388 lines
42 KiB
XML
388 lines
42 KiB
XML
<document id="C70F29A005591DAC976C293317429284" ID-CLB-Dataset="285349" ID-DOI="10.1016/j.phytochem.2015.02.014" ID-GBIF-Dataset="d30e1c4c-6a0f-4e42-97ec-8f9abb4e26ea" ID-ISSN="1873-3700" ID-Zenodo-Dep="10486867" IM.bibliography_approvedBy="guilherme" IM.illustrations_approvedBy="guilherme" IM.materialsCitations_approvedBy="felipe" IM.metadata_approvedBy="felipe" IM.tables_approvedBy="guilherme" IM.taxonomicNames_approvedBy="guilherme" IM.treatments_approvedBy="jonas" checkinTime="1704950218509" checkinUser="felipe" docAuthor="Epifano, Francesco, Fiorito, Serena, Genovese, Salvatore, Granica, Sebastian, Vitalini, Sara & Zidorn, Christian" docDate="2015" docId="03A0E701A37BFFB5FF970681FBE54784" docLanguage="en" docName="Phytochemistry.115.27-43.pdf" docOrigin="Phytochemistry 115 (1)" docSource="http://dx.doi.org/10.1016/j.phytochem.2015.02.014" docStyle="DocumentStyle:9E596C34F4E94307D29315B03ACE1007.6:Phytochemistry.2014-2019.journal_article" docStyleId="9E596C34F4E94307D29315B03ACE1007" docStyleName="Phytochemistry.2014-2019.journal_article" docStyleVersion="6" docTitle="Skimmia laureola Decne." docType="treatment" docVersion="6" lastPageNumber="35" masterDocId="FF999F79A37DFFBDFFE50019FFF4462D" masterDocTitle="Phytochemistry of the genus Skimmia (Rutaceae)" masterLastPageNumber="43" masterPageNumber="27" pageNumber="33" updateTime="1705416209838" updateUser="jonas">
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<mods:title id="5A5430E11B6BE35092B087684966881B">Phytochemistry of the genus Skimmia (Rutaceae)</mods:title>
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<mods:namePart id="4F2A87724BCF246371F9C08A2E86DC5B">Epifano, Francesco</mods:namePart>
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<mods:affiliation id="8DEECC6F01BAA1115A4194044450E9C2">Dipartimento di Farmacia, Università ‘‘ G. D’Annunzio’ ’ Chieti-Pescara, Via dei Vestini 31, 66013 Chieti Scalo, CH, Italy</mods:affiliation>
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<mods:namePart id="5711D48FFB9C5C2106E6BFE3BE3CB6B2">Fiorito, Serena</mods:namePart>
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<mods:namePart id="9C8247724D72A31CAFBFE6738305AA8C">Genovese, Salvatore</mods:namePart>
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<mods:namePart id="E35C5104F166352589D266BA9269820E">Granica, Sebastian</mods:namePart>
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<mods:namePart id="92446E3F710C2DD6280AC59517E364A8">Vitalini, Sara</mods:namePart>
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<mods:namePart id="84C2D3168601F63CB1B448443370AB15">Zidorn, Christian</mods:namePart>
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<mods:title id="AF8F0D63B38F3AD339E79BF14B4BFAF9">Phytochemistry</mods:title>
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<mods:date id="490630271985C3406E2C6FE72416A709">2015</mods:date>
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<mods:number id="55E764CA594B667BB7FC0A3966B63776">2015-07-31</mods:number>
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<mods:number id="1107972716C84FC014B6376E323BAECC">115</mods:number>
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<treatment id="03A0E701A37BFFB5FF970681FBE54784" LSID="urn:lsid:plazi:treatment:03A0E701A37BFFB5FF970681FBE54784" httpUri="http://treatment.plazi.org/id/03A0E701A37BFFB5FF970681FBE54784" lastPageId="8" lastPageNumber="35" pageId="6" pageNumber="33">
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<subSubSection id="C313059CA37BFFBBFF970681FF0B4081" box="[114,255,1688,1708]" pageId="6" pageNumber="33" type="nomenclature">
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<paragraph id="8BB65617A37BFFBBFF970681FF0B4081" blockId="6.[114,255,1688,1708]" box="[114,255,1688,1708]" pageId="6" pageNumber="33">
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<heading id="D0FEE17BA37BFFBBFF970681FF0B4081" box="[114,255,1688,1708]" fontSize="36" level="2" pageId="6" pageNumber="33" reason="3">
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<emphasis id="B97D8A05A37BFFBBFF970681FF0B4081" box="[114,255,1688,1708]" italics="true" pageId="6" pageNumber="33">
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3.5.
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<taxonomicName id="4C092D94A37BFFBBFF7E0681FF0B4081" ID-CoL="6YS9T" authority="(DC.) Decne." authorityName="Decne." baseAuthorityName="DC." box="[155,255,1688,1708]" class="Magnoliopsida" family="Rutaceae" genus="Skimmia" kingdom="Plantae" order="Sapindales" pageId="6" pageNumber="33" phylum="Tracheophyta" rank="species" species="laureola">S. laureola</taxonomicName>
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</emphasis>
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</heading>
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</paragraph>
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</subSubSection>
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<subSubSection id="C313059CA37BFFB5FF7406D6FBE54784" lastPageId="8" lastPageNumber="35" pageId="6" pageNumber="33" type="discussion">
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<paragraph id="8BB65617A37BFFBBFF7406D6FDC2418A" blockId="6.[113,783,1743,2015]" pageId="6" pageNumber="33">
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<taxonomicName id="4C092D94A37BFFBBFF7406D6FF0140CE" ID-CoL="6YS9T" box="[145,245,1743,1763]" class="Magnoliopsida" family="Rutaceae" genus="Skimmia" kingdom="Plantae" order="Sapindales" pageId="6" pageNumber="33" phylum="Tracheophyta" rank="species" species="laureola">
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<emphasis id="B97D8A05A37BFFBBFF7406D6FF0140CE" box="[145,245,1743,1763]" italics="true" pageId="6" pageNumber="33">S. laureola</emphasis>
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</taxonomicName>
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(syn.
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<taxonomicName id="4C092D94A37BFFBBFED106D6FDD640CE" ID-CoL="6QD33" authority="Blanco" authorityName="Blanco" box="[308,546,1743,1763]" class="Magnoliopsida" family="Rutaceae" genus="Limonia" kingdom="Plantae" order="Sapindales" pageId="6" pageNumber="33" phylum="Tracheophyta" rank="species" species="laureola">
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<emphasis id="B97D8A05A37BFFBBFED106D6FE2240CE" box="[308,470,1743,1763]" italics="true" pageId="6" pageNumber="33">Limonia laureola</emphasis>
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Blanco
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</taxonomicName>
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) is an evergreen shrub, native to Northern
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<collectingCountry id="F31E1687A37BFFBBFED406F5FE9E40D2" box="[305,362,1772,1791]" name="China" pageId="6" pageNumber="33">China</collectingCountry>
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and the Northern Himalayan region often cultivated for ornamental purposes, also as a bonsai (
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<bibRefCitation id="EF982BE6A37BFFBBFD4B0710FF50411A" author="He, M. & Zhang, H. & He, X. & Zhang, M." pageId="6" pageNumber="33" pagination="1122 - 1126" refId="ref15681" refString="He, M., Zhang, H., He, X., Zhang, M., 1995. Mass spectrometric study on two compounds from Skimmia laureola ssp. multinervia. Rapid Commun. Mass. Spectr. 9, 1122 - 1126." type="journal article" year="1995">He et al., 1995</bibRefCitation>
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). Leaves are consumed, after having been cooked, as a condiment in curries or as flavouring for other food by local populations in
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<collectingCountry id="F31E1687A37BFFBBFF750745FF3D4142" box="[144,201,1884,1903]" name="China" pageId="6" pageNumber="33">China</collectingCountry>
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and Himalayan region. Fresh leaves were used in the treatment of smallpox and smoke produced by burning the leaves is believed to purify the air (
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<bibRefCitation id="EF982BE6A37BFFBBFE73078DFDDD418B" author="He, M. & Zhang, H. & He, X. & Zhang, M." box="[406,553,1939,1959]" pageId="6" pageNumber="33" pagination="1122 - 1126" refId="ref15681" refString="He, M., Zhang, H., He, X., Zhang, M., 1995. Mass spectrometric study on two compounds from Skimmia laureola ssp. multinervia. Rapid Commun. Mass. Spectr. 9, 1122 - 1126." type="journal article" year="1995">He et al., 1995</bibRefCitation>
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).
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</paragraph>
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||
<paragraph id="8BB65617A37BFFBBFF7407A9FAE4401A" blockId="6.[113,783,1743,2015]" lastBlockId="6.[831,1501,1543,2010]" pageId="6" pageNumber="33">
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Together with
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<taxonomicName id="4C092D94A37BFFBBFEC107B6FE7F41EE" ID-CoL="6Z3Y4" box="[292,395,1967,1987]" class="Magnoliopsida" family="Rutaceae" genus="Skimmia" kingdom="Plantae" order="Sapindales" pageId="6" pageNumber="33" phylum="Tracheophyta" rank="species" species="japonica">
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<emphasis id="B97D8A05A37BFFBBFEC107B6FE7F41EE" box="[292,395,1967,1987]" italics="true" pageId="6" pageNumber="33">S. japonica</emphasis>
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</taxonomicName>
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,
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<taxonomicName id="4C092D94A37BFFBBFE7307B6FE0E41EE" ID-CoL="6QD33" box="[406,506,1967,1987]" class="Magnoliopsida" family="Rutaceae" genus="Limonia" kingdom="Plantae" order="Sapindales" pageId="6" pageNumber="33" phylum="Tracheophyta" rank="species" species="laureola">
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<emphasis id="B97D8A05A37BFFBBFE7307B6FE0E41EE" box="[406,506,1967,1987]" italics="true" pageId="6" pageNumber="33">S. laureola</emphasis>
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</taxonomicName>
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is the phytochemically and pharmacologically most intensely studied species of the genus
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<taxonomicName id="4C092D94A37BFFBBFCDA061EFC664036" ID-CoL="7HYL" box="[831,914,1543,1563]" class="Magnoliopsida" family="Rutaceae" genus="Skimmia" kingdom="Plantae" order="Sapindales" pageId="6" pageNumber="33" phylum="Tracheophyta" rank="genus">
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<emphasis id="B97D8A05A37BFFBBFCDA061EFC664036" box="[831,914,1543,1563]" italics="true" pageId="6" pageNumber="33">Skimmia</emphasis>
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</taxonomicName>
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.
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<taxonomicName id="4C092D94A37BFFBBFC7B061EFBF74036" ID-CoL="6QD33" box="[926,1027,1543,1563]" class="Magnoliopsida" family="Rutaceae" genus="Limonia" kingdom="Plantae" order="Sapindales" pageId="6" pageNumber="33" phylum="Tracheophyta" rank="species" species="laureola">
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<emphasis id="B97D8A05A37BFFBBFC7B061EFBF74036" box="[926,1027,1543,1563]" italics="true" pageId="6" pageNumber="33">S. laureola</emphasis>
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</taxonomicName>
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is a rich source of coumarins, alkaloids, triterpenes, and steroids and contains essential oil.
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</paragraph>
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<paragraph id="8BB65617A37BFFBBFCBB0659FB644147" blockId="6.[831,1501,1543,2010]" pageId="6" pageNumber="33">
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The first alkaloid isolated from
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<taxonomicName id="4C092D94A37BFFBBFB710626FA44407E" box="[1172,1456,1599,1619]" class="Magnoliopsida" family="Rutaceae" genus="Limonia" kingdom="Plantae" order="Sapindales" pageId="6" pageNumber="33" phylum="Tracheophyta" rank="subSpecies" species="laureola" subSpecies="multinervia">
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<emphasis id="B97D8A05A37BFFBBFB710626FB02407E" box="[1172,1270,1599,1619]" italics="true" pageId="6" pageNumber="33">S. laureola</emphasis>
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subsp.
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<emphasis id="B97D8A05A37BFFBBFAA50626FA44407E" box="[1344,1456,1599,1619]" italics="true" pageId="6" pageNumber="33">multinervia</emphasis>
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</taxonomicName>
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was evoxine
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<emphasis id="B97D8A05A37BFFBBFC7F0642FC474043" bold="true" box="[922,947,1627,1646]" pageId="6" pageNumber="33">17</emphasis>
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(
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<bibRefCitation id="EF982BE6A37BFFBBFC2D0645FB994043" author="He, M. & Zhang, H. & He, X. & Zhang, M." box="[968,1133,1627,1647]" pageId="6" pageNumber="33" pagination="1122 - 1126" refId="ref15681" refString="He, M., Zhang, H., He, X., Zhang, M., 1995. Mass spectrometric study on two compounds from Skimmia laureola ssp. multinervia. Rapid Commun. Mass. Spectr. 9, 1122 - 1126." type="journal article" year="1995">He et al., 1995</bibRefCitation>
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).
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<bibRefCitation id="EF982BE6A37BFFBBFB620645FA304042" author="Atta-ur-Rahman, A. & Sultana, N. & Choudhary, M. I. & Shah, P. M. & Khan, M. R." box="[1159,1476,1628,1647]" pageId="6" pageNumber="33" pagination="713 - 717" refId="ref14177" refString="Atta-ur-Rahman, A., Sultana, N., Choudhary, M. I., Shah, P. M., Khan, M. R., 1998 a. Isolation and structural studies on the chemical constituents of Skimmia laureola. J. Nat. Prod. 61, 713 - 717." type="journal article" year="1998">Atta-ur-Rahman et al. (1998a</bibRefCitation>
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,b) obtained four quinolone alkaloids from the ethanolic extract of leafy shoots and named them ptelefoliarine
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<emphasis id="B97D8A05A37BFFBBFAC7068AFADB408B" bold="true" box="[1314,1327,1683,1702]" pageId="6" pageNumber="33">6</emphasis>
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, acetoxyptelefoliarine
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<emphasis id="B97D8A05A37BFFBBFC6106B6FC6540EF" bold="true" box="[900,913,1711,1730]" pageId="6" pageNumber="33">7</emphasis>
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, acetoxyedulinine
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<emphasis id="B97D8A05A37BFFBBFBA806B6FBAE40EF" bold="true" box="[1101,1114,1711,1730]" pageId="6" pageNumber="33">8</emphasis>
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, and orixiarine
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<emphasis id="B97D8A05A37BFFBBFB1006B6FAF640EF" bold="true" box="[1269,1282,1711,1730]" pageId="6" pageNumber="33">9</emphasis>
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, and methyl isoplatydesmine
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<emphasis id="B97D8A05A37BFFBBFC7806D2FC4240F3" bold="true" box="[925,950,1739,1758]" pageId="6" pageNumber="33">20</emphasis>
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. Moreover, two additional quinoline alkaloids, acetyl ribalinine
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<emphasis id="B97D8A05A37BFFBBFC4D06FEFC3540D7" bold="true" box="[936,961,1767,1786]" pageId="6" pageNumber="33">10</emphasis>
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and ribaliprenylene
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<emphasis id="B97D8A05A37BFFBBFB7206FEFB4440D7" bold="true" box="[1175,1200,1767,1786]" pageId="6" pageNumber="33">11</emphasis>
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were isolated (
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<bibRefCitation id="EF982BE6A37BFFBBFAB706FEFC85413B" author="Sultana, N. & Khan, T. H." pageId="6" pageNumber="33" pagination="1186 - 1191" refId="ref18382" refString="Sultana, N., Atta-ur-Rahman, Khan, T. H., 2005. Tyrosinase inhibitor fatty ester and a quinoline alkaloid from Skimmia laureola. Z. Naturforsch. 60 b, 1186 - 1191." type="journal article" year="2005">Sultana et al., 2005</bibRefCitation>
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). In 2007 the same group provided evidence for the presence of yet two additional quinoline alkaloids in addition to
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<emphasis id="B97D8A05A37BFFBBFA860706FA7D411F" bold="true" box="[1379,1417,1823,1842]" pageId="6" pageNumber="33">6–8</emphasis>
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, and
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<emphasis id="B97D8A05A37BFFBBFA5B0706FA23411F" bold="true" box="[1470,1495,1823,1842]" pageId="6" pageNumber="33">11</emphasis>
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, methyl isoplatydesmine
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<emphasis id="B97D8A05A37BFFBBFBDD0722FBA54163" bold="true" box="[1080,1105,1851,1870]" pageId="6" pageNumber="33">20</emphasis>
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and dictamnine
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<emphasis id="B97D8A05A37BFFBBFB180722FAE24163" bold="true" box="[1277,1302,1851,1870]" pageId="6" pageNumber="33">12</emphasis>
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were isolated from aerial parts (
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<bibRefCitation id="EF982BE6A37BFFBBFC25074EFB764147" author="Sultana, N. & Choudhary, M. I. & Akhter, F." box="[960,1154,1879,1898]" pageId="6" pageNumber="33" pagination="194 - 197" refId="ref18421" refString="Sultana, N., Choudhary, M. I., Akhter, F., 2007. X-ray diffraction studies on inhibitor of platelet aggregation dictamnine. J. Chem. Soc. Pak. 29, 194 - 197." type="journal article" year="2007">Sultana et al., 2007</bibRefCitation>
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).
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</paragraph>
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<paragraph id="8BB65617A37BFFBAFCBB076BFB0347BA" blockId="6.[831,1501,1543,2010]" lastBlockId="7.[157,1271,183,407]" lastPageId="7" lastPageNumber="34" pageId="6" pageNumber="33">
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The first study describing the isolation and structural characterization of coumarins was published by Chatterjee and Bhattacharyya in two different papers in 1947 and 1953; leaves and bark yielded three coumarins, umbelliferone
|
||
<emphasis id="B97D8A05A37BFFBBFA5B07DFFA2341F4" bold="true" box="[1470,1495,1990,2009]" pageId="6" pageNumber="33">21</emphasis>
|
||
, O O β−D-glucopyranosyl H H COOH O
|
||
<emphasis id="B97D8A05A37AFFBAFB5A012DFF3B47A1" bold="true" pageId="7" pageNumber="34">O82</emphasis>
|
||
, limonin, MW 470
|
||
<emphasis id="B97D8A05A37AFFBAFDC70199FDC147BD" bold="true" box="[546,565,384,400]" pageId="7" pageNumber="34">83</emphasis>
|
||
, limonin 17-β−D-glucopyranoside, MW 650
|
||
<emphasis id="B97D8A05A37AFFBAFBE6019EFBE247BA" bold="true" box="[1027,1046,391,407]" pageId="7" pageNumber="34">84</emphasis>
|
||
, isoobacunoic acid, MW 472
|
||
</paragraph>
|
||
<paragraph id="8BB65617A37AFFBAFD020231FB1E44C6" blockId="7.[172,1342,459,747]" pageId="7" pageNumber="34">
|
||
β−D-glucopyranosyl HO O O COOH O O OHO O
|
||
<emphasis id="B97D8A05A37AFFBAFBFB028FFBC5448B" bold="true" box="[1054,1073,662,678]" pageId="7" pageNumber="34">87</emphasis>
|
||
, methyl isoobacunoate diosphenol
|
||
<emphasis id="B97D8A05A37AFFBAFF2002A9FF2C44ED" bold="true" box="[197,216,688,704]" pageId="7" pageNumber="34">85</emphasis>
|
||
, cyclocalamin,MW 502
|
||
<emphasis id="B97D8A05A37AFFBAFDFB02A9FDC544ED" bold="true" box="[542,561,688,704]" pageId="7" pageNumber="34">86</emphasis>
|
||
, cyclocalamin 17-β−D-glucopyranoside, MW 682 R =
|
||
<collectingCountry id="F31E1687A37AFFBAFB6F02B7FB574493" box="[1162,1187,686,702]" name="Switzerland" pageId="7" pageNumber="34">CH</collectingCountry>
|
||
3, MW 502
|
||
<emphasis id="B97D8A05A37AFFBAFBC202DCFBCE44F8" bold="true" box="[1063,1082,709,725]" pageId="7" pageNumber="34">88</emphasis>
|
||
, isoobacunoate acid diosphenol R = H, MW 486
|
||
</paragraph>
|
||
<paragraph id="8BB65617A37AFFBAFE53034FFDA54549" blockId="7.[148,1342,786,1020]" box="[438,593,852,868]" pageId="7" pageNumber="34">β−D-glucopyranosyl</paragraph>
|
||
<paragraph id="8BB65617A37AFFBAFF39039EFE2545A7" blockId="7.[148,1342,786,1020]" box="[220,465,890,919]" pageId="7" pageNumber="34">O COOH</paragraph>
|
||
<paragraph id="8BB65617A37AFFBAFD150392FACE45D1" blockId="7.[148,1342,786,1020]" pageId="7" pageNumber="34">
|
||
O
|
||
<emphasis id="B97D8A05A37AFFBAFC200392FF5345F2" bold="true" pageId="7" pageNumber="34">OOO89</emphasis>
|
||
, nomilin 17-β−D-glucopyranoside, R = acetyl MW 694
|
||
<emphasis id="B97D8A05A37AFFBAFD2003C8FD2C45CC" bold="true" box="[709,728,977,993]" pageId="7" pageNumber="34">91</emphasis>
|
||
, nomilin, R = acetyl MW 514
|
||
<emphasis id="B97D8A05A37AFFBAFF7103FFFF5345DB" bold="true" box="[148,167,998,1014]" pageId="7" pageNumber="34">90</emphasis>
|
||
, desacetylnomilin 17-β−D-glucopyranoside, R = H, MW 652
|
||
<emphasis id="B97D8A05A37AFFBAFD2003FFFD2C45DB" bold="true" box="[709,728,998,1014]" pageId="7" pageNumber="34">92</emphasis>
|
||
, desacetylnomilin,R = H, MW 472
|
||
<emphasis id="B97D8A05A37AFFBAFB9803F5FB6445D1" bold="true" box="[1149,1168,1004,1020]" pageId="7" pageNumber="34">93</emphasis>
|
||
, obacunone, MW 454
|
||
</paragraph>
|
||
<paragraph id="8BB65617A37AFFBAFB3A0473FBC64336" blockId="7.[161,1410,1064,1307]" pageId="7" pageNumber="34">
|
||
β−D-glucopyranosyl β−D-glucopyranosyl O O COOH COOH O O O OO O
|
||
<emphasis id="B97D8A05A37AFFBAFD5E04EDFD3A4329" bold="true" box="[699,718,1268,1284]" pageId="7" pageNumber="34">95</emphasis>
|
||
, retrocalamin, MW 462
|
||
<emphasis id="B97D8A05A37AFFBAFBF304EDFBDD4329" bold="true" box="[1046,1065,1268,1284]" pageId="7" pageNumber="34">96</emphasis>
|
||
, retrocalamin 17-β−D-glucopyranoside, MW
|
||
<emphasis id="B97D8A05A37AFFBAFF53051AFF3D433E" bold="true" box="[182,201,1283,1299]" pageId="7" pageNumber="34">94</emphasis>
|
||
, obacunone 17-β− D-glucopyranoside, MW 652 642
|
||
</paragraph>
|
||
<paragraph id="8BB65617A37AFFB5FCE2058BFF1B4503" blockId="7.[231,1323,1346,1583]" lastBlockId="8.[113,783,432,2014]" lastPageId="8" lastPageNumber="35" pageId="7" pageNumber="34">
|
||
β−D-glucopyranosyl COOH O HO HO O OOH O
|
||
<emphasis id="B97D8A05A37AFFBAFF1D0617FEFF4033" bold="true" box="[248,267,1550,1566]" pageId="7" pageNumber="34">97</emphasis>
|
||
, ichangensin, MW 444
|
||
<emphasis id="B97D8A05A37AFFBAFDA80602FD944006" bold="true" box="[589,608,1563,1579]" pageId="7" pageNumber="34">98</emphasis>
|
||
, ichangensin 17-β−D-glucopyranoside, MW 624
|
||
<emphasis id="B97D8A05A37AFFBAFB8F0606FB894002" bold="true" box="[1130,1149,1567,1583]" pageId="7" pageNumber="34">99</emphasis>
|
||
, calamin, MW 520 isopimpinellin
|
||
<emphasis id="B97D8A05A375FFB5FEE901A9FED147EE" bold="true" box="[268,293,432,451]" pageId="8" pageNumber="35">62</emphasis>
|
||
, and bergaptene
|
||
<emphasis id="B97D8A05A375FFB5FE3A01A9FE0C47EE" bold="true" box="[479,504,432,451]" pageId="8" pageNumber="35">46</emphasis>
|
||
. The same research group isolated scopoletin
|
||
<emphasis id="B97D8A05A375FFB5FED001D5FEBA47F2" bold="true" box="[309,334,460,479]" pageId="8" pageNumber="35">24</emphasis>
|
||
as an additional compound from an ethanol extract of the
|
||
<taxonomicName id="4C092D94A375FFB5FEED01F1FD6B47D6" authority="(Bhattacharjee and Mullick, 1960)" baseAuthorityName="Bhattacharjee and Mullick" baseAuthorityYear="1960" box="[264,671,488,507]" class="Magnoliopsida" family="Eucommiaceae" genus="Eucommia" kingdom="Plantae" order="Garryales" pageId="8" pageNumber="35" phylum="Tracheophyta" rank="species" species="bark">
|
||
bark (
|
||
<bibRefCitation id="EF982BE6A375FFB5FEA301F1FD6247D6" author="Bhattacharjee, S. R. & Mullick, D. K." box="[326,662,488,507]" pageId="8" pageNumber="35" pagination="420 - 422" refId="ref14475" refString="Bhattacharjee, S. R., Mullick, D. K., 1960. Isolation of scopoletin, skimming, and umbelliferone from the trunk-bark of Skimmia laureola. J. Ind. Chem. Soc. 37, 420 - 422." type="journal article" year="1960">Bhattacharjee and Mullick, 1960</bibRefCitation>
|
||
)
|
||
</taxonomicName>
|
||
. The same four coumarins were also obtained from apolar extracts of dry leaves (
|
||
<bibRefCitation id="EF982BE6A375FFB5FF210239FE49441E" author="Pathak, H. D. & Pant, J. N." box="[196,445,544,563]" pageId="8" pageNumber="35" pagination="45 - 51" refId="ref16985" refString="Pathak, H. D., Pant, J. N., 1972. Chemical examination of Skimmia laureola. Indian Perf. 16, 45 - 51." type="journal article" year="1972">Pathak and Pant, 1972</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="EF982BE6A375FFB5FE280239FCF6441E" author="Bhargava, K. K. & Seshadri, T. R." box="[461,770,544,563]" pageId="8" pageNumber="35" pagination="59 - 60" refId="ref14439" refString="Bhargava, K. K., Seshadri, T. R., 1973. Chemical examination of the leaf residues of Skimmia laureola. Curr. Sci. 42, 59 - 60." type="journal article" year="1973">Bhargava and Seshadri, 1973</bibRefCitation>
|
||
). Investigations of roots extract of
|
||
<taxonomicName id="4C092D94A375FFB5FE5F0222FDE94462" box="[442,541,571,591]" class="Magnoliopsida" family="Rutaceae" genus="Limonia" kingdom="Plantae" order="Sapindales" pageId="8" pageNumber="35" phylum="Tracheophyta" rank="species" species="laureola">
|
||
<emphasis id="B97D8A05A375FFB5FE5F0222FDE94462" box="[442,541,571,591]" italics="true" pageId="8" pageNumber="35">S. laureola</emphasis>
|
||
</taxonomicName>
|
||
afforded two additional coumarins, namely (+)-heraclenin
|
||
<emphasis id="B97D8A05A375FFB5FE29024EFE114447" bold="true" box="[460,485,599,618]" pageId="8" pageNumber="35">60</emphasis>
|
||
and isoimperatorin
|
||
<emphasis id="B97D8A05A375FFB5FD56024EFD384447" bold="true" box="[691,716,599,618]" pageId="8" pageNumber="35">47</emphasis>
|
||
, along with the glucoside of umbelliferone (skimmin)
|
||
<emphasis id="B97D8A05A375FFB5FDBC026AFD8644AB" bold="true" box="[601,626,627,646]" pageId="8" pageNumber="35">22</emphasis>
|
||
and scopoletin
|
||
<emphasis id="B97D8A05A375FFB5FF940296FF7E448F" bold="true" box="[113,138,655,674]" pageId="8" pageNumber="35">24</emphasis>
|
||
(
|
||
<bibRefCitation id="EF982BE6A375FFB5FF7F0296FEB7448F" author="Sood, S. & Gupta, B. D. & Banerjee, S. K." box="[154,323,655,675]" pageId="8" pageNumber="35" pagination="338 - 339" refId="ref18186" refString="Sood, S., Gupta, B. D., Banerjee, S. K., 1978. Constituents of Skimmia laureola. Planta Med. 34, 338 - 339." type="journal article" year="1978">Sood et al., 1978</bibRefCitation>
|
||
). Other coumarins, namely 7-methoxy-6-(2
|
||
<emphasis id="B97D8A05A375FFB5FCE40295FCF144B4" box="[769,773,652,665]" italics="true" pageId="8" pageNumber="35">
|
||
<superScript id="7C7CFB5FA375FFB5FCE40295FCF144B4" attach="none" box="[769,773,652,665]" fontSize="5" pageId="8" pageNumber="35">0</superScript>
|
||
</emphasis>
|
||
- methoxy-3
|
||
<emphasis id="B97D8A05A375FFB5FF0502B1FF104498" box="[224,228,680,693]" italics="true" pageId="8" pageNumber="35">
|
||
<superScript id="7C7CFB5FA375FFB5FF0502B1FF104498" attach="none" box="[224,228,680,693]" fontSize="5" pageId="8" pageNumber="35">0</superScript>
|
||
</emphasis>
|
||
-hydroxy-3
|
||
<emphasis id="B97D8A05A375FFB5FEB202B1FEAF4498" box="[343,347,680,693]" italics="true" pageId="8" pageNumber="35">
|
||
<superScript id="7C7CFB5FA375FFB5FEB202B1FEAF4498" attach="none" box="[343,347,680,693]" fontSize="5" pageId="8" pageNumber="35">0</superScript>
|
||
</emphasis>
|
||
-methylbutyl)-coumarin
|
||
<emphasis id="B97D8A05A375FFB5FD8402B2FD8E4493" bold="true" box="[609,634,683,702]" pageId="8" pageNumber="35">28</emphasis>
|
||
, isogospherol
|
||
<emphasis id="B97D8A05A375FFB5FF9402DEFF7E44F7" bold="true" box="[113,138,711,730]" pageId="8" pageNumber="35">59</emphasis>
|
||
, heraclenol
|
||
<emphasis id="B97D8A05A375FFB5FEEB02DEFED344F7" bold="true" box="[270,295,711,730]" pageId="8" pageNumber="35">61</emphasis>
|
||
, 5,8-dimethoxycoumarin
|
||
<emphasis id="B97D8A05A375FFB5FDD302DEFDBB44F7" bold="true" box="[566,591,711,730]" pageId="8" pageNumber="35">35</emphasis>
|
||
, 7-methoxy-6-[2
|
||
<emphasis id="B97D8A05A375FFB5FCE402DDFCF144FC" box="[769,773,708,721]" italics="true" pageId="8" pageNumber="35">
|
||
<superScript id="7C7CFB5FA375FFB5FCE402DDFCF144FC" attach="none" box="[769,773,708,721]" fontSize="5" pageId="8" pageNumber="35">0</superScript>
|
||
</emphasis>
|
||
- oxo-3
|
||
<emphasis id="B97D8A05A375FFB5FF4E02F9FF5B44C0" box="[171,175,736,749]" italics="true" pageId="8" pageNumber="35">
|
||
<superScript id="7C7CFB5FA375FFB5FF4E02F9FF5B44C0" attach="left" box="[171,175,736,749]" fontSize="5" pageId="8" pageNumber="35">0</superScript>
|
||
</emphasis>
|
||
-methylbutyl]-coumarin
|
||
<emphasis id="B97D8A05A375FFB5FE4B02FAFE3344DB" bold="true" box="[430,455,739,758]" pageId="8" pageNumber="35">29</emphasis>
|
||
, ulopterol
|
||
<emphasis id="B97D8A05A375FFB5FDD302FAFDBB44DB" bold="true" box="[566,591,739,758]" pageId="8" pageNumber="35">27</emphasis>
|
||
, and marmesin
|
||
<emphasis id="B97D8A05A375FFB5FD1002FAFCFA44DB" bold="true" box="[757,782,739,758]" pageId="8" pageNumber="35">52</emphasis>
|
||
were isolated from leaves (
|
||
<bibRefCitation id="EF982BE6A375FFB5FE7502E6FD42453F" author="Atta-ur-Rahman, A. & Sultana, N. & Riaz, M. & Choudhary, M. I." box="[400,694,767,786]" pageId="8" pageNumber="35" pagination="305 - 313" refId="ref14278" refString="Atta-ur-Rahman, A., Sultana, N., Riaz, M., Choudhary, M. I., 2002. Triterpene and coumarins from Skimmia laureola. Nat. Prod. Lett. 16, 305 - 313." type="journal article" year="2002">Atta-ur-Rahman et al., 2002</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="EF982BE6A375FFB5FD2102E6FF154503" author="Sultana, N. & Afza, N." pageId="8" pageNumber="35" pagination="271 - 274" refId="ref18350" refString="Sultana, N., Afza, N., Atta-ur-Rahman, 2004. Coumarin and quinoline alkaloids from Skimmia laureola. Sci. Int. 16, 271 - 274." type="journal article" year="2004">Sultana et al., 2004</bibRefCitation>
|
||
).
|
||
</paragraph>
|
||
<caption id="DF76069FA37AFFBAFF34076EFABC41A8" ID-DOI="http://doi.org/10.5281/zenodo.10486877" ID-Zenodo-Dep="10486877" box="[209,1352,1909,1925]" httpUri="https://zenodo.org/record/10486877/files/figure.png" pageId="7" pageNumber="34" startId="7.[209,235,1911,1925]" targetBox="[324,1222,1640,1879]" targetPageId="7" targetType="figure">
|
||
<paragraph id="8BB65617A37AFFBAFF34076EFABC41A8" blockId="7.[209,1352,1909,1925]" box="[209,1352,1909,1925]" pageId="7" pageNumber="34">
|
||
<emphasis id="B97D8A05A37AFFBAFF34076EFEF741A8" bold="true" box="[209,259,1911,1925]" pageId="7" pageNumber="34">Fig. 8.</emphasis>
|
||
Chemical structures and molecular weights of triterpene type limonoids detected in seeds of
|
||
<taxonomicName id="4C092D94A37AFFBAFBE1076CFB7A41A8" box="[1028,1166,1909,1925]" class="Magnoliopsida" family="Rutaceae" genus="Skimmia" kingdom="Plantae" order="Sapindales" pageId="7" pageNumber="34" phylum="Tracheophyta" rank="species" species="japonica">
|
||
<emphasis id="B97D8A05A37AFFBAFBE1076CFB7A41A8" box="[1028,1166,1909,1925]" italics="true" pageId="7" pageNumber="34">Skimmia japonica</emphasis>
|
||
</taxonomicName>
|
||
– compounds
|
||
<emphasis id="B97D8A05A37AFFBAFAE2076EFAB141A8" bold="true" box="[1287,1349,1911,1925]" pageId="7" pageNumber="34">82–102</emphasis>
|
||
.
|
||
</paragraph>
|
||
</caption>
|
||
<caption id="DF76069FA375FFB5FF9B0179FCF64743" ID-DOI="http://doi.org/10.5281/zenodo.10518982" ID-Zenodo-Dep="10518982" box="[126,770,352,366]" httpUri="https://zenodo.org/record/10518982/files/figure.png" pageId="8" pageNumber="35" startId="8.[126,152,352,366]" targetBox="[127,769,183,321]" targetPageId="8" targetType="figure">
|
||
<paragraph id="8BB65617A375FFB5FF9B0179FCF64743" blockId="8.[126,770,352,366]" box="[126,770,352,366]" pageId="8" pageNumber="35">
|
||
<emphasis id="B97D8A05A375FFB5FF9B0179FF444743" bold="true" box="[126,176,352,366]" pageId="8" pageNumber="35">Fig. 9.</emphasis>
|
||
Chemical structures and molecular weights of compounds
|
||
<emphasis id="B97D8A05A375FFB5FD7D0179FD434743" bold="true" box="[664,695,352,366]" pageId="8" pageNumber="35">103</emphasis>
|
||
and
|
||
<emphasis id="B97D8A05A375FFB5FD050179FD0B4743" bold="true" box="[736,767,352,366]" pageId="8" pageNumber="35">104</emphasis>
|
||
.
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="8BB65617A375FFB5FF74032CFE5242FC" blockId="8.[113,783,432,2014]" pageId="8" pageNumber="35">
|
||
<taxonomicName id="4C092D94A375FFB5FF74032CFF004564" ID-CoL="6QD33" box="[145,244,821,841]" class="Magnoliopsida" family="Rutaceae" genus="Limonia" kingdom="Plantae" order="Sapindales" pageId="8" pageNumber="35" phylum="Tracheophyta" rank="species" species="laureola">
|
||
<emphasis id="B97D8A05A375FFB5FF74032CFF004564" box="[145,244,821,841]" italics="true" pageId="8" pageNumber="35">S. laureola</emphasis>
|
||
</taxonomicName>
|
||
was also shown to be a rich source of triterpenes. The first phytochemical report concerning these secondary metabolites was
|
||
<emphasis id="B97D8A05A375FFB5FF400374FF4045AC" box="[165,180,877,897]" italics="true" pageId="8" pageNumber="35">O</emphasis>
|
||
-methyllaureolol
|
||
<emphasis id="B97D8A05A375FFB5FE8C0377FE7645AC" bold="true" box="[361,386,878,897]" pageId="8" pageNumber="35">74</emphasis>
|
||
(
|
||
<bibRefCitation id="EF982BE6A375FFB5FE720377FDA845AC" author="Zhang, H. J. & Gao, X. F. & Zhang, M. Z." box="[407,604,878,898]" pageId="8" pageNumber="35" pagination="873 - 874" refId="ref19439" refString="Zhang, H. J., Gao, X. F., Zhang, M. Z., 1995. O - Methyllaureolol from Skimmia laureola. Chin. Chem. Lett. 6, 873 - 874." type="journal article" year="1995">Zhang et al., 1995</bibRefCitation>
|
||
). Further details about the exact configuration were given by the same group two years later (
|
||
<bibRefCitation id="EF982BE6A375FFB5FF1103BFFE424594" author="Zhang, H. J. & Zhang, M. Z. & Gao, X. F." box="[244,438,934,954]" pageId="8" pageNumber="35" pagination="410 - 413" refId="ref19481" refString="Zhang, H. J., Zhang, M. Z., Gao, X. F., 1997. Structure determination of O - methyllaureolol from Skimmia laureola ssp. multinervia by 2 D HMQC and HMBC techniques. Magn. Res. Chem. 35, 410 - 413." type="journal article" year="1997">Zhang et al., 1997</bibRefCitation>
|
||
).
|
||
<bibRefCitation id="EF982BE6A375FFB5FE2B03BFFCFB4594" author="Atta-ur-Rahman, A. & Sultana, N. & Jahan, S. & Choudhary, M. I." box="[462,783,934,954]" pageId="8" pageNumber="35" pagination="223 - 229" refId="ref14235" refString="Atta-ur-Rahman, A., Sultana, N., Jahan, S., Choudhary, M. I., 1998 b. Phytochemical studies on Skimmia laureola. Nat. Prod. Lett. 12, 223 - 229." type="journal article" year="1998">Atta-ur-Rahman et al. (1998b)</bibRefCitation>
|
||
obtained 3-oxo-lanosta-20-25-diene-3-one
|
||
<emphasis id="B97D8A05A375FFB5FDD003DBFDBA45F8" bold="true" box="[565,590,962,981]" pageId="8" pageNumber="35">73</emphasis>
|
||
from aerial parts of
|
||
<taxonomicName id="4C092D94A375FFB5FF6B03C4FF0045DC" ID-CoL="6QD33" box="[142,244,989,1009]" class="Magnoliopsida" family="Rutaceae" genus="Limonia" kingdom="Plantae" order="Sapindales" pageId="8" pageNumber="35" phylum="Tracheophyta" rank="species" species="laureola">
|
||
<emphasis id="B97D8A05A375FFB5FF6B03C4FF0045DC" box="[142,244,989,1009]" italics="true" pageId="8" pageNumber="35">S. laureola</emphasis>
|
||
</taxonomicName>
|
||
. A series of other penta- and tetracyclic triterpenes were isolated in the following years: taraxerone
|
||
<emphasis id="B97D8A05A375FFB5FD8103E3FD894220" bold="true" box="[612,637,1018,1037]" pageId="8" pageNumber="35">81</emphasis>
|
||
(
|
||
<bibRefCitation id="EF982BE6A375FFB5FD6B03E3FF504204" author="Parvez, M. & Gul, W. & Yousaf, M. & Choudhary, M. I. & Riaz, M." pageId="8" pageNumber="35" pagination="213 - 215" refId="ref16898" refString="Parvez, M., Gul, W., Yousaf, M., Choudhary, M. I., Atta-Ur-Rahman, Riaz, M., 1999. Taraxerone. Acta Cryst. C 55, 213 - 215." type="journal article" year="1999">Parvez et al., 1999</bibRefCitation>
|
||
),
|
||
<emphasis id="B97D8A05A375FFB5FF59040CFF3F4204" box="[188,203,1045,1065]" italics="true" pageId="8" pageNumber="35">O</emphasis>
|
||
-methylcyclolaudenol
|
||
<emphasis id="B97D8A05A375FFB5FE54040FFE3E4204" bold="true" box="[433,458,1046,1065]" pageId="8" pageNumber="35">76</emphasis>
|
||
was obtained from the leaves and described by Atta-ur-Rahman et al. as well as by Hussain et al. in a number of reports published between 2002 and 2009. A derivative of the latter compound, namely 16,29-dihydroxy-20- ene-cyclolaudenol
|
||
<emphasis id="B97D8A05A375FFB5FED4049FFEBE42B4" bold="true" box="[305,330,1158,1177]" pageId="8" pageNumber="35">77</emphasis>
|
||
has been isolated in 2008 by Sultana et al., and finally 24-methyllanosta-7,25-dien-3-one
|
||
<emphasis id="B97D8A05A375FFB5FDBE04B8FD804299" bold="true" box="[603,628,1185,1204]" pageId="8" pageNumber="35">75</emphasis>
|
||
was obtained by
|
||
<bibRefCitation id="EF982BE6A375FFB5FF7404A4FE5542FD" author="Hussain, N. & Parvez, M." box="[145,417,1213,1233]" pageId="8" pageNumber="35" pagination="626" refId="ref15899" refString="Hussain, N., Parvez, M., 2010. 24 - Methyllanosta- 7,25 - dien- 3 - one. Acta Cryst. E 66, o 626." type="journal article" year="2010">Hussain and Parvez (2010)</bibRefCitation>
|
||
.
|
||
</paragraph>
|
||
<paragraph id="8BB65617A375FFB5FF7404C0FBE54784" blockId="8.[113,783,432,2014]" lastBlockId="8.[831,1501,181,425]" pageId="8" pageNumber="35">
|
||
The first investigation of
|
||
<taxonomicName id="4C092D94A375FFB5FE7404C1FE0242C1" ID-CoL="6QD33" box="[401,502,1240,1260]" class="Magnoliopsida" family="Rutaceae" genus="Limonia" kingdom="Plantae" order="Sapindales" pageId="8" pageNumber="35" phylum="Tracheophyta" rank="species" species="laureola">
|
||
<emphasis id="B97D8A05A375FFB5FE7404C1FE0242C1" box="[401,502,1240,1260]" italics="true" pageId="8" pageNumber="35">S. laureola</emphasis>
|
||
</taxonomicName>
|
||
essential oil was published in 1920 by Anon who reported some chemo-physical parameters (density, optical rotation, and solubility) of the essential oil obtained by steam distillation of the leaves. The chemical composition of the essential oil prepared from the same source was found to consist mainly of linalool and its acetate with smaller quantities of undefined sesquiterpenes (
|
||
<bibRefCitation id="EF982BE6A375FFB5FE780599FDCD43BE" author="Simonses, J. L." box="[413,569,1408,1427]" pageId="8" pageNumber="35" pagination="126 - 127" refId="ref18082" refString="Simonses, J. L., 1921. Essential oil from the leaves of Skimmia laureola. J. Soc. Chem. Ind. 40, 126 - 127." type="journal article" year="1921">Simonses, 1921</bibRefCitation>
|
||
). The composition of the essential oil of the leaves of
|
||
<taxonomicName id="4C092D94A375FFB5FE2A0582FDC24382" ID-CoL="6QD33" box="[463,566,1435,1455]" class="Magnoliopsida" family="Rutaceae" genus="Limonia" kingdom="Plantae" order="Sapindales" pageId="8" pageNumber="35" phylum="Tracheophyta" rank="species" species="laureola">
|
||
<emphasis id="B97D8A05A375FFB5FE2A0582FDC24382" box="[463,566,1435,1455]" italics="true" pageId="8" pageNumber="35">S. laureola</emphasis>
|
||
</taxonomicName>
|
||
was later refined in terms of percentages and phytochemicals in 1936 by Wienhaus and Rajdhan. These authors recorded the further presence of αpinene, β- phellandrene, azulene, and bergaptene. In 1966 Sharma et al. found geraniol, citronellyl formate, myrcene, methyl heptenone, nerol, citronellyl isobutirate, and citral as additional components. In 1972 Pathak and Pant revealed the presence of phenyl isobutyrate, camphene and furfural; these results were confirmed by
|
||
<bibRefCitation id="EF982BE6A375FFB5FEE50662FE8940A2" author="Sarin, Y. K." box="[256,381,1659,1679]" pageId="8" pageNumber="35" pagination="95 - 100" refId="ref17604" refString="Sarin, Y. K., 1977. Skimmia leaf: a potent source of essential oil from hill areas of Uttar Pradesh [India]. Adv. Essent. Oil Ind (Proc. Symp. Dev. Essent. Oil Uttar Pradesh), 95 - 100." type="book chapter" year="1977">Sarin (1977)</bibRefCitation>
|
||
and
|
||
<bibRefCitation id="EF982BE6A375FFB5FE570662FD8B40A2" author="Razdan, T. K. & Koul, G. L. & Kachroo, V." box="[434,639,1659,1679]" pageId="8" pageNumber="35" pagination="65 - 68" refId="ref17330" refString="Razdan, T. K., Koul, G. L., Kachroo, V., 1980. Colorimetric analysis of the constituents of essential oils - (1 °). Riv. It. Ess. 62, 65 - 68." type="journal article" year="1980">Razdan et al. (1980)</bibRefCitation>
|
||
. In 1989 Goel et al. identified citronellol as an additional component; and in 1992 Mathela et al. stated that pregeijerene and geijerene could be the most important compounds for the typical aroma of the essential oil of leaves of
|
||
<taxonomicName id="4C092D94A375FFB5FE8D06F3FE3840D3" ID-CoL="6QD33" box="[360,460,1770,1790]" class="Magnoliopsida" family="Rutaceae" genus="Limonia" kingdom="Plantae" order="Sapindales" pageId="8" pageNumber="35" phylum="Tracheophyta" rank="species" species="laureola">
|
||
<emphasis id="B97D8A05A375FFB5FE8D06F3FE3840D3" box="[360,460,1770,1790]" italics="true" pageId="8" pageNumber="35">S. laureola</emphasis>
|
||
</taxonomicName>
|
||
. In 2003 Shah et al. determined the seasonal variation of the proportions of linalool (ranging from 4% to 28%) and linalyl acetate (ranging from 37% to 64%) in the essential oil. In 2010 Jangwan et al. identified α- terpineol and geranyl acetate as additional components.
|
||
<bibRefCitation id="EF982BE6A375FFB5FDF10742FD254143" author="Shah, W. A. & Dar, M. Y. & Kuratull-Ain, R. & Manzoor, A. & Qurishi, M. A." box="[532,721,1883,1902]" pageId="8" pageNumber="35" pagination="116 - 121" refId="ref17794" refString="Shah, W. A., Dar, M. Y., Kuratull-Ain, R., Manzoor, A., Qurishi, M. A., 2012. Comparison of terpene composition of Skimmia laureola using hydrodistillation and HS- SPME techniques. J. Essent. Oil Bearing Plants 15, 116 - 121." type="journal article" year="2012">Shah et al. (2012)</bibRefCitation>
|
||
compared results of the quali-quantitative analysis of essential oil by ‘‘classic’’ hydro-distillation and head space-solid phase micro extraction; the main differences were observed in the percentages of linalool and its acetate, α- pinene, β- phellandrene, α- terpineol, and geyrene. Seeds of
|
||
<taxonomicName id="4C092D94A375FFB5FBC300ACFB7946E4" ID-CoL="6QD33" box="[1062,1165,181,201]" class="Magnoliopsida" family="Rutaceae" genus="Limonia" kingdom="Plantae" order="Sapindales" pageId="8" pageNumber="35" phylum="Tracheophyta" rank="species" species="laureola">
|
||
<emphasis id="B97D8A05A375FFB5FBC300ACFB7946E4" box="[1062,1165,181,201]" italics="true" pageId="8" pageNumber="35">S. laureola</emphasis>
|
||
</taxonomicName>
|
||
were shown to be a rich source of polyunsaturated fatty acids: the apolar extract, analyzed by GC–MS after derivatization as methyl esters, afforded the following percentages of the respective acids: palmitic 8.28%, stearic 1.47%, palmitoleic 2.57%, oleic 33.41%, linoleic 31.15%, and linolenic 23.12% (
|
||
<bibRefCitation id="EF982BE6A375FFB5FC73015BFBBA4778" author="Pasha, F. & Bhatty, M. K. & Khan, S. A." box="[918,1102,322,341]" pageId="8" pageNumber="35" pagination="214 - 216" refId="ref16941" refString="Pasha, F., Bhatty, M. K., Khan, S. A., 1966. Chemical investigations on Skimmia laureola seeds. Pak. J. Sci. Ind. Res. 9, 214 - 216." type="journal article" year="1966">Pasha et al., 1966</bibRefCitation>
|
||
). Skimmidiol fatty acid ester
|
||
<emphasis id="B97D8A05A375FFB5FA60015BFA5F4778" bold="true" box="[1413,1451,322,341]" pageId="8" pageNumber="35">104</emphasis>
|
||
was isolated from aerial parts (
|
||
<bibRefCitation id="EF982BE6A375FFB5FBB90147FADC475C" author="Sultana, N. & Khan, T. H." box="[1116,1320,350,369]" pageId="8" pageNumber="35" pagination="1186 - 1191" refId="ref18382" refString="Sultana, N., Atta-ur-Rahman, Khan, T. H., 2005. Tyrosinase inhibitor fatty ester and a quinoline alkaloid from Skimmia laureola. Z. Naturforsch. 60 b, 1186 - 1191." type="journal article" year="2005">Sultana et al., 2005</bibRefCitation>
|
||
) and the similar compound skimmilaureol
|
||
<emphasis id="B97D8A05A375FFB5FBA80160FB8747A1" bold="true" box="[1101,1139,377,396]" pageId="8" pageNumber="35">103</emphasis>
|
||
was isolated from leaf extracts by
|
||
<bibRefCitation id="EF982BE6A375FFB5FCDA018CFBF84784" author="Sultana, N. & Asaad, K." box="[831,1036,405,425]" pageId="8" pageNumber="35" pagination="37 - 47" refId="ref18464" refString="Sultana, N., Atta-ur-Rahman, Asaad, K., 2008. A new fatty ester and a new triterpene from Skimmia laureola. Nat. Prod. Res. 22, 37 - 47." type="journal article" year="2008">Sultana et al. (2008)</bibRefCitation>
|
||
.
|
||
</paragraph>
|
||
</subSubSection>
|
||
</treatment>
|
||
</document> |