc>
-glucose</td>
<td align="left"><p>T3</p>
<p>T40</p>
<p>T19</p>
<p>T17</p>
</td>
<td align="left"><p>F</p>
<p>B</p>
<p>F</p>
<p>F</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR154">154</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR41">41</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR120">120</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR159">159</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>113</bold>
</td>
<td align="left">Methyl 3,6-di-<italic>O</italic>
-galloyl-β-<sc>d</sc>
-glucoside</td>
<td align="left">T40</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR41">41</xref>
]</td>
</tr>
<tr><td align="left"> <bold>114</bold>
</td>
<td align="left">4,6 Bis hexahydroxydiphenyl-1-galloyl-glucose</td>
<td align="left">T4</td>
<td align="left">SB, L</td>
<td align="left">[<xref ref-type="bibr" rid="CR86">86</xref>
]</td>
</tr>
<tr><td align="left"> <bold>115</bold>
</td>
<td align="left">Sanguiin H-4</td>
<td align="left">T14 </td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR18">18</xref>
, <xref ref-type="bibr" rid="CR102">102</xref>
]</td>
</tr>
<tr><td align="left"> <bold>116</bold>
</td>
<td align="left">Corilagin</td>
<td align="left"><p>T3</p>
<p>T31</p>
<p>T16</p>
<p>T17</p>
<p>T19</p>
<p>T24</p>
<p>T32</p>
</td>
<td align="left"><p>F</p>
<p>R</p>
<p>L, B</p>
<p>F</p>
<p>F</p>
<p>F</p>
<p>L</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR154">154</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR101">101</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR41">41</xref>
, <xref ref-type="bibr" rid="CR106">106</xref>
, <xref ref-type="bibr" rid="CR107">107</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR21">21</xref>
, <xref ref-type="bibr" rid="CR118">118</xref>
, <xref ref-type="bibr" rid="CR119">119</xref>
, <xref ref-type="bibr" rid="CR159">159</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR120">120</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR126">126</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR135">135</xref>
, <xref ref-type="bibr" rid="CR136">136</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>117</bold>
</td>
<td align="left">Tercatain</td>
<td align="left"><p>T16</p>
<p>T17</p>
</td>
<td align="left"><p>B, L</p>
<p>F</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR41">41</xref>
, <xref ref-type="bibr" rid="CR106">106</xref>
, <xref ref-type="bibr" rid="CR107">107</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR159">159</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>118</bold>
</td>
<td align="left">1,3-Di-<italic>O</italic>
-galloyl-β-<sc>d</sc>
-glucose</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR159">159</xref>
]</td>
</tr>
<tr><td align="left"> <bold>119</bold>
</td>
<td align="left">2,3-<italic>O</italic>
-(<italic>S</italic>
)-HHDP-<sc>d</sc>
-glucose</td>
<td align="left"><p>T3</p>
<p>T14</p>
<p>T4</p>
<p>T16</p>
<p>T40</p>
<p>T36</p>
</td>
<td align="left"><p>F</p>
<p>L</p>
<p>B</p>
<p>B, L</p>
<p>B</p>
<p>L</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR154">154</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR102">102</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR104">104</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR41">41</xref>
, <xref ref-type="bibr" rid="CR107">107</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR41">41</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR38">38</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>120</bold>
</td>
<td align="left">2,3-(<italic>S</italic>
)-HHDP-6-<italic>O</italic>
-galloyl-<sc>d</sc>
-glucose</td>
<td align="left"><p>T3</p>
<p>T4</p>
<p>T40</p>
<p>T32</p>
</td>
<td align="left"><p>F</p>
<p>B</p>
<p>B</p>
<p>B</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR154">154</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR104">104</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR41">41</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR137">137</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>121</bold>
</td>
<td align="left">3,6-Di-<italic>O</italic>
-galloyl-<sc>d</sc>
-glucose</td>
<td align="left"><p>T3</p>
<p>T40</p>
<p>T17</p>
</td>
<td align="left"><p>F</p>
<p>B</p>
<p>F</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR154">154</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR41">41</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR159">159</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>122</bold>
</td>
<td align="left">3,4-Di-<italic>O</italic>
-galloyl-<sc>d</sc>
-glucose</td>
<td align="left">T3</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR154">154</xref>
]</td>
</tr>
<tr><td align="left"> <bold>123</bold>
</td>
<td align="left">6-<italic>O</italic>
-galloyl-<sc>d</sc>
-glucose</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR159">159</xref>
]</td>
</tr>
<tr><td align="left"> <bold>124</bold>
</td>
<td align="left">3,4,6-Tri-<italic>O</italic>
-galloyl-<sc>d</sc>
-glucose</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR159">159</xref>
]</td>
</tr>
<tr><td align="left"> <bold>125</bold>
</td>
<td align="left">Tellimagrandin I</td>
<td align="left"><p>T35</p>
<p>T17</p>
</td>
<td align="left"><p>L</p>
<p>F</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR139">139</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR159">159</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>126</bold>
</td>
<td align="left">Gemin D</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR159">159</xref>
]</td>
</tr>
<tr><td align="left"> <bold>127</bold>
</td>
<td align="left">Arjunin</td>
<td align="left"><p>T4</p>
<p>T17</p>
</td>
<td align="left"><p>L</p>
<p>F</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR65">65</xref>
, <xref ref-type="bibr" rid="CR86">86</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR115">115</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>128</bold>
</td>
<td align="left">Punicalin</td>
<td align="left"><p>T3</p>
<p>T4</p>
<p>T14</p>
<p>T40</p>
<p>T16</p>
<p>T17</p>
<p>T28</p>
<p>T49</p>
</td>
<td align="left"><p>F</p>
<p>L, B</p>
<p>L</p>
<p>B</p>
<p>L</p>
<p>L, F</p>
<p>SB</p>
<p>L</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR154">154</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR65">65</xref>
, <xref ref-type="bibr" rid="CR86">86</xref>
, <xref ref-type="bibr" rid="CR104">104</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR102">102</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR41">41</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR106">106</xref>
, <xref ref-type="bibr" rid="CR107">107</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR21">21</xref>
, <xref ref-type="bibr" rid="CR155">155</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR29">29</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR149">149</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>129</bold>
</td>
<td align="left">Casuarinin</td>
<td align="left"><p>T4</p>
<p>T16</p>
<p>T17</p>
</td>
<td align="left"><p>L, B</p>
<p>B</p>
<p>F</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR88">88</xref>
, <xref ref-type="bibr" rid="CR104">104</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR41">41</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR21">21</xref>
, <xref ref-type="bibr" rid="CR118">118</xref>
, <xref ref-type="bibr" rid="CR119">119</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>130</bold>
</td>
<td align="left">Casuariin</td>
<td align="left">T4</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR90">90</xref>
, <xref ref-type="bibr" rid="CR104">104</xref>
]</td>
</tr>
<tr><td align="left"> <bold>131</bold>
</td>
<td align="left">Terchebulin</td>
<td align="left"><p>T3</p>
<p>T4</p>
<p>T7</p>
<p>T12</p>
<p>T17</p>
<p>T31</p>
</td>
<td align="left"><p>F</p>
<p>B</p>
<p>SB</p>
<p>B</p>
<p>F</p>
<p>W</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR154">154</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR90">90</xref>
, <xref ref-type="bibr" rid="CR104">104</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR92">92</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR100">100</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR21">21</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR134">134</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>132</bold>
</td>
<td align="left">Castalagin</td>
<td align="left"><p>T4</p>
<p>T16, T40</p>
</td>
<td align="left"><p>B</p>
<p>B</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR90">90</xref>
, <xref ref-type="bibr" rid="CR104">104</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR41">41</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>133</bold>
</td>
<td align="left">Grandinin</td>
<td align="left">T16, T40</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR41">41</xref>
]</td>
</tr>
<tr><td align="left"> <bold>134</bold>
</td>
<td align="left">Castalin</td>
<td align="left">T16, T40</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR41">41</xref>
]</td>
</tr>
<tr><td align="left"> <bold>135</bold>
</td>
<td align="left">α/β-Punicalagin</td>
<td align="left"><p>T3</p>
<p>T7</p>
<p>T4</p>
<p>T11</p>
<p>T12</p>
<p>T31</p>
<p>T14</p>
<p>T16</p>
<p>T17</p>
<p>T40</p>
<p>T19</p>
<p>T28</p>
<p>T32</p>
<p>T35</p>
<p>T36</p>
<p>T38</p>
</td>
<td align="left"><p>F</p>
<p>SB</p>
<p>B</p>
<p>L</p>
<p>B</p>
<p>R</p>
<p>L</p>
<p>B</p>
<p>L, F</p>
<p>B</p>
<p>F</p>
<p>SB</p>
<p>B</p>
<p>L</p>
<p>L</p>
<p>L</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR154">154</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR92">92</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR104">104</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR35">35</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR100">100</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR101">101</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR18">18</xref>
, <xref ref-type="bibr" rid="CR103">103</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR41">41</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR21">21</xref>
, <xref ref-type="bibr" rid="CR106">106</xref>
, <xref ref-type="bibr" rid="CR119">119</xref>
, <xref ref-type="bibr" rid="CR155">155</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR41">41</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR120">120</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR29">29</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR137">137</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR139">139</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR38">38</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR39">39</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>136</bold>
</td>
<td align="left">1-α-<italic>O</italic>
-galloylpunicalagin</td>
<td align="left">T14 </td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR18">18</xref>
, <xref ref-type="bibr" rid="CR102">102</xref>
, <xref ref-type="bibr" rid="CR103">103</xref>
]</td>
</tr>
<tr><td align="left"> <bold>137</bold>
</td>
<td align="left">6′-<italic>O</italic>
-methyl neochebulagate</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR159">159</xref>
]</td>
</tr>
<tr><td align="left"> <bold>138</bold>
</td>
<td align="left">Dimethyl neochebulagate</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR159">159</xref>
]</td>
</tr>
<tr><td align="left"> <bold>139</bold>
</td>
<td align="left">Neochebulagic acid</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR159">159</xref>
]</td>
</tr>
<tr><td align="left"> <bold>140</bold>
</td>
<td align="left">Dimethyl 4′-epi-neochebulagate</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR159">159</xref>
]</td>
</tr>
<tr><td align="left"> <bold>141</bold>
</td>
<td align="left">Methyl chebulagate</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR159">159</xref>
]</td>
</tr>
<tr><td align="left"> <bold>142</bold>
</td>
<td align="left">Chebulagic acid</td>
<td align="left"><p>T3</p>
<p>T4</p>
<p>T8</p>
<p>T17</p>
<p>T16</p>
<p>T39</p>
<p>T20</p>
<p>T19</p>
<p>T32</p>
<p>T35</p>
</td>
<td align="left"><p>F</p>
<p>B, L, S</p>
<p>F, B, L, S</p>
<p>F, B, L, S, R</p>
<p>F, B, L, S, R</p>
<p>F, B, L, S, R</p>
<p>F, B, L, R</p>
<p>F</p>
<p>L</p>
<p>L</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR154">154</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
, <xref ref-type="bibr" rid="CR96">96</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR3">3</xref>
, <xref ref-type="bibr" rid="CR4">4</xref>
, <xref ref-type="bibr" rid="CR9">9</xref>
, <xref ref-type="bibr" rid="CR21">21</xref>
, <xref ref-type="bibr" rid="CR110">110</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR120">120</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR135">135</xref>
, <xref ref-type="bibr" rid="CR136">136</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR139">139</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>143</bold>
</td>
<td align="left">Chebulinic acid</td>
<td align="left"><p>T3</p>
<p>T4, T8, T16, T20, T39</p>
<p>T17</p>
<p>T32</p>
<p>T35</p>
</td>
<td align="left"><p>F</p>
<p>F, B, L, S, R</p>
<p>F, B, L, S, R</p>
<p>L</p>
<p>L</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR154">154</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR3">3</xref>
, <xref ref-type="bibr" rid="CR4">4</xref>
, <xref ref-type="bibr" rid="CR21">21</xref>
, <xref ref-type="bibr" rid="CR110">110</xref>
, <xref ref-type="bibr" rid="CR119">119</xref>
, <xref ref-type="bibr" rid="CR155">155</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR110">110</xref>
, <xref ref-type="bibr" rid="CR135">135</xref>
, <xref ref-type="bibr" rid="CR139">139</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>144</bold>
</td>
<td align="left">Chebulanin</td>
<td align="left"><p>T34, T11</p>
<p>T17</p>
</td>
<td align="left"><p>L</p>
<p>F</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR35">35</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR21">21</xref>
, <xref ref-type="bibr" rid="CR119">119</xref>
, <xref ref-type="bibr" rid="CR155">155</xref>
, <xref ref-type="bibr" rid="CR159">159</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>145</bold>
</td>
<td align="left">1,3-Di-<italic>O</italic>
-galloyl-2,4-chebuloyl-β-<sc>d</sc>
-glucose</td>
<td align="left">T3</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR154">154</xref>
]</td>
</tr>
<tr><td align="left"> <bold>146</bold>
</td>
<td align="left">1,6-Di-<italic>O</italic>
-galloyl-2,4-chebuloyl-β-<sc>d</sc>
-glucose</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR155">155</xref>
, <xref ref-type="bibr" rid="CR159">159</xref>
]</td>
</tr>
<tr><td align="left"> <bold>147</bold>
</td>
<td align="left">2-<italic>O</italic>
-galloylpunicalin</td>
<td align="left"><p>T14</p>
<p>T40</p>
<p>T32</p>
<p>T49</p>
</td>
<td align="left"><p>L</p>
<p>B</p>
<p>B</p>
<p>L</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR18">18</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR41">41</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR137">137</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR149">149</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>148</bold>
</td>
<td align="left">1-Desgalloyleugeniin</td>
<td align="left"><p>T14</p>
<p>T16</p>
</td>
<td align="left"><p>L</p>
<p>L</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR102">102</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR107">107</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>149</bold>
</td>
<td align="left">Eugeniin</td>
<td align="left">T14 </td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR102">102</xref>
]</td>
</tr>
<tr><td align="left"> <bold>150</bold>
</td>
<td align="left">Rugosin A</td>
<td align="left">T14 </td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR102">102</xref>
]</td>
</tr>
<tr><td align="left"> <bold>151</bold>
</td>
<td align="left">1(α)-<italic>O</italic>
-galloylpedunculagin</td>
<td align="left">T14 </td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR102">102</xref>
]</td>
</tr>
<tr><td align="left"> <bold>152</bold>
</td>
<td align="left">Praecoxin A</td>
<td align="left">T14 </td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR102">102</xref>
]</td>
</tr>
<tr><td align="left"> <bold>153</bold>
</td>
<td align="left">Calamansanin</td>
<td align="left">T14 </td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR102">102</xref>
]</td>
</tr>
<tr><td align="left"> <bold>154</bold>
</td>
<td align="left">Calamanin A</td>
<td align="left">T14 </td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR102">102</xref>
]</td>
</tr>
<tr><td align="left"> <bold>155</bold>
</td>
<td align="left">Calamanin B</td>
<td align="left">T14 </td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR102">102</xref>
]</td>
</tr>
<tr><td align="left"> <bold>156</bold>
</td>
<td align="left">Calamanin C</td>
<td align="left">T14 </td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR102">102</xref>
]</td>
</tr>
<tr><td align="left"> <bold>157</bold>
</td>
<td align="left">Terflavin C</td>
<td align="left"><p>T4</p>
<p>T14</p>
<p>T17</p>
</td>
<td align="left"><p>B</p>
<p>L</p>
<p>L</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR104">104</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR103">103</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR21">21</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>158</bold>
</td>
<td align="left">Terflavin A</td>
<td align="left"><p>T16</p>
<p>T17</p>
<p>T32</p>
</td>
<td align="left"><p>L</p>
<p>F</p>
<p>B</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR106">106</xref>
, <xref ref-type="bibr" rid="CR107">107</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR21">21</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR137">137</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>159</bold>
</td>
<td align="left">Terflavin B</td>
<td align="left"><p>T16</p>
<p>T17</p>
<p>T32</p>
</td>
<td align="left"><p>L</p>
<p>L, F</p>
<p>B</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR106">106</xref>
, <xref ref-type="bibr" rid="CR107">107</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR21">21</xref>
, <xref ref-type="bibr" rid="CR155">155</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR137">137</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>160</bold>
</td>
<td align="left">3-Methoxy-4-hydroxyphenol-1-<italic>O</italic>
-β-<sc>d</sc>
-(6′-<italic>O</italic>
-galloyl)-glucoside</td>
<td align="left">T16</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR41">41</xref>
]</td>
</tr>
<tr><td align="left"> <bold>161</bold>
</td>
<td align="left">3,5-Di-methoxy-4-hydroxyphenol-1-<italic>O</italic>
-β-<sc>d</sc>
-(6′-<italic>O</italic>
-galloyl)-glucoside</td>
<td align="left">T16</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR41">41</xref>
]</td>
</tr>
<tr><td align="left"> <bold>162</bold>
</td>
<td align="left">Acutissimin A</td>
<td align="left">T16</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR41">41</xref>
]</td>
</tr>
<tr><td align="left"> <bold>163</bold>
</td>
<td align="left">Eugenigrandin A</td>
<td align="left">T16</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR41">41</xref>
]</td>
</tr>
<tr><td align="left"> <bold>164</bold>
</td>
<td align="left">Catappanin A</td>
<td align="left">T16</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR41">41</xref>
]</td>
</tr>
<tr><td align="left"> <bold>165</bold>
</td>
<td align="left">Castamollinin</td>
<td align="left">T40</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR41">41</xref>
]</td>
</tr>
<tr><td align="left"> <bold>166</bold>
</td>
<td align="left">Tergallagin</td>
<td align="left">T16</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR106">106</xref>
, <xref ref-type="bibr" rid="CR107">107</xref>
]</td>
</tr>
<tr><td align="left"> <bold>167</bold>
</td>
<td align="left">Geraniin</td>
<td align="left">T16</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR107">107</xref>
]</td>
</tr>
<tr><td align="left"> <bold>168</bold>
</td>
<td align="left">Granatin B</td>
<td align="left">T16</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR107">107</xref>
]</td>
</tr>
<tr><td align="left"> <bold>169</bold>
</td>
<td align="left">Gallotannic (tannic acid)</td>
<td align="left"><p>T17,T8</p>
<p>T38</p>
</td>
<td align="left"><p>F</p>
<p>L</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR113">113</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR141">141</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>170</bold>
</td>
<td align="left">Chebulin</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR113">113</xref>
, <xref ref-type="bibr" rid="CR114">114</xref>
]</td>
</tr>
<tr><td align="left"> <bold>171</bold>
</td>
<td align="left">Terchebin</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR113">113</xref>
, <xref ref-type="bibr" rid="CR119">119</xref>
]</td>
</tr>
<tr><td align="left"> <bold>172</bold>
</td>
<td align="left">Neochebulinic acid</td>
<td align="left"><p>T3</p>
<p>T17</p>
</td>
<td align="left"><p>F</p>
<p>F</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR154">154</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR21">21</xref>
, <xref ref-type="bibr" rid="CR119">119</xref>
, <xref ref-type="bibr" rid="CR155">155</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>173</bold>
</td>
<td align="left">Chebumeinin A</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR118">118</xref>
]</td>
</tr>
<tr><td align="left"> <bold>174</bold>
</td>
<td align="left">Chebumeinin B</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR118">118</xref>
]</td>
</tr>
<tr><td align="left"> <bold>175</bold>
</td>
<td align="left">Isoterchebulin</td>
<td align="left">T32</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR137">137</xref>
]</td>
</tr>
<tr><td align="left"> <bold>176</bold>
</td>
<td align="left">Punicacortein C</td>
<td align="left"><p>T3</p>
<p>T32</p>
<p>T17</p>
</td>
<td align="left"><p>F</p>
<p>B</p>
<p>F</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR154">154</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR137">137</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR159">159</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>177</bold>
</td>
<td align="left">Punicacortein D</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR159">159</xref>
]</td>
</tr>
<tr><td align="left"> <bold>178</bold>
</td>
<td align="left">4,6-<italic>O</italic>
-Isoterchebuloyl-<sc>d</sc>
-glucose</td>
<td align="left">T32</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR137">137</xref>
]</td>
</tr>
<tr><td align="left"> <bold>179</bold>
</td>
<td align="left">Trigalloyl-β-<sc>d</sc>
-glucose</td>
<td align="left">T35</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR139">139</xref>
]</td>
</tr>
<tr><td align="left"> <bold>180</bold>
</td>
<td align="left">Tetragalloyl-β-<sc>d</sc>
-glucose</td>
<td align="left">T35</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR139">139</xref>
]</td>
</tr>
<tr><td align="left"> <bold>181</bold>
</td>
<td align="left">Pentagalloyl-β-<sc>d</sc>
-glucose</td>
<td align="left">T35</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR139">139</xref>
]</td>
</tr>
<tr><td align="left"> <bold>182</bold>
</td>
<td align="left">1,2,3-Tri-<italic>O</italic>
-galloyl-6-<italic>O</italic>
-cinnamoyl-β-<sc>d</sc>
-glucose</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR159">159</xref>
]</td>
</tr>
<tr><td align="left"> <bold>183</bold>
</td>
<td align="left">1,2,3,6-Tetra-<italic>O</italic>
-galloyl-4-<italic>O</italic>
-cinnamoyl-β-<sc>d</sc>
-glucose</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR159">159</xref>
]</td>
</tr>
<tr><td align="left"> <bold>184</bold>
</td>
<td align="left">1,6-Di-<italic>O</italic>
-galloyl-2-<italic>O</italic>
-cinnamoyl-β-<sc>d</sc>
-glucose</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR159">159</xref>
]</td>
</tr>
<tr><td align="left"> <bold>185</bold>
</td>
<td align="left">1,2-Di-<italic>O</italic>
-galloyl-6-<italic>O</italic>
-cinnamoyl-β-<sc>d</sc>
-glucose</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR159">159</xref>
]</td>
</tr>
<tr><td align="left"> <bold>186</bold>
</td>
<td align="left">4-<italic>O</italic>
-(2′′, 4′′-di-<italic>O</italic>
-galloyl-α-<sc>l</sc>
-rhamnosyl) ellagic acid</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR159">159</xref>
]</td>
</tr>
<tr><td align="left"> <bold>187</bold>
</td>
<td align="left">4-<italic>O</italic>
-(4′′-<italic>O</italic>
-galloyl-α-<sc>l</sc>
-rhamnosyl) ellagic acid</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR159">159</xref>
]</td>
</tr>
<tr><td align="left"> <bold>188</bold>
</td>
<td align="left">4-<italic>O</italic>
-(3′′, 4′′-di-<italic>O</italic>
-galloyl-α-<sc>l</sc>
-rhamnosyl) ellagic acid</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR159">159</xref>
]</td>
</tr>
<tr><td align="left"> <bold>189</bold>
</td>
<td align="left">1′-<italic>O</italic>
-methyl neochebulanin</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR159">159</xref>
]</td>
</tr>
<tr><td align="left"> <bold>190</bold>
</td>
<td align="left">Dimethyl neochebulinate</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR159">159</xref>
]</td>
</tr>
<tr><td align="left"> <bold>191</bold>
</td>
<td align="left">Phyllanemblinin E</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR159">159</xref>
]</td>
</tr>
<tr><td align="left"> <bold>192</bold>
</td>
<td align="left">1′-<italic>O</italic>
-methyl neochebulinate</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR159">159</xref>
]</td>
</tr>
<tr><td align="left"> <bold>193</bold>
</td>
<td align="left">Phyllanemblinin F</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR159">159</xref>
]</td>
</tr>
<tr><td align="left"> <bold>194</bold>
</td>
<td align="left">Procyanidin B-1</td>
<td align="left">T16</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR41">41</xref>
]</td>
</tr>
<tr><td align="left"> <bold>195</bold>
</td>
<td align="left">3′-<italic>O</italic>
-galloyl procyanidin B-2</td>
<td align="left">T16</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR41">41</xref>
]</td>
</tr>
<tr><td align="left" colspan="5">Flavonoids (45)</td>
</tr>
<tr><td align="left"> <bold>196</bold>
</td>
<td align="left">5,7,2′-Tri-<italic>O</italic>
-methylflavanone4′-<italic>O</italic>
-α-l-rhamnosyl-(1 → 4)-β-<sc>d</sc>
-glucoside</td>
<td align="left">T1</td>
<td align="left">R</td>
<td align="left">[<xref ref-type="bibr" rid="CR52">52</xref>
]</td>
</tr>
<tr><td align="left"> <bold>197</bold>
</td>
<td align="left">Arjunone</td>
<td align="left">T4</td>
<td align="left">B, F</td>
<td align="left">[<xref ref-type="bibr" rid="CR83">83</xref>
, <xref ref-type="bibr" rid="CR89">89</xref>
]</td>
</tr>
<tr><td align="left"> <bold>198</bold>
</td>
<td align="left">8-Methyl-5,7,2′,4′-tetramethoxy-flavanone </td>
<td align="left"><p>T1</p>
<p>T39</p>
</td>
<td align="left"><p>R</p>
<p>B</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR53">53</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR144">144</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>199</bold>
</td>
<td align="left">Naringin</td>
<td align="left"><p>T4</p>
<p>T8</p>
<p>T17</p>
<p>T39</p>
<p>T20</p>
</td>
<td align="left"><p>L, S, F</p>
<p>B, F</p>
<p>L, R, F</p>
<p>R, F</p>
<p>B, L, S, R</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>200</bold>
</td>
<td align="left">Eriodictyol</td>
<td align="left"><p>T4, T8, T17, T20, T39</p>
<p>T16</p>
</td>
<td align="left"><p>B, L, S, R, F</p>
<p>L, S, R, F</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>201</bold>
</td>
<td align="left">Hesperitin</td>
<td align="left">T24</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR122">122</xref>
]</td>
</tr>
<tr><td align="left"> <bold>202</bold>
</td>
<td align="left">Flavanone</td>
<td align="left">T24</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR122">122</xref>
]</td>
</tr>
<tr><td align="left"> <bold>203</bold>
</td>
<td align="left">Arjunolone (6,4-dihydroxy-7-methoxy flavone)</td>
<td align="left">T4</td>
<td align="left">SB</td>
<td align="left">[<xref ref-type="bibr" rid="CR64">64</xref>
]</td>
</tr>
<tr><td align="left"> <bold>204</bold>
</td>
<td align="left">Bicalein (5,6,7-trihydroxy flavone)</td>
<td align="left">T4</td>
<td align="left">SB</td>
<td align="left">[<xref ref-type="bibr" rid="CR64">64</xref>
]</td>
</tr>
<tr><td align="left"> <bold>205</bold>
</td>
<td align="left">Scutellarein</td>
<td align="left"><p>T4</p>
<p>T8, T17, T20</p>
<p>T16</p>
<p>T39</p>
</td>
<td align="left"><p>B, R</p>
<p>B, L, S, R, F</p>
<p>L, F</p>
<p>B, L, R, F</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>206</bold>
</td>
<td align="left">Luteolin</td>
<td align="left"><p>T4</p>
<p>T8, T20</p>
<p>T17</p>
<p>T16</p>
<p>T39</p>
<p>T24</p>
</td>
<td align="left"><p>B, L</p>
<p>L, S</p>
<p>R, L</p>
<p>L</p>
<p>L, S, F</p>
<p>F</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR23">23</xref>
, <xref ref-type="bibr" rid="CR65">65</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR122">122</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>207</bold>
</td>
<td align="left">Apigenin</td>
<td align="left"><p>T4</p>
<p>T8, T16, T17, T20, T39</p>
</td>
<td align="left"><p>B, L, S, R, F</p>
<p>B, L, S, R, F</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR23">23</xref>
, <xref ref-type="bibr" rid="CR66">66</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>208</bold>
</td>
<td align="left">Isoorientin</td>
<td align="left"><p>T11</p>
<p>T4, T8, T17, T16, T20, T39</p>
<p>T35</p>
<p>T36</p>
</td>
<td align="left"><p>L</p>
<p>B, L, S, R, F</p>
<p>L</p>
<p>L</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR35">35</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR139">139</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR38">38</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>209</bold>
</td>
<td align="left">Orientin</td>
<td align="left"><p>T11</p>
<p>T4</p>
<p>T8</p>
<p>T17</p>
<p>T16</p>
<p>T39</p>
<p>T20</p>
<p>T35</p>
<p>T36</p>
</td>
<td align="left"><p>L</p>
<p>L, F</p>
<p>B, S</p>
<p>B, L, S, R, F</p>
<p>L, R, F</p>
<p>B, S, F</p>
<p>L, S, F, R</p>
<p>L</p>
<p>L</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR35">35</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR139">139</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR38">38</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>210</bold>
</td>
<td align="left">Isovitexin</td>
<td align="left"><p>T11</p>
<p>T4</p>
<p>T17</p>
<p>T16</p>
<p>T39</p>
<p>T20</p>
<p>T35</p>
<p>T36</p>
</td>
<td align="left"><p>L</p>
<p>L, F</p>
<p>L, R, F</p>
<p>L</p>
<p>S, F</p>
<p>L, S, F</p>
<p>L</p>
<p>L</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR35">35</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
, <xref ref-type="bibr" rid="CR105">105</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR139">139</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR38">38</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>211</bold>
</td>
<td align="left">Apigenin-6-C-(2″-<italic>O</italic>
-galloyl)-β-<sc>d</sc>
-glucoside</td>
<td align="left">T16</td>
<td align="left">L</td>
<td align="left"><xref ref-type="bibr" rid="CR105">[105</xref>
]</td>
</tr>
<tr><td align="left"> <bold>212</bold>
</td>
<td align="left">Apigenin-8-C-(2″-<italic>O</italic>
-galloyl)-β-<sc>d</sc>
-glucoside</td>
<td align="left"><p>T16</p>
<p>T34</p>
</td>
<td align="left"><p>L</p>
<p>L</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR105">105</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR35">35</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>213</bold>
</td>
<td align="left">Vitexin</td>
<td align="left"><p>T4, T17, T20</p>
<p>T8</p>
<p>T16</p>
<p>T39</p>
<p>T35</p>
<p>T36</p>
</td>
<td align="left"><p>B, L, S, R, F</p>
<p>B, L, S, R</p>
<p>L, S, R, F</p>
<p>B, L, S, F</p>
<p>L</p>
<p>L</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR139">139</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR38">38</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>214</bold>
</td>
<td align="left">Amentoflavone</td>
<td align="left"><p>T8</p>
<p>T17</p>
<p>T20</p>
</td>
<td align="left"><p>L, S</p>
<p>L, R, F</p>
<p>L</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>215</bold>
</td>
<td align="left">Neosaponarin</td>
<td align="left">T36</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR38">38</xref>
]</td>
</tr>
<tr><td align="left"> <bold>216</bold>
</td>
<td align="left">(−)-Epicatechin</td>
<td align="left">T4</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR76">76</xref>
]</td>
</tr>
<tr><td align="left"> <bold>217</bold>
</td>
<td align="left">Epicatechin </td>
<td align="left"><p>T4, T8, T17, T20, T39</p>
<p>T16</p>
<p>T34</p>
</td>
<td align="left"><p>B, L, S, R, F</p>
<p>L, S, R, F</p>
<p>SB</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR35">35</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>218</bold>
</td>
<td align="left">Catechin</td>
<td align="left"><p>T34</p>
<p>T11</p>
<p>T4, T8, T16, T17, T20, T39</p>
<p>T44</p>
</td>
<td align="left"><p>SB</p>
<p>L</p>
<p>B, L, S, R, F</p>
<p>R</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR35">35</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR35">35</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR133">133</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>219</bold>
</td>
<td align="left">Catechin–epicatechin</td>
<td align="left">T44</td>
<td align="left">R</td>
<td align="left">[<xref ref-type="bibr" rid="CR43">43</xref>
]</td>
</tr>
<tr><td align="left"> <bold>220</bold>
</td>
<td align="left">Catechin–epigallocatechin</td>
<td align="left">T44</td>
<td align="left">R</td>
<td align="left">[<xref ref-type="bibr" rid="CR43">43</xref>
]</td>
</tr>
<tr><td align="left"> <bold>221</bold>
</td>
<td align="left">Epigallocatechin</td>
<td align="left">T34</td>
<td align="left">SB</td>
<td align="left">[<xref ref-type="bibr" rid="CR35">35</xref>
]</td>
</tr>
<tr><td align="left"> <bold>222</bold>
</td>
<td align="left">(−)-Epicatechin-3-<italic>O</italic>
-gallate</td>
<td align="left">T16</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR41">41</xref>
]</td>
</tr>
<tr><td align="left"> <bold>223</bold>
</td>
<td align="left">(−)-Epigallocatechin-3-<italic>O</italic>
-gallate</td>
<td align="left">T16</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR41">41</xref>
]</td>
</tr>
<tr><td align="left"> <bold>224</bold>
</td>
<td align="left">Flavanol</td>
<td align="left">T24</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR122">122</xref>
]</td>
</tr>
<tr><td align="left"> <bold>225</bold>
</td>
<td align="left">Gallocatechin</td>
<td align="left"><p>T34</p>
<p>T24</p>
</td>
<td align="left"><p>SB</p>
<p>F</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR35">35</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR126">126</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>226</bold>
</td>
<td align="left">Quercetin</td>
<td align="left"><p>T4</p>
<p>T8</p>
<p>T17</p>
<p>T16</p>
<p>T39</p>
<p>T20</p>
<p>T24</p>
<p>T49</p>
</td>
<td align="left"><p>B, L, R</p>
<p>R</p>
<p>S, R, F</p>
<p>L, S, F</p>
<p>L, B</p>
<p>F</p>
<p>F</p>
<p>L</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
, <xref ref-type="bibr" rid="CR142">142</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR124">124</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR124">124</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>227</bold>
</td>
<td align="left">Kaempferol</td>
<td align="left"><p>T4</p>
<p>T8</p>
<p>T16, T17</p>
<p>T20, T39</p>
<p>T24</p>
</td>
<td align="left"><p>B, L, S, R, F</p>
<p>B, L, S, F</p>
<p>B, L, S, R, F</p>
<p>L, S, R, F</p>
<p>F</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR23">23</xref>
, <xref ref-type="bibr" rid="CR66">66</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR122">122</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>228</bold>
</td>
<td align="left">Kaempferol-3-<italic>O</italic>
-β-<sc>d</sc>
-rutinoside</td>
<td align="left"><p>T4, T8, T17</p>
<p>T16</p>
<p>T39</p>
<p>T20</p>
<p>T36</p>
</td>
<td align="left"><p>B, L, S, R, F</p>
<p>L, S, F</p>
<p>L, R, F</p>
<p>L, S, R</p>
<p>L</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR38">38</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>229</bold>
</td>
<td align="left">Afzelin (kaempferol 3-<italic>O</italic>
-rhamnoside)</td>
<td align="left">T49</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR124">124</xref>
]</td>
</tr>
<tr><td align="left"> <bold>230</bold>
</td>
<td align="left">Rutin</td>
<td align="left"><p>T4, T16</p>
<p>T8</p>
<p>T17, T39</p>
<p>T20</p>
<p>T32</p>
<p>T36</p>
</td>
<td align="left"><p>B, L, S, F</p>
<p>L, S</p>
<p>B, L, S, R, F</p>
<p>L, S, F</p>
<p>L</p>
<p>L</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR135">135</xref>
, <xref ref-type="bibr" rid="CR136">136</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR38">38</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>231</bold>
</td>
<td align="left">Narcissin</td>
<td align="left">T32</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR135">135</xref>
, <xref ref-type="bibr" rid="CR136">136</xref>
]</td>
</tr>
<tr><td align="left"> <bold>232</bold>
</td>
<td align="left">Quercetin-3,4′-di-<italic>O</italic>
-glucoside</td>
<td align="left"><p>T4</p>
<p>T8</p>
<p>T16, T17, T20, T39</p>
</td>
<td align="left"><p>B, L, S, F</p>
<p>B, S, F</p>
<p>B, L, S, R, F</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>233</bold>
</td>
<td align="left">Quercetin-7-<italic>O</italic>
-rhamnoside</td>
<td align="left">T4</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR80">80</xref>
]</td>
</tr>
<tr><td align="left"> <bold>234</bold>
</td>
<td align="left">2-<italic>O</italic>
-β-glucosyloxy-4,6,2′,4′-tetramethoxychalcone</td>
<td align="left">T1</td>
<td align="left">R</td>
<td align="left">[<xref ref-type="bibr" rid="CR53">53</xref>
]</td>
</tr>
<tr><td align="left"> <bold>235</bold>
</td>
<td align="left">Cerasidin</td>
<td align="left">T4</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR80">80</xref>
]</td>
</tr>
<tr><td align="left"> <bold>236</bold>
</td>
<td align="left">Genistein</td>
<td align="left"><p>T4</p>
<p>T8, T16, T17, T20, T39</p>
</td>
<td align="left"><p>B, L, S, R, F</p>
<p>B, L, S, R, F</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR23">23</xref>
, <xref ref-type="bibr" rid="CR80">80</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>237</bold>
</td>
<td align="left">Cyaniding</td>
<td align="left">T4</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR66">66</xref>
]</td>
</tr>
<tr><td align="left"> <bold>238</bold>
</td>
<td align="left">Pelargonidin</td>
<td align="left">T4</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR66">66</xref>
]</td>
</tr>
<tr><td align="left"> <bold>239</bold>
</td>
<td align="left">Leucocyanidin</td>
<td align="left">T4</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR80">80</xref>
]</td>
</tr>
<tr><td align="left"> <bold>240</bold>
</td>
<td align="left">7-Hydroxy-3′,4-(methylenedioxy)flavan</td>
<td align="left">T8</td>
<td align="left">FR</td>
<td align="left">[<xref ref-type="bibr" rid="CR12">12</xref>
]</td>
</tr>
<tr><td align="left" colspan="5">Lignan (27)</td>
</tr>
<tr><td align="left"> <bold>241</bold>
</td>
<td align="left">Termilignan</td>
<td align="left"><p>T8</p>
<p>T39</p>
</td>
<td align="left"><p>FR</p>
<p>B</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR12">12</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR144">144</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>242</bold>
</td>
<td align="left">Anolignan B</td>
<td align="left"><p>T8</p>
<p>T44</p>
</td>
<td align="left"><p>FR</p>
<p>R</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR12">12</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR43">43</xref>
, <xref ref-type="bibr" rid="CR151">151</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>243</bold>
</td>
<td align="left">Thannilignan</td>
<td align="left">T8</td>
<td align="left">FR</td>
<td align="left">[<xref ref-type="bibr" rid="CR12">12</xref>
]</td>
</tr>
<tr><td align="left"> <bold>244</bold>
</td>
<td align="left">Termilignan B</td>
<td align="left">T44</td>
<td align="left">R</td>
<td align="left">[<xref ref-type="bibr" rid="CR133">133</xref>
]</td>
</tr>
<tr><td align="left"> <bold>245</bold>
</td>
<td align="left">Ferulic acid dehydrodimer</td>
<td align="left">T24</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR125">125</xref>
]</td>
</tr>
<tr><td align="left"> <bold>246</bold>
</td>
<td align="left">(7<italic>S</italic>
,8<italic>R</italic>
,7′<italic>R</italic>
,8′<italic>S</italic>
)-4′-hydroxy-4-methoxy-7,7′-epoxylignan</td>
<td align="left">T48</td>
<td align="left">SB</td>
<td align="left">[<xref ref-type="bibr" rid="CR50">50</xref>
]</td>
</tr>
<tr><td align="left"> <bold>247</bold>
</td>
<td align="left">Meso-(rel7<italic>S</italic>
,8<italic>R</italic>
,7′<italic>R</italic>
,8′<italic>S</italic>
)-4,4′-dimethoxy-7,7′-epoxylignan</td>
<td align="left">T48</td>
<td align="left">SB</td>
<td align="left">[<xref ref-type="bibr" rid="CR50">50</xref>
]</td>
</tr>
<tr><td align="left"> <bold>248</bold>
</td>
<td align="left">4′-<italic>O</italic>
-cinnamoyl cleomiscosin A</td>
<td align="left">T50</td>
<td align="left">R</td>
<td align="left">[<xref ref-type="bibr" rid="CR72">72</xref>
]</td>
</tr>
<tr><td align="left"> <bold>249</bold>
</td>
<td align="left">Diethylstilbestrol monosulphate</td>
<td align="left">T24</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR126">126</xref>
]</td>
</tr>
<tr><td align="left"> <bold>250</bold>
</td>
<td align="left">Terminaloside A</td>
<td align="left">T19</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR22">22</xref>
]</td>
</tr>
<tr><td align="left"> <bold>251</bold>
</td>
<td align="left">Terminaloside B</td>
<td align="left">T19</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR22">22</xref>
]</td>
</tr>
<tr><td align="left"> <bold>252</bold>
</td>
<td align="left">Terminaloside C</td>
<td align="left">T19</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR22">22</xref>
]</td>
</tr>
<tr><td align="left"> <bold>253</bold>
</td>
<td align="left">Terminaloside D</td>
<td align="left">T19</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR22">22</xref>
]</td>
</tr>
<tr><td align="left"> <bold>254</bold>
</td>
<td align="left">Terminaloside E</td>
<td align="left">T19</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR22">22</xref>
]</td>
</tr>
<tr><td align="left"> <bold>255</bold>
</td>
<td align="left">Terminaloside F</td>
<td align="left">T19</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR22">22</xref>
]</td>
</tr>
<tr><td align="left"> <bold>256</bold>
</td>
<td align="left">Terminaloside G</td>
<td align="left">T19</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR22">22</xref>
]</td>
</tr>
<tr><td align="left"> <bold>257</bold>
</td>
<td align="left">Terminaloside H</td>
<td align="left">T19</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR22">22</xref>
]</td>
</tr>
<tr><td align="left"> <bold>258</bold>
</td>
<td align="left">Terminaloside I</td>
<td align="left">T19</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR22">22</xref>
]</td>
</tr>
<tr><td align="left"> <bold>259</bold>
</td>
<td align="left">Terminaloside J</td>
<td align="left">T19</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR22">22</xref>
]</td>
</tr>
<tr><td align="left"> <bold>260</bold>
</td>
<td align="left">Terminaloside K</td>
<td align="left">T19</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR22">22</xref>
]</td>
</tr>
<tr><td align="left"> <bold>261</bold>
</td>
<td align="left">2-Epiterminaloside D</td>
<td align="left">T19</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR22">22</xref>
]</td>
</tr>
<tr><td align="left"> <bold>262</bold>
</td>
<td align="left">6-Epiterminaloside K</td>
<td align="left">T19</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR22">22</xref>
]</td>
</tr>
<tr><td align="left"> <bold>263</bold>
</td>
<td align="left">Terminaloside L</td>
<td align="left">T19</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR121">121</xref>
]</td>
</tr>
<tr><td align="left"> <bold>264</bold>
</td>
<td align="left">Terminaloside M</td>
<td align="left">T19</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR121">121</xref>
]</td>
</tr>
<tr><td align="left"> <bold>265</bold>
</td>
<td align="left">Terminaloside N</td>
<td align="left">T19</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR121">121</xref>
]</td>
</tr>
<tr><td align="left"> <bold>266</bold>
</td>
<td align="left">Terminaloside O</td>
<td align="left">T19</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR121">121</xref>
]</td>
</tr>
<tr><td align="left"> <bold>267</bold>
</td>
<td align="left">Terminaloside P</td>
<td align="left">T19</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR121">121</xref>
]</td>
</tr>
<tr><td align="left" colspan="5">Phenols and glycosides (52)</td>
</tr>
<tr><td align="left"> <bold>268</bold>
</td>
<td align="left">Ellagic acid</td>
<td align="left"><p>T1</p>
<p>T7</p>
<p>T10, TM, TT</p>
<p>T12</p>
<p>T40</p>
<p>T4, T8, T20</p>
<p>T17</p>
<p>T16</p>
<p>T39</p>
<p>T24</p>
<p>T25</p>
<p>T31</p>
<p>T28, T32</p>
<p>T35</p>
<p>T42</p>
<p>T30, T44</p>
<p>T36, T45, T46</p>
<p>T48</p>
<p>T49</p>
</td>
<td align="left"><p>B</p>
<p>SB</p>
<p>SB</p>
<p>B</p>
<p>B</p>
<p>B, L, S, R, F</p>
<p>L, SB, R F</p>
<p>SB, L, R, F</p>
<p>B, L, S, R, F, H</p>
<p>F</p>
<p>B, R, Rl</p>
<p>B</p>
<p>H</p>
<p>L, F</p>
<p>R, SB</p>
<p>R</p>
<p>L</p>
<p>SB</p>
<p>L</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR55">55</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR92">92</xref>
, <xref ref-type="bibr" rid="CR127">127</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR14">14</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR100">100</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR41">41</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
, <xref ref-type="bibr" rid="CR80">80</xref>
, <xref ref-type="bibr" rid="CR83">83</xref>
, <xref ref-type="bibr" rid="CR86">86</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR3">3</xref>
, <xref ref-type="bibr" rid="CR9">9</xref>
, <xref ref-type="bibr" rid="CR21">21</xref>
, <xref ref-type="bibr" rid="CR23">23</xref>
, <xref ref-type="bibr" rid="CR111">111</xref>
, <xref ref-type="bibr" rid="CR119">119</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR14">14</xref>
, <xref ref-type="bibr" rid="CR23">23</xref>
, <xref ref-type="bibr" rid="CR41">41</xref>
, <xref ref-type="bibr" rid="CR108">108</xref>
, <xref ref-type="bibr" rid="CR144">144</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
, <xref ref-type="bibr" rid="CR142">142</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR123">123</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR70">70</xref>
, <xref ref-type="bibr" rid="CR127">127</xref>
, <xref ref-type="bibr" rid="CR128">128</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR127">127</xref>
, <xref ref-type="bibr" rid="CR134">134</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR128">128</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR37">37</xref>
, <xref ref-type="bibr" rid="CR38">38</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR133">133</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR133">133</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR133">133</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR50">50</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR124">124</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>269</bold>
</td>
<td align="left">Methyl ellagic acid</td>
<td align="left">T4</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR90">90</xref>
]</td>
</tr>
<tr><td align="left"> <bold>270</bold>
</td>
<td align="left">3-<italic>O</italic>
-methylellagic acid</td>
<td align="left">T33</td>
<td align="left">SB</td>
<td align="left">[<xref ref-type="bibr" rid="CR158">158</xref>
]</td>
</tr>
<tr><td align="left"> <bold>271</bold>
</td>
<td align="left">3,3′-Di-<italic>O</italic>
-methylellagic acid</td>
<td align="left"><p>T28</p>
<p>T39</p>
<p>T48</p>
</td>
<td align="left"><p>SB</p>
<p>H,B</p>
<p>SB</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR29">29</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR8">8</xref>
, <xref ref-type="bibr" rid="CR9">9</xref>
, <xref ref-type="bibr" rid="CR143">143</xref>
, <xref ref-type="bibr" rid="CR144">144</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR50">50</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>272</bold>
</td>
<td align="left">3,3′-Di-<italic>O</italic>
-methylellagic acid 4-mono glucoside</td>
<td align="left">T39</td>
<td align="left">H</td>
<td align="left">[<xref ref-type="bibr" rid="CR147">147</xref>
, <xref ref-type="bibr" rid="CR148">148</xref>
]</td>
</tr>
<tr><td align="left"> <bold>273</bold>
</td>
<td align="left">Tetra-<italic>O</italic>
-methyl ellagic acid</td>
<td align="left">T39</td>
<td align="left">H</td>
<td align="left">[<xref ref-type="bibr" rid="CR148">148</xref>
]</td>
</tr>
<tr><td align="left"> <bold>274</bold>
</td>
<td align="left">3,3′-Di-<italic>O</italic>
-methylellagic acid 4-<italic>O</italic>
-β-<sc>d</sc>
-glucosyl-(1 → 4)-β-<sc>d</sc>
-glucosyl-(1 → 2)-α-<sc>l</sc>
-arabinoside</td>
<td align="left">T1</td>
<td align="left">R</td>
<td align="left">[<xref ref-type="bibr" rid="CR52">52</xref>
]</td>
</tr>
<tr><td align="left"> <bold>275</bold>
</td>
<td align="left">3,4,3′-Tri-<italic>O</italic>
-methylflavellagic acid</td>
<td align="left"><p>T7</p>
<p>T12</p>
<p>T24</p>
<p>T25</p>
<p>T31</p>
<p>T28</p>
<p>T32</p>
<p>T39</p>
</td>
<td align="left"><p>B</p>
<p>B</p>
<p>F</p>
<p>L, B, R, Rl</p>
<p>B</p>
<p>SB, H</p>
<p>H, B</p>
<p>H</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR126">126</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR100">100</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR126">126</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR26">26</xref>
, <xref ref-type="bibr" rid="CR70">70</xref>
, <xref ref-type="bibr" rid="CR127">127</xref>
, <xref ref-type="bibr" rid="CR128">128</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR127">127</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR29">29</xref>
, <xref ref-type="bibr" rid="CR128">128</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR128">128</xref>
, <xref ref-type="bibr" rid="CR138">138</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR143">143</xref>
, <xref ref-type="bibr" rid="CR148">148</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>276</bold>
</td>
<td align="left">3,3′,4-<italic>O</italic>
-trimethyl-4′-<italic>O</italic>
-β-<sc>d</sc>
-glucosylellagic acid</td>
<td align="left">T28</td>
<td align="left">SB</td>
<td align="left">[<xref ref-type="bibr" rid="CR29">29</xref>
]</td>
</tr>
<tr><td align="left"> <bold>277</bold>
</td>
<td align="left">3,3′-Di-<italic>O</italic>
-methyl ellagic acid 4′-<italic>O</italic>
-β-<sc>d</sc>
-xyloside</td>
<td align="left">T48</td>
<td align="left">SB</td>
<td align="left">[<xref ref-type="bibr" rid="CR50">50</xref>
]</td>
</tr>
<tr><td align="left"> <bold>278</bold>
</td>
<td align="left">3,4′-Di-<italic>O</italic>
-methylellagic acid 3′-<italic>O</italic>
-β-<sc>d</sc>
-xyloside</td>
<td align="left">T48</td>
<td align="left">SB</td>
<td align="left">[<xref ref-type="bibr" rid="CR153">153</xref>
]</td>
</tr>
<tr><td align="left"> <bold>279</bold>
</td>
<td align="left">4′-<italic>O</italic>
-galloy-3,3′-di-<italic>O</italic>
-methylellagic acid 4-<italic>O</italic>
-β-<sc>d</sc>
-xyloside</td>
<td align="left">T48</td>
<td align="left">SB</td>
<td align="left">[<xref ref-type="bibr" rid="CR153">153</xref>
]</td>
</tr>
<tr><td align="left"> <bold>280</bold>
</td>
<td align="left">Flavogallonic acid</td>
<td align="left"><p>T7</p>
<p>T40</p>
<p>T31</p>
<p>T12</p>
<p>T36</p>
</td>
<td align="left"><p>SB</p>
<p>B</p>
<p>W</p>
<p>R</p>
<p>L</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR92">92</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR41">41</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR134">134</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR101">101</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR38">38</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>281</bold>
</td>
<td align="left">Methyl (<italic>S</italic>
)-flavogallonate</td>
<td align="left">T36</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR38">38</xref>
]</td>
</tr>
<tr><td align="left"> <bold>282</bold>
</td>
<td align="left">Vanillic acid 4-<italic>O</italic>
-β-<sc>d</sc>
-(6′-<italic>O</italic>
-galloyl) glucoside</td>
<td align="left">T32</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR138">138</xref>
]</td>
</tr>
<tr><td align="left"> <bold>283</bold>
</td>
<td align="left">3-<italic>O</italic>
-methylellagic acid 4′-<italic>O</italic>
-α-<sc>l</sc>
-rhamnoside</td>
<td align="left"><p>T4</p>
<p>T34</p>
<p>T33</p>
</td>
<td align="left"><p>B</p>
<p>SB</p>
<p>SB</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR76">76</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR35">35</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR158">158</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>284</bold>
</td>
<td align="left">Eschweilenol C (ellagic acid 4-<italic>O</italic>
-α-<sc>l</sc>
-rhamnoside)</td>
<td align="left"><p>T12</p>
<p>T17</p>
</td>
<td align="left"><p>B</p>
<p>F</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR100">100</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR164">164</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>285</bold>
</td>
<td align="left">3-<italic>O</italic>
-methylellagic acid 4′-<italic>O</italic>
-xyloside</td>
<td align="left">T31</td>
<td align="left">R</td>
<td align="left">[<xref ref-type="bibr" rid="CR101">101</xref>
]</td>
</tr>
<tr><td align="left"> <bold>286</bold>
</td>
<td align="left">Brevifolincarboxylic acid</td>
<td align="left">T35</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR139">139</xref>
]</td>
</tr>
<tr><td align="left"></td>
<td align="left"></td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR159">159</xref>
]</td>
</tr>
<tr><td align="left"> <bold>287</bold>
</td>
<td align="left">Terflavin D</td>
<td align="left">T17</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR21">21</xref>
]</td>
</tr>
<tr><td align="left"> <bold>288</bold>
</td>
<td align="left">Gallic acid</td>
<td align="left"><p>T3</p>
<p>T4, T8, T20, T39</p>
<p>T10, TM, TT</p>
<p>T17</p>
<p>T16</p>
<p>T34</p>
<p>T12</p>
<p>T31</p>
<p>T40</p>
<p>T24</p>
<p>T30</p>
<p>T35</p>
<p>T36</p>
<p>T38</p>
<p>T42</p>
<p>T44</p>
<p>T45, T46</p>
<p>T48</p>
<p>T49</p>
</td>
<td align="left"><p>F</p>
<p>B, L, S, R, F</p>
<p>SB</p>
<p>SB, F, R, L</p>
<p>SB, F, R, L</p>
<p>L</p>
<p>B</p>
<p>R, W</p>
<p>B</p>
<p>F</p>
<p>R</p>
<p>L</p>
<p>L</p>
<p>L</p>
<p>R, SB</p>
<p>R</p>
<p>L</p>
<p>SB</p>
<p>L</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR154">154</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
, <xref ref-type="bibr" rid="CR80">80</xref>
, <xref ref-type="bibr" rid="CR83">83</xref>
, <xref ref-type="bibr" rid="CR86">86</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR14">14</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR14">14</xref>
, <xref ref-type="bibr" rid="CR21">21</xref>
, <xref ref-type="bibr" rid="CR23">23</xref>
, <xref ref-type="bibr" rid="CR118">118</xref>
, <xref ref-type="bibr" rid="CR119">119</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR14">14</xref>
, <xref ref-type="bibr" rid="CR23">23</xref>
, <xref ref-type="bibr" rid="CR41">41</xref>
, <xref ref-type="bibr" rid="CR108">108</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR35">35</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR100">100</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR101">101</xref>
, <xref ref-type="bibr" rid="CR134">134</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR41">41</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR123">123</xref>
, <xref ref-type="bibr" rid="CR125">125</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR133">133</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR139">139</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR38">38</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR141">141</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR133">133</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR133">133</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR133">133</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR50">50</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR124">124</xref>
]</p>
</td>
</tr>
<tr><td align="left"><bold>289</bold>
</td>
<td align="left">Phyllemblin (ethyl gallate isomers1 progallin A)</td>
<td align="left"><p>T4</p>
<p>T8</p>
<p>T24</p>
<p>T28</p>
<p>T36</p>
</td>
<td align="left"><p>B</p>
<p>F</p>
<p>F</p>
<p>SB</p>
<p>L</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR86">86</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR96">96</xref>
, <xref ref-type="bibr" rid="CR113">113</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR126">126</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR29">29</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR38">38</xref>
]</p>
</td>
</tr>
<tr><td align="left"><bold>290</bold>
</td>
<td align="left">Monogalloyl glucose</td>
<td align="left"><p>T3</p>
<p>T8</p>
<p>T17</p>
<p>T31</p>
</td>
<td align="left"><p>F</p>
<p>F</p>
<p>F</p>
<p>R</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR154">154</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR113">113</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR21">21</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR101">101</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>291</bold>
</td>
<td align="left">Methyl gallate</td>
<td align="left"><p>T14</p>
<p>T8</p>
<p>T32</p>
<p>T36</p>
<p>T48</p>
<p>T49</p>
</td>
<td align="left"><p>L</p>
<p>F</p>
<p>L</p>
<p>L</p>
<p>SB</p>
<p>L</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR18">18</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR113">113</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR135">135</xref>
, <xref ref-type="bibr" rid="CR136">136</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR38">38</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR50">50</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR124">124</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>292</bold>
</td>
<td align="left">Shikimic acid</td>
<td align="left">T32</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR135">135</xref>
, <xref ref-type="bibr" rid="CR136">136</xref>
]</td>
</tr>
<tr><td align="left"> <bold>293</bold>
</td>
<td align="left">5-<italic>O</italic>
-galloyl-(−)-shikimic acid</td>
<td align="left"><p>T3</p>
<p>T17</p>
</td>
<td align="left"><p>F</p>
<p>F</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR118">118</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR154">154</xref>
, <xref ref-type="bibr" rid="CR159">159</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>294</bold>
</td>
<td align="left">4-<italic>O</italic>
-galloyl-(−)-shikimic acid</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR159">159</xref>
]</td>
</tr>
<tr><td align="left"> <bold>295</bold>
</td>
<td align="left">3,5-Di-<italic>O</italic>
-galloyl-(−)-shikimic acid</td>
<td align="left">T3</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR154">154</xref>
]</td>
</tr>
<tr><td align="left"> <bold>296</bold>
</td>
<td align="left">Digallic acid</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR159">159</xref>
]</td>
</tr>
<tr><td align="left"> <bold>297</bold>
</td>
<td align="left">Ethyl gallate isomers2</td>
<td align="left">T24</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR126">126</xref>
]</td>
</tr>
<tr><td align="left"> <bold>298</bold>
</td>
<td align="left">Ethyl gallate isomers3</td>
<td align="left">T24</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR126">126</xref>
]</td>
</tr>
<tr><td align="left"> <bold>299</bold>
</td>
<td align="left">Dimethyl gallic acid</td>
<td align="left">T35</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR139">139</xref>
]</td>
</tr>
<tr><td align="left"> <bold>300</bold>
</td>
<td align="left">Chebulic acid</td>
<td align="left"><p>T3</p>
<p>T17</p>
<p>T24</p>
<p>T35</p>
</td>
<td align="left"><p>F</p>
<p>F</p>
<p>F</p>
<p>L</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR154">154</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR4">4</xref>
, <xref ref-type="bibr" rid="CR9">9</xref>
, <xref ref-type="bibr" rid="CR112">112</xref>
, <xref ref-type="bibr" rid="CR119">119</xref>
, <xref ref-type="bibr" rid="CR159">159</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR125">125</xref>
, <xref ref-type="bibr" rid="CR126">126</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR139">139</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>301</bold>
</td>
<td align="left">6′-<italic>O</italic>
-methyl chebulate</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR159">159</xref>
]</td>
</tr>
<tr><td align="left"> <bold>302</bold>
</td>
<td align="left">7′-<italic>O</italic>
-methyl chebulate</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR159">159</xref>
]</td>
</tr>
<tr><td align="left"> <bold>303</bold>
</td>
<td align="left">Chebulic acid trimethyl ester</td>
<td align="left">T32</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR135">135</xref>
, <xref ref-type="bibr" rid="CR136">136</xref>
]</td>
</tr>
<tr><td align="left"> <bold>304</bold>
</td>
<td align="left">Terminalin</td>
<td align="left"><italic>T38</italic>
</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR39">39</xref>
]</td>
</tr>
<tr><td align="left"> <bold>305</bold>
</td>
<td align="left">Decarboxyellagic acid</td>
<td align="left">T3</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR154">154</xref>
]</td>
</tr>
<tr><td align="left"> <bold>306</bold>
</td>
<td align="left">3-<italic>O</italic>
-galloyl-<sc>d</sc>
-glucose</td>
<td align="left">T3</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR154">154</xref>
]</td>
</tr>
<tr><td align="left"> <bold>307</bold>
</td>
<td align="left">6-<italic>O</italic>
-galloyl-<sc>d</sc>
-glucose</td>
<td align="left"><p>T3</p>
<p>T17</p>
</td>
<td align="left"><p>F</p>
<p>F</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR154">154</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR159">159</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>308</bold>
</td>
<td align="left">Vanillic acid</td>
<td align="left"><p>T4, T8, T20, T39</p>
<p>T17</p>
<p>T16</p>
<p>T44</p>
</td>
<td align="left"><p>B, L, S, R, F</p>
<p>B</p>
<p>S, R, B, F</p>
<p>R</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
, <xref ref-type="bibr" rid="CR117">117</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR43">43</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>309</bold>
</td>
<td align="left">Benzoic acid</td>
<td align="left"><p>T44</p>
<p>T24</p>
</td>
<td align="left"><p>R</p>
<p>F</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR43">43</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR122">122</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>310</bold>
</td>
<td align="left">Hydrocinnamic acid</td>
<td align="left">T44</td>
<td align="left">R</td>
<td align="left">[<xref ref-type="bibr" rid="CR43">43</xref>
]</td>
</tr>
<tr><td align="left"> <bold>311</bold>
</td>
<td align="left">Gentisic acid</td>
<td align="left">T16</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR108">108</xref>
]</td>
</tr>
<tr><td align="left"> <bold>312</bold>
</td>
<td align="left">Protocatechuic acid</td>
<td align="left">T4, T8, T16, T17, T20, T39</td>
<td align="left">B, L, S, R, F</td>
<td align="left">[<xref ref-type="bibr" rid="CR23">23</xref>
]</td>
</tr>
<tr><td align="left"> <bold>313</bold>
</td>
<td align="left">2,3-Di-hydroxyphenyl β-<sc>d</sc>
-glucosiduronic acid</td>
<td align="left">T24</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR125">125</xref>
]</td>
</tr>
<tr><td align="left"> <bold>314</bold>
</td>
<td align="left">Quinic acid</td>
<td align="left"><p>T4, T8, T16, T17, T20, T39</p>
<p>T24</p>
</td>
<td align="left">B, L, S, R, F</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR125">125</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>315</bold>
</td>
<td align="left"><italic>p</italic>
-Coumaric acid</td>
<td align="left"><p>T17</p>
<p>T44</p>
</td>
<td align="left"><p>WP</p>
<p>R</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR117">117</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR43">43</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>316</bold>
</td>
<td align="left">Caffeic acid</td>
<td align="left"><p>T4, T8</p>
<p>T17</p>
<p>T16</p>
<p>T39</p>
<p>T20</p>
<p>T44</p>
</td>
<td align="left"><p>L, S</p>
<p>L, S, R</p>
<p>L</p>
<p>B, L, S, R, F</p>
<p>B</p>
<p>R</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR43">43</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>317</bold>
</td>
<td align="left">Chlorogenic acid</td>
<td align="left"><p>T4</p>
<p>T17</p>
<p>T16, T39</p>
<p>T20</p>
</td>
<td align="left"><p>L, S</p>
<p>S, R, F, L</p>
<p>L</p>
<p>B</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>318</bold>
</td>
<td align="left">Ferulic acid</td>
<td align="left"><p>T4</p>
<p>T8, T17, T20, T39</p>
<p>T16</p>
</td>
<td align="left"><p>B, L, S, F</p>
<p>B, L, S, R, F</p>
<p>L, S, R</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>319</bold>
</td>
<td align="left">Sinapic acid</td>
<td align="left"><p>T4, T16, T20, T39</p>
<p>T8</p>
<p>T17</p>
</td>
<td align="left"><p>B, L, S, R, F</p>
<p>S, R, F</p>
<p>B, S, R, F</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
</td>
</tr>
<tr><td align="left" colspan="5">Steroids (8), polyols (9) and esters (6)</td>
</tr>
<tr><td align="left"> <bold>320</bold>
</td>
<td align="left">β-Sitosterol</td>
<td align="left"><p>T1</p>
<p>T4</p>
<p>T8</p>
<p>T12</p>
<p>T16</p>
<p>T48</p>
<p>T25</p>
<p>T36</p>
<p>T39</p>
<p>T44</p>
</td>
<td align="left"><p>B, H</p>
<p>S, F</p>
<p>F</p>
<p>F</p>
<p>B, SB</p>
<p>H</p>
<p>H</p>
<p>SB</p>
<p>B</p>
<p>H, SB, R</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR55">55</xref>
, <xref ref-type="bibr" rid="CR56">56</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR57">57</xref>
, <xref ref-type="bibr" rid="CR83">83</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR96">96</xref>
, <xref ref-type="bibr" rid="CR113">113</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR99">99</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR128">128</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR128">128</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR129">129</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR140">140</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR147">147</xref>
, <xref ref-type="bibr" rid="CR148">148</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR43">43</xref>
, <xref ref-type="bibr" rid="CR133">133</xref>
, <xref ref-type="bibr" rid="CR152">152</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>321</bold>
</td>
<td align="left">β-Sitosterol-3-acetate</td>
<td align="left">T44</td>
<td align="left">SB, R</td>
<td align="left">[<xref ref-type="bibr" rid="CR43">43</xref>
]</td>
</tr>
<tr><td align="left"> <bold>322</bold>
</td>
<td align="left">β-Sitosteryl palmitate</td>
<td align="left"><p>T16</p>
<p>T25, T31</p>
</td>
<td align="left"><p>SB, H</p>
<p>L,F</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR128">128</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR128">128</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>323</bold>
</td>
<td align="left">Stigmasterol 3-<italic>O</italic>
-β-<sc>d</sc>
-glucoside</td>
<td align="left"><p>T4</p>
<p>T33</p>
</td>
<td align="left"><p>F</p>
<p>SB</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR80">80</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR158">158</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>324</bold>
</td>
<td align="left">Stigmasterol</td>
<td align="left"><p>T12</p>
<p>T25</p>
<p>T33</p>
<p>T44</p>
</td>
<td align="left"><p>B</p>
<p>SB</p>
<p>SB</p>
<p>RB</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR99">99</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR129">129</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR158">158</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR133">133</xref>
, <xref ref-type="bibr" rid="CR152">152</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>325</bold>
</td>
<td align="left">Stigma-4-ene-3-one</td>
<td align="left">T44</td>
<td align="left">RB</td>
<td align="left">[<xref ref-type="bibr" rid="CR43">43</xref>
]</td>
</tr>
<tr><td align="left"> <bold>326</bold>
</td>
<td align="left">16,17-Dihydroneridienone 3<italic>O</italic>
-β-<sc>d</sc>
-glucosyl-(1 → 6)-<italic>O</italic>
-β-<sc>d</sc>
-galactoside</td>
<td align="left">T4</td>
<td align="left">R</td>
<td align="left">[<xref ref-type="bibr" rid="CR59">59</xref>
]</td>
</tr>
<tr><td align="left"> <bold>327</bold>
</td>
<td align="left">Cannogenol 3-<italic>O</italic>
-β-<sc>d</sc>
-galactosyl-(1 → 4)-<italic>O</italic>
-α-<sc>l</sc>
-rhamno-side</td>
<td align="left">T8</td>
<td align="left">Se</td>
<td align="left">[<xref ref-type="bibr" rid="CR94">94</xref>
]</td>
</tr>
<tr><td align="left"> <bold>328</bold>
</td>
<td align="left">2-Hexanol</td>
<td align="left">T9</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR13">13</xref>
]</td>
</tr>
<tr><td align="left"> <bold>329</bold>
</td>
<td align="left">Octanol</td>
<td align="left">T9</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR13">13</xref>
]</td>
</tr>
<tr><td align="left"> <bold>330</bold>
</td>
<td align="left">Methoxycarbonyloxymethyl methylcarbonate</td>
<td align="left">T24</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR125">125</xref>
]</td>
</tr>
<tr><td align="left"> <bold>331</bold>
</td>
<td align="left">Ribonolactone</td>
<td align="left">T24</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR125">125</xref>
]</td>
</tr>
<tr><td align="left"> <bold>332</bold>
</td>
<td align="left">Apionic acid</td>
<td align="left">T24</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR125">125</xref>
]</td>
</tr>
<tr><td align="left"> <bold>333</bold>
</td>
<td align="left">Ascorbic acid</td>
<td align="left">T24</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR125">125</xref>
]</td>
</tr>
<tr><td align="left"> <bold>334</bold>
</td>
<td align="left">Gluconolactone</td>
<td align="left">T24</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR125">125</xref>
]</td>
</tr>
<tr><td align="left"> <bold>335</bold>
</td>
<td align="left">Glucohepatonic acid-1,4-lactone</td>
<td align="left">T24</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR125">125</xref>
]</td>
</tr>
<tr><td align="left"> <bold>336</bold>
</td>
<td align="left">Galacturonic acid</td>
<td align="left">T44</td>
<td align="left">R</td>
<td align="left">[<xref ref-type="bibr" rid="CR43">43</xref>
]</td>
</tr>
<tr><td align="left"> <bold>337</bold>
</td>
<td align="left">Geranyl formate</td>
<td align="left">T9</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR13">13</xref>
]</td>
</tr>
<tr><td align="left"> <bold>338</bold>
</td>
<td align="left">Citronellyl acetate</td>
<td align="left">T9</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR13">13</xref>
]</td>
</tr>
<tr><td align="left"> <bold>339</bold>
</td>
<td align="left">Geranyl acetate</td>
<td align="left">T9</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR13">13</xref>
]</td>
</tr>
<tr><td align="left"> <bold>340</bold>
</td>
<td align="left">Geranyl tiglate</td>
<td align="left">T9</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR13">13</xref>
]</td>
</tr>
<tr><td align="left"> <bold>341</bold>
</td>
<td align="left">Laxiflorin</td>
<td align="left">T31</td>
<td align="left">RB</td>
<td align="left">[<xref ref-type="bibr" rid="CR127">127</xref>
]</td>
</tr>
<tr><td align="left"> <bold>342</bold>
</td>
<td align="left">(1<italic>S</italic>
,5<italic>R</italic>
)-4-oxo-6,8-dioxabicyclo[3.2.1]oct-2-ene-2-carboxylic acid</td>
<td align="left">T24</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR125">125</xref>
]</td>
</tr>
<tr><td align="left" colspan="5">Others (26)</td>
</tr>
<tr><td align="left"> <bold>343</bold>
</td>
<td align="left">Glucuronic acid</td>
<td align="left">T24</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR125">125</xref>
]</td>
</tr>
<tr><td align="left"> <bold>344</bold>
</td>
<td align="left">Coumarin</td>
<td align="left">T45</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR133">133</xref>
]</td>
</tr>
<tr><td align="left"> <bold>345</bold>
</td>
<td align="left">Eujavonic acid</td>
<td align="left">T24</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR125">125</xref>
]</td>
</tr>
<tr><td align="left"> <bold>346</bold>
</td>
<td align="left">Purine</td>
<td align="left">T24</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR125">125</xref>
]</td>
</tr>
<tr><td align="left"> <bold>347</bold>
</td>
<td align="left">5-(4-Hydroxy-2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid (gemfibrozil M1)</td>
<td align="left">T24</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR125">125</xref>
]</td>
</tr>
<tr><td align="left"> <bold>348</bold>
</td>
<td align="left"><italic>p</italic>
-Hydroxytiaprofenic acid</td>
<td align="left">T24</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR125">125</xref>
]</td>
</tr>
<tr><td align="left"> <bold>349</bold>
</td>
<td align="left"><italic>Cis</italic>
-polyisoprene</td>
<td align="left">T32</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR135">135</xref>
]</td>
</tr>
<tr><td align="left"> <bold>350</bold>
</td>
<td align="left">Arachidic acid</td>
<td align="left">T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR113">113</xref>
]</td>
</tr>
<tr><td align="left"> <bold>351</bold>
</td>
<td align="left">Behenic acid</td>
<td align="left">T8, T17</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR113">113</xref>
]</td>
</tr>
<tr><td align="left"> <bold>352</bold>
</td>
<td align="left">Arjunaphthanoloside</td>
<td align="left">T4</td>
<td align="left">SB</td>
<td align="left">[<xref ref-type="bibr" rid="CR87">87</xref>
]</td>
</tr>
<tr><td align="left"> <bold>353</bold>
</td>
<td align="left">Resveratrol (3′,4,5′-trihydroxystilbene)</td>
<td align="left"><p>T24</p>
<p>T44</p>
</td>
<td align="left"><p>F</p>
<p>R</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR126">126</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR43">43</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>354</bold>
</td>
<td align="left">Resveratrol glucoside (piceid)</td>
<td align="left"><p>T24</p>
<p>T44</p>
</td>
<td align="left"><p>F</p>
<p>RB</p>
</td>
<td align="left"><p><xref ref-type="bibr" rid="CR126">[126</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR152">152</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>355</bold>
</td>
<td align="left">Resveratrol-β-<sc>d</sc>
-glucoside</td>
<td align="left">T44</td>
<td align="left">RB</td>
<td align="left">[<xref ref-type="bibr" rid="CR152">152</xref>
]</td>
</tr>
<tr><td align="left"> <bold>356</bold>
</td>
<td align="left">Combretastatin</td>
<td align="left">T24</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR126">126</xref>
]</td>
</tr>
<tr><td align="left"> <bold>357</bold>
</td>
<td align="left">Combretastatin A1</td>
<td align="left">T24</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR126">126</xref>
]</td>
</tr>
<tr><td align="left"> <bold>358</bold>
</td>
<td align="left">(<italic>Z</italic>
)-Stilbene</td>
<td align="left">T44</td>
<td align="left">R</td>
<td align="left">[<xref ref-type="bibr" rid="CR133">133</xref>
]</td>
</tr>
<tr><td align="left"> <bold>359</bold>
</td>
<td align="left">(<italic>E</italic>
)-Stilbene</td>
<td align="left">T44</td>
<td align="left">R</td>
<td align="left">[<xref ref-type="bibr" rid="CR133">133</xref>
]</td>
</tr>
<tr><td align="left"> <bold>360</bold>
</td>
<td align="left">3′5′-Dihydroxy-4-(2-hydroxyethoxy) resveratrol-3-<italic>O</italic>
-β-rutinoside</td>
<td align="left">T44</td>
<td align="left">R, RB</td>
<td align="left">[<xref ref-type="bibr" rid="CR43">43</xref>
, <xref ref-type="bibr" rid="CR152">152</xref>
]</td>
</tr>
<tr><td align="left"> <bold>361</bold>
</td>
<td align="left">Resveratrol-3-β-rutinoside glycoside</td>
<td align="left">T44</td>
<td align="left">R, RB</td>
<td align="left">[<xref ref-type="bibr" rid="CR43">43</xref>
, <xref ref-type="bibr" rid="CR152">152</xref>
]</td>
</tr>
<tr><td align="left"> <bold>362</bold>
</td>
<td align="left">1,4-Cineole</td>
<td align="left">T9</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR13">13</xref>
]</td>
</tr>
<tr><td align="left"> <bold>363</bold>
</td>
<td align="left">Terpinen-4-ol</td>
<td align="left">T9</td>
<td align="left">L</td>
<td align="left">[<xref ref-type="bibr" rid="CR13">13</xref>
]</td>
</tr>
<tr><td align="left"> <bold>364</bold>
</td>
<td align="left">Terminalianone</td>
<td align="left">T12</td>
<td align="left">B</td>
<td align="left">[<xref ref-type="bibr" rid="CR98">98</xref>
]</td>
</tr>
<tr><td align="left"> <bold>365</bold>
</td>
<td align="left">Termicalcicolanone A</td>
<td align="left">T15</td>
<td align="left">WP</td>
<td align="left">[<xref ref-type="bibr" rid="CR19">19</xref>
]</td>
</tr>
<tr><td align="left"> <bold>366</bold>
</td>
<td align="left">Termicalcicolanone B</td>
<td align="left">T15</td>
<td align="left">WP</td>
<td align="left">[<xref ref-type="bibr" rid="CR19">19</xref>
]</td>
</tr>
<tr><td align="left"> <bold>367</bold>
</td>
<td align="left">Mangiferin</td>
<td align="left"><p>T4</p>
<p>T8</p>
<p>T17</p>
<p>T16</p>
<p>T39</p>
<p>T20</p>
</td>
<td align="left"><p>B, S, F</p>
<p>B, R, F</p>
<p>B, L, S, R, F</p>
<p>L, R, F</p>
<p>B, L, S, F</p>
<p>L, S, R</p>
</td>
<td align="left"><p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
<p>[<xref ref-type="bibr" rid="CR23">23</xref>
]</p>
</td>
</tr>
<tr><td align="left"> <bold>368</bold>
</td>
<td align="left">Benzoyl-β-<sc>d</sc>
-(4′ → 10″geranilanoxy)-pyranoside</td>
<td align="left">T8</td>
<td align="left">F</td>
<td align="left">[<xref ref-type="bibr" rid="CR160">160</xref>
]</td>
</tr>
</tbody>
</table>
<table-wrap-foot><p><italic>R</italic>
root, <italic>SB</italic>
stem bark, <italic>B</italic>
bark, <italic>F</italic>
fruit, <italic>S</italic>
stem, <italic>H</italic>
heartwood, <italic>RB</italic>
root bark, <italic>Rl</italic>
rootlet, <italic>Se</italic>
seed, <italic>FR</italic>
fruit rind, <italic>WP</italic>
whole plant, <italic>T1</italic>
–<italic>T50</italic>
plants from Table <xref rid="Tab1" ref-type="table">1</xref>
, <italic>TM T. manii</italic>
, <italic>TT T. tomentosa</italic>
</p>
</table-wrap-foot>
</table-wrap>
<table-wrap id="Tab3"><label>Table 3</label>
<caption><p>The numbers and main types of compounds reported from different <italic>Terminalia</italic>
species</p>
</caption>
<table frame="hsides" rules="groups"><thead><tr><th align="left">No.</th>
<th align="left">Plant</th>
<th align="left">Plant organs</th>
<th align="left">Numbers</th>
<th align="left">Main types</th>
</tr>
</thead>
<tbody><tr><td align="left">T1</td>
<td align="left"><italic>T. alata</italic>
</td>
<td align="left">Roots, barks</td>
<td char="." align="char">18</td>
<td align="left">Triterpenes</td>
</tr>
<tr><td align="left">T3</td>
<td align="left"><italic>T. arborea</italic>
</td>
<td align="left">Fruits</td>
<td char="." align="char">24</td>
<td align="left">Hydrolysable tannin</td>
</tr>
<tr><td align="left">T4</td>
<td align="left"><italic>T. arjuna</italic>
</td>
<td align="left">Whole plants</td>
<td char="." align="char">93</td>
<td align="left">Triterpenes, tannins, flavonoids</td>
</tr>
<tr><td align="left">T7</td>
<td align="left"><italic>T. avicennioides</italic>
</td>
<td align="left">Barks</td>
<td char="." align="char">10</td>
<td align="left">Triterpenes, tannins</td>
</tr>
<tr><td align="left">T8</td>
<td align="left"><italic>T. bellirica</italic>
</td>
<td align="left">Fruits, barks</td>
<td char="." align="char">45</td>
<td align="left">Triterpenes, flavonoids, lignin, simple phenols</td>
</tr>
<tr><td align="left">T9</td>
<td align="left"><italic>T. bentzoe</italic>
</td>
<td align="left">Leaves</td>
<td char="." align="char">29</td>
<td align="left">Monoterpenoids, sesquiterpenoid</td>
</tr>
<tr><td align="left">T11</td>
<td align="left"><italic>T. brachystemma</italic>
</td>
<td align="left">Leaves</td>
<td char="." align="char">8</td>
<td align="left">Flavonoids</td>
</tr>
<tr><td align="left">T12</td>
<td align="left"><italic>T. brownii</italic>
</td>
<td align="left">Leaves</td>
<td char="." align="char">13</td>
<td align="left">Triterpenes</td>
</tr>
<tr><td align="left">T14</td>
<td align="left"><italic>T. calamansanai</italic>
</td>
<td align="left">Leaves</td>
<td char="." align="char">18</td>
<td align="left">Hydrolysable tannin</td>
</tr>
<tr><td align="left">T16</td>
<td align="left"><italic>T. catappa</italic>
</td>
<td align="left">Whole plants</td>
<td char="." align="char">64</td>
<td align="left">Triterpenes, tannins, flavonoids, simple phenols</td>
</tr>
<tr><td align="left">T17</td>
<td align="left"><italic>T. chebula</italic>
</td>
<td align="left">Whole plants</td>
<td char="." align="char">120</td>
<td align="left">Triterpenes, tannins, flavonoids, simple phenols</td>
</tr>
<tr><td align="left">T19</td>
<td align="left"><italic>T. citrina</italic>
</td>
<td align="left">Fruits, leaves</td>
<td char="." align="char">23</td>
<td align="left">Lignan</td>
</tr>
<tr><td align="left">T20</td>
<td align="left"><italic>T. elliptica</italic>
</td>
<td align="left">Whole plants</td>
<td char="." align="char">36</td>
<td align="left">Flavonoids</td>
</tr>
<tr><td align="left">T24</td>
<td align="left"><italic>T. ferdinandiana</italic>
</td>
<td align="left">Fruits</td>
<td char="." align="char">35</td>
<td align="left">Flavonoids, simple phenols, polyols</td>
</tr>
<tr><td align="left">T25</td>
<td align="left"><italic>T. glaucescens</italic>
</td>
<td align="left">Barks</td>
<td char="." align="char">19</td>
<td align="left">Triterpenes</td>
</tr>
<tr><td align="left">T28</td>
<td align="left"><italic>T. ivorensis</italic>
</td>
<td align="left">Barks</td>
<td char="." align="char">18</td>
<td align="left">Triterpenes</td>
</tr>
<tr><td align="left">T31</td>
<td align="left"><italic>T. laxiflora</italic>
</td>
<td align="left">Roots</td>
<td char="." align="char">13</td>
<td align="left">Tannins</td>
</tr>
<tr><td align="left">T32</td>
<td align="left"><italic>T. macroptera</italic>
</td>
<td align="left">Whole plants</td>
<td char="." align="char">28</td>
<td align="left">Triterpenes, tannins, simple phenols</td>
</tr>
<tr><td align="left">T33</td>
<td align="left"><italic>T. mantaly</italic>
</td>
<td align="left">Stem barks</td>
<td char="." align="char">7</td>
<td align="left">Triterpenes, simple phenols</td>
</tr>
<tr><td align="left">T34</td>
<td align="left"><italic>T. mollis</italic>
</td>
<td align="left">Barks</td>
<td char="." align="char">12</td>
<td align="left">Triterpenes, flavonoids</td>
</tr>
<tr><td align="left">T35</td>
<td align="left"><italic>T. muelleri</italic>
</td>
<td align="left">Leaves</td>
<td char="." align="char">16</td>
<td align="left">Hydrolysable tannin, flavonoids, simple phenols</td>
</tr>
<tr><td align="left">T36</td>
<td align="left"><italic>T. myriocarpa</italic>
</td>
<td align="left">Leaves, barks</td>
<td char="." align="char">21</td>
<td align="left">Triterpenes, flavonoids, simple phenols</td>
</tr>
<tr><td align="left">T39</td>
<td align="left"><italic>T. paniculata</italic>
</td>
<td align="left">Barks</td>
<td char="." align="char">43</td>
<td align="left">Triterpenes, flavonoids, simple phenols</td>
</tr>
<tr><td align="left">T40</td>
<td align="left"><italic>T. parviflora</italic>
</td>
<td align="left">Barks</td>
<td char="." align="char">16</td>
<td align="left">Tannins</td>
</tr>
<tr><td align="left">T44</td>
<td align="left"><italic>T. sericea</italic>
</td>
<td align="left">Roots</td>
<td char="." align="char">32</td>
<td align="left">Triterpenes, simple phenols, other compounds</td>
</tr>
<tr><td align="left">T48</td>
<td align="left"><italic>T. superba</italic>
</td>
<td align="left">Barks</td>
<td char="." align="char">15</td>
<td align="left">Triterpenes, simple phenols</td>
</tr>
</tbody>
</table>
<table-wrap-foot><p>Chemical components identified from the other 12 species, including <italic>T. bialata</italic>
(T10), <italic>T. calcicola</italic>
(T15), <italic>T. kaiserana</italic>
(T30), <italic>T. manii</italic>
(TM), <italic>T. macroptera</italic>
(T32), <italic>T. oblongata</italic>
(T38), <italic>T. sambesiaca</italic>
(T42), <italic>T. spinosa</italic>
(T45), <italic>T. stenostachya</italic>
(T46), <italic>T. stuhlmannii</italic>
(T47), <italic>T. triflora</italic>
(T49), <italic>T. tropophylla</italic>
(T50) were less than 6 compounds</p>
</table-wrap-foot>
</table-wrap>
</p>
<sec id="Sec4"><title>Terpenoids</title>
<p id="Par28">So far, 104 terpenoids (Fig. <xref rid="Fig1" ref-type="fig">1</xref>
) including 86 triterpenes (<bold>1–86</bold>
), 14 monoterpenes (<bold>87–100</bold>
), 4 sesquiterpenes (<bold>101–104</bold>
) have been reported from the genus <italic>Terminalia</italic>
. The triterpenoids are mainly oleanane, ursane and lupine types, and their glycosides. Particularly, Atta-ur-Rahman et al. isolated a new <italic>seco</italic>
-triterpene terminalin A (<bold>81</bold>
) possessing a novel rearranged <italic>seco</italic>
-glutinane structure with a pyran ring-A and an isopropanol moiety from the stem barks of <italic>T. glaucescens</italic>
[<xref ref-type="bibr" rid="CR129">129</xref>
]. Ponou et al. found two dimeric triterpenoid glucosides, ivorenosides A and B (<bold>49–50</bold>
) possessing an unusual skeleton [<xref ref-type="bibr" rid="CR131">131</xref>
], and two new oleanane type triterpenes, 3-oxo-type ivorengenin A (<bold>41</bold>
) and 3,24-dinor-2,4-secooleanane-type ivorengenin B (<bold>53</bold>
) from the barks of <italic>T. ivorensis</italic>
[<xref ref-type="bibr" rid="CR132">132</xref>
]. Compounds <bold>41</bold>
, <bold>49</bold>
and <bold>53</bold>
showed significant anticancer activities. Wang et al. isolated five new 18,19-secooleanane type triterpene glycosyl esters, namely arjunasides A–E (<bold>82–86</bold>
) from the MeOH extract of <italic>T. arjuna</italic>
’<italic>s</italic>
barks, TaBs [<xref ref-type="bibr" rid="CR68">68</xref>
]. Moreover, five ursane type triterpene glucosyl esters (<bold>64–68</bold>
) were also obtained for the first time [<xref ref-type="bibr" rid="CR76">76</xref>
]. From the fruits of <italic>T. chebula</italic>
, 23-<italic>O</italic>
-neochebuloylarjungenin 28-<italic>O</italic>
-β-<sc>d</sc>
-glycosyl ester (<bold>21</bold>
) and 23-<italic>O</italic>
-4′-<italic>epi</italic>
-neochebuloylarjungenin (<bold>22</bold>
) with novel substituents at C-23 were reported, in addition to compounds <bold>23–24</bold>
, <bold>30–32</bold>
and <bold>63</bold>
, whose C-23 substituents were gallate. Compounds <bold>30</bold>
and <bold>31</bold>
had strong hypoglycemic effect [<xref ref-type="bibr" rid="CR146">146</xref>
]. Furthermore, compound <bold>40</bold>
was obtained from the barks of <italic>T. arjuna</italic>
[<xref ref-type="bibr" rid="CR85">85</xref>
], while friedelin (<bold>79</bold>
) with 3-oxo moiety was reported from the fruits of <italic>T. arjuna</italic>
[<xref ref-type="bibr" rid="CR83">83</xref>
], the root barks of <italic>T. avicennioides</italic>
[<xref ref-type="bibr" rid="CR93">93</xref>
], and the stem barks of <italic>T. glaucescens</italic>
[<xref ref-type="bibr" rid="CR130">130</xref>
] and <italic>T. mollis</italic>
[<xref ref-type="bibr" rid="CR35">35</xref>
].<fig id="Fig1"><label>Fig. 1</label>
<caption><p>The structures of terpenoids <bold>1–104</bold>
</p>
</caption>
<graphic xlink:href="13659_2019_222_Fig1a_HTML" id="MO1"></graphic>
<graphic xlink:href="13659_2019_222_Fig1b_HTML" id="MO100"></graphic>
<graphic xlink:href="13659_2019_222_Fig1c_HTML" id="MO102"></graphic>
</fig>
</p>
</sec>
<sec id="Sec5"><title>Tannins</title>
<p id="Par29">As the main secondary metabolites, 91 tannins (<bold>105–195</bold>
) were reported from the genus <italic>Terminalia</italic>
(Fig. <xref rid="Fig2" ref-type="fig">2</xref>
), including ellagitannins, gallotannins, dimeric, and trimeric tannins. Four cinnamoyl-containing gallotannins (<bold>182–185</bold>
) were discovered firstly from the fruits of <italic>T. chebula</italic>
, and 1,2,3,6-tetra-<italic>O</italic>
-galloyl-4-<italic>O</italic>
-cinnamoyl-β-<sc>d</sc>
-glucose (<bold>183</bold>
) and 4-<italic>O</italic>
-(2″,4″-di-<italic>O</italic>
-galloyl-α-<sc>l</sc>
-rhamnosyl) ellagic acid (<bold>186</bold>
) showed significant inhibitory activity on α-glucosidase with IC<sub>50</sub>
values of 2.9 and 6.4 μM, respectively [<xref ref-type="bibr" rid="CR159">159</xref>
].<fig id="Fig2"><label>Fig. 2</label>
<caption><p>The structures of tannins <bold>105–195</bold>
</p>
</caption>
<graphic xlink:href="13659_2019_222_Fig2a_HTML" id="MO2"></graphic>
<graphic xlink:href="13659_2019_222_Fig2b_HTML" id="MO200"></graphic>
<graphic xlink:href="13659_2019_222_Fig2c_HTML" id="MO201"></graphic>
</fig>
</p>
<p id="Par30">Tannins possess not only liver and kidney protection properties, but also anti-diarrhea, anticancer, antibacterial and hypoglycemic activities [<xref ref-type="bibr" rid="CR133">133</xref>
]. However, a condensed tannin terminalin (<bold>186</bold>
) from <italic>T. oblongata</italic>
was reported to have severe hepatorenal toxicity and even caused renal necrosis [<xref ref-type="bibr" rid="CR39">39</xref>
].</p>
</sec>
<sec id="Sec6"><title>Flavonoids</title>
<p id="Par31">The <italic>Terminalia</italic>
genus are rich in flavonoids (Fig. <xref rid="Fig3" ref-type="fig">3</xref>
) comprising of flavanones (<bold>196–202</bold>
), flavones (<bold>203–215</bold>
), flavan-3-ols (<bold>216–225</bold>
), and flavonols (<bold>226–233</bold>
). Among them, cerasidin (<bold>235</bold>
) of chalcone, genistein (<bold>236</bold>
) of isoflavone, and leucocyanidin (<bold>239</bold>
) of flavan-3,4-diol from <italic>T. arjuna</italic>
[<xref ref-type="bibr" rid="CR80">80</xref>
] were described as rare structural types in the <italic>Terminalia</italic>
genus. Moreover, a new chalcone glycoside 2-<italic>O</italic>
-β-glucosyloxy-4,6,2′,4′-tetramethoxychalchone (<bold>234</bold>
) was reported from the roots of <italic>T. alata</italic>
[<xref ref-type="bibr" rid="CR53">53</xref>
]. In addition, anthocyanidin cyanidin (<bold>237</bold>
) and pelargonidin (<bold>238</bold>
), flavanoid 7-hydroxy-3′,4-(methylenedioxy)flavan (<bold>240</bold>
) and other structure were reported [<xref ref-type="bibr" rid="CR12">12</xref>
, <xref ref-type="bibr" rid="CR23">23</xref>
, <xref ref-type="bibr" rid="CR66">66</xref>
]. Compounds <bold>209–213</bold>
, <bold>215</bold>
were <italic>C</italic>
-glycosides at C-6 or C-8 of ring A.<fig id="Fig3"><label>Fig. 3</label>
<caption><p>The structures of flavonoids <bold>197–240</bold>
</p>
</caption>
<graphic xlink:href="13659_2019_222_Fig3_HTML" id="MO3"></graphic>
</fig>
</p>
</sec>
<sec id="Sec7"><title>Lignans</title>
<p id="Par32">Twenty-seven lignans (<bold>241–267</bold>
) were reported from the genus <italic>Terminalia</italic>
(Fig. <xref rid="Fig4" ref-type="fig">4</xref>
). A new lignan 4′-<italic>O</italic>
-cinnamoyl cleomiscosin A (<bold>248</bold>
) was reported from the ethanol extract of <italic>T. tropophylla</italic>
roots [<xref ref-type="bibr" rid="CR72">72</xref>
]. Moreover, 13 new furofuran lignan glucosides, terminalosides A–K (<bold>250–260</bold>
), 2-epiterminaloside D (<bold>261</bold>
), 6-epiterminaloside K (<bold>262</bold>
) and 5 new polyalkoxylated furofuranone lignan glucosides, terminalosides L–P (<bold>263–267</bold>
) were obtained from the leaves of <italic>T. citrina</italic>
. All of them were tested for their estrogenic and/or antiestrogenic activities using estrogen responsive breast cancer cell lines T47D and MCF-7, and showed varying degrees of inhibitory activity. Among them, terminalosides B (<bold>251</bold>
), G (<bold>256</bold>
), L (<bold>263</bold>
) and M (<bold>264</bold>
) inhibited cell growth by up to 90% at a minimum concentration of 10 nM [<xref ref-type="bibr" rid="CR22">22</xref>
, <xref ref-type="bibr" rid="CR121">121</xref>
].<fig id="Fig4"><label>Fig. 4</label>
<caption><p>The structures of lignans <bold>241–267</bold>
</p>
</caption>
<graphic xlink:href="13659_2019_222_Fig4_HTML" id="MO4"></graphic>
</fig>
</p>
</sec>
<sec id="Sec8"><title>Phenols and Glycosides</title>
<p id="Par33">There are 52 phenols and glycosides reported in the <italic>Terminalia</italic>
genus (Fig. <xref rid="Fig5" ref-type="fig">5</xref>
), in which ellagic acid (<bold>268</bold>
) and gallic acid (<bold>289</bold>
) are present in almost all species. Studies have shown that most of the simple phenolic compounds have antioxidant, antibacterial, hypoglycemic, liver and kidney protection [<xref ref-type="bibr" rid="CR23">23</xref>
].<fig id="Fig5"><label>Fig. 5</label>
<caption><p>The structures of phenols and glycosides (<bold>268–319</bold>
)</p>
</caption>
<graphic xlink:href="13659_2019_222_Fig5_HTML" id="MO5"></graphic>
</fig>
</p>
</sec>
<sec id="Sec9"><title>Sterols and Cardiac Glycosides</title>
<p id="Par34">Only 6 sterols (<bold>320–325</bold>
) and 2 cardiac glycosides (<bold>326-327</bold>
) were isolated from the genus <italic>Terminalia</italic>
before 2001 (Fig. <xref rid="Fig6" ref-type="fig">6</xref>
).<fig id="Fig6"><label>Fig. 6</label>
<caption><p>The structures of steroids (<bold>320–325</bold>
) and cardiac glycosides (<bold>326–327</bold>
)</p>
</caption>
<graphic xlink:href="13659_2019_222_Fig6_HTML" id="MO6"></graphic>
</fig>
</p>
</sec>
<sec id="Sec10"><title>Polyols and Esters</title>
<p id="Par35">Polyols and lipids were reported to be abundant in the genus <italic>Terminalia</italic>
and concentrated mainly in fruits and leaves [<xref ref-type="bibr" rid="CR125">125</xref>
]. So far, 9 polyol (<bold>328–336</bold>
) and 6 esters (<bold>337–342</bold>
) have been documented (Fig. <xref rid="Fig7" ref-type="fig">7</xref>
).<fig id="Fig7"><label>Fig. 7</label>
<caption><p>The structures of polyols and esters (<bold>328–342</bold>
)</p>
</caption>
<graphic xlink:href="13659_2019_222_Fig7_HTML" id="MO7"></graphic>
</fig>
</p>
</sec>
<sec id="Sec11"><title>Other Compounds</title>
<p id="Par36">Other compounds featured in the <italic>Terminalia</italic>
genus are shown in Fig. <xref rid="Fig8" ref-type="fig">8</xref>
and are mostly styrenes. Cao et al. isolated two new cytotoxic xanthones - termicalcicolanone A (<bold>365</bold>
), termicalcicolanone B (<bold>366</bold>
) in <italic>T. calcicola</italic>
, and found an inhibitory effect on ovarian cancer [<xref ref-type="bibr" rid="CR19">19</xref>
]. Hiroko Negishi et al. obtained a new chromone derivative - terminalianone (<bold>364</bold>
) from the barks of <italic>Terminalia brownii</italic>
[<xref ref-type="bibr" rid="CR98">98</xref>
]. Ansari et al. isolated the novel compound, 4′-substituted benzoyl-β-<sc>d</sc>
glycoside (<bold>368</bold>
), from the fruits of <italic>T. bellirica</italic>
and illustrated its potential for anticoagulation [<xref ref-type="bibr" rid="CR160">160</xref>
].<fig id="Fig8"><label>Fig. 8</label>
<caption><p>The structures of other compounds (<bold>343–368</bold>
)</p>
</caption>
<graphic xlink:href="13659_2019_222_Fig8_HTML" id="MO8"></graphic>
</fig>
</p>
<p id="Par37">Moreover, chlorophyll and various vitamins were reported from the genus <italic>Terminalia</italic>
.</p>
</sec>
</sec>
<sec id="Sec12"><title>Pharmacological Activities</title>
<p id="Par38">The pharmacological activities of the genus <italic>Terminalia</italic>
, mainly including antimicrobial, antioxidant, cytotoxicity, anti-inflammatory, hypoglycemic, cardiovascular, mosquitocidal and antiviral, have been extensively studied.</p>
<sec id="Sec13"><title>Antimicrobial</title>
<p id="Par39">Extracts of several <italic>Terminalia</italic>
species exhibit antimicrobial activity against various microbes. For example, methanol and aqueous extracts of <italic>T. australis</italic>
were demonstrated antimicrobial activity against <italic>Ca. albicans</italic>
(MIC = 180 and 250 µg/mL, resp.) and <italic>Ca. kruzzei</italic>
(MIC = 250 and 300 µg/mL, resp.) [<xref ref-type="bibr" rid="CR8">8</xref>
]. Aqueous extracts of the stem barks, woods and whole roots of <italic>T. brownii</italic>
showed antibacterial activity against standard strains of <italic>Sta. aureus</italic>
(14.0 ± 1.1 µg/mL), <italic>Escherichia coli</italic>
, <italic>Ps. aeruginosa</italic>
(12.0 ± 1.1 µg/mL), <italic>Klebsiella pneumonia</italic>
(6.0 ± 1.0 µg/mL), <italic>Sa. typhi</italic>
and <italic>Bacillus anthracis</italic>
(13.0 ± 1.0 µg/mL), as well as fungi <italic>Ca. albicans</italic>
(12.3 ± 1.5 µg/mL) and <italic>Cr. neoformans</italic>
(9.7 ± 1.1 µg/mL) [<xref ref-type="bibr" rid="CR16">16</xref>
]. Ethanol extracts of the root barks and leaves of <italic>T. schimperiana</italic>
were against <italic>Sta. aureus</italic>
, <italic>Ps. aeruginosa</italic>
and <italic>Sa. typhi</italic>
(MIC = 0.058–2.089 mg/mL), with inhibition zone diameters (IZDs) of 17.2 to 10.0 mm, compared to gentamicin (IZD = 21.8–10 mm). The results supported the efficacy of the extracts in the folkloric treatment of burns wounds, bronchitis and dysentery, respectively [<xref ref-type="bibr" rid="CR42">42</xref>
]. Antibacterial tests on <italic>Mycobacterium smegmatis</italic>
ATCC 14468 showed that methanol extract of <italic>T. sambesiaca</italic>
roots and stem barks had promising effects (MIC = 1.25 mg/mL, both) [<xref ref-type="bibr" rid="CR133">133</xref>
].</p>
<p id="Par40">Ellagitannin punicalagin (<bold>133</bold>
) obtained from the stem barks of <italic>T. mollis</italic>
demonstrated crucial activity against <italic>Ca. parapsilosis</italic>
and <italic>Ca. krusei</italic>
(MIC = 6.25 μg/mL), as well as <italic>Ca. albicans</italic>
(MIC = 12.5 μg/mL) [<xref ref-type="bibr" rid="CR35">35</xref>
]. 7-Hydroxy-3′,4′-(methylenedioxy) flavan (<bold>240</bold>
), termilignan (<bold>241</bold>
), anolignan B (<bold>242</bold>
) and thannilignan (<bold>243</bold>
) isolated from the fruit rinds of <italic>T. bellirica</italic>
displayed significant antifungal activity against <italic>Penicillium expansum</italic>
(MIC = 1.0, 2.0, 3.0 and 4.0 µg/mL, resp.), also with <bold>240</bold>
and <bold>241</bold>
against <italic>Ca. albicans</italic>
at 10 and 6 µg/mL, resp. [<xref ref-type="bibr" rid="CR12">12</xref>
]. The antimycobacterial activity of friedelin (<bold>79</bold>
) furnished from the root barks of <italic>T. avicennioides</italic>
was 4.9 μg/mL in terms of MIC value [<xref ref-type="bibr" rid="CR93">93</xref>
]. <italic>β</italic>
-Arjungenin (<bold>16</bold>
), betulinic acid (<bold>74</bold>
), sitosterol (<bold>319</bold>
) and stigmasterol (<bold>323</bold>
) from <italic>T. brownii</italic>
were proved to possess antibacterial activity, with <bold>74</bold>
the most active against <italic>A. niger</italic>
and <italic>S. ipomoea</italic>
(MIC = 50 μg/ml) [<xref ref-type="bibr" rid="CR99">99</xref>
].</p>
</sec>
<sec id="Sec14"><title>Antioxidant</title>
<p id="Par41"><italic>Terminalia</italic>
species have also illustrated some interesting antioxidant properties [<xref ref-type="bibr" rid="CR161">161</xref>
]. By a 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay, relatively high anti-oxidant activities of the methanol extracts of <italic>T. alata</italic>
, <italic>T. bellirica</italic>
and <italic>T. corticosa</italic>
trunk-barks were found (IC<sub>50</sub>
= 0.24, 1.02 and 0.25 mg/mL, resp.), compared to the positive control, <sc>l</sc>
-ascorbic acid (IC<sub>50</sub>
= 0.24 mg/mL) [<xref ref-type="bibr" rid="CR2">2</xref>
].</p>
<p id="Par42">Flavonoid glycosides, apigenin-6-<italic>C</italic>
- (<bold>211</bold>
) and apigenin-8-<italic>C</italic>
- (<bold>212</bold>
) (2″-<italic>O</italic>
-galloy1)-<italic>β</italic>
-<sc>d</sc>
-glucoside, isolated from dried fallen leaves of <italic>T. catappa</italic>
, showed significant antioxidative effects (IC<sub>50</sub>
= 2.1 and 4.5 µM, resp.) on Cu<sup>2+</sup>
/0<sup>2</sup>
-induced low density lipoprotein lipid peroxidation, with probucol (IC<sub>50</sub>
= 4.0 µM) as positive control [<xref ref-type="bibr" rid="CR105">105</xref>
].</p>
<p id="Par43">Arjunaphthanoloside (<bold>351</bold>
), isolated from the stem barks of <italic>T. arjuna</italic>
showed potent antioxidant activity and inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated rat peritoneal macrophages [<xref ref-type="bibr" rid="CR87">87</xref>
], while ivorenosides B (<bold>51</bold>
) and C (<bold>52</bold>
), two triterpenoid saponins from <italic>T. ivorensis</italic>
, exhibited scavenging activities against DPPH and ABTS<sup>+</sup>
radicals [<xref ref-type="bibr" rid="CR131">131</xref>
].</p>
<p id="Par44">The antioxidant potential of <italic>T. paniculata</italic>
(TPW) was investigated by DPPH, ABTS<sup>2−</sup>
, NO, superoxide (O<sup>2−</sup>
), Fe<sup>2+</sup>
chelating and ferric reducing/antioxidant power (FRAP) assays. TPW showed maximum superoxide, ABTS<sup>2−</sup>
, NO, DPPH inhibition, and Fe<sup>2+</sup>
-chelating property at 400 µg/mL, resp. FRAP value was 4.5 ± 0.25 µg Fe(II)/g, which demonstrated the efficacy of aqueous barks extract of <italic>T. paniculata</italic>
as a potential antioxidant and analgesic agent [<xref ref-type="bibr" rid="CR142">142</xref>
].</p>
<p id="Par45">TaB contains various natural antioxidants and has been used to protect animal cells against oxidative stress. The alleviating effect of TaB aqueous extract against Ni toxicity in rice (<italic>Oryza sativa</italic>
L.) suggested that TaB extract considerably alleviated Ni toxicity in rice seedlings by preventing Ni uptake and reducing oxidative stress in the seedlings [<xref ref-type="bibr" rid="CR162">162</xref>
]. Behavioral paradigms and PCR studies of TaB extract against picrotoxin-induced anxiety showed that TaB supplementation increased locomotion towards open arm (EPM), illuminated area (light–dark box test), and increased rearing frequency (open field test) in a dose dependent manner, compared to picrotoxin (P < 0.05). Furthermore, alcoholic extract of TaB showed protective activity against picrotoxin in mice by modulation of genes related to synaptic plasticity, neurotransmitters, and antioxidant enzymes [<xref ref-type="bibr" rid="CR174">174</xref>
].</p>
</sec>
<sec id="Sec15"><title>Cytotoxicity</title>
<p id="Par46">70% Acetone extracts of <italic>T. calamansanai</italic>
leaves inhibited the viability of human promyelocytic leukemia HL-60 cells. Sanguiin H-4 (<bold>115</bold>
), 1-<italic>α</italic>
-<italic>O</italic>
-galloylpunicalagin (<bold>136</bold>
), punicalagin (<bold>135</bold>
), 2-<italic>O</italic>
-galloylpunicalin (<bold>147</bold>
) and methyl gallate (<bold>290</bold>
) were the main components isolated from <italic>T. calamansanai</italic>
with the IC<sub>50</sub>
values of 65.2, 74.8, 42.2, 38.0 and > 100 µM, respectively, for HL-60 cells. Apoptosis of HL-60 cells treated with 1-<italic>α</italic>
-<italic>O</italic>
-galloylpunicalagin, <bold>115</bold>
, <bold>135</bold>
, and <bold>147</bold>
was noted by the appearance of a sub-G1 peak in flow cytometric analysis and DNA fragmentation by gel electrophoresis. <bold>115</bold>
and <bold>147</bold>
induced a decrease of the human poly (ADP-ribose) polymerase (PARP) cleavage-related procaspase-3 and elevated activity of caspase-3 in HL-60 cells, but not normal human peripheral blood mononuclear cells, PBMCs [<xref ref-type="bibr" rid="CR18">18</xref>
].</p>
<p id="Par47">Terminaliaside A (<bold>60</bold>
), an oleanane-type triterpenoid saponin isolated from the roots of <italic>T. tropophylla</italic>
showed antiproliferative activity against the A2780 human ovarian cancer cell line with an IC<sub>50</sub>
value of 1.2 µM [<xref ref-type="bibr" rid="CR72">72</xref>
]. The 70% methanolic extract of <italic>T. chebula</italic>
fruits was found to decrease cell viability, inhibit cell proliferation, and induce cell death of human (MCF-7) and mouse (S115) breast cancer, human osteosarcoma (HOS-1), human prostate cancer (PC-3) and a non-tumorigenic, immortalized human prostate (PNT1A) cell lines. Flow cytometry and other analyses showed that some apoptosis was induced by the extract at lower concentrations, but at higher concentrations, necrosis was the major mechanism of cell death. Chebulinic acid (<bold>143</bold>
) and ellagic acid (<bold>186</bold>
) were tested by ATP assay on HOS-1 cell line in comparison with three known antigrowth phenolics of <italic>Terminalia</italic>
, gallic acid (<bold>287</bold>
), methyl gallate (<bold>290</bold>
), luteolin (<bold>206</bold>
), and tannic acid (<bold>169</bold>
). Results showed that the most growth inhibitory phenolics in <italic>T. chebula</italic>
fruits were chebulinic acid (IC<sub>50</sub>
= 53.2 µM ±/0.16) >/tannic acid (IC<sub>50</sub>
= 59.0 mg/mL ±/0.19) > ellagic acid (IC<sub>50</sub>
= 78.5 µM ±/0.24) [<xref ref-type="bibr" rid="CR111">111</xref>
].</p>
<p id="Par48">Aqueous and ethanolic extracts of <italic>T. citrina</italic>
fruits were revealed to exhibit significant mutagenicity in tested strains of baby hamster kidney cell line (BHK-21). Ethanolic extract showed higher mutagenicity in TA 100 strain, whereas aqueous extract exhibited higher mutagenicity in TA 102 strain than TA 100. Both extracts showed dose-dependent mutagenicity. Fifty percent cell viability was exhibited by 260 and 545 μg/mL of ethanolic and aqueous extracts respectively [<xref ref-type="bibr" rid="CR169">169</xref>
]. Moreover, ivorenoside A (<bold>50</bold>
) showed antiproliferative activity against MDA-MB-231 and HCT116 human cancer cell lines with IC<sub>50</sub>
values of 3.96 and 3.43 µM, respectively [<xref ref-type="bibr" rid="CR131">131</xref>
].</p>
</sec>
<sec id="Sec16"><title>Anti-inflammatory</title>
<p id="Par49">Inflammation has been considered as a major risk factor for various kinds of human diseases. Macrophages play substantial roles in host defense against infection. It can be activated by LPS, the major component of the outer membrane of Gram-negative bacteria. An investigation was carried out to determine anti-inflammatory potential of ethyl acetate fraction isolated from <italic>T. bellirica</italic>
(EFTB) in LPS stimulated RAW 264.7 macrophage cell lines. EFTB (100 μg/mL) inhibited all inflammatory markers in dose dependent manner. Moreover, EFTB down regulated the mRNA expression of TNF-α, IL-6, COX-2 and NF-κB against LPS stimulation. These results demonstrated that EFTB is able to attenuate inflammatory response possibly via suppression of ROS and NO species, inhibiting the production of arachidonic acid metabolites, proinflammatory mediators and cytokines release [<xref ref-type="bibr" rid="CR165">165</xref>
].</p>
<p id="Par50">Anolignan B (<bold>242</bold>
) isolated from roots of <italic>T. sericea</italic>
was tested for anti-inflammatory activity using the cyclooxygenase enzyme assays (COX-1 and COX-2) It showed activity against both COX-1 (IC<sub>50</sub>
= 1.5 mM) and COX-2 (IC<sub>50</sub>
= 7.5 mM) enzymes [<xref ref-type="bibr" rid="CR151">151</xref>
]. Termiarjunosides I (<bold>47</bold>
) and II (<bold>48</bold>
) isolated from stem barks of <italic>T. arjuna</italic>
inhibited aggregation of platelets and suppressed the release of NO and superoxide from macrophages [<xref ref-type="bibr" rid="CR156">156</xref>
].</p>
<p id="Par51">The anti-inflammatory activities of a polyphenol-rich fraction (TMEF) obtained from <italic>T. muelleri</italic>
was assessed using carrageenan-induced paw edema model by measuring PGE2, TNF-α, IL-1b, and IL-6 plasma levels as well as the paw thickness. The group treated with 400 mg/kg of TMEF showed a greater inhibition in the number of writhes (by 63%) than the standard treated group (61%). TMEF pretreatment reduced the edema thickness by 48, 53, and 62% at the tested doses, respectively. TMEF administration inhibited the carrageenan-induced elevations in PGE2 (by 34, 43, and 47%), TNF-α (18, 28, and 41%), IL-1β (14, 22, and 29%), and IL-6 (26, 31, and 46%) [<xref ref-type="bibr" rid="CR166">166</xref>
].</p>
</sec>
<sec id="Sec17"><title>Hypoglycemic</title>
<p id="Par52">Some species and isolates from <italic>Terminalia</italic>
have indicated possession of α-glucosidase inhibitory capabilities. Gallic acid (<bold>287</bold>
) and methyl gallate (<bold>290</bold>
), from stem barks of <italic>T. superba</italic>
, showed significant activity (IC<sub>50</sub>
= 5.2 ± 0.2 and 11.5 ± 0.1 μM, resp.). Arjunic acid (<bold>5</bold>
) and glaucinoic acid (<bold>46</bold>
) from stem barks of <italic>T. glaucescens</italic>
showed significant <italic>β</italic>
-glucuronidase inhibitory activity with IC<sub>50</sub>
value 80.1 and 500 μM, resp., against <italic>β</italic>
-glucuronidase [<xref ref-type="bibr" rid="CR130">130</xref>
].</p>
<p id="Par53">In a study to investigate <italic>α</italic>
-glucosidase inhibition of extracts and isolated compounds from <italic>T. macroptera</italic>
leaves, chebulagic acid (<bold>142</bold>
) showed an IC<sub>50</sub>
value of 0.05 µM towards <italic>α</italic>
-glucosidase and 24.9 ± 0.4 µM towards 15-lipoxygenase (15-LO), in contrast to positive controls (acarbose: IC<sub>50</sub>
= 201 ± 28 µM towards <italic>α</italic>
-glucosidase, quercetin: IC<sub>50</sub>
= 93 ± 3 µM towards 15-LO). Corilagin (<bold>116</bold>
) and narcissin (<bold>231</bold>
) were good 15-LO and <italic>α</italic>
-glucosidase inhibitors. Rutin (<bold>230</bold>
) was a good <italic>α</italic>
-glucosidase inhibitor (IC<sub>50</sub>
ca. 3 µM), but less active towards 15-LO [<xref ref-type="bibr" rid="CR136">136</xref>
].</p>
<p id="Par54">From the fruits of <italic>T. chebula</italic>
, 23-<italic>O</italic>
-galloylarjunolic acid (<bold>30</bold>
) and 23-<italic>O</italic>
-galloylarjunolic acid 28-<italic>O</italic>
-<italic>β</italic>
-<sc>d</sc>
-glucosyl ester (<bold>31</bold>
) were afforded and showed potent inhibitory activities with IC<sub>50</sub>
values of 21.7 (<bold>30</bold>
) and 64.2 (<bold>31</bold>
) µM, resp., against Baker’s yeast <italic>α</italic>
-glucosidase, compared to the positive control, acarbose (IC<sub>50</sub>
174.0 µM) [<xref ref-type="bibr" rid="CR146">146</xref>
].</p>
<p id="Par55">Hydrolyzable tannins, 1,2,3,6-tetra-<italic>O</italic>
-galloyl-4-<italic>O</italic>
-cinnamoyl-<italic>β</italic>
-<sc>d</sc>
-glucose (<bold>183</bold>
) and 4-<italic>O</italic>
-(2″,4″-di-<italic>O</italic>
-galloyl-α-<sc>l</sc>
-rhamnosyl) ellagic acid (<bold>186</bold>
) from the fruits of <italic>T. chebula</italic>
, showed significant <italic>α</italic>
-glucosidase inhibitory activities with IC<sub>50</sub>
values of 2.9 and 6.4 µM, resp. In addition, inhibition kinetic studies showed that both compounds have mixed-type inhibitory activities with the inhibition constants (Ki) of 1.9 and 4.0 µM, respectively [<xref ref-type="bibr" rid="CR159">159</xref>
].</p>
</sec>
<sec id="Sec18"><title>Cardiovascular</title>
<p id="Par56">A few species of <italic>Terminalia</italic>
have demonstrated cardiovascular activities. It was reported that the barks of <italic>T. arjuna</italic>
possessed significant inotropic and hypotensive effect, mild diuretic, antithrombotic, prostaglandin E2 enhancing and hypolipidaemic activities [<xref ref-type="bibr" rid="CR66">66</xref>
].</p>
<p id="Par57">Ethanolic extract of <italic>T. pallida</italic>
fruits (TpFE) were studied to determine their cardioprotection against isoproterenol (ISO)-administered rats. The supplementation of TpFE dose-dependently exerts notable protection on myocardium by virtue of its strong antioxidant activity. It could be used as a medicinal food for the treatment of cardiovascular ailments [<xref ref-type="bibr" rid="CR163">163</xref>
].</p>
</sec>
<sec id="Sec19"><title>Mosquitocidal</title>
<p id="Par58">Insect-borne diseases remain to this day a major source of illness and can cause death worldwide. The resistance to chemical insecticides among mosquito species has been a major problem in vector control. The larvicidal and ovicidal activities of crude benzene, hexane, ethyl acetate, chloroform and methanol extracts of <italic>T. chebula</italic>
were tested for their toxicity against three important vector mosquitoes, viz., <italic>Anopheles stephensi</italic>
, <italic>Aedes aegypti</italic>
and <italic>Culex quinquefasciatus</italic>
. All extracts showed moderate larvicidal effects, the highest larval mortality was found in the methanol extract of <italic>T. chebula</italic>
against the larvae of <italic>A. stephensi</italic>
, <italic>A. aegypti</italic>
, and <italic>C. quinquefasciatus</italic>
with the LC<sub>50</sub>
values of 87.13, 93.24 and 111.98 ppm, respectively. Mean percent hatchability of the ovicidal activity was observed 48 h post treatment. All the five solvent extracts showed moderate ovicidal activity. The maximum egg mortality (zero hatchability) was observed in the methanol extract of <italic>T. chebula</italic>
at 200 and 250 ppm against <italic>A. stephensi</italic>
, while <italic>A. aegypti</italic>
and <italic>C. quinquefasciatus</italic>
showed 100% mortality at 300 ppm. No mortality was observed in the control group. The finding of the investigation revealed that the leaf extract of <italic>T. chebula</italic>
possesses remarkable larvicidal and ovicidal activity against medically important vector mosquitoes [<xref ref-type="bibr" rid="CR167">167</xref>
, <xref ref-type="bibr" rid="CR168">168</xref>
].</p>
</sec>
<sec id="Sec20"><title>Antiviral</title>
<p id="Par59">Termilignan (<bold>241</bold>
) and anolignan B (<bold>242</bold>
), obtained from <italic>T. bellirica</italic>
exhibited antimalarial activity against the chloroquine-susceptible strain 3D7 of <italic>Plasmodium falciparum</italic>
(IC<sub>50</sub>
= 9.6 ± 1.2 μM)[<xref ref-type="bibr" rid="CR12">12</xref>
]. Casuarinin (<bold>129</bold>
), chebulagic acid (<bold>142</bold>
) from the fruits of <italic>T. chebula</italic>
possessed hepatitis C virus inhibition activities (IC<sub>50</sub>
= 9.6 and 5.2 μM, resp.) [<xref ref-type="bibr" rid="CR118">118</xref>
]. Punicalin (<bold>128</bold>
) and 2-<italic>O</italic>
-galloylpunicalin (<bold>147</bold>
), isolated from aqueous extract of <italic>T. triflora</italic>
leaves, showed inhibitory activity on HIV-1 reverse transcriptase with IC<sub>50</sub>
of 0.11 μg/mL (0.14 μM) and 0.10 μg/mL (0.11 μM), resp. [<xref ref-type="bibr" rid="CR149">149</xref>
].</p>
<p id="Par60">In vitro anti-HIV-1 activity of acetone and methanol extracts of <italic>T. paniculata</italic>
fruits was studied by Durge A. et al. Cytotoxicity tests were conducted on TZM-bl cells and PBMCs, the CC<sub>50</sub>
values of both extracts were ≥ 260 μg/mL. By using TZM-bl cells, the extracts were tested for their ability to inhibit replication of two primary isolates HIV-1 (X4, Subtype D) and HIV-1 (R5, Subtype C). The activity against HIV-1 primary isolate (R5, Subtype C) was confirmed by using activated PBMC and quantification of HIV-1 p24 antigen. Both the extracts showed anti-HIV-1 activity in a dose-dependent manner. The EC<sub>50</sub>
values of the acetone and methanol extracts of <italic>T. paniculata</italic>
were ≤ 10.3 μg/mL. Furthermore, the enzymatic assays were performed to determine the mechanism of action which indicated that the anti-HIV-1 activity might be due to inhibition of reverse transcriptase (≥ 77.7% inhibition) and protease (≥ 69.9% inhibition) enzymes [<xref ref-type="bibr" rid="CR172">172</xref>
].</p>
<p id="Par61">Kesharwani A. et al. investigated anti-HSV-2 activity of <italic>T. chebula</italic>
extract and its constituents, chebulagic acid (<bold>142</bold>
) and chebulinic acid (<bold>143</bold>
). Cytotoxicity assay using Vero cells revealed CC<sub>50</sub>
= 409.71 ± 47.70 μg/mL for the extract whereas <bold>142</bold>
and <bold>143</bold>
showed more than 95% cell viability up to 200 μg/mL. The extract from <italic>T. chebula</italic>
(IC<sub>50</sub>
= 0.01 ± 0.0002 μg/mL), chebulagic (IC<sub>50</sub>
= 1.41 ± 0.51 μg/mL) and chebulinic acids (IC<sub>50</sub>
= 0.06 ± 0.002 μg/mL) showed dose dependent in vitro anti-viral activity against HSV-2, which can also effectively prevent the attachment and penetration of the HSV-2 to Vero cells. In comparison, acyclovir showed poor direct anti-viral activity and failed to significantly (p > 0.05) prevent the attachment as well as penetration of HSV-2 to Vero cells when tested up to 50 μg/mL. Besides, in post-infection plaque reduction assay, <italic>T. chebula</italic>
extract, chebulagic and chebulinic acids showed IC<sub>50</sub>
values of 50.06 ± 6.12, 31.84 ± 2.64, and 8.69 ± 2.09 μg/mL, resp., which were much lower than acyclovir (71.80 ± 19.95 μg/mL) [<xref ref-type="bibr" rid="CR173">173</xref>
].</p>
</sec>
<sec id="Sec21"><title>Others</title>
<p id="Par62"><italic>Terminalia</italic>
species were also reported to be used in the treatment of diarrhea [<xref ref-type="bibr" rid="CR95">95</xref>
], Alzheimer’s disease [<xref ref-type="bibr" rid="CR112">112</xref>
], psoriasis [<xref ref-type="bibr" rid="CR164">164</xref>
], liver disease [<xref ref-type="bibr" rid="CR170">170</xref>
], kidney disease [<xref ref-type="bibr" rid="CR171">171</xref>
], etc. Terminalosides A–K (<bold>249–259</bold>
) from the leaves of the Bangladeshi medicinal plant <italic>T. citrina</italic>
possess estrogen-inhibitory properties. Among them, Terminaloside E (<bold>253</bold>
) showed inhibitory activity against the T47D cell line, such terminalosides C (<bold>252</bold>
), F (<bold>255</bold>
), and I (<bold>258</bold>
). Besides, 6-epiterminaloside K (<bold>262</bold>
) displayed antiestrogenic activity against MCF-7 cells [<xref ref-type="bibr" rid="CR22">22</xref>
].</p>
</sec>
</sec>
<sec id="Sec22"><title>Conclusion and Future Prospects</title>
<p id="Par63">The genus <italic>Terminalia</italic>
contains not only a large number of tannins, simple phenolics, but also a lot of terpenoids, flavonoids, lignans and other compounds. Most tannins, simple phenolics and flavonoids have antioxidation, antibacterial, antiinflammatory and anticancer activities. The plants of the genus <italic>Terminalia</italic>
have exhibited positive effect on immune regulation, cardiovascular disease and diabetes, and can accelerate wound healing [<xref ref-type="bibr" rid="CR157">157</xref>
]. Therefore, the <italic>Terminalia</italic>
genus has great medicinal potential. However, most of the chemical composition of species is still unknown, we should use modern advanced technology such as LC–MS to continue to isolate its compounds, and determine their pharmacological activities and mechanism of action, to explore other possible greater medicinal value.</p>
</sec>
</body>
<back><glossary><title>Abbreviations</title>
<def-list><def-item><term><italic>A.</italic>
</term>
<def><p id="Par2"><italic>Aspergillus</italic>
</p>
</def>
</def-item>
<def-item><term>BCG</term>
<def><p id="Par3"><italic>Bacillus Calmette Guerin</italic>
</p>
</def>
</def-item>
<def-item><term>BMM</term>
<def><p id="Par4">Broth microdilution method</p>
</def>
</def-item>
<def-item><term><italic>Ca.</italic>
</term>
<def><p id="Par5"><italic>Candida</italic>
</p>
</def>
</def-item>
<def-item><term><italic>Cr.</italic>
</term>
<def><p id="Par6"><italic>Cryptococcus</italic>
</p>
</def>
</def-item>
<def-item><term>CC<sub>50</sub>
</term>
<def><p id="Par7">Cytotoxic concentration of the extracts to cause death to 50% of host’s viable cells</p>
</def>
</def-item>
<def-item><term>DPPH</term>
<def><p id="Par8">2,2-Diphenyl-1-picrylhydrazyl</p>
</def>
</def-item>
<def-item><term><italic>E.</italic>
</term>
<def><p id="Par9"><italic>Escherichia</italic>
</p>
</def>
</def-item>
<def-item><term>EC<sub>50</sub>
</term>
<def><p id="Par10">Half maximal effective concentration</p>
</def>
</def-item>
<def-item><term>FRAP</term>
<def><p id="Par11">Ferric reducing/antioxidant power</p>
</def>
</def-item>
<def-item><term>GABA</term>
<def><p id="Par12">Neurotransmitter gamma-aminobutyric acid</p>
</def>
</def-item>
<def-item><term>IC<sub>50</sub>
</term>
<def><p id="Par13">Minimum inhibition concentration for inhibiting 50% of the pathogen</p>
</def>
</def-item>
<def-item><term><italic>K.</italic>
</term>
<def><p id="Par14"><italic>Klebsiella</italic>
</p>
</def>
</def-item>
<def-item><term>MIC</term>
<def><p id="Par15">Minimum inhibitory concentration</p>
</def>
</def-item>
<def-item><term>MTT</term>
<def><p id="Par16">3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide</p>
</def>
</def-item>
<def-item><term><italic>Ps.</italic>
</term>
<def><p id="Par17"><italic>Pseudomonas</italic>
</p>
</def>
</def-item>
<def-item><term><italic>Sa.</italic>
</term>
<def><p id="Par18"><italic>Salmonella</italic>
</p>
</def>
</def-item>
<def-item><term><italic>Sta.</italic>
</term>
<def><p id="Par19"><italic>Staphylococcus</italic>
</p>
</def>
</def-item>
<def-item><term><italic>Str.</italic>
</term>
<def><p id="Par20"><italic>Streptomyces</italic>
</p>
</def>
</def-item>
</def-list>
</glossary>
<ack><title>Acknowledgements</title>
<p>This work was supported by the Key Projects of Yunnan Science and Technology, and Yunnan Key Laboratory of Natural Medicinal Chemistry (S2017-ZZ14).</p>
</ack>
<notes><title>Conflict of interest</title>
<notes notes-type="COI-statement"><p>All authors declare no conflict of interest.</p>
</notes>
</notes>
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