Chemical Constituents of Dichloromethane Extract of Cultivated Satureja khuzistanica
Identifieur interne : 000F01 ( Pmc/Corpus ); précédent : 000F00; suivant : 000F02Chemical Constituents of Dichloromethane Extract of Cultivated Satureja khuzistanica
Auteurs : Firouz Matloubi Moghaddam ; Mahdi Moridi Farimani ; Sabah Salahvarzi ; Gholamreza AminSource :
- Evidence-based Complementary and Alternative Medicine [ 1741-427X ] ; 2006.
Abstract
Four compounds β-sitosterol, β-sitosterol-3-
Url:
DOI: 10.1093/ecam/nel065
PubMed: 17342246
PubMed Central: 1810368
Links to Exploration step
PMC:1810368Le document en format XML
<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Chemical Constituents of Dichloromethane Extract of Cultivated <italic>Satureja khuzistanica</italic></title><author><name sortKey="Moghaddam, Firouz Matloubi" sort="Moghaddam, Firouz Matloubi" uniqKey="Moghaddam F" first="Firouz Matloubi" last="Moghaddam">Firouz Matloubi Moghaddam</name><affiliation><nlm:aff wicri:cut=" and" id="AFF1">Department of Chemistry, Sharif University of Technology</nlm:aff></affiliation></author><author><name sortKey="Farimani, Mahdi Moridi" sort="Farimani, Mahdi Moridi" uniqKey="Farimani M" first="Mahdi Moridi" last="Farimani">Mahdi Moridi Farimani</name><affiliation><nlm:aff wicri:cut=" and" id="AFF1">Department of Chemistry, Sharif University of Technology</nlm:aff></affiliation></author><author><name sortKey="Salahvarzi, Sabah" sort="Salahvarzi, Sabah" uniqKey="Salahvarzi S" first="Sabah" last="Salahvarzi">Sabah Salahvarzi</name><affiliation><nlm:aff wicri:cut=" and" id="AFF1">Department of Chemistry, Sharif University of Technology</nlm:aff></affiliation></author><author><name sortKey="Amin, Gholamreza" sort="Amin, Gholamreza" uniqKey="Amin G" first="Gholamreza" last="Amin">Gholamreza Amin</name><affiliation><nlm:aff id="AFF1">Department of Pharmacognosy, Faculty of Pharmacy, Tehran University of Medical Science Tehran, Iran</nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">17342246</idno><idno type="pmc">1810368</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1810368</idno><idno type="RBID">PMC:1810368</idno><idno type="doi">10.1093/ecam/nel065</idno><date when="2006">2006</date><idno type="wicri:Area/Pmc/Corpus">000F01</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Chemical Constituents of Dichloromethane Extract of Cultivated <italic>Satureja khuzistanica</italic></title><author><name sortKey="Moghaddam, Firouz Matloubi" sort="Moghaddam, Firouz Matloubi" uniqKey="Moghaddam F" first="Firouz Matloubi" last="Moghaddam">Firouz Matloubi Moghaddam</name><affiliation><nlm:aff wicri:cut=" and" id="AFF1">Department of Chemistry, Sharif University of Technology</nlm:aff></affiliation></author><author><name sortKey="Farimani, Mahdi Moridi" sort="Farimani, Mahdi Moridi" uniqKey="Farimani M" first="Mahdi Moridi" last="Farimani">Mahdi Moridi Farimani</name><affiliation><nlm:aff wicri:cut=" and" id="AFF1">Department of Chemistry, Sharif University of Technology</nlm:aff></affiliation></author><author><name sortKey="Salahvarzi, Sabah" sort="Salahvarzi, Sabah" uniqKey="Salahvarzi S" first="Sabah" last="Salahvarzi">Sabah Salahvarzi</name><affiliation><nlm:aff wicri:cut=" and" id="AFF1">Department of Chemistry, Sharif University of Technology</nlm:aff></affiliation></author><author><name sortKey="Amin, Gholamreza" sort="Amin, Gholamreza" uniqKey="Amin G" first="Gholamreza" last="Amin">Gholamreza Amin</name><affiliation><nlm:aff id="AFF1">Department of Pharmacognosy, Faculty of Pharmacy, Tehran University of Medical Science Tehran, Iran</nlm:aff></affiliation></author></analytic><series><title level="j">Evidence-based Complementary and Alternative Medicine</title><idno type="ISSN">1741-427X</idno><idno type="eISSN">1741-4288</idno><imprint><date when="2006">2006</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>Four compounds β-sitosterol, β-sitosterol-3-<italic>O</italic>-β-<sc>d</sc>-glucopyranoside, ursolic acid and 4′,5,6-trihydroxy-3′, 7-dimethoxyflavone were characterized from the dichloromethane extract of the aerial parts of <italic>Satureja khuzistanica</italic> (Lamiaceae), a native medicinal plant growing in Iran, on the basis of spectral analysis and comparing with the data in literature. The natural occurrence of these compounds can be conclusive for the chemotaxonomic characterization of the genus <italic>Satureja.</italic></p></div></front><back><div1 type="bibliography"><listBibl><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct></listBibl></div1></back></TEI><pmc article-type="research-article"><pmc-dir>properties open_access</pmc-dir>
<front><journal-meta><journal-id journal-id-type="nlm-ta">Evid Based Complement Alternat Med</journal-id><journal-id journal-id-type="publisher-id">eCAM</journal-id><journal-id journal-id-type="publisher-id">Evidence-based Complementary and Alternative Medicine</journal-id><journal-title>Evidence-based Complementary and Alternative Medicine</journal-title><issn pub-type="ppub">1741-427X</issn><issn pub-type="epub">1741-4288</issn><publisher><publisher-name>Oxford University Press</publisher-name></publisher></journal-meta><article-meta><article-id pub-id-type="pmid">17342246</article-id><article-id pub-id-type="pmc">1810368</article-id><article-id pub-id-type="doi">10.1093/ecam/nel065</article-id><article-categories><subj-group subj-group-type="heading"><subject>Original Articles - Basic Science</subject></subj-group></article-categories><title-group><article-title>Chemical Constituents of Dichloromethane Extract of Cultivated <italic>Satureja khuzistanica</italic></article-title></title-group><contrib-group><contrib contrib-type="author" corresp="yes"><name><surname>Moghaddam</surname><given-names>Firouz Matloubi</given-names></name><xref rid="AFF1" ref-type="aff"><sup>1</sup></xref></contrib><contrib contrib-type="author"><name><surname>Farimani</surname><given-names>Mahdi Moridi</given-names></name><xref rid="AFF1" ref-type="aff"><sup>1</sup></xref></contrib><contrib contrib-type="author"><name><surname>Salahvarzi</surname><given-names>Sabah</given-names></name><xref rid="AFF1" ref-type="aff"><sup>1</sup></xref></contrib><contrib contrib-type="author"><name><surname>Amin</surname><given-names>Gholamreza</given-names></name><xref rid="AFF1" ref-type="aff"><sup>2</sup></xref></contrib></contrib-group><aff id="AFF1"><sup>1</sup>Department of Chemistry, Sharif University of Technology and<sup>2</sup>Department of Pharmacognosy, Faculty of Pharmacy, Tehran University of Medical Science Tehran, Iran</aff><author-notes><corresp>For reprints and all correspondence: Professor Firouz Matloubi Moghaddam, Department of Chemistry, Sharif University of Technology, Azadi Avenue, Tehran 11365-9516, Iran. Tel: +98-21-66165309; Fax: +98-21-66012983; E-mail: <email>matloubi@sharif.edu</email></corresp></author-notes><pub-date pub-type="ppub"><month>3</month><year>2007</year></pub-date><pub-date pub-type="epub"><day>26</day><month>9</month><year>2006</year></pub-date><volume>4</volume><issue>1</issue><fpage>95</fpage><lpage>98</lpage><history><date date-type="received"><day>16</day><month>1</month><year>2006</year></date><date date-type="accepted"><day>22</day><month>8</month><year>2006</year></date></history><copyright-statement>© 2006 The Author(s).</copyright-statement><copyright-year>2006</copyright-year><license license-type="openaccess"><p>This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/2.0/uk/) which permits unrestricted non-commerical use, distribution, and reproduction in any medium, provided the original work is properly cited.</p></license><abstract><p>Four compounds β-sitosterol, β-sitosterol-3-<italic>O</italic>-β-<sc>d</sc>-glucopyranoside, ursolic acid and 4′,5,6-trihydroxy-3′, 7-dimethoxyflavone were characterized from the dichloromethane extract of the aerial parts of <italic>Satureja khuzistanica</italic> (Lamiaceae), a native medicinal plant growing in Iran, on the basis of spectral analysis and comparing with the data in literature. The natural occurrence of these compounds can be conclusive for the chemotaxonomic characterization of the genus <italic>Satureja.</italic></p></abstract><kwd-group><kwd>daucosterin</kwd><kwd>Lamiaceae</kwd><kwd><italic>Satureja khuzistanica</italic></kwd><kwd>sitosterol</kwd><kwd>4′,5,6-trihydroxy-3′, 7-dimethoxyflavone</kwd><kwd>ursolic acid</kwd></kwd-group></article-meta></front><body><sec sec-type="intro"><title>Introduction</title><p>Medicinal and aromatic plants have been used for many centuries and are still popular in today's alternative therapies. Herbal remedies and alternative medicines are used throughout the world and in the past herbs often represented the original sources of most drugs (<xref ref-type="bibr" rid="B1">1</xref>). <italic>Satureja khuzistanica</italic> Jamzad (Marzeh Khuzistani in Persian, family of Lamiaceae) is an endemic plant that is widely distributed in the southern parts of Iran (<xref ref-type="bibr" rid="B2">2</xref>). It is a subshrub, branched stem ∼30 cm high, densely leafly, broadly ovaiate-orbicular covered with white hairs. Base of the leaves is attenuate and petioliform.</p><p>This plant has been used as analgesic and antiseptic among the inhabitants of southern parts of Iran. Infusion of aerial parts of this plant is credited in folk medicine to relieve toothache. The composition of the essential oils of wild and cultivated <italic>S. khuzistanica</italic> has already been investigated (<xref ref-type="bibr" rid="B3">3</xref>). Antimicrobial activity, anti-inflammatory, antinociceptive effects and antioxidant, antidiabetic, antihyperlipidemic and reproduction stimulatory properties of this plant have been recently reported from Iran (<xref ref-type="bibr" rid="B4 B5 B6">4–6</xref>).</p><p>The chemical composition of the crude extract of this species has not yet been investigated. The current work examined the composition of dichloromethane extract of the aerial parts of cultivated <italic>S. khuzistanica</italic>.</p></sec><sec sec-type="methods"><title>Methods</title><sec><title>General</title><p>Melting points were determined with a Buchi B-540 melting point apparatus. <sup>1</sup>H, <sup>13</sup>C-NMR (DEPT) and 2D-NMR were recorded on Bruker (DRX-500 Avance) NMR spectrometer. Silica gel (kieselgel 60, 70–230 mesh, Merck) was used for column chromatography. Spots were detected on TLC under UV or by heating after spraying with 5% phosphomolybdic acid in C<sub>2</sub>H<sub>5</sub>OH.</p></sec><sec><title>Plant Material</title><p>Aerial parts of cultivated <italic>S. khuzistanica</italic> in flowering stage from open field were prepared by Khorraman Company in industrial village of Khoramabad, Lorestan Province, Iran, November 2005 (<xref ref-type="fig" rid="F1">Fig. 1</xref>). The plant was authenticated by herbal museum of the Faculty of Pharmacy, Tehran University of Medical Science, Tehran, Iran and a voucher specimen (No. 6650-THE) is deposited.
<chem-struct id="C1"><label>(1)</label><graphic xlink:href="nel065c1.jpg" mimetype="image" position="float"></graphic></chem-struct><chem-struct id="C2"><label>(2)</label><graphic xlink:href="nel065c2.jpg" mimetype="image" position="float"></graphic></chem-struct><chem-struct id="C3"><label>(3)</label><graphic xlink:href="nel065c3.jpg" mimetype="image" position="float"></graphic></chem-struct><chem-struct id="C4"><label>(4)</label><graphic xlink:href="nel065c4.jpg" mimetype="image" position="float"></graphic></chem-struct></p></sec><sec><title>Extraction and Isolation</title><p>The air-dried aerial parts of cultivated <italic>S. khuzistanica</italic> (1 kg) was crushed and extracted with CH<sub>2</sub>Cl<sub>2</sub> (3 × 3 liters) at room temperature for 6 days. The CH<sub>2</sub>Cl<sub>2</sub> extracts were combined and concentrated <italic>in vacuo</italic> to yield a gummy extract. This residue treated with MeOH to remove waxy compounds.</p><p>The MeOH soluble portion (33.2 g) was subjected to a silica gel column chromatography (70–230 mesh, 800 g) with a gradient of hexane–EtOAc and then EtOAc–MeOH as eluent. Eight fractions were collected according to TLC analysis. The fraction of hexane–EtOAc (75:25) was subjected to another column chromatography using hexane–EtOAc (10:1) as the eluent. After recrystallization from MeOH, we obtained 75 mg of compound (<xref ref-type="chem" rid="C1">1</xref>). The fraction of hexane–EtOAc (70:30) was rechromatographed over silica gel and eluted with hexane–EtOAc (9:1) to give 150 mg of compound (<xref ref-type="chem" rid="C2">2</xref>). The fraction of hexane–EtOAc (60:40) was separated on another column chromatography and eluted with hexane–EtOAc (9:1) to give 270 mg of compound (<xref ref-type="chem" rid="C3">3</xref>). From the fraction of EtOAc–MeOH (20:1), crude crystals were obtained, which gave after recrystallization from pyridine/MeOH 40 mg of pure compound (<xref ref-type="chem" rid="C4">4</xref>).</p></sec></sec><sec sec-type="results"><title>Results</title><sec><title>Isolation and Identification of Compounds</title><p>In this study, for the first time we investigated the chemical composition of cultivated <italic>S. khuzistanica</italic>, a plant that was used very extensively in folk medicine of southern parts of Iran.</p><p>Dichloromethane extract of aerial parts of this plant was fractionated under silica gel column chromatography and resulted in isolation of four compounds.</p><p>Compound (<xref ref-type="chem" rid="C1">1</xref>) was obtained as colorless needles with a melting point of 133–135°C. According to the <sup>1</sup>H, <sup>13</sup>C, 2D NMR (H,H-COSY, HMQC, HMBC) experiments and also MS spectra and by comparing these spectroscopic data with those reported in the literatures, this compound was assigned to be β-sitosterol (<xref ref-type="bibr" rid="B7 B8 B9">7–9</xref>).</p><p>The second compound was isolated as brown crystals with a melting point of 253–255°C. By comparing the spectral data of this compound with those reported in the literatures, it was identified as 4′,5,6-trihydroxy-3′,7-dimethoxyflavone (<xref ref-type="bibr" rid="B10">10</xref>,<xref ref-type="bibr" rid="B11">11</xref>).</p><p>Compound (<xref ref-type="chem" rid="C3">3</xref>) was obtained as a white powder with a melting point of 267–269°C. The <sup>1</sup>H NMR and <sup>13</sup>C NMR data of this compound were consistent with the reported data of ursolic acid (<xref ref-type="bibr" rid="B12 B13 B14">12–14</xref>).</p><p>The structure of compound (<xref ref-type="chem" rid="C4">4</xref>), isolated as colorless needles (mp: 275–277°C) was established as β-sitosterol-3-<italic>O</italic>-β-<sc>d</sc>-glucopyranoside (daucosterin) by comparison of its spectral data with literature values (<xref ref-type="bibr" rid="B15">15</xref>,<xref ref-type="bibr" rid="B16">16</xref>).</p><sec><title>β-Sitosterol (1)</title><p>Colorless needles, mp 133–135°C; <sup>1</sup>H NMR (500 MHz, CDCl<sub>3</sub>) δ 5.39 (1H, <italic>m</italic>, H-6), 3.56 (1H, <italic>m</italic>, H-3), 1.05 (3H, <italic>s</italic>, Me-19), 0.96 (3H, <italic>d</italic>, <italic>J</italic> = 6.5 Hz, Me-21), 0.89 (3H, <italic>t</italic>, <italic>J</italic> = 7.4 Hz, Me-29), 0.87 (3H, <italic>d</italic>, <italic>J</italic> = 6.7 Hz, Me-26), 0.85 (3H, <italic>d</italic>, <italic>J</italic> = 6.7 Hz, Me-27), 0.72 (3H, <italic>s</italic>, Me-18); <sup>13</sup>C NMR (125 MHz, CDCl<sub>3</sub>, based on DEPT, HMQC, HMBC experiments) see <xref ref-type="table" rid="T1">Table 1</xref>; EIMS <italic>m/z</italic> 414 [M]<sup>+</sup> (39), 396 (100), 381 (21), 329 (17), 303 (19), 273 (11), 255 (24), 213 (20), 161 (18), 145 (22), 107 (22), 95 (23), 55 (21).
</p></sec><sec><title>4′,5,6-Trihydroxy-3′,7-dimethoxyflavone (2)</title><p>Brown crystals, mp 253–255°C; <sup>1</sup>H NMR (500 MHz, DMSO-d<sub>6</sub>) δ 12.67 (1H, <italic>brs</italic>, OH-5), 7.60 (1H, <italic>dd</italic>, <italic>J</italic> = 7.6 Hz, 2.0 Hz, H-6′), 7.58 (1H, <italic>d</italic>, <italic>J</italic> = 2.0 Hz, H-2′), 6.95 (1H, <italic>d</italic>, <italic>J</italic> = 7.6 Hz, H-5′), 6.93 (1H, <italic>s</italic>, H-8), 6.91 (1H, <italic>s</italic>, H-3), 3.92 (3H, <italic>s</italic>, OMe), 3.90 (3H, <italic>s</italic>, OMe′); <sup>13</sup>C NMR (125 MHz, DMSO-d<sub>6</sub>, based on DEPT, HMQC, HMBC experiments) see <xref ref-type="table" rid="T1">Table 1</xref>; EIMS <italic>m/z</italic> 330 [M]<sup>+</sup> (100), 312 (29), 284 (34), 248 (7), 148 (7), 69 (8).</p></sec><sec><title>Ursolic acid (3)</title><p>White powder, mp 267–269°C; <sup>1</sup>H NMR (500 MHz, DMSO-d<sub>6</sub>) δ 5.13 (1H, <italic>m</italic>, H-12), 4.31 (1H, <italic>brs</italic>, D<sub>2</sub>O exchangeable, OH), 3.00 (1H, <italic>m</italic>, H-3), 2.10 (1H, <italic>d</italic>, <italic>J</italic> = 11.25 Hz, H-18), 1.04 (3H, <italic>s</italic>, Me-27), 0.92 (3H, <italic>d</italic>, <italic>J</italic> = 6.5 Hz, Me-30), 0.89 (3H, <italic>s</italic>, Me-24), 0.87 (3H, <italic>s</italic>, Me-25), 0.81 (3H, <italic>d</italic>, <italic>J</italic> = 6.25 Hz, Me-29), 0.75 (3H, <italic>s</italic>, Me-26), 0.68 (3H, <italic>s</italic>, Me-23); <sup>13</sup>C NMR (125 MHz, DMSO-d<sub>6</sub>, based on DEPT, HMQC, HMBC experiments) see <xref ref-type="table" rid="T1">Table 1</xref>; EIMS <italic>m/z</italic> 456 [M]<sup>+</sup> (5), 248 (100), 219 (6), 207 (23), 203 (33), 190 (11), 189 (13), 133 (23), 119 (10), 85 (10), 71 (14), 69 (10), 57 (19).</p></sec><sec><title>Daucosterin (4)</title><p>White powder, mp 275–277°C; <sup>1</sup>H NMR (500 MHz, C<sub>5</sub>D<sub>5</sub>N) δ 5.31 (1H, <italic>m</italic>, H-6), 5.02 (1H, <italic>d</italic>, <italic>J</italic> = 7.7 Hz, H-1′), 4.52 (1H, <italic>dd</italic>, <italic>J</italic> = 11.6 Hz, 2.1 Hz, H-6′β), 4.43 (1H, <italic>dd</italic>, <italic>J</italic> = 11.7 Hz, 5.2Hz, H-6′α), 4.23 (2H, <italic>m</italic>, H-3′, H-4′), 4.00 (1H, <italic>t</italic>, <italic>J</italic> = 7.9 Hz, H-2′), 3.92 (1H, <italic>m</italic>, H-5′), 3.87 (1H, <italic>m</italic>, H-3), 0.91 (3H, <italic>d</italic>, <italic>J</italic> = 6.4 Hz, Me-21), 0.86 (3H, <italic>s</italic>, Me-19),0.82 (3H, <italic>t</italic>, <italic>J</italic> = 7.3 Hz, Me-29), 0.80 (3H, <italic>d</italic>, <italic>J</italic> = 6.8 Hz, Me-26), 0.78 (3H, <italic>d</italic>, <italic>J</italic> = 6.9 Hz, Me-27), 0.58 (3H, <italic>s</italic>, Me-18); <sup>13</sup>C NMR (125 MHz, DMSO-d<sub>6</sub>, based on DEPT, HMQC, HMBC experiments), see <xref ref-type="table" rid="T1">Table 1</xref>.</p></sec></sec></sec><sec sec-type="discussion"><title>Discussion</title><p>Herbal remedies used in the traditional folk medicine provide an interesting and still largely unexplored source for the creation and development of potentially new drugs. But it is necessary to reveal the active principles by isolation and characterization of their constituents and to validate their possible toxicity (<xref ref-type="bibr" rid="B17">17</xref>,<xref ref-type="bibr" rid="B18">18</xref>). The chemistry of the genus <italic>Satureja</italic> has not been thoroughly analyzed. Previous studies on the chemical composition of this genus indicate the occurrence of flavonoids in <italic>Satureja thymbra</italic> and <italic>Satureja spinosa</italic> (<xref ref-type="bibr" rid="B11">11</xref>). Iridoid glucosides have also been reported from <italic>Satureja vulgaris</italic> (<xref ref-type="bibr" rid="B19">19</xref>). Mono and sesquiterpenoids and also diterpenoids belonging to labdane, isopimarene and rearranged isopimarene groups were detected in <italic>Satureja gilliesii</italic> (<xref ref-type="bibr" rid="B20">20</xref>,<xref ref-type="bibr" rid="B21">21</xref>). Oleanolic acid, ursolic acid, β-sitosterol-β-<sc>d</sc>-glucoside and flavanone glycosides have been isolated from <italic>Satureja acinos</italic>, <italic>Satureja montana</italic> and <italic>Satureja obovata</italic> (<xref ref-type="bibr" rid="B22">22</xref>). Two 3,4-secotriterpenoids along with a mixture of three sterols have been reported from <italic>Satureja calamintha</italic> and <italic>Satureja graeca</italic> (<xref ref-type="bibr" rid="B23">23</xref>,<xref ref-type="bibr" rid="B24">24</xref>).</p><p>From four compounds isolated from <italic>S. khuzistanica</italic>, β-sitosterol has been previously reported from <italic>S. calamintha</italic> and <italic>S. graeca</italic> (<xref ref-type="bibr" rid="B23">23</xref>). 4′,5,6-Trihydroxy-3′,7-dimethoxyflavone has been isolated from <italic>S. thymbra</italic> and <italic>S. spinosa</italic> (<xref ref-type="bibr" rid="B11">11</xref>). Also ursolic acid has been reported from <italic>S. acinos</italic> (<xref ref-type="bibr" rid="B22">22</xref>) and <italic>S. graeca</italic> (<xref ref-type="bibr" rid="B23">23</xref>). And β-sitosterol-β-<sc>d</sc>-glucoside has been isolated from <italic>S. acinos</italic>, <italic>S. montana</italic> and <italic>S. obovata</italic> (<xref ref-type="bibr" rid="B22">22</xref>).</p><p>The occurrence of these compounds in <italic>S. khuzistanica</italic> confirms the presence of flavones, triterpenoids and steroids in the genus <italic>Satureja</italic> (Lamiaceae). The natural occurrence of these compounds can be conclusive for the chemotaxonomic characterization of this genus.</p><p>With respect to numerous uses of this plant in folk medicine and great experiments that have been accomplished to investigate its biological properties, we decided to study the chemical composition of the crude extract. This process resulted in isolation of four known compounds. Nevertheless, we cannot attribute biological properties of <italic>S. khuzistanica</italic> to one of these compounds. Ursolic acid has been long recognized to have anti-inflammatory, antihyperlipidemic properties in laboratory animals. Recently, it has also been noted for its antitumor promotion effects (<xref ref-type="bibr" rid="B25">25</xref>). With regard to excessive amount of ursolic acid in <italic>S. khuzistanica</italic>, therapeutic effects of the plant may be related to the presence of ursolic acid. This compound has also been found plentifully in other species of Lamiaceae family and exact assessment of its biological effects in these species has not been reported, therefore, we believe that the biological effects of <italic>S. khuzistanica</italic> are due to all existing compounds on this plant.</p></sec></body><back><ack><p>The authors would like to thank Prof. Dr P. Ruedi, University of Zurich, for the MS spectra and also Dr A.N. Salehinia, Khorraman Co., for providing cultivated plants.</p></ack><ref-list><title>References</title><ref id="B1"><label>1</label><citation citation-type="journal"><person-group person-group-type="author"><name><surname>Saad</surname><given-names>B</given-names></name><name><surname>Azaizeh</surname><given-names>H</given-names></name><name><surname>Said</surname><given-names>O</given-names></name></person-group><article-title>Tradition and perspectives of Arab herbal medicine: a review</article-title><source>Evid Based Complement Alternat Med</source><year>2005</year><volume>2</volume><fpage>475</fpage><lpage>9</lpage><pub-id pub-id-type="pmid">16322804</pub-id></citation></ref><ref id="B2"><label>2</label><citation citation-type="journal"><person-group person-group-type="author"><name><surname>Jamzad</surname><given-names>Z</given-names></name></person-group><article-title>A new species of the genus <italic>Satureja</italic> (Labiatae) from Iran</article-title><source>Iran J Bot</source><year>1994</year><volume>6</volume><fpage>215</fpage><lpage>8</lpage></citation></ref><ref id="B3"><label>3</label><citation citation-type="journal"><person-group person-group-type="author"><name><surname>Farsam</surname><given-names>H</given-names></name><name><surname>Amanlou</surname><given-names>M</given-names></name><name><surname>Radpour</surname><given-names>MR</given-names></name><name><surname>Salehinia</surname><given-names>AN</given-names></name><name><surname>Shafiee</surname><given-names>A</given-names></name></person-group><article-title>Composition of the essential oils of wild and cultivated <italic>Satureuja khuzistanica</italic> Jamzad from Iran</article-title><source>Flavour Fragr J</source><year>2004</year><volume>19</volume><fpage>308</fpage><lpage>10</lpage></citation></ref><ref id="B4"><label>4</label><citation citation-type="journal"><person-group person-group-type="author"><name><surname>Amanlou</surname><given-names>M</given-names></name><name><surname>Fazeli</surname><given-names>MR</given-names></name><name><surname>Arvin</surname><given-names>A</given-names></name><name><surname>Amin</surname><given-names>HG</given-names></name><name><surname>Farsam</surname><given-names>H</given-names></name></person-group><article-title>Antimicrobial activity of crude methanolic extract of <italic>Satureja khuzistanica</italic></article-title><source>Fitoterapia</source><year>2004</year><volume>75</volume><fpage>768</fpage><lpage>70</lpage><pub-id pub-id-type="pmid">15567261</pub-id></citation></ref><ref id="B5"><label>5</label><citation citation-type="journal"><person-group person-group-type="author"><name><surname>Amanlou</surname><given-names>M</given-names></name><name><surname>Dadkhah</surname><given-names>F</given-names></name><name><surname>Salehinia</surname><given-names>AN</given-names></name><name><surname>Farsam</surname><given-names>H</given-names></name><name><surname>Dehpour</surname><given-names>AR</given-names></name></person-group><article-title>An anti-inflammatory and anti-nociceptive effect of hydroalcoholic extract of <italic>Satureja khuzistanica</italic> Jamzad extract</article-title><source>J Pharm Pharmceut Sci</source><year>2005</year><volume>8</volume><fpage>102</fpage><lpage>6</lpage></citation></ref><ref id="B6"><label>6</label><citation citation-type="journal"><person-group person-group-type="author"><name><surname>Abdollahi</surname><given-names>M</given-names></name><name><surname>Salehnia</surname><given-names>A</given-names></name><name><surname>Mortazavi</surname><given-names>SH</given-names></name><name><surname>Ebrahimi</surname><given-names>M</given-names></name><name><surname>Shafiee</surname><given-names>A</given-names></name></person-group><article-title>Antioxidant, antidiabetic, antihyperlipidemic, reproduction stimulatory properties and safety of essential oil of <italic>Satureja khuzistanica</italic> in rat <italic>in vivo</italic>: an oxicopharmacological study</article-title><source>Med Sci Monit</source><year>2003</year><volume>9</volume><fpage>BR331</fpage><lpage>5</lpage><pub-id pub-id-type="pmid">12960922</pub-id></citation></ref><ref id="B7"><label>7</label><citation citation-type="journal"><person-group person-group-type="author"><name><surname>Manoharan</surname><given-names>KP</given-names></name><name><surname>Huat Benny</surname><given-names>TK</given-names></name><name><surname>Yang</surname><given-names>D</given-names></name></person-group><article-title>Cycloartane type triterpenoids from the rhizomes of <italic>Polygonum bistorta</italic></article-title><source>Phytochemistry</source><year>2005</year><volume>66</volume><fpage>1168</fpage><lpage>73</lpage><pub-id pub-id-type="pmid">15922377</pub-id></citation></ref><ref id="B8"><label>8</label><citation citation-type="journal"><person-group person-group-type="author"><name><surname>Nes</surname><given-names>WD</given-names></name><name><surname>Nortom</surname><given-names>RA</given-names></name><name><surname>Benson</surname><given-names>M</given-names></name></person-group><article-title>Carbon-13 NMR studies on sitosterol biosynthesized from [<sup>13</sup>C] mevalonates</article-title><source>Phytochemistry</source><year>1992</year><volume>66</volume><fpage>805</fpage><lpage>11</lpage></citation></ref><ref id="B9"><label>9</label><citation citation-type="journal"><person-group person-group-type="author"><name><surname>Greca</surname><given-names>MD</given-names></name><name><surname>Monaco</surname><given-names>M</given-names></name><name><surname>Previtra</surname><given-names>L</given-names></name></person-group><article-title>Stigmasterols from <italic>Typha latifolia</italic></article-title><source>J Nat Prod</source><year>1990</year><volume>53</volume><fpage>1430</fpage><lpage>5</lpage></citation></ref><ref id="B10"><label>10</label><citation citation-type="journal"><person-group person-group-type="author"><name><surname>Miski</surname><given-names>M</given-names></name><name><surname>Ulubelen</surname><given-names>A</given-names></name><name><surname>Mabry</surname><given-names>TJ</given-names></name></person-group><article-title>6-Hydroxyflavones from <italic>Thymbra spicata</italic></article-title><source>Phytochemistry</source><year>1983</year><volume>22</volume><fpage>2093</fpage><lpage>4</lpage></citation></ref><ref id="B11"><label>11</label><citation citation-type="journal"><person-group person-group-type="author"><name><surname>Skoula</surname><given-names>M</given-names></name><name><surname>Grayer</surname><given-names>RJ</given-names></name><name><surname>Kite</surname><given-names>GC</given-names></name></person-group><article-title>Surface flavonoids in <italic>Satureja thymbra</italic> and <italic>Satureja spinosa</italic></article-title><source>Biochem Syst Ecol</source><year>2005</year><volume>33</volume><fpage>541</fpage><lpage>4</lpage></citation></ref><ref id="B12"><label>12</label><citation citation-type="journal"><person-group person-group-type="author"><name><surname>Chiang</surname><given-names>YM</given-names></name><name><surname>Chang</surname><given-names>JY</given-names></name><name><surname>Kuo</surname><given-names>CC</given-names></name><name><surname>Chang</surname><given-names>CY</given-names></name><name><surname>Kuo</surname><given-names>YH</given-names></name></person-group><article-title>Cytotoxic triterpenes from the aerial roots of <italic>Ficus microcarpa</italic></article-title><source>Phytochemistry</source><year>2005</year><volume>66</volume><fpage>495</fpage><lpage>501</lpage><pub-id pub-id-type="pmid">15694457</pub-id></citation></ref><ref id="B13"><label>13</label><citation citation-type="journal"><person-group person-group-type="author"><name><surname>Kriwacki</surname><given-names>RW</given-names></name><name><surname>Pitner</surname><given-names>TP</given-names></name></person-group><article-title>Current aspects of practical two dimentional (2D) nuclear magnetic resonance (NMR) spectroscopy, application to structure elucidation</article-title><source>Pharm Res</source><year>1989</year><volume>6</volume><fpage>531</fpage><lpage>700</lpage><pub-id pub-id-type="pmid">2678077</pub-id></citation></ref><ref id="B14"><label>14</label><citation citation-type="journal"><person-group person-group-type="author"><name><surname>Romeo</surname><given-names>G</given-names></name><name><surname>Giannetto</surname><given-names>P</given-names></name><name><surname>Aversa</surname><given-names>MC</given-names></name></person-group><article-title>Constituents of <italic>Satureia calamintha</italic>, application of Eu(fod)2 to the assignments of methyl resonances of triterpenes related to 12-ursene</article-title><source>Org Magn Reson</source><year>1977</year><volume>9</volume><fpage>29</fpage><lpage>34</lpage></citation></ref><ref id="B15"><label>15</label><citation citation-type="journal"><person-group person-group-type="author"><name><surname>Schwarzmaier</surname><given-names>U</given-names></name></person-group><article-title>Prunasin, daucosterin and sitosterol from the bitter seeds of <italic>prunus amygdalus</italic></article-title><source>Phytochemistry</source><year>1972</year><volume>11</volume><fpage>2358</fpage></citation></ref><ref id="B16"><label>16</label><citation citation-type="journal"><person-group person-group-type="author"><name><surname>Swift</surname><given-names>LJ</given-names></name></person-group><article-title>Isolation of β-sitostryl-<sc>d</sc>-glucoside from the juice of flurida <italic>Valencia oranges</italic> (<italic>Citrus sinensis</italic> L.)</article-title><source>J Am Chem Soc</source><year>1952</year><volume>74</volume><fpage>1099</fpage><lpage>100</lpage></citation></ref><ref id="B17"><label>17</label><citation citation-type="journal"><person-group person-group-type="author"><name><surname>Lindequist</surname><given-names>U</given-names></name><name><surname>Niedermeyer</surname><given-names>THJ</given-names></name><name><surname>Jülich</surname><given-names>WD</given-names></name></person-group><article-title>The pharmacological potential of mushrooms</article-title><source>Evid Based Complement Alternat Med</source><year>2005</year><volume>2</volume><fpage>285</fpage><lpage>99</lpage><pub-id pub-id-type="pmid">16136207</pub-id></citation></ref><ref id="B18"><label>18</label><citation citation-type="journal"><person-group person-group-type="author"><name><surname>Al-Fatimi</surname><given-names>MAA</given-names></name><name><surname>Jülich</surname><given-names>WD</given-names></name><name><surname>Jansen</surname><given-names>R</given-names></name><name><surname>Lindequist</surname><given-names>U</given-names></name></person-group><article-title>Bioactive components of the traditionally used mushroom <italic>Podaxis pistillaris</italic></article-title><source>Evid Based Complement Alternat Med</source><year>2006</year><volume>3</volume><fpage>87</fpage><lpage>92</lpage><pub-id pub-id-type="pmid">16550228</pub-id></citation></ref><ref id="B19"><label>19</label><citation citation-type="journal"><person-group person-group-type="author"><name><surname>Bianco</surname><given-names>A</given-names></name><name><surname>Lamesi</surname><given-names>S</given-names></name><name><surname>Passacantilli</surname><given-names>P</given-names></name></person-group><article-title>Iridoid glucosides from <italic>Satureja vulgaris</italic></article-title><source>Phytochemistry</source><year>1984</year><volume>23</volume><fpage>121</fpage><lpage>3</lpage></citation></ref><ref id="B20"><label>20</label><citation citation-type="journal"><person-group person-group-type="author"><name><surname>Labbe</surname><given-names>C</given-names></name><name><surname>Castillo</surname><given-names>M</given-names></name><name><surname>Connolly</surname><given-names>JD</given-names></name></person-group><article-title>Mono and sesquiterpenoids from <italic>Satureja gilliesii</italic></article-title><source>Phytochemistry</source><year>1993</year><volume>2</volume><fpage>441</fpage><lpage>4</lpage></citation></ref><ref id="B21"><label>21</label><citation citation-type="journal"><person-group person-group-type="author"><name><surname>Labbe</surname><given-names>C</given-names></name><name><surname>Castillo</surname><given-names>M</given-names></name><name><surname>Fainia</surname><given-names>F</given-names></name><name><surname>Coll</surname><given-names>J</given-names></name><name><surname>Connolly</surname><given-names>JD</given-names></name></person-group><article-title>Rearranged isopimarenes and other diterpenoids from <italic>Satureja gilliesii</italic></article-title><source>Phytochemistry</source><year>1994</year><volume>36</volume><fpage>735</fpage><lpage>8</lpage></citation></ref><ref id="B22"><label>22</label><citation citation-type="journal"><person-group person-group-type="author"><name><surname>Escudero</surname><given-names>J</given-names></name><name><surname>Lopez</surname><given-names>C</given-names></name><name><surname>Rabanal</surname><given-names>RM</given-names></name><name><surname>Valverde</surname><given-names>S</given-names></name></person-group><article-title>Secondary metabolites from <italic>Satureja</italic> species. New triterpenoid from <italic>Satureja acinos</italic></article-title><source>J Nat Prod</source><year>1985</year><volume>48</volume><fpage>128</fpage><lpage>31</lpage></citation></ref><ref id="B23"><label>23</label><citation citation-type="journal"><person-group person-group-type="author"><name><surname>Giannetto</surname><given-names>P</given-names></name><name><surname>Romeo</surname><given-names>G</given-names></name><name><surname>Aversa</surname><given-names>MC</given-names></name></person-group><article-title>Calaminthadiol, a new 3,4-secotriterpenoid from <italic>Satureia calamintha</italic> and <italic>Satureia graeca</italic></article-title><source>Phytochemistry</source><year>1979</year><volume>18</volume><fpage>1203</fpage><lpage>5</lpage></citation></ref><ref id="B24"><label>24</label><citation citation-type="journal"><person-group person-group-type="author"><name><surname>Romeo</surname><given-names>G</given-names></name><name><surname>Giannetto</surname><given-names>P</given-names></name><name><surname>Aversa</surname><given-names>MC</given-names></name></person-group><article-title>A new 3,4-secopentacyclic triterpenoid from the genus <italic>satureia</italic></article-title><source>Phytochemistry</source><year>1980</year><volume>19</volume><fpage>437</fpage><lpage>9</lpage></citation></ref><ref id="B25"><label>25</label><citation citation-type="journal"><person-group person-group-type="author"><name><surname>Liu</surname><given-names>J</given-names></name></person-group><article-title>Pharmacology of oleanolic acid and ursolic acid</article-title><source>J Ethnopharmacol</source><year>1995</year><volume>49</volume><fpage>57</fpage><lpage>68</lpage><pub-id pub-id-type="pmid">8847885</pub-id></citation></ref></ref-list><sec sec-type="display-objects"><title>Figures and Tables</title><fig id="F1" position="float"><label>Figure 1.</label><caption><p><italic>Satureja khuzistanica</italic> Jamzad.</p></caption><graphic xlink:href="nel065f1"></graphic></fig><table-wrap id="T1" position="float"><label>Table 1.</label><caption><p><sup>13</sup>C-NMR spectroscopic data for compounds <xref ref-type="chem" rid="C1 C2 C3 C4">1–4</xref></p></caption><table frame="hsides" rules="groups"><thead align="left"><tr><th rowspan="1" colspan="1"></th><th rowspan="1" colspan="1">1</th><th rowspan="1" colspan="1">2</th><th rowspan="1" colspan="1">3</th><th rowspan="1" colspan="1">4</th></tr></thead><tbody align="left"><tr><td rowspan="1" colspan="1">1</td><td rowspan="1" colspan="1">37.7<italic>t</italic></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">39.2<italic>t</italic></td><td rowspan="1" colspan="1">38.8<italic>t</italic></td></tr><tr><td rowspan="1" colspan="1">2</td><td rowspan="1" colspan="1">32.3<italic>t</italic></td><td rowspan="1" colspan="1">164.6<italic>s</italic></td><td rowspan="1" colspan="1">27.8<italic>t</italic></td><td rowspan="1" colspan="1">33.5<italic>t</italic></td></tr><tr><td rowspan="1" colspan="1">3</td><td rowspan="1" colspan="1">72.2<italic>d</italic></td><td rowspan="1" colspan="1">103.8<italic>d</italic></td><td rowspan="1" colspan="1">77.7<italic>d</italic></td><td rowspan="1" colspan="1">79.8<italic>d</italic></td></tr><tr><td rowspan="1" colspan="1">4</td><td rowspan="1" colspan="1">42.8<italic>t</italic></td><td rowspan="1" colspan="1">183.1<italic>s</italic></td><td rowspan="1" colspan="1">39.2<italic>s</italic></td><td rowspan="1" colspan="1">41.3<italic>t</italic></td></tr><tr><td rowspan="1" colspan="1">5</td><td rowspan="1" colspan="1">141.2<italic>s</italic></td><td rowspan="1" colspan="1">147.1<italic>s</italic></td><td rowspan="1" colspan="1">55.6<italic>d</italic></td><td rowspan="1" colspan="1">142.3<italic>s</italic></td></tr><tr><td rowspan="1" colspan="1">6</td><td rowspan="1" colspan="1">122.1<italic>d</italic></td><td rowspan="1" colspan="1">130.8<italic>s</italic></td><td rowspan="1" colspan="1">18.9<italic>t</italic></td><td rowspan="1" colspan="1">123.2<italic>d</italic></td></tr><tr><td rowspan="1" colspan="1">7</td><td rowspan="1" colspan="1">32.1<italic>t</italic></td><td rowspan="1" colspan="1">155.2<italic>s</italic></td><td rowspan="1" colspan="1">33.6<italic>t</italic></td><td rowspan="1" colspan="1">31.6<italic>t</italic></td></tr><tr><td rowspan="1" colspan="1">8</td><td rowspan="1" colspan="1">32.3<italic>d</italic></td><td rowspan="1" colspan="1">92.0<italic>d</italic></td><td rowspan="1" colspan="1">40.0<italic>s</italic></td><td rowspan="1" colspan="1">33.4<italic>d</italic></td></tr><tr><td rowspan="1" colspan="1">9</td><td rowspan="1" colspan="1">50.6<italic>d</italic></td><td rowspan="1" colspan="1">150.5<italic>s</italic></td><td rowspan="1" colspan="1">47.9<italic>d</italic></td><td rowspan="1" colspan="1">51.7<italic>d</italic></td></tr><tr><td rowspan="1" colspan="1">10</td><td rowspan="1" colspan="1">36.9<italic>s</italic></td><td rowspan="1" colspan="1">105.9<italic>s</italic></td><td rowspan="1" colspan="1">37.4<italic>s</italic></td><td rowspan="1" colspan="1">38.2<italic>s</italic></td></tr><tr><td rowspan="1" colspan="1">11</td><td rowspan="1" colspan="1">21.5<italic>t</italic></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">23.7<italic>t</italic></td><td rowspan="1" colspan="1">22.7<italic>t</italic></td></tr><tr><td rowspan="1" colspan="1">12</td><td rowspan="1" colspan="1">40.2<italic>t</italic></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">125.4<italic>d</italic></td><td rowspan="1" colspan="1">40.7<italic>t</italic></td></tr><tr><td rowspan="1" colspan="1">13</td><td rowspan="1" colspan="1">42.8<italic>s</italic></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">139.0<italic>s</italic></td><td rowspan="1" colspan="1">43.8<italic>s</italic></td></tr><tr><td rowspan="1" colspan="1">14</td><td rowspan="1" colspan="1">57.2<italic>d</italic></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">42.5<italic>s</italic></td><td rowspan="1" colspan="1">58.1<italic>d</italic></td></tr><tr><td rowspan="1" colspan="1">15</td><td rowspan="1" colspan="1">24.7<italic>t</italic></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">28.4<italic>t</italic></td><td rowspan="1" colspan="1">25.8<italic>t</italic></td></tr><tr><td rowspan="1" colspan="1">16</td><td rowspan="1" colspan="1">28.7<italic>t</italic></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">24.7<italic>t</italic></td><td rowspan="1" colspan="1">29.9<italic>t</italic></td></tr><tr><td rowspan="1" colspan="1">17</td><td rowspan="1" colspan="1">56.5<italic>d</italic></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">47.7<italic>s</italic></td><td rowspan="1" colspan="1">57.7<italic>d</italic></td></tr><tr><td rowspan="1" colspan="1">18</td><td rowspan="1" colspan="1">12.4<italic>q</italic></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">53.2<italic>d</italic></td><td rowspan="1" colspan="1">13.5<italic>q</italic></td></tr><tr><td rowspan="1" colspan="1">19</td><td rowspan="1" colspan="1">19.8<italic>q</italic></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">39.4<italic>d</italic></td><td rowspan="1" colspan="1">20.7<italic>q</italic></td></tr><tr><td rowspan="1" colspan="1">20</td><td rowspan="1" colspan="1">36.6<italic>d</italic></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">39.3<italic>d</italic></td><td rowspan="1" colspan="1">37.7<italic>d</italic></td></tr><tr><td rowspan="1" colspan="1">21</td><td rowspan="1" colspan="1">19.2<italic>q</italic></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">31.1<italic>t</italic></td><td rowspan="1" colspan="1">20.3<italic>q</italic></td></tr><tr><td rowspan="1" colspan="1">22</td><td rowspan="1" colspan="1">34.4<italic>t</italic></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">37.2<italic>t</italic></td><td rowspan="1" colspan="1">35.5<italic>t</italic></td></tr><tr><td rowspan="1" colspan="1">23</td><td rowspan="1" colspan="1">26.5<italic>t</italic></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">29.1<italic>q</italic></td><td rowspan="1" colspan="1">27.7<italic>t</italic></td></tr><tr><td rowspan="1" colspan="1">24</td><td rowspan="1" colspan="1">46.2<italic>d</italic></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">16.1<italic>q</italic></td><td rowspan="1" colspan="1">47.4<italic>d</italic></td></tr><tr><td rowspan="1" colspan="1">25</td><td rowspan="1" colspan="1">29.6<italic>d</italic></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">16.9<italic>q</italic></td><td rowspan="1" colspan="1">30.7<italic>d</italic></td></tr><tr><td rowspan="1" colspan="1">26</td><td rowspan="1" colspan="1">20.2<italic>q</italic></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">17.8<italic>q</italic></td><td rowspan="1" colspan="1">21.3<italic>q</italic></td></tr><tr><td rowspan="1" colspan="1">27</td><td rowspan="1" colspan="1">19.5<italic>q</italic></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">24.1<italic>q</italic></td><td rowspan="1" colspan="1">20.5<italic>q</italic></td></tr><tr><td rowspan="1" colspan="1">28</td><td rowspan="1" colspan="1">23.5<italic>t</italic></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">179.1<italic>s</italic></td><td rowspan="1" colspan="1">24.7<italic>t</italic></td></tr><tr><td rowspan="1" colspan="1">29</td><td rowspan="1" colspan="1">12.3<italic>q</italic></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">17.9<italic>q</italic></td><td rowspan="1" colspan="1">13.3<italic>q</italic></td></tr><tr><td rowspan="1" colspan="1">30</td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">21.9<italic>q</italic></td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">1′</td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">122.5<italic>s</italic></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">103.9<italic>d</italic></td></tr><tr><td rowspan="1" colspan="1">2′</td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">110.8<italic>d</italic></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">76.7<italic>d</italic></td></tr><tr><td rowspan="1" colspan="1">3′</td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">151.5<italic>s</italic></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">79.9<italic>d</italic></td></tr><tr><td rowspan="1" colspan="1">4′</td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">148.9<italic>s</italic></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">73.0<italic>d</italic></td></tr><tr><td rowspan="1" colspan="1">5′</td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">116.6<italic>d</italic></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">79.4<italic>d</italic></td></tr><tr><td rowspan="1" colspan="1">6′</td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">121.2<italic>d</italic></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">64.1<italic>t</italic></td></tr><tr><td rowspan="1" colspan="1">OMe</td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">57.1<italic>q</italic></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">OMe'</td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1">56.8<italic>q</italic></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td></tr></tbody></table></table-wrap></sec></back></pmc></record>Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=$WICRI_ROOT/Wicri/Bois/explor/OrangerV1/Data/Pmc/Corpus
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 000F01 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/Pmc/Corpus/biblio.hfd -nk 000F01 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien
|wiki= Wicri/Bois
|area= OrangerV1
|flux= Pmc
|étape= Corpus
|type= RBID
|clé= PMC:1810368
|texte= Chemical Constituents of Dichloromethane Extract of Cultivated Satureja khuzistanica
}}
Pour générer des pages wiki
HfdIndexSelect -h $EXPLOR_AREA/Data/Pmc/Corpus/RBID.i -Sk "pubmed:17342246" \
| HfdSelect -Kh $EXPLOR_AREA/Data/Pmc/Corpus/biblio.hfd \
| NlmPubMed2Wicri -a OrangerV1
| This area was generated with Dilib version V0.6.25. |  |