Phytochemical profile of Paulownia tomentosa (Thunb). Steud.
Identifieur interne : 000402 ( Pmc/Corpus ); précédent : 000401; suivant : 000403Phytochemical profile of Paulownia tomentosa (Thunb). Steud.
Auteurs : Krist Na Schneiderová ; Karel ŠmejkalSource :
- Phytochemistry Reviews [ 1568-7767 ] ; 2014.
Abstract
Url:
DOI: 10.1007/s11101-014-9376-y
PubMed: NONE
PubMed Central: 7089068
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PMC:7089068Le document en format XML
<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Phytochemical profile of <italic>Paulownia tomentosa</italic> (Thunb). Steud.</title><author><name sortKey="Schneiderova, Krist Na" sort="Schneiderova, Krist Na" uniqKey="Schneiderova K" first="Krist Na" last="Schneiderová">Krist Na Schneiderová</name><affiliation><nlm:aff id="Aff1"></nlm:aff></affiliation></author><author><name sortKey="Smejkal, Karel" sort="Smejkal, Karel" uniqKey="Smejkal K" first="Karel" last="Šmejkal">Karel Šmejkal</name><affiliation><nlm:aff id="Aff1"></nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmc">7089068</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7089068</idno><idno type="RBID">PMC:7089068</idno><idno type="doi">10.1007/s11101-014-9376-y</idno><idno type="pmid">NONE</idno><date when="2014">2014</date><idno type="wicri:Area/Pmc/Corpus">000402</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000402</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Phytochemical profile of <italic>Paulownia tomentosa</italic> (Thunb). Steud.</title><author><name sortKey="Schneiderova, Krist Na" sort="Schneiderova, Krist Na" uniqKey="Schneiderova K" first="Krist Na" last="Schneiderová">Krist Na Schneiderová</name><affiliation><nlm:aff id="Aff1"></nlm:aff></affiliation></author><author><name sortKey="Smejkal, Karel" sort="Smejkal, Karel" uniqKey="Smejkal K" first="Karel" last="Šmejkal">Karel Šmejkal</name><affiliation><nlm:aff id="Aff1"></nlm:aff></affiliation></author></analytic><series><title level="j">Phytochemistry Reviews</title><idno type="ISSN">1568-7767</idno><idno type="eISSN">1572-980X</idno><imprint><date when="2014">2014</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p><italic>Paulownia tomentosa</italic>, a member of the plant family Paulowniaceae and a rich source of biologically active secondary metabolites, is traditionally used in Chinese herbal medicine. Flavonoids, lignans, phenolic glycosides, quinones, terpenoids, glycerides, phenolic acids, and miscellaneous other compounds have been isolated from different parts of <italic>P. tomentosa</italic> plant. Recent interest in this species has focused on isolating and identifying of prenylated flavonoids, that exhibit potent antioxidant, antibacterial, and antiphlogistic activities and inhibit severe acute respiratory syndrome coronavirus papain-like protease. They show cytotoxic activity against various human cancer cell lines and inhibit the effects of human cholinesterase, butyrylcholinesterase, and bacterial neuraminidases. Most of the compounds considered here have never been isolated from any other species of plant. This review summarizes the information about the isolated compounds that are active, their bioactivities, and the structure–activity relationships that have been worked out for them.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Adriani, C" uniqKey="Adriani C">C Adriani</name></author><author><name sortKey="Bonini, C" uniqKey="Bonini C">C Bonini</name></author><author><name sortKey="Iavarone, C" uniqKey="Iavarone C">C Iavarone</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Ahmad, M" uniqKey="Ahmad M">M Ahmad</name></author><author><name sortKey="Rizwani, Gh" uniqKey="Rizwani G">GH Rizwani</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Akbay, P" uniqKey="Akbay P">P Akbay</name></author><author><name sortKey="Calis, I" uniqKey="Calis I">I Calis</name></author><author><name sortKey=" Ndeger, " uniqKey=" Ndeger ">Ű 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<front><journal-meta><journal-id journal-id-type="nlm-ta">Phytochem Rev</journal-id><journal-id journal-id-type="iso-abbrev">Phytochem Rev</journal-id><journal-title-group><journal-title>Phytochemistry Reviews</journal-title></journal-title-group><issn pub-type="ppub">1568-7767</issn><issn pub-type="epub">1572-980X</issn><publisher><publisher-name>Springer Netherlands</publisher-name><publisher-loc>Dordrecht</publisher-loc></publisher></journal-meta><article-meta><article-id pub-id-type="pmc">7089068</article-id><article-id pub-id-type="publisher-id">9376</article-id><article-id pub-id-type="doi">10.1007/s11101-014-9376-y</article-id><article-categories><subj-group subj-group-type="heading"><subject>Article</subject></subj-group></article-categories><title-group><article-title>Phytochemical profile of <italic>Paulownia tomentosa</italic> (Thunb). Steud.</article-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Schneiderová</surname><given-names>Kristýna</given-names></name><xref ref-type="aff" rid="Aff1"></xref></contrib><contrib contrib-type="author" corresp="yes"><name><surname>Šmejkal</surname><given-names>Karel</given-names></name><address><phone>+ 420 541 562 839</phone><email>karel.mejkal@post.cz</email></address><xref ref-type="aff" rid="Aff1"></xref></contrib><aff id="Aff1"><institution-wrap><institution-id institution-id-type="GRID">grid.412968.0</institution-id><institution-id institution-id-type="ISNI">0000000110092154</institution-id><institution>Department of Natural Drugs, Faculty of Pharmacy,</institution><institution>University of Veterinary and Pharmaceutical Sciences Brno,</institution></institution-wrap>Palackého 1/3, 612 42 Brno, Czech Republic</aff></contrib-group><pub-date pub-type="epub"><day>29</day><month>8</month><year>2014</year></pub-date><pub-date pub-type="ppub"><year>2015</year></pub-date><volume>14</volume><issue>5</issue><fpage>799</fpage><lpage>833</lpage><history><date date-type="received"><day>25</day><month>4</month><year>2014</year></date><date date-type="accepted"><day>2</day><month>8</month><year>2014</year></date></history><permissions><copyright-statement>© Springer Science+Business Media Dordrecht 2014</copyright-statement><license><license-p>This article is made available via the PMC Open Access Subset for unrestricted research re-use and secondary analysis in any form or by any means with acknowledgement of the original source. These permissions are granted for the duration of the World Health Organization (WHO) declaration of COVID-19 as a global pandemic.</license-p></license></permissions><abstract id="Abs1"><p><italic>Paulownia tomentosa</italic>, a member of the plant family Paulowniaceae and a rich source of biologically active secondary metabolites, is traditionally used in Chinese herbal medicine. Flavonoids, lignans, phenolic glycosides, quinones, terpenoids, glycerides, phenolic acids, and miscellaneous other compounds have been isolated from different parts of <italic>P. tomentosa</italic> plant. Recent interest in this species has focused on isolating and identifying of prenylated flavonoids, that exhibit potent antioxidant, antibacterial, and antiphlogistic activities and inhibit severe acute respiratory syndrome coronavirus papain-like protease. They show cytotoxic activity against various human cancer cell lines and inhibit the effects of human cholinesterase, butyrylcholinesterase, and bacterial neuraminidases. Most of the compounds considered here have never been isolated from any other species of plant. This review summarizes the information about the isolated compounds that are active, their bioactivities, and the structure–activity relationships that have been worked out for them.</p></abstract><kwd-group xml:lang="en"><title>Keywords</title><kwd><italic>Bignonia tomentosa</italic></kwd><kwd>Flavonoid</kwd><kwd>Lignan</kwd><kwd><italic>Paulownia tomentosa</italic></kwd><kwd>Paulowniaceae</kwd><kwd>Phenolic glycosides</kwd></kwd-group><custom-meta-group><custom-meta><meta-name>issue-copyright-statement</meta-name><meta-value>© Springer Science+Business Media Dordrecht 2015</meta-value></custom-meta></custom-meta-group></article-meta></front><body><sec id="Sec1" sec-type="introduction"><title>Introduction</title><p>The plant <italic>Paulownia tomentosa</italic> (Thunb.) Siebold & Zucc. ex Steud. is a very adaptable and extremely fast-growing timber tree native to central and western China traditionally used in Chinese Medicine. This deciduous tree is now grown in many areas worldwide, mostly as a decorative ornamental tree (Erbar and Gűlden <xref ref-type="bibr" rid="CR45">2011</xref>; Zhu et al. <xref ref-type="bibr" rid="CR255">1986</xref>).</p><p>Two related varieties of <italic>P. tomentosa</italic> have been described—var. <italic>tsinlingensis</italic> has a round to shallowly cordate leaf base and a glabrous or sparsely hairy lower leaf surface, whereas var. <italic>tomentosa</italic> is characterized by a cordate leaf blade base and an abaxial surface that is densely hairy when mature (Hong et al. <xref ref-type="bibr" rid="CR67">1998</xref>).</p><p><italic>Paulownia</italic> was named <italic>paulownia</italic> in honour of Anna Paulowna (1795–1865), queen consort of The Netherlands and a daughter of Tsar Paul I of Russia. Nowadays, it is commonly known under its synonym <italic>Bignonia tomentosa</italic> (Zhu et al. <xref ref-type="bibr" rid="CR255">1986</xref>) or as the princess-tree, empress-tree, foxglove tree, royal paulownia, kiri, or mao pao tong (yuan bian zhong) (Erbar and Gűlden <xref ref-type="bibr" rid="CR45">2011</xref>; Hong et al. <xref ref-type="bibr" rid="CR67">1998</xref>).</p><p>The genus <italic>Paulownia</italic> was first assigned to family Bignoniaceae by Swiss botanist Thunberg (1781). It was then transferred to the Scrophulariaceae family by the Dutch scholars Zuccarini and Siebold (1835) (Zhu et al. <xref ref-type="bibr" rid="CR255">1986</xref>). At last, Paulownia has been categorized as a family of its own, Paulowniaceae, based on data from the latest molecular phylogenetic studies. This family includes only one genus and between six and ten species. It was originally introduced in 1949 by the research of Nakai (Erbar and Gűlden <xref ref-type="bibr" rid="CR45">2011</xref>).</p></sec><sec id="Sec2"><title>Biological activity and traditional uses of <italic>P. tomentosa</italic> extracts</title><p>According to both legends and records, people were already using Paulownia for various purposes about 2,600 years ago. Chinese herbal medicine has used <italic>P. tomentosa</italic> traditionally to relieve bronchitis, especially by reducing coughing, asthma, and phlegm (Zhu et al. <xref ref-type="bibr" rid="CR255">1986</xref>). It has also been used to treat conjunctivitis, dysentery, enteritis, erysipelas, gonorrhea, hemorrhoids, parotitis, traumatic bleeding, and tonsillitis (Jiang et al. <xref ref-type="bibr" rid="CR78">2004</xref>; Si et al. <xref ref-type="bibr" rid="CR197">2009</xref>). Solutions prepared from the leaves and fruit extracted in water have been used in daily applications to promote the healthy growth of hair and turn grey hair dark. An extract prepared from the wood and leaves may relieve swollen feet. Pharmacological experiments have shown that extracts from the fruit can reduce blood pressure. Nowadays, injections and tablets prepared from <italic>Paulownia</italic> flowers and fruit are used for the herbal treatment of chronic bronchitis and other kinds of inflammation (Zhu et al. <xref ref-type="bibr" rid="CR255">1986</xref>).</p><p>More than 130 physiologically active constituents have been isolated from different parts of the <italic>Paulownia</italic> plant. Their biological activity has been tested using both the isolated compounds and different types of extracts. For example, <italic>n</italic>-butanol, EtOAc, and MeOH extracts obtained from the fruit have displayed antiradical activity in anti-DPPH and peroxynitrite assays, due to mainly the presence of flavonoids and phenolic glycosides, but not of all compounds present in these extracts have been identified) (Šmejkal et al. <xref ref-type="bibr" rid="CR204">2007b</xref>). An MeOH extract obtained from the fruit inhibited hAChE (IC<sub>50</sub> = 1.44 mg/ml) and BChE (IC<sub>50</sub> = 0.97 mg/ml) significantly more strongly than CHCl<sub>3</sub> and water extracts (possibly due to the content of phenolic glycosides and <italic>C</italic>-prenylated dihydroflavonols and flavanones) (Cho et al. <xref ref-type="bibr" rid="CR31">2012</xref>). Significant concentration-dependent anti-inflammatory properties of EtOH extracts of the bark of the tree have also been observed recently using a lipopolysaccharide (LPS)-induced nitric oxide production inhibition model in the murine macrophages cell line RAW264.7 (Si et al. <xref ref-type="bibr" rid="CR198">2011a</xref>). Kim et al. (<xref ref-type="bibr" rid="CR92">2010a</xref>, <xref ref-type="bibr" rid="CR93">b</xref>) showed potential of aqueous extract of <italic>P. tomentosa</italic> to suppress glutamate induced toxicity in primary cultured rat cortical cells (with possible sesquiterpene lactone as active substance). The bio-activities of individual compounds and, where possible, the structure–activity relationships are in Tables <xref rid="Tab1" ref-type="table">1</xref>, <xref rid="Tab2" ref-type="table">2</xref>, <xref rid="Tab3" ref-type="table">3</xref> and <xref rid="Tab4" ref-type="table">4</xref> and discussed in separate chapters.<table-wrap id="Tab1"><label>Table 1</label><caption><p>Non-prenylated flavonoid aglycones isolated from <italic>P. tomentosa</italic></p></caption><table frame="hsides" rules="groups"><thead><tr><th align="left">Name of compound and ID</th><th align="left">Isolation source</th><th align="left">Biological activity</th><th align="left" colspan="5">Chemical structure</th></tr></thead><tbody><tr><td align="left">Matteucinol (syn. 4′-<italic>O</italic>-methylfarrerol) (<bold>1</bold>) (2<italic>S</italic>)</td><td align="left">Leaves (Zhu et al. <xref ref-type="bibr" rid="CR255">1986</xref>)</td><td align="left">Weak cytotoxic activity in vitro against human leukaemia (HL-60) and human hepatoma (SMMC-7721) cell lines (Zhao et al. <xref ref-type="bibr" rid="CR253">2012</xref>); no α-glucosidase inhibitory effect (Zhao et al. <xref ref-type="bibr" rid="CR252">2009</xref>); weak aldose-reductase inhibitory activity (Kadota et al. <xref ref-type="bibr" rid="CR83">1994</xref>); moderate inhibitory effect on human immunodeficiency virus-1 protease (Lee et al. <xref ref-type="bibr" rid="CR108">2008</xref>); no activity against lipopolysaccharide (LPS)-induced NO production in RAW 264.7 macrophages (Li et al. <xref ref-type="bibr" rid="CR114">2011</xref>)</td><td align="left" colspan="5"><inline-graphic xlink:href="11101_2014_9376_Figa_HTML.gif" id="d29e421"></inline-graphic></td></tr><tr><td align="left"></td><td align="left"></td><td align="left"></td><td align="left" colspan="5"><inline-graphic xlink:href="11101_2014_9376_Figb_HTML.gif" id="d29e431"></inline-graphic></td></tr></tbody></table><table frame="hsides" rules="groups"><thead><tr><th align="left"></th><th align="left"></th><th align="left"></th><th align="left">R1</th><th align="left">R2</th><th align="left">R3</th><th align="left">R4</th><th align="left">R5</th></tr></thead><tbody><tr><td align="left">Apigenin (<bold>2</bold>)</td><td align="left">Leaves (Zhao et al. <xref ref-type="bibr" rid="CR253">2012</xref>), flowers (Chen et al. <xref ref-type="bibr" rid="CR27">2009</xref>; Jiang et al. <xref ref-type="bibr" rid="CR78">2004</xref>)</td><td align="left">Antioxidant (Prince Vijeya Singh et al. <xref ref-type="bibr" rid="CR167">2004</xref>); antibacterial, anti-inflammatory, antispasmodic, antidiarrhoic, antiproliferative, vasorelaxant (Jiang et al. <xref ref-type="bibr" rid="CR78">2004</xref>); neuroprotective (Losi et al. <xref ref-type="bibr" rid="CR123">2004</xref>); cardioprotective (Psotová et al. <xref ref-type="bibr" rid="CR168">2004</xref>); chemopreventive activity against skin cancer (Chen et al. <xref ref-type="bibr" rid="CR27">2009</xref>); activity reviewed by Shukla and Gupta (<xref ref-type="bibr" rid="CR192">2009</xref>) and Patel et al. (<xref ref-type="bibr" rid="CR159">2007</xref>)</td><td align="left">H</td><td align="left">H</td><td align="left">OH</td><td align="left">H</td><td align="left">OH</td></tr><tr><td align="left">Kaempferol (<bold>3</bold>)</td><td align="left">Leaves (Si et al. <xref ref-type="bibr" rid="CR193">2008a</xref>)</td><td align="left">Cytotoxic, pro-apoptic (suppresses cell metastasis via inhibition of the ERK-p38-JNK and AP-1 signaling pathways in U-2 OS human osteosarcoma cells) (Chen et al. <xref ref-type="bibr" rid="CR29">2013</xref>); antioxidant (e.g., attenuates bladder hyperactivity caused by potassium chloride after protamine sulphate-induced bladder injury) (Huang et al. <xref ref-type="bibr" rid="CR73">2014</xref>); impact on human health and cancer chemoprevention reviewed by Chen and Chen (<xref ref-type="bibr" rid="CR24">2013</xref>), and Calderon-Montano et al. (<xref ref-type="bibr" rid="CR19">2011</xref>)</td><td align="left">OH</td><td align="left">H</td><td align="left">OH</td><td align="left">H</td><td align="left">OH</td></tr><tr><td align="left">Luteolin (<bold>4</bold>)</td><td align="left">Leaves (Si et al. <xref ref-type="bibr" rid="CR193">2008a</xref>; Zhang and Li <xref ref-type="bibr" rid="CR249">2011</xref>)</td><td align="left">Memory-improving (Yoo et al. <xref ref-type="bibr" rid="CR242">2013</xref>); inhibition of α-amylase activity (Funke and Melzig <xref ref-type="bibr" rid="CR51">2005</xref>); cytotoxic (BGC-823 gastric carcinoma xenografts in nude mice) (Lu et al. <xref ref-type="bibr" rid="CR124">2013</xref>); vascular protective (Si et al. <xref ref-type="bibr" rid="CR200">2013</xref>); biological activity reviewed by Lopez-Lazaro (<xref ref-type="bibr" rid="CR121">2009</xref>)</td><td align="left">H</td><td align="left">OH</td><td align="left">OH</td><td align="left">H</td><td align="left">OH</td></tr><tr><td align="left">Quercetin (<bold>5</bold>)</td><td align="left">Bark (Si et al. <xref ref-type="bibr" rid="CR199">2011b</xref>), leaves (Si et al. <xref ref-type="bibr" rid="CR193">2008a</xref>)</td><td align="left">Antifibrotic (Yoon et al. <xref ref-type="bibr" rid="CR243">2012</xref>); antioxidant, antiproliferative, anti-inflammatory, cardioprotective (Chen et al. <xref ref-type="bibr" rid="CR29">2013</xref>); neuroprotective (Ghosh et al. <xref ref-type="bibr" rid="CR53">2013</xref>); anti-diabetic [dose-dependent inhibition of both Na<sup>+</sup>/K<sup>+</sup> ATPase and sodium hydrogen exchanger in type 2 diabetic erythrocytes (Mishra and Rizvi <xref ref-type="bibr" rid="CR133">2012</xref>); inhibition of PI3K (Koch et al. <xref ref-type="bibr" rid="CR96">2013</xref>)]; antiviral [anti HCV (Khachatoorian et al. <xref ref-type="bibr" rid="CR88">2012</xref>); HCMV (Cotin et al. <xref ref-type="bibr" rid="CR35">2012</xref>)]; no anti-HIV activity in vitro tested on H9 cells in the absence of toxicity (Tang et al. <xref ref-type="bibr" rid="CR216">1994</xref>); review of bioactivities by Russo et al. (<xref ref-type="bibr" rid="CR177">2012</xref>)</td><td align="left">OH</td><td align="left">H</td><td align="left">OH</td><td align="left">OH</td><td align="left">OH</td></tr><tr><td align="left">7,3′-Dimethylquercetin (syn. rhamnazin) (<bold>6</bold>)</td><td align="left" rowspan="4">Leaves, green immature fruit (Wollenweber et al. <xref ref-type="bibr" rid="CR231">2008</xref>)</td><td align="left">Antimicrobial activity, poor antifungal effect (Omosa et al. <xref ref-type="bibr" rid="CR146">2014</xref>); low antimicrobial activity, low toxicity against human lymphocytes and monocytes, antioxidant/anti-inflammatory activity (Martini et al. <xref ref-type="bibr" rid="CR126">2004</xref>; Pelzer et al. <xref ref-type="bibr" rid="CR161">1998</xref>); low affinity to acetylcholinesterase (Remya et al. <xref ref-type="bibr" rid="CR171">2012</xref>); low inhibitory effect on NO production in RAW264.7 cells (Sudsai et al. <xref ref-type="bibr" rid="CR209">2013</xref>); no activity against HSV-1, low toxicity against Vero cells (Tian et al. <xref ref-type="bibr" rid="CR219">2009</xref>); no antioxidant activity (Takamatsu et al. <xref ref-type="bibr" rid="CR214">2003</xref>); no trypanocidal activity (Grael et al. <xref ref-type="bibr" rid="CR55">2000</xref>); activity against lipid peroxidation in rat liver microsomes (Yun et al. <xref ref-type="bibr" rid="CR246">2000</xref>); cytotoxicity against TK-10, MCF-7 and UACC-62 cells (Lopez-Lazaro et al. <xref ref-type="bibr" rid="CR122">2000</xref>); no inhibition of glycolysis in various tumor cells (Suolinna et al. <xref ref-type="bibr" rid="CR212">1975</xref>)</td><td align="left">OH</td><td align="left">OMe</td><td align="left">OH</td><td align="left">H</td><td align="left">OMe</td></tr><tr><td align="left">7,3′,4′-Trimethylquercetin (<bold>7</bold>)</td><td align="left">Thrombin inhibition (Shi et al. <xref ref-type="bibr" rid="CR190">2012</xref>); inhibition of IL-4 synthesis in basophils (Hirano et al. <xref ref-type="bibr" rid="CR65">2006</xref>); weak trypanocidal activity (Jordao et al. <xref ref-type="bibr" rid="CR81">2004</xref>); weak inhibition of NO production in LPS-activated mouse peritoneal macrophages (Matsuda et al. <xref ref-type="bibr" rid="CR130">2003</xref>); weak inhibition of degranulation of RBL-2H3 cells (Mastuda et al. <xref ref-type="bibr" rid="CR128">2002</xref>); inhibition of Pgp activity (Scambia et al. <xref ref-type="bibr" rid="CR182">1994</xref>); no inhibition of glycolysis in a variety of tumor cells (Suolinna et al. <xref ref-type="bibr" rid="CR212">1975</xref>)</td><td align="left">OH</td><td align="left">OMe</td><td align="left">OMe</td><td align="left">H</td><td align="left">OMe</td></tr><tr><td align="left">7,3′,4′-Trimethylmyricetin (<bold>8</bold>)</td><td align="left">Weak inhibition of NO production in LPS-activated mouse peritoneal macrophages (Matsuda et al. <xref ref-type="bibr" rid="CR130">2003</xref>); weak inhibition of degranulation of RBL-2H3 cells (Mastuda et al. <xref ref-type="bibr" rid="CR128">2002</xref>)</td><td align="left">OH</td><td align="left">OMe</td><td align="left">OMe</td><td align="left">OH</td><td align="left">OMe</td></tr><tr><td align="left">7,3′,4′,5′-Tetramethylmyricetin (<bold>9</bold>)</td><td align="left"></td><td align="left">OH</td><td align="left">OMe</td><td align="left">OMe</td><td align="left">OMe</td><td align="left">OMe</td></tr><tr><td align="left"></td><td align="left"></td><td align="left"></td><td align="left" colspan="5"> <inline-graphic xlink:href="11101_2014_9376_Figc_HTML.gif" id="d29e856"></inline-graphic></td></tr></tbody></table><table frame="hsides" rules="groups"><thead><tr><th align="left"></th><th align="left"></th><th align="left"></th><th align="left">R<sub>1</sub></th><th align="left">R<sub>2</sub></th><th align="left">R<sub>3</sub></th><th align="left">R<sub>4</sub></th><th align="left">R<sub>5</sub></th></tr></thead><tbody><tr><td align="left">(+)-Catechin (<bold>10</bold>) (2<italic>R</italic>, 3<italic>S</italic>)</td><td align="left">Leaves (Si et al. <xref ref-type="bibr" rid="CR193">2008a</xref>)</td><td align="left">Antiviral (HCV) (Khachatoorian et al. <xref ref-type="bibr" rid="CR88">2012</xref>); antimicrobial (Mankovskaia et al. <xref ref-type="bibr" rid="CR125">2013</xref>); antioxidant, e.g., adjunctive therapy for the treatment of Parkinson’s disease (Teixeira et al. <xref ref-type="bibr" rid="CR218">2013</xref>); osteogenic (Wei et al. <xref ref-type="bibr" rid="CR228">2011</xref>); anti-proliferative, anti-inflammatory, antifibrotic (GRX cells) (Bragança de Moraes et al. <xref ref-type="bibr" rid="CR15">2012</xref>); activity reviewed, for example, by Bansal et al. (<xref ref-type="bibr" rid="CR11">2013</xref>)</td><td align="left">OH</td><td align="left">H</td><td align="left">OH</td><td align="left">OH</td><td align="left">OH</td></tr><tr><td align="left">Dihydrotricin (<bold>11</bold>) (2<italic>S</italic>)</td><td align="left">Fruits (Šmejkal et al. <xref ref-type="bibr" rid="CR203">2007a</xref>)</td><td align="left">Antioxidant, vasorelaxant, low anti-platelet aggregation activity (Chang et al. <xref ref-type="bibr" rid="CR22">2010</xref>)</td><td align="left">H</td><td align="left">OMe</td><td align="left">OH</td><td align="left">OMe</td><td align="left">OH</td></tr><tr><td align="left">(−)-Epicatechin (<bold>12</bold>) (2<italic>R</italic>, 3<italic>R</italic>)</td><td align="left">Leaves (Si et al. <xref ref-type="bibr" rid="CR193">2008a</xref>)</td><td align="left">Antifungal (Betts et al. <xref ref-type="bibr" rid="CR13">2013</xref>); improves muscle mitochondrial structure (Taub et al. <xref ref-type="bibr" rid="CR217">2012</xref>); antioxidant, cardioprotective (Paneerselvam et al. <xref ref-type="bibr" rid="CR153">2010</xref>); cytotoxic (HT29 human colon adenocarcinoma cells) (Sánchez-Tena et al. <xref ref-type="bibr" rid="CR179">2013</xref>); anti-inflammatory (Fu et al. <xref ref-type="bibr" rid="CR50">2013</xref>); activity reviewed, for example, by Fraga and Oteiza (<xref ref-type="bibr" rid="CR47">2011</xref>)</td><td align="left">OH</td><td align="left">H</td><td align="left">OH</td><td align="left">OH</td><td align="left">OH</td></tr><tr><td align="left">Homoeriodictyol (syn. hesperetin) (<bold>13</bold>) (2<italic>S</italic>)</td><td align="left">Leaves (Zhang and Li <xref ref-type="bibr" rid="CR249">2011</xref>)</td><td align="left">Major flavonoid of citrus, activity reviewed by Khan and Zill-E-Huma (<xref ref-type="bibr" rid="CR89">2014</xref>)</td><td align="left">H</td><td align="left">H</td><td align="left">OH</td><td align="left">OMe</td><td align="left">OH</td></tr><tr><td align="left">Naringenin (<bold>14</bold>) (2<italic>S</italic>)</td><td align="left">Bark (Si et al. <xref ref-type="bibr" rid="CR199">2011b</xref>), leaves (Si et al. <xref ref-type="bibr" rid="CR193">2008a</xref>)</td><td align="left">Anti-diabetic (inhibition of PI3K) (Koch et al. <xref ref-type="bibr" rid="CR96">2013</xref>); antiviral [anti HCV (Khachatoorian et al. <xref ref-type="bibr" rid="CR88">2012</xref>), HCMV (Cotin et al. <xref ref-type="bibr" rid="CR35">2012</xref>)]; antimicrobial (de Aguiar et al. <xref ref-type="bibr" rid="CR38">2013</xref>); anti-inflammatory (Jayaraman et al. <xref ref-type="bibr" rid="CR77">2012</xref>); antioxidant (Wang et al. <xref ref-type="bibr" rid="CR226">2012</xref>); cytotoxic (ERα-transfected HeLA cells, ERα-containing HepG2 cells) (Bulzomi et al. <xref ref-type="bibr" rid="CR16">2010</xref>); no antiparasitic activity against <italic>Leishmania</italic> spp. (<italic>major</italic>, <italic>chagasi</italic>, <italic>braziliensis</italic>, <italic>amazonensis</italic>), <italic>Trypanosoma cruzi</italic> (Grecco Sdos et al. <xref ref-type="bibr" rid="CR56">2012</xref>); major flavonoid of citrus, activity reviewed by Khan and Zill-E-Huma (<xref ref-type="bibr" rid="CR89">2014</xref>)</td><td align="left">H</td><td align="left">H</td><td align="left">OH</td><td align="left">H</td><td align="left">OH</td></tr><tr><td align="left">Taxifolin (<bold>15</bold>) (2<italic>R</italic>, 3<italic>R</italic>)</td><td align="left">Leaves (Si et al. <xref ref-type="bibr" rid="CR193">2008a</xref>)</td><td align="left">Inhibition of β-amyloid aggregation (Sato et al. <xref ref-type="bibr" rid="CR181">2013</xref>); potential for atopic dermatitis treatment (blocks hERG K<sup>+</sup> channels) (Yun et al. <xref ref-type="bibr" rid="CR247">2013</xref>); cytotoxic, pro-apoptotic (DU145 human prostate carcinoma cells) (Zhang and Coultas <xref ref-type="bibr" rid="CR248">2013</xref>); hypotensive (ACEI), anti-inflammatory, antioxidant (diminished 5-lipoxygenase and NADPH oxidase activity) (Arutyunyan et al. <xref ref-type="bibr" rid="CR6">2012</xref>); activity reviewed by Weidmann (<xref ref-type="bibr" rid="CR229">2012</xref>)</td><td align="left">OH</td><td align="left">OH</td><td align="left">OH</td><td align="left">H</td><td align="left">OH</td></tr><tr><td align="left">5,4′-Dihydroxy-7,3′-dimethoxyflavanone (<bold>16</bold>) (2<italic>S</italic>)</td><td align="left">Flowers (Chen et al. <xref ref-type="bibr" rid="CR27">2009</xref>; Jiang et al. <xref ref-type="bibr" rid="CR78">2004</xref>; Kim et al. <xref ref-type="bibr" rid="CR92">2010a</xref>, <xref ref-type="bibr" rid="CR93">b</xref>)</td><td align="left">Inactive against glutamate-induced neurotoxicity studied in primary-cultured rat cortical cells (Kim et al. <xref ref-type="bibr" rid="CR92">2010a</xref>, <xref ref-type="bibr" rid="CR93">b</xref>); no trypanocidal activity (Grael et al. <xref ref-type="bibr" rid="CR55">2000</xref>)</td><td align="left">H</td><td align="left">H</td><td align="left">OH</td><td align="left">OMe</td><td align="left">OMe</td></tr><tr><td align="left">5-Hydroxy-7,3′,4′-trimethoxyflavanone (<bold>17</bold>) (2<italic>S</italic>)</td><td align="left">Flowers (Kim et al. <xref ref-type="bibr" rid="CR92">2010a</xref>, <xref ref-type="bibr" rid="CR93">b</xref>)</td><td align="left">Inactive against glutamate-induced neurotoxicity studied in primary-cultured rat cortical cells (Kim et al. <xref ref-type="bibr" rid="CR92">2010a</xref>, <xref ref-type="bibr" rid="CR93">b</xref>); inhibition of inflammation by induction of synovial apoptosis of fibroblast-like synoviocytes through caspase 3 activation in rats with adjuvant arthritis (Li et al. <xref ref-type="bibr" rid="CR113">2010</xref>, <xref ref-type="bibr" rid="CR116">2013</xref>); inhibition of JAK2-STAT3 signal pathway in rats (Li et al. <xref ref-type="bibr" rid="CR115">2012</xref>); inhibition of phosphodiesterase 4 (Yang et al. <xref ref-type="bibr" rid="CR237">2011</xref>); low toxicity on B16F10 and SK-MEL-1 melanoma cells (Rodriguez et al. <xref ref-type="bibr" rid="CR173">2002</xref>); antimutagenic activity (Miyazawa et al. <xref ref-type="bibr" rid="CR134">2000</xref>)</td><td align="left">H</td><td align="left">H</td><td align="left">OMe</td><td align="left">OMe</td><td align="left">OMe</td></tr><tr><td align="left">7-Caffeoyl-acacetin (syn. 7-caffeoyl-4′-methoxyapigenin) (<bold>18</bold>)</td><td align="left">Stem bark (Si et al. <xref ref-type="bibr" rid="CR197">2009</xref>)</td><td align="left"></td><td align="left" colspan="5"><inline-graphic xlink:href="11101_2014_9376_Figd_HTML.gif" id="d29e1361"></inline-graphic></td></tr></tbody></table></table-wrap><table-wrap id="Tab2"><label>Table 2</label><caption><p><italic>C</italic>-prenylated flavonoids isolated from <italic>P. tomentosa</italic></p></caption><table frame="hsides" rules="groups"><thead><tr><th align="left">Name of compound and ID</th><th align="left">Isolation</th><th align="left">Biological activity</th><th align="left">Chemical structure</th></tr></thead><tbody><tr><td align="left"></td><td align="left"></td><td align="left"></td><td align="left"> <inline-graphic xlink:href="11101_2014_9376_Fige_HTML.gif" id="d29e1406"></inline-graphic></td></tr></tbody></table><table frame="hsides" rules="groups"><thead><tr><th align="left"></th><th align="left"></th><th align="left"></th><th align="left">R</th></tr></thead><tbody><tr><td align="left">6-Isopentenyl-3′-<italic>O</italic>-methyltaxifolin (<bold>19</bold>) (2<italic>R</italic>, 3<italic>R</italic>)</td><td align="left">Fruit (Šmejkal et al. <xref ref-type="bibr" rid="CR203">2007a</xref>)</td><td align="left"></td><td align="left">H</td></tr><tr><td align="left">3,4′,5,5′,7-Pentahydroxy-3′-methoxy-6-(3-methyl-2-butenyl) flavanone (<bold>20</bold>) (2<italic>R</italic>, 3<italic>R</italic>)</td><td align="left">Fruit (Asai et al. <xref ref-type="bibr" rid="CR7">2008</xref>)</td><td align="left">Antioxidant (Asai et al. <xref ref-type="bibr" rid="CR7">2008</xref>); cytotoxic (A2780 human ovarian cancer cell line) (Murphy et al. <xref ref-type="bibr" rid="CR137">2005</xref>, <xref ref-type="bibr" rid="CR138">2006</xref>)</td><td align="left">OH</td></tr></tbody></table></table-wrap><table-wrap id="Tab3"><label>Table 3</label><caption><p><italic>C</italic>-geranylated flavonoids isolated from <italic>P. tomentosa</italic></p></caption><table frame="hsides" rules="groups"><thead><tr><th align="left">Name of compound and ID</th><th align="left">Isolation</th><th align="left">Biological activity</th><th align="left" colspan="4">Chemical structure</th></tr></thead><tbody><tr><td align="left"></td><td align="left"></td><td align="left"></td><td align="left" colspan="4"> <inline-graphic xlink:href="11101_2014_9376_Figf_HTML.gif" id="d29e1527"></inline-graphic></td></tr></tbody></table><table frame="hsides" rules="groups"><thead><tr><th align="left"></th><th align="left"></th><th align="left"></th><th align="left">R<sub>1</sub></th><th align="left">R<sub>2</sub></th><th align="left">R<sub>3</sub></th><th align="left">R<sub>4</sub></th></tr></thead><tbody><tr><td align="left">Mimulone (syn. 6-geranylnaringenin, bonannione A) (<bold>21</bold>) (2<italic>S</italic>)</td><td align="left">Flowers (Chen et al. <xref ref-type="bibr" rid="CR27">2009</xref>; Jiang et al. <xref ref-type="bibr" rid="CR78">2004</xref>; Kim et al. <xref ref-type="bibr" rid="CR92">2010a</xref>, <xref ref-type="bibr" rid="CR93">b</xref>), fruit (Asai et al. <xref ref-type="bibr" rid="CR7">2008</xref>; Cho et al. <xref ref-type="bibr" rid="CR31">2012</xref>, <xref ref-type="bibr" rid="CR32">2013</xref>; Lee et al. <xref ref-type="bibr" rid="CR111">2014</xref>; Šmejkal et al. <xref ref-type="bibr" rid="CR203">2007a</xref>, <xref ref-type="bibr" rid="CR206">2008b</xref>)</td><td align="left">Antioxidant (Šmejkal et al. <xref ref-type="bibr" rid="CR204">2007b</xref>; Zima et al. <xref ref-type="bibr" rid="CR256">2010</xref>), antioxidant and anti-inflammatory properties in vitro in S100B-induced human monocytes (Lin et al. <xref ref-type="bibr" rid="CR118">2011</xref>), anti-inflammatory activity in LPS-activated THP-1 cells (Peluso et al. <xref ref-type="bibr" rid="CR160">2010</xref>); antimicrobial against seven Gram-positive bacteria, no antimicrobial activity against three types of Gram-negative bacteria or yeast (Šmejkal et al. <xref ref-type="bibr" rid="CR206">2008b</xref>), antimicrobial against <italic>S. aureus</italic> and various methicillin resistatant strains of <italic>S. aureus</italic> (MRSA 287, MRSA 4211, MRSA, 6975, MRSA 630, MRSA 62059) (Navrátilová et al. <xref ref-type="bibr" rid="CR141">2013</xref>); cytotoxic [epithelioid cell line WB344 (Šmejkal et al. <xref ref-type="bibr" rid="CR204">2007b</xref>), human erythro-leukaemia cell line K562 (Šmejkal et al. <xref ref-type="bibr" rid="CR205">2008a</xref>), human ovarian cancer cell line A2780 (Murphy et al. <xref ref-type="bibr" rid="CR137">2005</xref>, <xref ref-type="bibr" rid="CR138">2006</xref>; Yoder et al. <xref ref-type="bibr" rid="CR241">2007</xref>), KB, KB-VIN, A549, DU145 (Rosselli et al. <xref ref-type="bibr" rid="CR176">2011</xref>), low activity against T-lymphoblastic leukaemia CEM, multiple myeloma RPMI 8226 and U266 cell lines, BJ human fibroblast cell line (Šmejkal et al. <xref ref-type="bibr" rid="CR207">2010</xref>)]; SARS-CoV PLpro activity (Cho et al. <xref ref-type="bibr" rid="CR32">2013</xref>); hAChE, BChE inhibitor (Cho et al. <xref ref-type="bibr" rid="CR31">2012</xref>); significant inhibitory effects against <italic>Cp</italic>-NanI (a sialidase from <italic>C. perfringens</italic>) (Lee et al. <xref ref-type="bibr" rid="CR111">2014</xref>); weak estrogenic, no progestogenic and androgenic activity (Milligan et al. <xref ref-type="bibr" rid="CR131">2000</xref>); inactive against glutamate-induced neurotoxicity studied in primary-cultured rat cortical cells (Kim et al. <xref ref-type="bibr" rid="CR92">2010a</xref>, <xref ref-type="bibr" rid="CR93">b</xref>)</td><td align="left">H</td><td align="left">H</td><td align="left">OH</td><td align="left">H</td></tr><tr><td align="left">Diplacone (syn. propolin C, nymphaeol A) (<bold>22</bold>) (2<italic>S</italic>)</td><td align="left">Flowers (Chen et al. <xref ref-type="bibr" rid="CR27">2009</xref>; Jiang et al. <xref ref-type="bibr" rid="CR78">2004</xref>; Kim et al. <xref ref-type="bibr" rid="CR92">2010a</xref>, <xref ref-type="bibr" rid="CR93">b</xref>), fruit (Asai et al. <xref ref-type="bibr" rid="CR7">2008</xref>; Cho et al. <xref ref-type="bibr" rid="CR31">2012</xref>, <xref ref-type="bibr" rid="CR32">2013</xref>; Lee et al. <xref ref-type="bibr" rid="CR111">2014</xref>; Šmejkal et al. <xref ref-type="bibr" rid="CR203">2007a</xref>, <xref ref-type="bibr" rid="CR206">2008b</xref>)</td><td align="left">Antioxidant (Kumazawa et al. <xref ref-type="bibr" rid="CR102">2007</xref>; Asai et al. <xref ref-type="bibr" rid="CR7">2008</xref>; Šmejkal et al. <xref ref-type="bibr" rid="CR204">2007b</xref>; Zima et al. <xref ref-type="bibr" rid="CR256">2010</xref>; Trusheva et al. <xref ref-type="bibr" rid="CR222">2011</xref>), prooxidant and anti-inflammatory (Hošek et al. <xref ref-type="bibr" rid="CR70">2013</xref>); antiherbivore (Kobayashi et al. <xref ref-type="bibr" rid="CR95">2008</xref>); antimicrobial against seven Gram-positive bacteria, no antimicrobial activity against three types of Gram-negative bacteria or yeast (Šmejkal et al. <xref ref-type="bibr" rid="CR206">2008b</xref>), antimicrobial against <italic>S. aureus</italic>, various methicillin resistant strains of <italic>S. aureus</italic> (MRSA 287, MRSA 4211, MRSA, 6975, MRSA 630, MRSA 62059)—most potent together with <bold>31</bold> (Navrátilová et al. <xref ref-type="bibr" rid="CR141">2013</xref>) and methicillin-susceptible <italic>S. aureus</italic> strain. Anti-MRSA, inactive against <italic>P. auruginosa</italic> (Raghukumar et al. <xref ref-type="bibr" rid="CR169">2010</xref>); antiphlogistic (TNF-α, similar to indomethacin) (Hošek et al. <xref ref-type="bibr" rid="CR69">2010</xref>), but no anti-inflammatory effect was observed in COX-2 inhibition assay (Phommart et al. <xref ref-type="bibr" rid="CR163">2005</xref>); cytotoxic (epithelioid cell line WB344 (Šmejkal et al. <xref ref-type="bibr" rid="CR203">2007a</xref>), T-lymphoblastic leukaemia CEM, multiple myeloma RPMI 8226 and U266 cell lines, BJ human fibroblast cell line (Šmejkal et al. <xref ref-type="bibr" rid="CR207">2010</xref>), human erythro-leukaemia cell line K562 (Šmejkal et al. <xref ref-type="bibr" rid="CR205">2008a</xref>), KB human oral carcinoma, human breast cancer, human small cell lung cancer NCI-H187 (Phommart et al. <xref ref-type="bibr" rid="CR163">2005</xref>), induction of apoptosis via caspase activation, bid and cytochrome c release in human melanoma cells (Chen et al. <xref ref-type="bibr" rid="CR26">2004</xref>), human ovarian cancer cell line A2780 (Murphy et al. <xref ref-type="bibr" rid="CR137">2005</xref>, <xref ref-type="bibr" rid="CR138">2006</xref>; Yoder et al. <xref ref-type="bibr" rid="CR241">2007</xref>), PC-3, DU-145, Hep-3B cell line (Chen et al. <xref ref-type="bibr" rid="CR28">2012</xref>)); hAChE, BChE inhibitor (Cho et al. <xref ref-type="bibr" rid="CR31">2012</xref>), SARS-CoV PLpro activity (Cho et al. <xref ref-type="bibr" rid="CR32">2013</xref>); significant inhibitory effects against <italic>Cp</italic>-NanI (a sialidase from <italic>C. perfringens</italic>) (Lee et al. <xref ref-type="bibr" rid="CR111">2014</xref>); selective docking to <italic>Leishmania major</italic> N-myristoyltransferase (Ogungbe et al. <xref ref-type="bibr" rid="CR145">2014</xref>); antileishmanial activity (<italic>L. donovani</italic> amastigotes) (Salem et al. <xref ref-type="bibr" rid="CR178">2011</xref>); inactive against glutamate-induced neurotoxicity studied in primary-cultured rat cortical cells (Kim et al. <xref ref-type="bibr" rid="CR92">2010a</xref>, <xref ref-type="bibr" rid="CR93">b</xref>)</td><td align="left">H</td><td align="left">OH</td><td align="left">OH</td><td align="left">H</td></tr><tr><td align="left">Diplacol (<bold>23</bold>) (2<italic>R</italic>, 3<italic>R</italic>)</td><td align="left">Fruit (Asai et al. <xref ref-type="bibr" rid="CR7">2008</xref>), flowers, leaves (Kobayashi et al. <xref ref-type="bibr" rid="CR95">2008</xref>)</td><td align="left">Antioxidant (Asai et al. <xref ref-type="bibr" rid="CR7">2008</xref>); cytotoxic (human ovarian cancer cell line A2780) (Murphy et al. <xref ref-type="bibr" rid="CR138">2006</xref>; Yoder et al. <xref ref-type="bibr" rid="CR241">2007</xref>), low activity against T-lymphoblastic leukaemia CEM, multiple myeloma RPMI 8226 and U266 cell lines, BJ human fibroblast cell line (Šmejkal et al. <xref ref-type="bibr" rid="CR207">2010</xref>)</td><td align="left">OH</td><td align="left">OH</td><td align="left">OH</td><td align="left">H</td></tr><tr><td align="left">3′-<italic>O</italic>-methyldiplacone (<bold>24</bold>)</td><td align="left">Fruit (Asai et al. <xref ref-type="bibr" rid="CR7">2008</xref>; Cho et al. <xref ref-type="bibr" rid="CR31">2012</xref>, <xref ref-type="bibr" rid="CR32">2013</xref>; Lee et al. <xref ref-type="bibr" rid="CR111">2014</xref>; Šmejkal et al. <xref ref-type="bibr" rid="CR203">2007a</xref>, <xref ref-type="bibr" rid="CR206">2008b</xref>), flowers and leaves (Kobayashi et al. <xref ref-type="bibr" rid="CR95">2008</xref>)</td><td align="left">Antioxidant (Šmejkal et al. <xref ref-type="bibr" rid="CR203">2007a</xref>; Yazaki et al. <xref ref-type="bibr" rid="CR240">2009</xref>); SARS-CoV PLpro activity (Cho et al. <xref ref-type="bibr" rid="CR32">2013</xref>); weak hAChE, BChE inhibitor (Cho et al. <xref ref-type="bibr" rid="CR31">2012</xref>); significant inhibitory effects against <italic>Cp</italic>-NanI (a sialidase from <italic>C. perfringens</italic>) (Lee et al. <xref ref-type="bibr" rid="CR111">2014</xref>); strong docking energy to <italic>L. major</italic> pteridine reductase 1, selective docking to glycerol-3-phosphate dehydrogenase (Ogungbe et al. <xref ref-type="bibr" rid="CR145">2014</xref>), antileishmanial activity (<italic>L. donovani</italic> amastigotes) (Salem et al. <xref ref-type="bibr" rid="CR178">2011</xref>); activity against lymphoblastic leukaemia CEM, multiple myeloma RPMI 8226 and U266 cell lines, BJ human fibroblast cell line (Šmejkal et al. <xref ref-type="bibr" rid="CR207">2010</xref>), human erythro-leukaemia cell line K562 (Šmejkal et al. <xref ref-type="bibr" rid="CR205">2008a</xref>); weak antimicrobial against seven Gram-positive bacteria, no antimicrobial activity against three types of Gram-negative bacteria or yeast (Šmejkal et al. <xref ref-type="bibr" rid="CR206">2008b</xref>), weak antimicrobial activity against <italic>S. aureus</italic>, various methicillin resistant strains of <italic>S. aureus</italic> (MRSA 287, MRSA 4211, MRSA, 6975, MRSA 630, MRSA 62059) (Navrátilová et al. <xref ref-type="bibr" rid="CR141">2013</xref>)</td><td align="left">H</td><td align="left">OMe</td><td align="left">OH</td><td align="left">H</td></tr><tr><td align="left">3′-<italic>O</italic>-methyldiplacol (syn. diplacol 3′-<italic>O</italic>-methylether) (<bold>25</bold>) (2<italic>R</italic>, 3<italic>R</italic>)</td><td align="left">Flowers (Kobayashi et al. <xref ref-type="bibr" rid="CR95">2008</xref>), fruit (Asai et al. <xref ref-type="bibr" rid="CR7">2008</xref>; Cho et al. <xref ref-type="bibr" rid="CR31">2012</xref>, <xref ref-type="bibr" rid="CR32">2013</xref>; Šmejkal et al. <xref ref-type="bibr" rid="CR206">2008b</xref>)</td><td align="left">Antioxidant (Asai et al. <xref ref-type="bibr" rid="CR7">2008</xref>; Yazaki et al. <xref ref-type="bibr" rid="CR240">2009</xref>), antimicrobial against seven Gram-positive bacteria, no antimicrobial activity against three types of Gram-negative bacteria or yeast (Šmejkal et al. <xref ref-type="bibr" rid="CR206">2008b</xref>), antimicrobial against <italic>S. aureus</italic> and various methicillin resistant strains of <italic>S. aureus</italic> (MRSA 287, MRSA 4211, MRSA, 6975, MRSA 630, MRSA 62059)—most potent together with <bold>27</bold> (Navrátilová et al. <xref ref-type="bibr" rid="CR141">2013</xref>); cytotoxic (human erythro-leukaemia cell line K562) (Šmejkal et al. <xref ref-type="bibr" rid="CR205">2008a</xref>), low activity against T-lymphoblastic leukaemia CEM, multiple myeloma RPMI 8226 and U266 cell lines, BJ human fibroblast cell line (Šmejkal et al. <xref ref-type="bibr" rid="CR207">2010</xref>); SARS-CoV PLpro activity (Cho et al. <xref ref-type="bibr" rid="CR32">2013</xref>); hAChE, BChE inhibitor (Cho et al. <xref ref-type="bibr" rid="CR31">2012</xref>); antileishmanial activity (<italic>L. donovani</italic> amastigotes) (Salem et al. <xref ref-type="bibr" rid="CR178">2011</xref>), selective docking to <italic>L</italic>. <italic>major</italic> methionyl tRNA synthetase (Ogungbe et al. <xref ref-type="bibr" rid="CR145">2014</xref>)</td><td align="left">OH</td><td align="left">OMe</td><td align="left">OH</td><td align="left">H</td></tr><tr><td align="left">3′-<italic>O</italic>-methyl-5′-<italic>O</italic>-methyldiplacone (syn. 6-geranyl-4′,5,7-trihydroxy-3′,5′-dimethoxyflavanone) (<bold>26</bold>) (2<italic>S</italic>)</td><td align="left">Fruit (Asai et al. <xref ref-type="bibr" rid="CR7">2008</xref>; Cho et al. <xref ref-type="bibr" rid="CR31">2012</xref>, <xref ref-type="bibr" rid="CR32">2013</xref>; Šmejkal et al. <xref ref-type="bibr" rid="CR206">2008b</xref>)</td><td align="left">Antioxidant (Yazaki et al. <xref ref-type="bibr" rid="CR240">2009</xref>), antimicrobial against seven Gram-positive bacteria, no antimicrobial activity against three types of Gram-negative bacteria or yeast (Šmejkal et al. <xref ref-type="bibr" rid="CR206">2008b</xref>), antimicrobial against <italic>S. aureus</italic> and various methicillin resistant strains of <italic>S. aureus</italic> (MRSA 287, MRSA 4211, MRSA, 6975, MRSA 630, MRSA 62059) (Navrátilová et al. <xref ref-type="bibr" rid="CR141">2013</xref>); cytotoxic (multiple myeloma RPMI 8226 and U266 cell lines, human cervical cancer cells HeLa, BJ human fibroblast cell line (Šmejkal et al. <xref ref-type="bibr" rid="CR207">2010</xref>), human erythro-leukaemia cell line K562) (Šmejkal et al. <xref ref-type="bibr" rid="CR205">2008a</xref>); SARS-CoV PLpro activity (Cho et al. <xref ref-type="bibr" rid="CR32">2013</xref>); hAChE, BChE inhibitor (Cho et al. <xref ref-type="bibr" rid="CR31">2012</xref>)</td><td align="left">H</td><td align="left">OMe</td><td align="left">OH</td><td align="left">OMe</td></tr><tr><td align="left">3′-<italic>O</italic>-methyl-5′-hydroxydiplacone (syn. 6-geranyl-4′,5,5′,7-tetrahydroxy-3′-methoxyflavanone) (<bold>27</bold>) (2<italic>S</italic>)</td><td align="left">Immature fruit (Asai et al. <xref ref-type="bibr" rid="CR7">2008</xref>), fruit (Šmejkal et al. <xref ref-type="bibr" rid="CR206">2008b</xref>), leaves (Kobayashi et al. <xref ref-type="bibr" rid="CR95">2008</xref>)</td><td align="left">Antioxidant (Asai et al. <xref ref-type="bibr" rid="CR7">2008</xref>; Yazaki et al. <xref ref-type="bibr" rid="CR240">2009</xref>; Zima et al. <xref ref-type="bibr" rid="CR256">2010</xref>); antimicrobial activity against seven Gram-positive bacteria, no antimicrobial activity against three types of Gram-negative bacteria or yeast (Šmejkal et al. <xref ref-type="bibr" rid="CR206">2008b</xref>), antimicrobial against <italic>S. aureus</italic> and various methicillin resistant strains of <italic>S. aureus</italic> (MRSA 287, MRSA 4211, MRSA, 6975, MRSA 630, MRSA 62059) (Navrátilová et al. <xref ref-type="bibr" rid="CR141">2013</xref>); cytotoxic (human erythro-leukamia cell line K562) (Šmejkal et al. <xref ref-type="bibr" rid="CR205">2008a</xref>), activity against T-lymphoblastic leukaemia CEM, multiple myeloma RPMI 8226 and U266 cell lines, BJ human fibroblast cell line (Šmejkal et al. <xref ref-type="bibr" rid="CR207">2010</xref>)</td><td align="left">H</td><td align="left">OMe</td><td align="left">OH</td><td align="left">OH</td></tr><tr><td align="left">3′-<italic>O</italic>-methyl-5′-methoxydiplacol (<bold>28</bold>) (racemic mixture of 2<italic>R</italic>, 3<italic>R</italic> and 2<italic>S</italic>, 3<italic>S</italic>)</td><td align="left">Fruit (Šmejkal et al. <xref ref-type="bibr" rid="CR203">2007a</xref>)</td><td align="left"></td><td align="left">OH</td><td align="left">OMe</td><td align="left">OH</td><td align="left">OMe</td></tr><tr><td align="left">6-Geranyl-5,7-dihydroxy-3′,4′-dimethoxyflavanone (<bold>29</bold>) (2<italic>S</italic>)</td><td align="left">Immature fruit (Asai et al. <xref ref-type="bibr" rid="CR7">2008</xref>)</td><td align="left">Antioxidant (Asai et al. <xref ref-type="bibr" rid="CR7">2008</xref>)</td><td align="left">H</td><td align="left">H</td><td align="left">OMe</td><td align="left">OMe</td></tr><tr><td align="left">6-Geranyl-3′,5,7-tri-hydroxy-4′-methoxyflavanone (syn. 4′-<italic>O</italic>-methyldiplacone) (<bold>30</bold>) (2<italic>S</italic>)</td><td align="left">Immature fruit (Asai et al. <xref ref-type="bibr" rid="CR7">2008</xref>), fruits (Cho et al. <xref ref-type="bibr" rid="CR31">2012</xref>, <xref ref-type="bibr" rid="CR32">2013</xref>; Lee et al. <xref ref-type="bibr" rid="CR111">2014</xref>)</td><td align="left">Antioxidant (Asai et al. <xref ref-type="bibr" rid="CR7">2008</xref>); SARS-CoV PLpro activity (Cho et al. <xref ref-type="bibr" rid="CR32">2013</xref>); hAChE, BChE inhibitor (Cho et al. <xref ref-type="bibr" rid="CR31">2012</xref>); significant inhibitory effects against <italic>Cp</italic>-NanI (a sialidase from <italic>C. perfringens</italic>) (Lee et al. <xref ref-type="bibr" rid="CR111">2014</xref>); antileishmanial activity (<italic>L. donovani</italic> amastigotes) (Salem et al. <xref ref-type="bibr" rid="CR178">2011</xref>)</td><td align="left">H</td><td align="left">H</td><td align="left">OMe</td><td align="left">OH</td></tr><tr><td align="left">6-Geranyl-3,3′,5,7-tetrahydroxy-4′-methoxyflavanone (syn. 4′-<italic>O</italic>-methyldiplacol) (<bold>31</bold>) (2<italic>R</italic>, 3<italic>R</italic>)</td><td align="left">Immature fruit (Asai et al. <xref ref-type="bibr" rid="CR7">2008</xref>), fruit (Cho et al. <xref ref-type="bibr" rid="CR31">2012</xref>, <xref ref-type="bibr" rid="CR32">2013</xref>)</td><td align="left">Antioxidant (Asai et al. <xref ref-type="bibr" rid="CR7">2008</xref>), SARS-CoV PLpro activity (Cho et al. <xref ref-type="bibr" rid="CR32">2013</xref>); hAChE, BChE inhibitor (Cho et al. <xref ref-type="bibr" rid="CR31">2012</xref>)</td><td align="left">OH</td><td align="left">H</td><td align="left">OMe</td><td align="left">OH</td></tr><tr><td align="left">Schizolaenone C (<bold>32</bold>) (2<italic>S</italic>)</td><td align="left">Fruit (Šmejkal et al. <xref ref-type="bibr" rid="CR207">2010</xref>)</td><td align="left">Cytotoxic (T-lymphoblastic leukaemia CEM, multiple myeloma RPMI 8226 and U266 cell lines, human cervical cancer cells HeLa, BJ human fibroblast cell line) (Šmejkal et al. <xref ref-type="bibr" rid="CR207">2010</xref>), cytotoxic (human ovarian cancer cell line A2780) (Murphy et al. <xref ref-type="bibr" rid="CR138">2006</xref>; antioxidant (Zima et al. <xref ref-type="bibr" rid="CR256">2010</xref>)</td><td align="left">H</td><td align="left">OH</td><td align="left">H</td><td align="left">OH</td></tr><tr><td align="left">6-Geranyl-3,3′,5,5′,7-pentahydroxy-4′-methoxyflavanone (<bold>33</bold>) (2<italic>R</italic>, 3<italic>R</italic>)</td><td align="left" rowspan="2">Fruit (Cho et al. <xref ref-type="bibr" rid="CR31">2012</xref>)</td><td align="left" rowspan="2">hAChE, BChE inhibitor (Cho et al. <xref ref-type="bibr" rid="CR31">2012</xref>)</td><td align="left">OH</td><td align="left">OH</td><td align="left">OMe</td><td align="left">OH</td></tr><tr><td align="left">6-Geranyl-3′,5,5′,7-tetrahydroxy-4′-methoxyflavanone (<bold>34</bold>) (2<italic>S</italic>)</td><td align="left">H</td><td align="left">OH</td><td align="left">OMe</td><td align="left">OH</td></tr><tr><td align="left">Tomentodiplacone B (<bold>35</bold>) (2<italic>S</italic>)</td><td align="left">Fruits (Šmejkal et al. <xref ref-type="bibr" rid="CR206">2008b</xref>)</td><td align="left">Antioxidant (Yazaki et al. <xref ref-type="bibr" rid="CR240">2009</xref>; Zima et al. <xref ref-type="bibr" rid="CR256">2010</xref>); low direct cytotoxicity (human erythro-leukamia cell line K562) (Šmejkal et al. <xref ref-type="bibr" rid="CR205">2008a</xref>); low direct activity against T-lymphoblastic leukaemia CEM, multiple myeloma RPMI 8226 and U266 cell lines, BJ human fibroblast cell line (Šmejkal et al. <xref ref-type="bibr" rid="CR207">2010</xref>), effect on cell cycle (THP-1 human monocytic leukaemia cells) (Kollár et al. <xref ref-type="bibr" rid="CR97">2011</xref>); antimicrobial against <italic>S. aureus</italic> and various methicillin resistant strains of <italic>S. aureus</italic> (MRSA 287, MRSA 4211, MRSA, 6975, MRSA 630, MRSA 62059) (Navrátilová et al. <xref ref-type="bibr" rid="CR141">2013</xref>), no antimicrobial activity on Gram-negative bacteria or yeast and on seven Gram-positive bacteria (Navrátilová et al. <xref ref-type="bibr" rid="CR141">2013</xref>; Šmejkal et al. <xref ref-type="bibr" rid="CR206">2008b</xref>)</td><td align="left" colspan="4"><inline-graphic xlink:href="11101_2014_9376_Figg_HTML.gif" id="d29e2620"></inline-graphic></td></tr><tr><td align="left"></td><td align="left"></td><td align="left"></td><td align="left" colspan="4"><inline-graphic xlink:href="11101_2014_9376_Figh_HTML.gif" id="d29e2630"></inline-graphic></td></tr></tbody></table><table frame="hsides" rules="groups"><thead><tr><th align="left"></th><th align="left"></th><th align="left"></th><th align="left" colspan="4">R</th></tr></thead><tbody><tr><td align="left">3,3′,4′, 5,7-Pentahydroxy-6-[7-hydroxy-3,7-dimethyl-2(<italic>E</italic>)octenyl] flavanone (<bold>36</bold>) (2<italic>R</italic>, 3<italic>R</italic>)</td><td align="left">Immature fruit (Asai et al. <xref ref-type="bibr" rid="CR7">2008</xref>)</td><td align="left">Antioxidant (Asai et al. <xref ref-type="bibr" rid="CR7">2008</xref>)</td><td align="left" colspan="4">OH</td></tr><tr><td align="left">Prokinawan (<bold>37</bold>) (2<italic>S</italic>)</td><td align="left">Flowers (Kobayashi et al. <xref ref-type="bibr" rid="CR95">2008</xref>), immature fruit (Asai et al. <xref ref-type="bibr" rid="CR7">2008</xref>)</td><td align="left">Antioxidant (Asai et al. <xref ref-type="bibr" rid="CR7">2008</xref>)</td><td align="left" colspan="4">H</td></tr><tr><td align="left"></td><td align="left"></td><td align="left"></td><td align="left" colspan="4"> <inline-graphic xlink:href="11101_2014_9376_Figi_HTML.gif" id="d29e2716"></inline-graphic></td></tr></tbody></table><table frame="hsides" rules="groups"><thead><tr><th align="left"></th><th align="left"></th><th align="left"></th><th align="left">R1</th><th align="left">R2</th><th align="left">R3</th></tr></thead><tbody><tr><td align="left">Tomentodiplacone (<bold>38</bold>) (2<italic>S</italic>)</td><td align="left">Fruit (Šmejkal et al. <xref ref-type="bibr" rid="CR206">2008b</xref>)</td><td align="left">Antioxidant (Yazaki et al. <xref ref-type="bibr" rid="CR240">2009</xref>); antimicrobial against seven Gram-positive bacteria, no antimicrobial activity against three types of Gram-negative bacteria or yeast (Šmejkal et al. <xref ref-type="bibr" rid="CR206">2008b</xref>), weak erythroid differentiation activity (Šmejkal et al. <xref ref-type="bibr" rid="CR205">2008a</xref>)</td><td align="left">H</td><td align="left">OMe</td><td align="left">H</td></tr><tr><td align="left">Tomentodiplacol (<bold>39</bold>) (2<italic>R</italic>, 3<italic>R</italic>)</td><td align="left">Fruit (Šmejkal et al. <xref ref-type="bibr" rid="CR203">2007a</xref>)</td><td align="left">Antioxidant (Šmejkal et al. <xref ref-type="bibr" rid="CR203">2007a</xref>)</td><td align="left">OH</td><td align="left">OMe</td><td align="left">H</td></tr><tr><td align="left">4′,5,5′,7-Tetrahydroxy-6-[6-hydroxy-3,7-dimethyl-2(<italic>E</italic>),7-octadienyl]-3′-methoxyflavanone (<bold>40</bold>) (2<italic>S</italic>)</td><td align="left">Immature fruit (Asai et al. <xref ref-type="bibr" rid="CR7">2008</xref>)</td><td align="left">Antioxidant (Asai et al. <xref ref-type="bibr" rid="CR7">2008</xref>)</td><td align="left">H</td><td align="left">OMe</td><td align="left">OH</td></tr><tr><td align="left">3,3′,4′,5,7-Pentahydroxy-6-[6-hydroxy-3,7-dimethyl-2(<italic>E</italic>),7-octadienyl]flavanone (<bold>41</bold>) (2<italic>R</italic>, 3<italic>R</italic>)</td><td align="left">Immature fruit (Asai et al. <xref ref-type="bibr" rid="CR7">2008</xref>)</td><td align="left">Antioxidant (Asai et al. <xref ref-type="bibr" rid="CR7">2008</xref>)</td><td align="left">OH</td><td align="left">OH</td><td align="left">H</td></tr><tr><td align="left">Tanariflavanone D (<bold>42</bold>) (2<italic>S</italic>)</td><td align="left">Immature fruit (Asai et al. <xref ref-type="bibr" rid="CR7">2008</xref>), fruit (Schneiderová et al. <xref ref-type="bibr" rid="CR185">2013</xref>)</td><td align="left">Antioxidant (Asai et al. <xref ref-type="bibr" rid="CR7">2008</xref>; Phommart et al. <xref ref-type="bibr" rid="CR163">2005</xref>); cytotoxic (human breast cancer cell line BC) (Phommart et al. <xref ref-type="bibr" rid="CR163">2005</xref>); no anti-inflammatory effect in COX-2 inhibition assay (Phommart et al. <xref ref-type="bibr" rid="CR163">2005</xref>)</td><td align="left">H</td><td align="left">H</td><td align="left">OH</td></tr><tr><td align="left">Tomentomimulol (<bold>43</bold>) (<italic>2R</italic>, <italic>3R</italic>)</td><td align="left">Fruit (Schneiderová et al. <xref ref-type="bibr" rid="CR185">2013</xref>)</td><td align="left"></td><td align="left">OH</td><td align="left">H</td><td align="left">H</td></tr><tr><td align="left">Mimulone B (<bold>44</bold>) (2<italic>S</italic>)</td><td align="left">Fruit (Schneiderová et al. <xref ref-type="bibr" rid="CR185">2013</xref>)</td><td align="left"></td><td align="left">H</td><td align="left">H</td><td align="left">H</td></tr><tr><td align="left"></td><td align="left"></td><td align="left"></td><td align="left" colspan="3"> <inline-graphic xlink:href="11101_2014_9376_Figj_HTML.gif" id="d29e2988"></inline-graphic></td></tr></tbody></table><table frame="hsides" rules="groups"><thead><tr><th align="left"></th><th align="left"></th><th align="left"></th><th align="left">R</th></tr></thead><tbody><tr><td align="left">Tomentodiplacone C (<bold>45</bold>) (racemic mixture of 2<italic>R</italic>, 2<italic>S</italic>)</td><td align="left">Fruit (Navrátilová et al. <xref ref-type="bibr" rid="CR141">2013</xref>)</td><td align="left">Antimicrobial against <italic>S. aureus</italic> and various methicillin resistant strains of <italic>S. aureus</italic> (MRSA 287, MRSA 4211, MRSA, 6975, MRSA 630, MRSA 62059), no antimicrobial activity on Gram-negative bacteria, minor ability to affect the initiation of eukaryotic translation via dual-luciferase reported assay (firefly and renilla) in comparison with anisomycin (Navrátilová et al. <xref ref-type="bibr" rid="CR141">2013</xref>)</td><td align="left">OMe</td></tr><tr><td align="left">Mimulone E (<bold>46</bold>) (2<italic>S</italic>)</td><td align="left">Fruit (Navrátilová et al. <xref ref-type="bibr" rid="CR141">2013</xref>)</td><td align="left"></td><td align="left">H</td></tr><tr><td align="left"></td><td align="left"></td><td align="left"></td><td align="left"> <inline-graphic xlink:href="11101_2014_9376_Figk_HTML.gif" id="d29e3066"></inline-graphic></td></tr></tbody></table><table frame="hsides" rules="groups"><thead><tr><th align="left"></th><th align="left"></th><th align="left"></th><th align="left">R</th></tr></thead><tbody><tr><td align="left">Tomentodiplacone D (<bold>47</bold>) (2<italic>S</italic>)</td><td align="left">Fruit (Navrátilová et al. <xref ref-type="bibr" rid="CR141">2013</xref>)</td><td align="left" rowspan="2">Antimicrobial against <italic>S. aureus</italic> and various methicillin resistant strains of <italic>S. aureus</italic> (MRSA 287, MRSA 4211, MRSA, 6975, MRSA 630, MRSA 62059), no antimicrobial activity on Gram-negative bacteria, no ability to affect the initiation of eukaryotic translation via dual-luciferase reported assay (firefly and renilla) (Navrátilová et al. <xref ref-type="bibr" rid="CR141">2013</xref>)</td><td align="left"> <inline-graphic xlink:href="11101_2014_9376_Figl_HTML.gif" id="d29e3114"></inline-graphic></td></tr><tr><td align="left">Tomentodiplacone E (<bold>48</bold>) (2<italic>S</italic>)</td><td align="left">Fruit (Navrátilová et al. <xref ref-type="bibr" rid="CR141">2013</xref>)</td><td align="left"> <inline-graphic xlink:href="11101_2014_9376_Figm_HTML.gif" id="d29e3136"></inline-graphic></td></tr><tr><td align="left">Tomentodiplacone F (<bold>49</bold>) (2<italic>S</italic>)</td><td align="left">Fruit (Navrátilová et al. <xref ref-type="bibr" rid="CR141">2013</xref>)</td><td align="left"></td><td align="left"> <inline-graphic xlink:href="11101_2014_9376_Fign_HTML.gif" id="d29e3159"></inline-graphic></td></tr><tr><td align="left">Tomentodiplacone G (<bold>50</bold>) (2<italic>S</italic>)</td><td align="left">Fruit (Navrátilová et al. <xref ref-type="bibr" rid="CR141">2013</xref>)</td><td align="left">Antimicrobial against <italic>S. aureus</italic> and various methicillin resistant strains of <italic>S. aureus</italic> (MRSA 287, MRSA 4211, MRSA, 6975, MRSA 630, MRSA 62059), no antimicrobial activity on Gram-negative bacteria, no ability to affect the initiation of eukaryotic translation via dual-luciferase reported assay (firefly and renilla) (Navrátilová et al. <xref ref-type="bibr" rid="CR141">2013</xref>)</td><td align="left"> <inline-graphic xlink:href="11101_2014_9376_Figo_HTML.gif" id="d29e3193"></inline-graphic></td></tr><tr><td align="left">Tomentodiplacone H (<bold>51</bold>) (racemic mixture 2<italic>R</italic>, 2<italic>S</italic>)</td><td align="left">Fruit (Navrátilová et al. <xref ref-type="bibr" rid="CR141">2013</xref>)</td><td align="left"></td><td align="left"> <inline-graphic xlink:href="11101_2014_9376_Figp_HTML.gif" id="d29e3219"></inline-graphic></td></tr><tr><td align="left">Tomentodiplacone I (<bold>52</bold>) (racemic mixture of 2<italic>R</italic>, 2<italic>S</italic>)</td><td align="left">Fruit (Navrátilová et al. <xref ref-type="bibr" rid="CR141">2013</xref>)</td><td align="left"></td><td align="left"> <inline-graphic xlink:href="11101_2014_9376_Figq_HTML.gif" id="d29e3245"></inline-graphic></td></tr><tr><td align="left">Mimulone C (<bold>53</bold>) (2<italic>S</italic>)</td><td align="left">Fruit (Navrátilová et al. <xref ref-type="bibr" rid="CR141">2013</xref>)</td><td align="left" rowspan="2">Antimicrobial against <italic>S. aureus</italic> and various methicillin resistant strains of <italic>S. aureus</italic> (MRSA 287, MRSA 4211, MRSA, 6975, MRSA 630, MRSA 62059), no antimicrobial activity on Gram-negative bacteria, <bold>53</bold> has no ability to affect the initiation of eukaryotic translation via dual-luciferase reported assay (firefly and renilla) (Navrátilová et al. <xref ref-type="bibr" rid="CR141">2013</xref>)</td><td align="left"> <inline-graphic xlink:href="11101_2014_9376_Figr_HTML.gif" id="d29e3282"></inline-graphic></td></tr><tr><td align="left">Mimulone D (<bold>54</bold>) (2<italic>S</italic>)</td><td align="left">Fruit (Navrátilová et al. <xref ref-type="bibr" rid="CR141">2013</xref>)</td><td align="left"> <inline-graphic xlink:href="11101_2014_9376_Figs_HTML.gif" id="d29e3304"></inline-graphic></td></tr><tr><td align="left"></td><td align="left"></td><td align="left"></td><td align="left"> <inline-graphic xlink:href="11101_2014_9376_Figt_HTML.gif" id="d29e3314"></inline-graphic></td></tr></tbody></table><table frame="hsides" rules="groups"><thead><tr><th align="left"></th><th align="left"></th><th align="left"></th><th align="left">R1</th><th align="left">R2</th><th align="left">R3</th><th align="left">R4</th></tr></thead><tbody><tr><td align="left">Tomentin A (<bold>55</bold>) (2<italic>S</italic>)</td><td align="left" rowspan="5">Fruit (Cho et al. <xref ref-type="bibr" rid="CR32">2013</xref>)</td><td align="left" rowspan="5">Activity against Severe acute respiratory syndrome corona virus (SARS-CoV PLpro, a reversible inhibitor <bold>63</bold> was the most potent compound tested (Cho et al. <xref ref-type="bibr" rid="CR32">2013</xref>)</td><td align="left">H</td><td align="left">H</td><td align="left">OH</td><td align="left">OH</td></tr><tr><td align="left">Tomentin B (<bold>56</bold>) (2<italic>S</italic>)</td><td align="left">H</td><td align="left">H</td><td align="left">OMe</td><td align="left">OH</td></tr><tr><td align="left">Tomentin C (<bold>57</bold>) (2<italic>S</italic>)</td><td align="left">H</td><td align="left">OH</td><td align="left">OMe</td><td align="left">OMe</td></tr><tr><td align="left">Tomentin D (<bold>58</bold>) (2<italic>S</italic>)</td><td align="left">H</td><td align="left">OMe</td><td align="left">OH</td><td align="left">OMe</td></tr><tr><td align="left">Tomentin E (<bold>59</bold>) (2<italic>R</italic>, 3<italic>S</italic>)</td><td align="left">OH</td><td align="left">H</td><td align="left">OH</td><td align="left">OMe</td></tr></tbody></table></table-wrap><table-wrap id="Tab4"><label>Table 4</label><caption><p>Phenolic glycosides isolated from <italic>P. tomentosa</italic></p></caption><table frame="hsides" rules="groups"><thead><tr><th align="left">Name of compound and ID</th><th align="left">Isolation</th><th align="left">Biological activity</th><th align="left">Chemical structure</th></tr></thead><tbody><tr><td align="left"></td><td align="left"></td><td align="left"></td><td align="left"> <inline-graphic xlink:href="11101_2014_9376_Figu_HTML.gif" id="d29e3509"></inline-graphic></td></tr></tbody></table><table frame="hsides" rules="groups"><thead><tr><th align="left"></th><th align="left"></th><th align="left"></th><th align="left">R</th></tr></thead><tbody><tr><td align="left">Coniferin (syn. abietin, coniferosid, laricin) (<bold>69</bold>)</td><td align="left">Bark (Sticher and Lahloub <xref ref-type="bibr" rid="CR208">1982</xref>; Zhu et al. <xref ref-type="bibr" rid="CR255">1986</xref>)</td><td align="left">Antiphlogistic (Choi et al. <xref ref-type="bibr" rid="CR33">2004</xref>), low COX-2/1 and 5-LOX inhibition (Wang et al. <xref ref-type="bibr" rid="CR227">2013</xref>; Diaz Lanza et al. <xref ref-type="bibr" rid="CR42">2001</xref>); low antioxidant activity in vitro (DPPH) (She et al. <xref ref-type="bibr" rid="CR189">2013</xref>); stimulation osteoblastic bone formation in vitro (Ding et al. <xref ref-type="bibr" rid="CR43">2010</xref>); concentration-dependent contractions in rat aortic rings (Deliorman et al. <xref ref-type="bibr" rid="CR40">2000</xref>); inhibition of ADP-induced platelet aggregation (Panossian et al. <xref ref-type="bibr" rid="CR155">1998</xref>); hypotensive in rats (Matsubara et al. <xref ref-type="bibr" rid="CR129">1991</xref>)</td><td align="left">H</td></tr><tr><td align="left">Syringin (syn. eleutherosid B) (<bold>70</bold>)</td><td align="left">Bark (Sticher and Lahloub <xref ref-type="bibr" rid="CR208">1982</xref>; Zhu et al. <xref ref-type="bibr" rid="CR255">1986</xref>)</td><td align="left">Antidepressant (Kurkin et al. <xref ref-type="bibr" rid="CR104">2006</xref>), antiphlogistic, antinociceptive (Choi et al. <xref ref-type="bibr" rid="CR33">2004)</xref>; peroxyl radical scavenging capacity (Kim et al. <xref ref-type="bibr" rid="CR92">2010a</xref>, <xref ref-type="bibr" rid="CR93">b</xref>), inhibition of NO production in LPS-induced RAW 264.7 cells (Lee et al. <xref ref-type="bibr" rid="CR109">2009</xref>); enhances memory in aged rats (Huang et al. <xref ref-type="bibr" rid="CR71">2013a</xref>, <xref ref-type="bibr" rid="CR72">b</xref>); protective effects against Aβ(25–35)-induced atrophies of axons and dendrites (Bai et al. <xref ref-type="bibr" rid="CR10">2011</xref>; Tohda et al. <xref ref-type="bibr" rid="CR220">2008</xref>); immunomodulatory activity in PMN phagocytic function test (Sharma et al. <xref ref-type="bibr" rid="CR188">2012</xref>); hepatoprotective in mice (Gong et al. <xref ref-type="bibr" rid="CR54">2014</xref>); adiponectin receptor 2 agonist (Sun et al. <xref ref-type="bibr" rid="CR211">2013</xref>); low COX and 5-LOX inhibition (Diaz Lanza et al. <xref ref-type="bibr" rid="CR42">2001</xref>); concentration-dependent contractions in rat aortic rings (Deliorman et al. <xref ref-type="bibr" rid="CR40">2000</xref>); inhibition of ADP-induced platelet aggregation (Panossian et al. <xref ref-type="bibr" rid="CR155">1998</xref>; Iizuka et al. <xref ref-type="bibr" rid="CR75">2005</xref>); moderate in vitro cytotoxic activities against A549 and HL-60 (Yang et al. <xref ref-type="bibr" rid="CR238">2012</xref>); antitumour activity in sarcoma S180 transplanted mice (Zhang et al. <xref ref-type="bibr" rid="CR250">2007</xref>); weak inhibition of snake PDE I (Chai et al. <xref ref-type="bibr" rid="CR21">2009</xref>); hypoglycemic effect (Liu et al. <xref ref-type="bibr" rid="CR119">2008</xref>; Niu et al. <xref ref-type="bibr" rid="CR143">2008a</xref>, <xref ref-type="bibr" rid="CR144">b</xref>; Niu et al. <xref ref-type="bibr" rid="CR142">2007</xref>); adaptogenic activity reviewed by Panossian and Wagner (<xref ref-type="bibr" rid="CR154">2005</xref>)</td><td align="left">OMe</td></tr><tr><td align="left"></td><td align="left"></td><td align="left"></td><td align="left"> <inline-graphic xlink:href="11101_2014_9376_Figv_HTML.gif" id="d29e3678"></inline-graphic></td></tr></tbody></table><table frame="hsides" rules="groups"><thead><tr><th align="left"></th><th align="left"></th><th align="left"></th><th align="left">R1</th><th align="left">R2</th><th align="left">R3</th></tr></thead><tbody><tr><td align="left">Acteoside (syn. verbascoside) (<bold>71</bold>)</td><td align="left">Bark (Si et al. <xref ref-type="bibr" rid="CR199">2011b</xref>; Sticher and Lahloub <xref ref-type="bibr" rid="CR208">1982</xref>; Zhu et al. <xref ref-type="bibr" rid="CR255">1986</xref>), wood (Si et al. <xref ref-type="bibr" rid="CR196">2008d</xref>), sapwood (Ota et al. <xref ref-type="bibr" rid="CR148">1993</xref>), fruit (Šmejkal et al. <xref ref-type="bibr" rid="CR204">2007b</xref>), leaves (Schilling et al. <xref ref-type="bibr" rid="CR183">1982</xref>), young plant (Damtoft and Jensen <xref ref-type="bibr" rid="CR37">1993</xref>)</td><td align="left">Antioxidant, anti-inflammatory (Lin et al. <xref ref-type="bibr" rid="CR117">2006</xref>; Šmejkal et al. <xref ref-type="bibr" rid="CR204">2007b</xref>); antihepatotoxic (Xiong et al. <xref ref-type="bibr" rid="CR235">1998</xref>), antimicrobial (Kurkin <xref ref-type="bibr" rid="CR103">2003</xref>), antiviral (Kim et al. <xref ref-type="bibr" rid="CR91">2001</xref>); immuno-modulatory (Akbay et al. <xref ref-type="bibr" rid="CR3">2002</xref>); antihypertensive (Ahmad and Rizwani <xref ref-type="bibr" rid="CR2">1995</xref>); neuroprotective (Koo et al. <xref ref-type="bibr" rid="CR99">2005</xref>); cytotoxic (e.g., human erythro-leukemia cell line K562 (Šmejkal et al. <xref ref-type="bibr" rid="CR205">2008a</xref>), antiestrogen in breast cancer cells MCF7 and osteoblast without any effect on endometrial cancer cells Ishikawa (Papoutsi et al. <xref ref-type="bibr" rid="CR156">2006</xref>), bioactivities reviewed by He et al. (<xref ref-type="bibr" rid="CR63">2011</xref>)</td><td align="left">OH</td><td align="left">OH</td><td align="left">H</td></tr><tr><td align="left"><italic>β</italic>-Oxoacteoside (syn. tomentoside A) (<bold>72</bold>)</td><td align="left"></td><td align="left">Antioxidant (Tozuka et al. <xref ref-type="bibr" rid="CR221">2005</xref>)</td><td align="left">OH</td><td align="left">OH</td><td align="left">=O</td></tr><tr><td align="left">Martynoside (<bold>73</bold>)</td><td align="left">Stem (Kang et al. <xref ref-type="bibr" rid="CR84">1994</xref>)</td><td align="left">Antioxidant (Jimenéz and Riguera <xref ref-type="bibr" rid="CR79">1994</xref>); antihypertensive (Kang et al. <xref ref-type="bibr" rid="CR86">2003</xref>); cytotoxic (antiestrogen in breast cancer cells MCF7 via the ER-pathway, osteoblasts KS483, endometrial cancer cells Ishikawa) (Papoutsi et al. <xref ref-type="bibr" rid="CR156">2006</xref>)</td><td align="left">OMe</td><td align="left">OMe</td><td align="left">H</td></tr><tr><td align="left">Campneoside I (<bold>74</bold>)</td><td align="left">Wood (Si et al. <xref ref-type="bibr" rid="CR196">2008d</xref>), stem (Kang et al. <xref ref-type="bibr" rid="CR84">1994</xref>)</td><td align="left">Antibacterial against <italic>Staphylococcus</italic> and <italic>Streptococcus</italic> species (MIC 150 μg/ml) (Kang et al. <xref ref-type="bibr" rid="CR84">1994</xref>)</td><td align="left">OH</td><td align="left">OH</td><td align="left">OMe</td></tr><tr><td align="left">Campneoside II (syn. <italic>β</italic>-hydroxy-acteoside) (<bold>75</bold>)</td><td align="left">Bark (Si et al. <xref ref-type="bibr" rid="CR199">2011b</xref>), wood (Si et al. <xref ref-type="bibr" rid="CR194">2008b</xref>)</td><td align="left">Antibacterial, anti-inflammatory (Jimenéz and Riguera <xref ref-type="bibr" rid="CR79">1994</xref>), anticomplement (Si et al. <xref ref-type="bibr" rid="CR194">2008b</xref>)</td><td align="left">OH</td><td align="left">OH</td><td align="left">OH</td></tr><tr><td align="left">Ilicifolioside A (<bold>76</bold>)</td><td align="left">wood (Si et al. <xref ref-type="bibr" rid="CR194">2008b</xref>)</td><td align="left">Anticomplement (Si et al. <xref ref-type="bibr" rid="CR194">2008b</xref>)</td><td align="left">OH</td><td align="left">OH</td><td align="left">OEt</td></tr><tr><td align="left"></td><td align="left"></td><td align="left"></td><td align="left" colspan="3"> <inline-graphic xlink:href="11101_2014_9376_Figw_HTML.gif" id="d29e3953"></inline-graphic></td></tr></tbody></table><table frame="hsides" rules="groups"><thead><tr><th align="left"></th><th align="left"></th><th align="left"></th><th align="left">R</th></tr></thead><tbody><tr><td align="left">Isoacteoside (syn. isoverbascoside) (<bold>77</bold>)</td><td align="left">Bark (Si et al. <xref ref-type="bibr" rid="CR199">2011b</xref>), wood (Si et al. <xref ref-type="bibr" rid="CR196">2008d</xref>), sapwood (Ota et al. <xref ref-type="bibr" rid="CR148">1993</xref>), fruit (Šmejkal et al. <xref ref-type="bibr" rid="CR204">2007b</xref>), leaves (Schilling et al. <xref ref-type="bibr" rid="CR183">1982</xref>), young plant (Damtoft and Jensen <xref ref-type="bibr" rid="CR37">1993</xref>)</td><td align="left">Antioxidant (Šmejkal et al. <xref ref-type="bibr" rid="CR204">2007b</xref>), xanthine oxidase inhibition (Kong et al. <xref ref-type="bibr" rid="CR98">1999</xref>); suppression of glutamate induced neurotoxicity (Koo et al. <xref ref-type="bibr" rid="CR99">2005</xref>); antioxidant, immunosuppressive (Jimenéz and Riguera <xref ref-type="bibr" rid="CR79">1994</xref>); cytotoxic (e.g., human erythro-leukemia cell line K562) (Šmejkal et al. <xref ref-type="bibr" rid="CR205">2008a</xref>)</td><td align="left">H</td></tr><tr><td align="left">Isocampneoside I (<bold>78</bold>)</td><td align="left">Wood (mixture of <italic>R</italic>- and <italic>S</italic>-epimers) (Si et al. <xref ref-type="bibr" rid="CR196">2008d</xref>)</td><td align="left">Inhibition of D-galactosamine induced cytotoxicity in primary cultured mouse hepatocytes (Pan et al. <xref ref-type="bibr" rid="CR151">2010</xref>)</td><td align="left">OMe</td></tr><tr><td align="left">Isocampneoside II (<bold>79</bold>)</td><td align="left">Bark (Si et al. <xref ref-type="bibr" rid="CR199">2011b</xref>), wood (Si et al. <xref ref-type="bibr" rid="CR194">2008b</xref>)</td><td align="left">Aldose reductase inhibitor (potential against diabetic complications) (Kim et al. <xref ref-type="bibr" rid="CR94">2011</xref>); anticomplement (Si et al. <xref ref-type="bibr" rid="CR194">2008b</xref>); antioxidant, neuro-protective on hydrogen peroxide-induced oxidative injury in PC12 cells (Si et al. <xref ref-type="bibr" rid="CR200">2013</xref>).</td><td align="left">OH</td></tr><tr><td align="left">Isoilicifolioside A (<bold>80</bold>)</td><td align="left">Wood (Si et al. <xref ref-type="bibr" rid="CR194">2008b</xref>)</td><td align="left">Anticomplement (Si et al. <xref ref-type="bibr" rid="CR194">2008b</xref>)</td><td align="left">OEt</td></tr><tr><td align="left">Cistanoside F (<bold>81</bold>)</td><td align="left">Bark (Si et al. <xref ref-type="bibr" rid="CR199">2011b</xref>)</td><td align="left">Antioxidant (Xiong et al. <xref ref-type="bibr" rid="CR234">1996</xref>); vasorelaxant (Yoshikawa et al. <xref ref-type="bibr" rid="CR244">2006</xref>); interaction with bovine serum albumin (Wu et al. <xref ref-type="bibr" rid="CR233">2012</xref>)</td><td align="left"> <inline-graphic xlink:href="11101_2014_9376_Figx_HTML.gif" id="d29e4129"></inline-graphic></td></tr></tbody></table></table-wrap></p></sec><sec id="Sec3"><title><italic>P. tomentosa</italic> flavonoids and their biological activity</title><p>Flavonoids represent the most numerous group of secondary metabolites isolated from <italic>P. tomentosa</italic>. They can be divided into simple non-prenylated flavonoids <bold>1</bold>–<bold>18</bold> (Table <xref rid="Tab1" ref-type="table">1</xref>), <italic>C</italic>-prenylated and <italic>C</italic>-geranylated flavonoids <bold>19</bold>–<bold>59</bold> (Tables <xref rid="Tab2" ref-type="table">2</xref>, <xref rid="Tab3" ref-type="table">3</xref>, respectively), and flavonoid glycosides <bold>60</bold>–<bold>65</bold>. Compounds <bold>16</bold>, <bold>17</bold>, <bold>19</bold>, <bold>20</bold>, <bold>25</bold>–<bold>31</bold>, <bold>33</bold>–<bold>36</bold>, <bold>38</bold>–<bold>59</bold> have never been isolated from any other species. Most of the isolated flavanones are characterized by a <italic>2S</italic> configuration in contrast to the dihydroflavonols, for which <italic>2R</italic>, <italic>3R</italic> isomer is often observed.</p><p>Some of the flavonoid compounds found in <italic>P. tomentosa</italic> have been categorized as dietary flavonoids. Consuming these compounds is believed to deliver health benefits. The activities of these flavonoids are frequently been reviewed, for example in the papers of Romano et al. (<xref ref-type="bibr" rid="CR174">2013</xref>), Marzocchella et al. (<xref ref-type="bibr" rid="CR127">2011</xref>), Ross and Kasum (<xref ref-type="bibr" rid="CR175">2002</xref>), and Havsteen (<xref ref-type="bibr" rid="CR62">2002</xref>). Some simple flavonoid substances isolated from fruit of <italic>P. tomentosa</italic> are commonly observed as the lipophilic components of different plant exudates. Flavonoids <bold>1</bold>–<bold>18</bold> show broad-spectrum pharmacological activities (Table <xref rid="Tab1" ref-type="table">1</xref>). Many papers report their potential role as anticancer compounds for use against human cervical and breast (Bulzomi et al. <xref ref-type="bibr" rid="CR16">2010</xref>, <xref ref-type="bibr" rid="CR17">2012</xref>), hepatoma, leukemic (Zhao et al. <xref ref-type="bibr" rid="CR253">2012</xref>), osteosarcoma (Chen et al. <xref ref-type="bibr" rid="CR29">2013</xref>), gastric carcinoma (Lu et al. <xref ref-type="bibr" rid="CR124">2013</xref>), colon adenocarcinoma (Sánchez-Tena et al. <xref ref-type="bibr" rid="CR179">2013</xref>), or prostatic (Zhang and Coultas <xref ref-type="bibr" rid="CR248">2013</xref>) cancer cell lines. Their antioxidant properties could explain their promising cardioprotective (Paneerselvam et al. <xref ref-type="bibr" rid="CR153">2010</xref>; Psotová et al. <xref ref-type="bibr" rid="CR168">2004</xref>) and neuroprotective effects (Losi et al. <xref ref-type="bibr" rid="CR123">2004</xref>). Antimicrobial (Betts et al. <xref ref-type="bibr" rid="CR13">2013</xref>; Jiang et al. <xref ref-type="bibr" rid="CR78">2004</xref>; Mankovskaia et al. <xref ref-type="bibr" rid="CR125">2013</xref>) and antiviral (Khachatoorian et al. <xref ref-type="bibr" rid="CR88">2012</xref>) bio-activities against different pathogens have also been discovered. In some cases, no specific biological activity has been observed (Kim et al. <xref ref-type="bibr" rid="CR92">2010a</xref>, <xref ref-type="bibr" rid="CR93">2010b</xref>; Tang et al. <xref ref-type="bibr" rid="CR216">1994</xref>).</p><p><italic>Paulownia tomentosa</italic> is also a rich source of prenylated and geranylated flavonoids (<bold>19</bold>–<bold>59</bold>), whose occurrence is limited to relatively a few plant families (Yazaki et al. <xref ref-type="bibr" rid="CR240">2009</xref>). There are sometimes misunderstandings in the naming of these compounds. A compound containing both a phenolic skeleton and a terpenoid side chain is often designated as a “prenylated” phenolic substance, even though it contains not a prenyl, but rather a geranyl or other type of terpenoid side-chain. Prenylated flavonoids are biosynthesized by a combination of several pathways: the acetate, shikimate, and mevalonate (Fig. <xref rid="Fig1" ref-type="fig">1</xref>). It is now known that the prenyl and geranyl moieties are biosynthesized via mevalonate or deoxyxylulose pathway. The connection of terpenoid and flavonoid biosynthetic pathways is provided by prenyltransferases (Šmejkal <xref ref-type="bibr" rid="CR202">2014</xref>; Andersen and Markham <xref ref-type="bibr" rid="CR4">2006</xref>; Kuzuyama et al. <xref ref-type="bibr" rid="CR106">2005</xref>). The side chain can later be converted into different moieties by several reactions. It is unclear, whether the described modifications of the prenyl side-chain are natural—sunlight, the presence of oxygen and an elevated temperature can all affect the terpenoid metabolism—or are artefacts of isolation. Some of the changes in the prenyl moiety have been observed after treatment of an extract, or during the separation of a mixture in the acidic environment of silica gel (Navrátilová et al. <xref ref-type="bibr" rid="CR141">2013</xref>; Šmejkal <xref ref-type="bibr" rid="CR202">2014</xref>) (Fig. <xref rid="Fig2" ref-type="fig">2</xref>). <fig id="Fig1"><label>Fig. 1</label><caption><p>Schematic of the pathways of the biosynthesis of geranylated flavonoids</p></caption><graphic xlink:href="11101_2014_9376_Fig1_HTML" id="MO1"></graphic></fig><fig id="Fig2"><label>Fig. 2</label><caption><p>Flavonoid glycosides</p></caption><graphic xlink:href="11101_2014_9376_Fig2_HTML" id="MO2"></graphic></fig></p><p>Most of the prenylated flavonoids isolated from <italic>P. tomentosa</italic> belong to <italic>C</italic>-geranylated group of flavonoids (<bold>21</bold>–<bold>52</bold>). Some of them have their side-chain further modified by hydroxylation (<bold>35</bold>–<bold>44</bold>, <bold>50</bold>, <bold>51</bold>, <bold>53</bold>–<bold>59</bold>), methoxylation (<bold>45</bold>–<bold>47</bold>, <bold>49</bold>, <bold>50</bold>), oxidation (<bold>47</bold>, <bold>48</bold>, <bold>52</bold>), cyclization (<bold>51</bold>, <bold>53</bold>–<bold>59</bold>), or reduction (<bold>19</bold>, <bold>20</bold>, <bold>47</bold>–<bold>52</bold>). Interestingly, these compounds have been isolated from the leaves, flowers and fruit, but they are most commonly isolated from the roots, root bark, or bark of different plants (Botta et al. <xref ref-type="bibr" rid="CR14">2005</xref>). Compounds <bold>23</bold>, <bold>24</bold>, and <bold>28</bold> have been found in the yellow dendritic trichomes on the adaxial side of the <italic>P. tomentosa</italic> leaves. On the other hand, no significant detected concentration of secondary metabolites has been detected in the white dendritic trichomes on the adaxial side of the leaves or the brown dendritic trichomes on the flower buds (Kobayashi et al. <xref ref-type="bibr" rid="CR95">2008</xref>). Glandular hairs found on the young reproductive organs of <italic>P. tomentosa</italic> are rich in flavonoids, with concentrations over 1,000 times greater than those on the surfaces of the young leaves (Kobayashi et al. <xref ref-type="bibr" rid="CR95">2008</xref>). Some seasonal variations in the appropriate time for harvesting the fruit have been discovered. Autumn is the best time to obtain high concentrations of flavonoids whereas early summer is better for phenylpropanoid glycosides (Holubová and Šmejkal <xref ref-type="bibr" rid="CR66">2011</xref>).</p><p>The antioxidant (Asai et al. <xref ref-type="bibr" rid="CR7">2008</xref>; Šmejkal et al. <xref ref-type="bibr" rid="CR203">2007a</xref>, <xref ref-type="bibr" rid="CR204">b</xref>; Zima et al. <xref ref-type="bibr" rid="CR256">2010</xref>), antibacterial (Navrátilová et al. <xref ref-type="bibr" rid="CR141">2013</xref>; Šmejkal et al. <xref ref-type="bibr" rid="CR206">2008b</xref>), antiphlogistic (Hošek et al. <xref ref-type="bibr" rid="CR69">2010</xref>), cytotoxic (Kollár et al. <xref ref-type="bibr" rid="CR97">2011</xref>; Šmejkal et al. <xref ref-type="bibr" rid="CR203">2007a</xref>, <xref ref-type="bibr" rid="CR205">2008a</xref>, <xref ref-type="bibr" rid="CR207">2010</xref>), and severe acute respiratory syndrome coronavirus papain-like protease (SARS-CoV PLpro) activities (Cho et al. <xref ref-type="bibr" rid="CR32">2013</xref>) of isolated geranylated flavonoids have been described recently, together with their inhibitory effect on both human acetylcholinesterase and butyrylcholinesterase (Cho et al. <xref ref-type="bibr" rid="CR31">2012</xref>). The great ability of several geranylated flavanones to interact with bacterial sialidase isolated from <italic>Clostridum perfringens</italic> (<italic>Cp</italic>-NanI), a bacterium causing various gastrointestinal diseases, has recently been reported (Lee et al. <xref ref-type="bibr" rid="CR111">2014</xref>).</p><p>Possible relationships between structure and activity have been proposed for each of these biological activities. Nevertheless, it is difficult to evaluate real structure–activity relationships only by comparing the published studies, because the study conditions and the assays employed are often different. Generally, the addition of an isoprenoid chain renders the derivate molecule more pharmacologically effective than the parent compound, probably because the prenyl group increases the lipophilicity and confers a strong affinity for biological membranes (Botta et al. <xref ref-type="bibr" rid="CR14">2005</xref>; Epifano et al. <xref ref-type="bibr" rid="CR44">2007</xref>; Chen et al. <xref ref-type="bibr" rid="CR30">2014</xref>).</p><p>Interestingly, neither the geranyl side-chain nor its substitution affects the antioxidant activity of flavonoids. The spatial arrangement of the substitution of the flavanone skeleton is more important. For example, the antiradical activity is increased by 2′-hydroxyl substitution of the ring B, whereas 4′-methoxyl substitution diminishes it. The general rules postulated for the antioxidant activity of flavonoids in vitro are applicable (Havsteen <xref ref-type="bibr" rid="CR62">2002</xref>; Chen et al. <xref ref-type="bibr" rid="CR25">2002</xref>), there are many review publications that touch on this topic, and it is not aim of this paper to delve deeply into this (Plaza et al. <xref ref-type="bibr" rid="CR165">2014</xref>). The type of antioxidant assays used for the experiment could also be a factor that significantly affects this activity (Zima et al. <xref ref-type="bibr" rid="CR256">2010</xref>).</p><p>Numerous reports about structure related antimicrobial activity have been published, but comparison shows the results to be widely conflicting (Cushnie and Lamb <xref ref-type="bibr" rid="CR36">2005</xref>). Based on several studies, it has been postulated that hydroxylation at position C-5 or C-7 of ring A and positions C-2′ or C-4′ of ring B increases the antibacterial activity (Šmejkal et al. <xref ref-type="bibr" rid="CR206">2008b</xref>; Navrátilová et al. <xref ref-type="bibr" rid="CR141">2013</xref>). However, contrary to this assumption, <bold>45</bold> and <bold>50</bold> had no significant antibacterial activity (Navrátilová et al. <xref ref-type="bibr" rid="CR141">2013</xref>). Interestingly, some C-geranylated flavonoids do not able inhibit the growth of Gram-negative bacteria (<bold>21</bold>, <bold>22</bold>, <bold>25</bold>–<bold>27</bold>, <bold>35</bold>, <bold>38</bold>, <bold>45</bold>, <bold>47</bold>–<bold>48</bold>, <bold>50</bold>, <bold>53</bold>, and <bold>54</bold>). Resistance to these compounds is probably due to the more complex structure and hydrophilic nature of G-cell walls (Navrátilová et al. <xref ref-type="bibr" rid="CR141">2013</xref>; Šmejkal et al. <xref ref-type="bibr" rid="CR206">2008b</xref>). Furthermore, substitution of the geranyl side-chain with carbonyl, hydroxyl or methoxyl groups diminishes the antibacterial activity in a manner similar to what is seen when the geranyl substituent at C-6 forms a ring by reacting with the hydroxyl group at C-7. Compounds <bold>45</bold>, <bold>47</bold>, <bold>48</bold>, <bold>50</bold>, <bold>53</bold>, and <bold>54</bold> exhibit some degree of activity in the range of the concentrations tested on the Gram-positive bacteria <italic>Staphyloccocus aureus</italic> and various methicillin resistant strains of <italic>S. aureus</italic>. The level of activity varied in depending on both the structure and the bacterial strain used in the assay. Flavonoid structures like <bold>24</bold> are more effective in protecting plants from water loss because of their reduced polarity (Kobayashi et al. <xref ref-type="bibr" rid="CR95">2008</xref>; Navrátilová et al. <xref ref-type="bibr" rid="CR141">2013</xref>). Compounds <bold>45</bold>, <bold>47</bold>, <bold>48</bold>, <bold>50</bold>, and <bold>53</bold> were also tested for their ability to affect the initiation of the eukaryotic translation via dual-luciferase reported assay (firefly and renilla), but only <bold>45</bold> showed a modest activity in comparison with anisomycin (Navrátilová et al. <xref ref-type="bibr" rid="CR141">2013</xref>).</p><p>The cytotoxicity of the prenylated flavonoids obtained from <italic>P. tomentosa</italic> has been tested in more than 20 different cell lines. The type of prenylation strongly affects the cytotoxicity of a flavonoid in the traditional P-388 murine leukemia model. The unmodified 3-prenyl group and the presence of corresponding <italic>ortho</italic>-dihydroxy or trihydroxy substitution of the flavonoid ring B are crucial to its activity against P-388 as compared with other prenyl substituents (Hakim et al. <xref ref-type="bibr" rid="CR59">1999</xref>, <xref ref-type="bibr" rid="CR60">2002</xref>, <xref ref-type="bibr" rid="CR61">2006</xref>). Similar findings have been observed for modified C-6 geranyl groups and the substitution of the ring B for other cell lines tested (Šmejkal et al. <xref ref-type="bibr" rid="CR207">2010</xref>). However, replacing the <italic>para</italic>-hydroxy group of the ring B of a C-8 prenylated flavanone with several different acyl substituents resulted in greater cytotoxicity (Aniol et al. <xref ref-type="bibr" rid="CR5">2012</xref>; Šmejkal <xref ref-type="bibr" rid="CR202">2014</xref>). It has also been found that cytotoxic activity is diminished by the presence of a C-3 hydroxyl substituent on the ring C, 4′-methoxy substitution of the ring B or a <italic>para</italic>-hydroxy substituted ring B (Šmejkal et al. <xref ref-type="bibr" rid="CR205">2008a</xref>). For this reason, it is important to emphasize that the relative importance of the substitution of ring B can differ according to the cell line used. Modification of a prenyl or geranyl side-chain can not only change the direct cytotoxicity, but it may also affect the proliferation cells or trigger apoptosis (Kollár et al. <xref ref-type="bibr" rid="CR97">2011</xref>; Šmejkal et al. <xref ref-type="bibr" rid="CR203">2007a</xref>, <xref ref-type="bibr" rid="CR205">2008a</xref>, <xref ref-type="bibr" rid="CR207">2010</xref>; Šmejkal <xref ref-type="bibr" rid="CR202">2014</xref>).</p><p>Prenylated flavonoids <bold>55</bold>–<bold>59</bold>, modified with an unusual 3,4-dihydro-2<italic>H</italic>-pyran moiety, have been found to inhibit the severe acute respiratory syndrome corona virus PLpro enzyme more effectively than their parent compounds, the precursors from which were they derived (Cho et al. <xref ref-type="bibr" rid="CR32">2013</xref>).</p><p>The presence of a geranyl group at the C-6 position (<bold>21</bold>, <bold>22</bold>, <bold>24</bold>–<bold>26</bold>, <bold>30</bold>, <bold>31</bold>, <bold>33</bold>, and <bold>34</bold>) seems to be crucial for the hAChE and BChE inhibitory effects. The most effective inhibitor was <bold>22</bold>. All of the geranylated flavonoids, apart from <bold>26</bold>, inhibited hAChE dose-dependently. It appears that greater inhibition is observed when ring B of the flavanone bears free hydroxyl groups (Cho et al. <xref ref-type="bibr" rid="CR31">2012</xref>).</p><p>The crystal structure of the bacterial sialidase <italic>Cp</italic>-NanI catalytic domain in a complex with the geranylated flavonoid diplacone (<bold>22</bold>) provides structural insights into the binding mode of natural flavonoid-based inhibitors at atomic resolution. It shows how the geranyl and C-3′ hydroxyl groups of <bold>22</bold> contribute to the stability of the enzyme-inhibitor complex. Time-dependent competitive inhibition patterns have been observed. Structural comparison of the human sialidases Neu1–Neu4 with the <italic>Cp</italic>-NanI–diplacone (<bold>22</bold>) complex suggests that the interaction between human sialidases and <bold>22</bold> is likely to be unfavourable because of polar or ionic repulsion (Lee et al. <xref ref-type="bibr" rid="CR111">2014</xref>).</p><p>Six flavonoid glycosides have been extracted from the stem bark <bold>60</bold>–<bold>62</bold> (Si et al. <xref ref-type="bibr" rid="CR197">2009</xref>) and flowers <bold>63</bold>–<bold>66</bold> (Scogin <xref ref-type="bibr" rid="CR186">1980</xref>) of <italic>P. tomentosa</italic>. Apigenin-7-<italic>O</italic>-<italic>β</italic>-<sc>d</sc>-glucopyranoside (synonym: cosmosiin) (Kurkina et al. <xref ref-type="bibr" rid="CR105">2011</xref>) (<bold>60</bold>) shows anti-HIV activity in vitro on H9 cells (Tang et al. <xref ref-type="bibr" rid="CR216">1994</xref>) and enhances the secretion of adiponectin, the phosphorylation of the tyrosine residue of insulin receptor-β, and the translocation of GLUT5 (Rao et al. <xref ref-type="bibr" rid="CR170">2011</xref>). Compound <bold>60</bold> shows no significant hepatic Glc-6-phosphatase inhibitory activity in vitro (Kumar et al. <xref ref-type="bibr" rid="CR101">2010</xref>). Apigenin-7-<italic>O</italic>-<italic>β</italic>-<sc>d</sc>-glucuronopyranoside (<bold>61</bold>) was more potent than apigenin (<bold>2</bold>) and omeprazole in an assay analysing the inhibition of reflux esophagitis and gastritis promoted surgically and by application of indomethacine in rats (Min et al. <xref ref-type="bibr" rid="CR132">2005</xref>). No information about the biological activity of apigenin-7-<italic>O</italic>-[<italic>β</italic>-<sc>d</sc>-glucuronopyranosyl (1 → 2)-<italic>O</italic>-<italic>β</italic>-<sc>d</sc>-glucuronopyranoside] (<bold>62</bold>) has been found in the literature. Delphinidin-3-<italic>O</italic>-glucoside (synonym: myrtillin) (<bold>63</bold>) protects microglia from inflammation-induced stress signaling (Carey et al. <xref ref-type="bibr" rid="CR20">2013</xref>), is cytotoxic against the MCF-7 (breast) cancer cell line (Vareed et al. <xref ref-type="bibr" rid="CR224">2006</xref>), and has an the affinity for the estrogenic ERβ receptor (Hidalgo et al. <xref ref-type="bibr" rid="CR64">2012</xref>). Delphinidin-3,5-di-<italic>O</italic>-glucoside (<bold>64</bold>) and cyanidin-3,5-di-<italic>O</italic>-glucoside (<bold>65</bold>) are potent antioxidants (Lee et al. <xref ref-type="bibr" rid="CR110">2011</xref>; Tanaka et al. <xref ref-type="bibr" rid="CR215">2013</xref>). Compounds <bold>63</bold> and <bold>65</bold> are potent ACE inhibitors in vitro (Hidalgo et al. <xref ref-type="bibr" rid="CR64">2012</xref>; Persson et al. <xref ref-type="bibr" rid="CR162">2009</xref>).</p></sec><sec id="Sec4"><title><italic>P. tomentosa</italic> lignans and their biological activity</title><p>Only three lignans: (+)-paulownin (<bold>66</bold>), (+)-sesamin (<bold>67</bold>), (+)-piperitol (<bold>68</bold>) have been isolated from the wood of <italic>P. tomentosa</italic> (Ina et al. <xref ref-type="bibr" rid="CR76">1987</xref>; Takahashi and Nakagawa <xref ref-type="bibr" rid="CR213">1966</xref>; Zhu et al. <xref ref-type="bibr" rid="CR255">1986</xref>) (Fig. <xref rid="Fig3" ref-type="fig">3</xref>). Several reports have described their pharmacological effects (Zhang et al. <xref ref-type="bibr" rid="CR251">2014</xref>; Pan et al. <xref ref-type="bibr" rid="CR150">2009</xref>). Compound <bold>66</bold> is a promising antifungal agent that acts against the basidiomycetes <italic>Fomitopsis palustris</italic> and <italic>Trametes versicolor</italic> (Kawamura et al. <xref ref-type="bibr" rid="CR87">2004</xref>). Sesamin (<bold>67</bold>) has been previously isolated from the wood of <italic>P. tomentosa</italic>, and <italic>P. kawakamii</italic> and the hybrid of <italic>P. elongata</italic> × <italic>P. fortunei</italic> (Takahashi and Nakagawa <xref ref-type="bibr" rid="CR213">1966</xref>; Zhu et al. <xref ref-type="bibr" rid="CR255">1986</xref>). Compound <bold>67</bold> is the major lignan in sesame, and has various biological activities, such as antioxidant, angiogenic (Chung et al. <xref ref-type="bibr" rid="CR34">2010</xref>), antiphlogistic (Chatrattanakunchai et al. <xref ref-type="bibr" rid="CR23">2000</xref>), antihypertensive (Nakano et al. <xref ref-type="bibr" rid="CR139">2006</xref>), insecticidal (Nascimento et al. <xref ref-type="bibr" rid="CR140">2004</xref>), neuroprotective (Khan et al. <xref ref-type="bibr" rid="CR90">2010</xref>), and anticarcinogenic (Yasuda and Sakaki <xref ref-type="bibr" rid="CR239">2012</xref>). However, this compound showed no significant ability to reduce the formation of atherosclerotic lesions in the ApoE (−/−) gene-knockout mouse, whereas specific dietary polyphenols, especially quercetin and theaflavin were more active (Loke et al. <xref ref-type="bibr" rid="CR120">2010</xref>). It has been suggested that some of the biological effects attributed to sezamine (<bold>67</bold>) may, in fact, be caused by its metabolites and that <bold>67</bold> may be acting as a proactive substance in the body (Yasuda and Sakaki <xref ref-type="bibr" rid="CR239">2012</xref>). The metabolism of sesamim (<bold>67</bold>) by cytochrome P450 and UDP-glucuronosyltransferase has been found remarkably different in humans as compared to other animals. Further investigation into the safety of taking sesamin (<bold>67</bold>) with therapeutic drugs that are metabolised by CYP2C9 is also needed (Yasuda and Sakaki <xref ref-type="bibr" rid="CR239">2012</xref>).<fig id="Fig3"><label>Fig. 3</label><caption><p>Lignans</p></caption><graphic xlink:href="11101_2014_9376_Fig3_HTML" id="MO3"></graphic></fig></p></sec><sec id="Sec5"><title><italic>P. tomentosa</italic> phenolic glycosides and their biological activity</title><p>A total of thirteen phenylpropanoid glycosides (<bold>69</bold>–<bold>81</bold>) with multifarious bioactivities, natural compounds derived biosynthetically from the amino acid phenylalanine, have been isolated from different parts of the <italic>P. tomentosa</italic> plant (Table <xref rid="Tab4" ref-type="table">4</xref>) (Damtoft and Jensen <xref ref-type="bibr" rid="CR37">1993</xref>; Kang et al. <xref ref-type="bibr" rid="CR84">1994</xref>; Ota et al. <xref ref-type="bibr" rid="CR148">1993</xref>; Schilling et al. <xref ref-type="bibr" rid="CR183">1982</xref>; Si et al. <xref ref-type="bibr" rid="CR194">2008b</xref>, <xref ref-type="bibr" rid="CR196">d</xref>, Si et al. <xref ref-type="bibr" rid="CR199">2011b</xref>; Sticher and Lahloub <xref ref-type="bibr" rid="CR208">1982</xref>; Šmejkal et al. <xref ref-type="bibr" rid="CR204">2007b</xref>; Zhu et al. <xref ref-type="bibr" rid="CR255">1986</xref>). Phenylpropanoids are of great interest for fabricating effective tonic, anticancer, hepatoprotective, immunostimulating, antimicrobial, and anti-inflammatory phytopreparations (Kurkin <xref ref-type="bibr" rid="CR103">2003</xref>; Galvez et al. <xref ref-type="bibr" rid="CR52">2006</xref>; Panossian and Wagner <xref ref-type="bibr" rid="CR154">2005</xref>; Fu et al. <xref ref-type="bibr" rid="CR49">2008</xref>; Pan et al. <xref ref-type="bibr" rid="CR149">2003</xref>).</p></sec><sec id="Sec6"><title><italic>P. tomentosa</italic> quinones and their biological activity</title><p>A new furanoquinone, methyl-5-hydroxy-dinaphthol[1,2–2′,3′]furan-7,12-dione-6-carboxylate (MHDDC) (<bold>82</bold>) (Fig. <xref rid="Fig4" ref-type="fig">4</xref>) identified in <italic>P. tomentosa</italic> stem bark (MeOH extract) has been shown to possess antiviral activity against poliovirus types 1 and 3, using HeLa cells in vitro (Kang et al. <xref ref-type="bibr" rid="CR85">1999</xref>). Its cathepsin K and L inhibitory activities in vitro have recently been discovered. The 5-OH functional group may have a favourable effect on this reduction potential which prevents the degradation of bone the matrix carried out by osteoclasts (Park et al. <xref ref-type="bibr" rid="CR158">2009</xref>).<fig id="Fig4"><label>Fig. 4</label><caption><p>Quinones</p></caption><graphic xlink:href="11101_2014_9376_Fig4_HTML" id="MO4"></graphic></fig></p><p>The naphtoquinone plumbagin (<bold>83</bold>) has been detected in the leaves and fruit of <italic>P. tomentosa</italic> (Babula et al. <xref ref-type="bibr" rid="CR9">2006</xref>). It has been used in traditional systems of medicine since ancient times (Pile et al. <xref ref-type="bibr" rid="CR164">2013</xref>). It has exhibited promising antimalarial activity in vitro with IC<sub>50</sub> of 580 (270–640) nM and 370 (270–490) nM, respectively, against 3D7 chloroquine-sensitive <italic>P. falciparum</italic> and K1 chloroquine-resistant <italic>P. falciparum</italic> clones, using an assay based on SYBR Green I. Toxicity testing indicated relatively low toxicity at dose levels up to 100 mg/kg body weight (for a single oral dose) and 25 mg/kg (for daily dose given for consecutive 14 days) for acute and subacute toxicity, respectively. Based on the results of in vivo antimalarial testing, plumbagin administered at a the dose of 25 mg/kg of body weight for 4 consecutive days exhibited moderate to weak antimalarial activity with regard to its ability to reduce parasitaemia and prolong survival time (Sumsakul et al. <xref ref-type="bibr" rid="CR210">2014</xref>). Other published studies of plumbagin (<bold>83</bold>) described effects such as antifungal, antibacterial, cytotoxic (Krishnaswamy and Purushothaman <xref ref-type="bibr" rid="CR100">1980</xref>), anticoagulant (Santhakumari et al. <xref ref-type="bibr" rid="CR180">1978</xref>), anthelmintic (antischistosomal) (Zhang and Coultas <xref ref-type="bibr" rid="CR248">2013</xref>) and an anti-inflammatory effect on the amelioration of experimental ulcerative colitis in mice at a dose of 8–10 mg/kg (Pile et al. <xref ref-type="bibr" rid="CR164">2013</xref>).</p></sec><sec id="Sec7"><title><italic>P. tomentosa</italic> terpenoids and their biological activity</title><p>Six iridoids: 7-<italic>β</italic>-hydroxyharpagide (<bold>84</bold>), paulownioside (<bold>85</bold>), catalpol (<bold>86</bold>), aucubin (<bold>87</bold>), tomentoside (<bold>88</bold>) and 7-hydroxytomentoside (<bold>89</bold>) have been isolated from the leaves of <italic>P. tomentosa</italic> (<bold>84</bold>–<bold>87</bold>) (Adriani et al. <xref ref-type="bibr" rid="CR1">1981</xref>; Franzyk et al. <xref ref-type="bibr" rid="CR48">1999</xref>), the bark of the trunk and roots (<bold>86</bold>) (Plouvier <xref ref-type="bibr" rid="CR166">1971</xref>) and parts of the young plant (<bold>85</bold>, <bold>86</bold>, <bold>88</bold>, and <bold>89</bold>) (Damtoft and Jensen <xref ref-type="bibr" rid="CR37">1993</xref>) (Fig. <xref rid="Fig5" ref-type="fig">5</xref>). Compound <bold>86</bold> shows neuroprotective activity (Li et al. <xref ref-type="bibr" rid="CR112">2004</xref>), a cardioprotective effect against myocardial infarction—specifically reperfusion damage (Huang et al. <xref ref-type="bibr" rid="CR71">2013a</xref>, <xref ref-type="bibr" rid="CR72">b</xref>), and radioprotective effects (Chen et al. <xref ref-type="bibr" rid="CR29">2013</xref>). It also increases glucose utilization by increasing the secretion of β-endorphin from the adrenal gland (Shieh et al. <xref ref-type="bibr" rid="CR191">2011</xref>). Compounds <bold>86</bold> and <bold>87</bold> possess antispasmodic activity (Deurbina et al. <xref ref-type="bibr" rid="CR41">1994</xref>). Aucubin (<bold>87</bold>) had antioxidant and pancreas-protective effects on streptozotocin-induced diabetes in rats (Jin et al. <xref ref-type="bibr" rid="CR80">2008</xref>) and it may improve obesity-induced atherosclerosis by attenuating the TNF-α-induced inflammatory response (Park <xref ref-type="bibr" rid="CR157">2013</xref>). A weak antibacterial effect (against <italic>Streptococcus pneumoniae</italic> and MG-hemolytic streptococcus, MIC 28.946 mg/ml) (Zheng et al. <xref ref-type="bibr" rid="CR254">2012</xref>) and neuroprotective effects of <bold>87</bold> on diabetes and diabetic encephalopathy (Xue et al. <xref ref-type="bibr" rid="CR236">2012</xref>) have also been observed.<fig id="Fig5"><label>Fig. 5</label><caption><p>Terpenoids</p></caption><graphic xlink:href="11101_2014_9376_Fig5_HTML" id="MO5"></graphic></fig></p><p>The sesquiterpenic lacton isoatriplicolide tiglate (<bold>90</bold>) has been isolated from <italic>P. tomentosa</italic> flowers. It has neuroprotective effects against glutamate-induced neurotoxicity (Kim et al. <xref ref-type="bibr" rid="CR92">2010a</xref>, <xref ref-type="bibr" rid="CR93">2010b</xref>) and cytotoxic activity against several cancer cell lines: A549 lung carcinoma; SK-OV-3 adenocarcinoma; SK-Mel-2 malignant melanoma; XF498 central nervous system tumors; HCT15 colon adenocarcinoma, against which its effect is comparable to that of reference substance adriamycin (Moon and Zee <xref ref-type="bibr" rid="CR136">2001</xref>); human breast cancers MDA-MB-231, MCF7, HS578T, and T47D; and the HeLa, SiHa and C33A cervical cancer cell lines (Jung et al. <xref ref-type="bibr" rid="CR82">2012</xref>).</p><p>Seven phytosterols have been isolated from <italic>P. tomentosa</italic> leaves: ursolic acid (<bold>91</bold>) (Zhu et al. <xref ref-type="bibr" rid="CR255">1986</xref>; Zhang and Li <xref ref-type="bibr" rid="CR249">2011</xref>), 3-epiursolic acid (<bold>92</bold>), pomolic acid (<bold>93</bold>), corosolic acid (<bold>94</bold>), maslinic acid (<bold>95</bold>), <italic>β</italic>-sitosterol (<bold>96</bold>), and daucosterol (<bold>97</bold>) (Zhang and Li <xref ref-type="bibr" rid="CR249">2011</xref>). Most of these show various biological activities, e.g., <bold>91</bold> is a potentially useful for treating Alzheimer’s disease (because of its ability to block the interactions of the amyloid β-CD36) (Wilkinson et al. <xref ref-type="bibr" rid="CR230">2011</xref>). It can prevent the recruitment of the monocytes that accelerate atherosclerosis, a major complication of diabetes, in mice (Ullevig et al. <xref ref-type="bibr" rid="CR223">2011</xref>), and it also possesses antibacterial (Wong et al. <xref ref-type="bibr" rid="CR232">2012</xref>), anti-trypanosomal, and anti-leishmanial properties (Bero et al. <xref ref-type="bibr" rid="CR12">2011</xref>). Compound <bold>91</bold> has also shown cytotoxic effects against K562 and K562/ADR human chronic myelogenous leukaemia, HL60 and HL60/ADR human acute myelocytic leukemia cancer cells, and the human colon cancer cell lines SW480 and SW620 (Shan et al. <xref ref-type="bibr" rid="CR187">2011</xref>). Compounds <bold>93</bold>–<bold>96</bold> also show promising cytotoxic potential, e.g., <bold>93</bold> is effective against the human chronic myelogenous leukaemia cell line 562 and also against cells derived from chronic myeloid leukaemia patients (Vasconcelos et al. <xref ref-type="bibr" rid="CR225">2007</xref>). Compound <bold>94</bold> shows cytotoxic effects against osteosarcoma MG-63 cells (Cai et al. <xref ref-type="bibr" rid="CR18">2011</xref>) and immunosuppressive activity on myeloid-derived suppressor cells in the murine sarcoma model (Horland et al. <xref ref-type="bibr" rid="CR68">2013</xref>). Compound <bold>95</bold> is effective against HT29 human colon cancer cells (Reyes-Zurita et al. <xref ref-type="bibr" rid="CR172">2011</xref>) and <bold>96</bold> promotes apoptosis in various cancer cells (Hac-Wydro <xref ref-type="bibr" rid="CR58">2013</xref>). Anti-inflammatory activities have been revealed for compounds <bold>91</bold>, <bold>92</bold>, and <bold>96</bold> (Deepak and Handa <xref ref-type="bibr" rid="CR39">2000</xref>), and <bold>93</bold> (Schinella et al. <xref ref-type="bibr" rid="CR184">2008</xref>). An immunomodulatory effect of <bold>97</bold> in protecting mice against candidiasis disseminated by the CD4+ Th1 immune response has been seen (Lee et al. <xref ref-type="bibr" rid="CR107">2007</xref>). Other recently discovered pharmacological effects include antimalarial (<bold>95</bold>) (Moneriz et al. <xref ref-type="bibr" rid="CR135">2011</xref>), hypotensive and endothelium-dependent vasorelaxant effects (<bold>93</bold>) (Estrada et al. <xref ref-type="bibr" rid="CR46">2011</xref>). Compound <bold>95</bold> is potentially useful for treating cerebral ischemic injuries (Guan et al. <xref ref-type="bibr" rid="CR57">2011</xref>), and <bold>94</bold> has promising antidiabetic effects (Sivakumar et al. <xref ref-type="bibr" rid="CR201">2009</xref>).</p></sec><sec id="Sec8"><title><italic>P. tomentosa</italic> glycerides and their biological activity</title><p>Thirty acylglycerols (<bold>98</bold>–<bold>127</bold>) belonging to 1,3-di-<italic>O</italic>-acetyl-2-<italic>O</italic>-(acyl)-glycerols, 1-<italic>O</italic>-acetyl-2-<italic>O</italic>-(acyl)-<italic>sn</italic>-glycerols and 2-<italic>O</italic>-(acyl)-glycerols, including only five known compounds (<bold>99</bold>, <bold>106</bold>, <bold>108</bold>, <bold>114</bold>, and <bold>119</bold>), have been identified in the exudates secreted from the glandular trichomes on the leaves: 1,3-di-<italic>O</italic>-acetyl-2-<italic>O</italic>-[(3<italic>R</italic>,6<italic>S</italic>)-3-(acetyloxy)-6-hydroxyeicosanoyl]-glycerol (<bold>98</bold>), 1-<italic>O</italic>-acetyl-2-<italic>O</italic>-[(3<italic>R</italic>)-3-(acetyloxy)octa-decanoyl]-<italic>sn</italic>-glycerol (<bold>99</bold>), 1-<italic>O</italic>-acetyl-2-<italic>O</italic>-[(3<italic>R</italic>,7<italic>R</italic>)-3,7-<italic>bis</italic>(acetyloxy)octadecanoyl]-<italic>sn</italic>-glycerol (<bold>100</bold>), 1-<italic>O</italic>-acetyl-2-<italic>O</italic>-[(3<italic>R</italic>,6<italic>S</italic>)-3-(acetyloxy)-6-hydroxyoctadecanoyl]-<italic>sn</italic>-glycerol (<bold>101</bold>), 2-<italic>O</italic>-[(3<italic>R</italic>,7<italic>R</italic>)-3,7-dihydroxy-eicosanoyl]-glycerol (<bold>102</bold>), 2-<italic>O</italic>-[(3<italic>R</italic>,6<italic>S</italic>)-3,6-dihydroxy-eicosanoyl]-glycerol (<bold>103</bold>), 2-<italic>O</italic>-[(3<italic>R</italic>,8<italic>R</italic>)-3,8-dihydroxy-eicosanoyl]-glycerol (<bold>104</bold>), 2-<italic>O</italic>-[(3<italic>R</italic>,9<italic>R</italic>)-3,9-dihydroxy-eicosanoyl]-glycerol (<bold>105</bold>), 1-<italic>O</italic>-acetyl-2-<italic>O</italic>-[(3<italic>R</italic>)-3-(acetyloxy) eicosanoyl]-<italic>sn</italic>-glycerol (<bold>106</bold>), 1-<italic>O</italic>-acetyl-2-<italic>O</italic>-[(3<italic>R</italic>,6<italic>S</italic>)-3,6-<italic>bis</italic>(acetyloxy)eicosanoyl]-<italic>sn</italic>-glycerol (<bold>107</bold>), 1-<italic>O</italic>-acetyl-2-<italic>O</italic>-[(3<italic>R</italic>,7<italic>R</italic>)-3,7-<italic>bis</italic>(acetyloxy)eicosanoyl]-<italic>sn</italic>-glycerol (<bold>108</bold>), 1-<italic>O</italic>-acetyl-2-<italic>O</italic>-[(3<italic>R</italic>,8<italic>R</italic>)-3,8-<italic>bis</italic>(acetyloxy)eicosanoyl]-<italic>sn</italic>-glycerol (<bold>109</bold>), 1-<italic>O</italic>-acetyl-2-<italic>O</italic>-[(3<italic>R</italic>,9<italic>R</italic>)-3,9-<italic>bis</italic>(acetyloxy)eicosanoyl]-<italic>sn</italic>-glycerol (<bold>110</bold>), 1-<italic>O</italic>-acetyl-2-<italic>O</italic>-[(3<italic>R</italic>,6<italic>S</italic>)-3-(acetyloxy)-6-hydroxyeicosanoyl]-<italic>sn</italic>-glycerol (<bold>111</bold>), 1-<italic>O</italic>-acetyl-2-<italic>O</italic>-[(3<italic>R</italic>,8<italic>R</italic>)-3-(acetyloxy)-8-hydroxyeicosanoyl]-<italic>sn</italic>-glycerol (<bold>112</bold>), 1-<italic>O</italic>-acetyl-2-<italic>O</italic>-[(3<italic>R</italic>,9<italic>R</italic>)-3-(acetyloxy)-9-hydroxyeicosanoyl]-<italic>sn</italic>-glycerol (<bold>113</bold>), 2-<italic>O</italic>-[(3<italic>R</italic>)-3-(acetyloxy)octadecanoyl]-glycerol (<bold>114</bold>), 2-<italic>O</italic>-[(3<italic>R</italic>,6<italic>S</italic>)-3-(acetyloxy)-6-hydroxy-octadecanoyl]-glycerol) (<bold>115</bold>), 2-<italic>O</italic>-[(3<italic>R</italic>,7<italic>R</italic>)-3-(acetyloxy)-7-hydroxy-octadecanoyl]-glycerol (<bold>116</bold>), 2-<italic>O</italic>-[(3<italic>R</italic>,8<italic>R</italic>)-3-(acetyloxy)-8-hydroxy-octadecanoyl]-glycerol (<bold>117</bold>), 2-<italic>O</italic>-[(3<italic>R</italic>,9<italic>R</italic>)-3-(acetyloxy)-9-hydroxy-octadecanoyl]-glycerol (<bold>118</bold>), 2-<italic>O</italic>-[(3<italic>R</italic>,7<italic>R</italic>)-3,7-<italic>bis</italic>(acetyloxy) octadecanoyl]-glycerol (<bold>119</bold>), 2-<italic>O</italic>-[(3<italic>R</italic>,8<italic>R</italic>)-3,8-<italic>bis</italic>(acetyloxy)octadecanoyl]-glycerol (<bold>120</bold>), 2-<italic>O</italic>-[(3<italic>R</italic>)-3-(acetyloxy)eicosanoyl]-glycerol (<bold>121</bold>), 2-<italic>O</italic>-[(3<italic>R</italic>,6<italic>S</italic>)-3-(acetyloxy)-6-hydroxy-eicosanoyl]-glycerol (<bold>122</bold>), 2-<italic>O</italic>-[(3<italic>R</italic>,7<italic>R</italic>)-3-(acetyloxy)-7-hydroxy-eicosanoyl]-glycerol (<bold>123</bold>), 2-<italic>O</italic>-[(3<italic>R</italic>,8<italic>R</italic>)-3-(acetyloxy)-8-hydroxy-eicosanoyl]-glycerol (<bold>124</bold>), 2-<italic>O</italic>-[(3<italic>R</italic>,9<italic>R</italic>)-3-(acetyloxy)-9-hydroxy-eicosanoyl]-glycerol (<bold>125</bold>), 2-<italic>O</italic>-[(3<italic>R</italic>,8<italic>R</italic>)-3,8-<italic>bis</italic>(acetyloxy)eicosanoyl]-glycerol (<bold>126</bold>), 2-<italic>O</italic>-[(3<italic>R</italic>,9<italic>R</italic>)-3,9-<italic>bis</italic>(acetyloxy)eicosanoyl]-glycerol (<bold>127</bold>). The relatively most abundant constituents were <bold>111</bold> (20 % of the total glycerides), <bold>126</bold> (14 %), and <bold>120</bold> and <bold>127</bold> (12 %) (Asai et al. <xref ref-type="bibr" rid="CR8">2009</xref>). Another analysis of the secretions of the glandular hairs on the leaves of both bud flushes and adult trees as well as the flowers of adult trees showed that these secretions contain ten glycerides (<bold>106</bold>, <bold>108</bold>–<bold>110</bold>, <bold>118</bold>, <bold>122</bold>, <bold>124</bold>–<bold>127</bold>). These compounds showed sticky character, but they were not toxic to several insects. Therefore, the glandular hairs on the leaves and flowers may serve only to physically deter herbivores (Kobayashi et al. <xref ref-type="bibr" rid="CR95">2008</xref>) (Fig. <xref rid="Fig6" ref-type="fig">6</xref>).<fig id="Fig6"><label>Fig. 6</label><caption><p>Glycerides</p></caption><graphic xlink:href="11101_2014_9376_Fig6_HTML" id="MO6"></graphic></fig></p></sec><sec id="Sec9"><title>Miscellaneous <italic>P. tomentosa</italic> compounds and their biological activity</title><p>Six known phenolic acids, namely <italic>p</italic>-hydroxybenzoic acid (<bold>128</bold>), vanillic acid (<bold>129</bold>), gallic acid (<bold>130</bold>), cinnamic acid (<bold>131</bold>), <italic>p</italic>-coumaric acid (<bold>132</bold>), and caffeic acid (<bold>133</bold>) have been identified in the leaves of <italic>P. tomentosa</italic> (<bold>128</bold>–<bold>133</bold>), bark (<bold>130</bold> and <bold>131</bold>) and wood (<bold>133</bold>) (Ota et al. <xref ref-type="bibr" rid="CR148">1993</xref>; Si et al. <xref ref-type="bibr" rid="CR195">2008c</xref>, <xref ref-type="bibr" rid="CR199">2011b</xref>), and <italic>p</italic>-ethoxybenzaldehyde (<bold>134</bold>) is present in flowers (Yuan et al. <xref ref-type="bibr" rid="CR245">2009</xref>). The 5,7-dihydroxy-6-geranylchromone (<bold>135</bold>) isolated from fruits shows only moderate cytotoxic activity against a suspension culture of <italic>Nicotiana tabacum</italic> cv. Bright Yellow (BY-2), which confirms that ring B of the flavonoid skeleton is important for this activity (Šmejkal et al. <xref ref-type="bibr" rid="CR205">2008a</xref>). A large group of essential oil substances found in the flowers of <italic>P. tomentosa</italic> have also been identified (Oprea et al. <xref ref-type="bibr" rid="CR147">2004</xref>; Ibrahim et al. <xref ref-type="bibr" rid="CR74">2013</xref>) (Fig. <xref rid="Fig7" ref-type="fig">7</xref>).<fig id="Fig7"><label>Fig. 7</label><caption><p>Miscellaneous compounds</p></caption><graphic xlink:href="11101_2014_9376_Fig7_HTML" id="MO7"></graphic></fig></p></sec><sec id="Sec10" sec-type="conclusion"><title>Conclusions</title><p>Plants are still highly esteemed all over the world as rich sources of therapeutic agents. In this context, traditional Chinese herbal medicines, such as <italic>Paulownia</italic> continue to influence a modern healthcare. It has been estimated that approximately 420,000 plant species exist on Earth, but little is known about the phytochemical or therapeutic qualities of most of them. Thanks to the development of the spectral and other analytical methods used in modern phytochemistry, many of the principal physiologically active secondary metabolites have been identified and researched in detail. The accumulated knowledge of traditional medicine is therefore, playing an important role in enhancing the success of drug discovery in herbal medicine. Approximately 80 % of the currently known antimicrobial, cardiovascular, immunosuppressive, and anticancer drugs are of plant origin (Pan et al. <xref ref-type="bibr" rid="CR152">2013</xref>).</p><p>As mentioned in this review, <italic>P. tomentosa</italic> is a rich source of multifarious secondary metabolites, mainly prenylated flavonoids. As of today 135 compounds, including flavonoids, lignans, phenolic glycosides, quinones, terpenoids, glycerides, phenolic acids, and other miscellaneous compounds have been isolated from various extracts of this plant.</p><p>Of increasing interest are the isolation and identification of <italic>P. tomentosa</italic> prenylated flavonoids, as they have shown promising pharmacological effects. In the first experiments, their antioxidant, antibacterial, antiphlogistic, cytotoxic, and SARS-CoV PL activities have been discovered along with inhibitory effects on human acetylcholinesterase, butyrylcholinesterase, and bacterial neuraminidases. More than 40 compounds with modified prenyl or geranyl side-chains attached at C-6 of the flavonoid skeleton have been isolated from the flowers, fruit, and leaves of <italic>P. tomentosa</italic>. Only two of these compounds have shown the presence of a five-carbon side-chain; for the others a ten-carbon side-chain is typical. Further, only a few compounds have shown a geranyl moiety modified by hydroxylation at C-6″ or C-7″. Some compounds have a geranyl group modified by formating a heterocyclic moiety, which is also unusual. Most of them have never been isolated from any other plant species. However, further in vivo pharmacology studies are needed to precisely elucidate biological mechanism of action, efficacy, and toxicity of these promising therapeutic agents. Elucidation of the structure–activity relationships is also crucial for their further total syntheses and introduction into medical practice. 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