410 lines
41 KiB
XML
410 lines
41 KiB
XML
<document id="859C1FCD3FD52405AC93E9C2DCA452C9" ID-CLB-Dataset="285324" ID-DOI="10.1016/j.phytochem.2016.01.008" ID-GBIF-Dataset="065ebbec-6b75-4e30-b7bd-2517a94d3cca" ID-ISSN="1873-3700" ID-Zenodo-Dep="10485291" IM.bibliography_approvedBy="felipe" IM.illustrations_approvedBy="julia" IM.materialsCitations_approvedBy="felipe" IM.metadata_approvedBy="julia" IM.tables_approvedBy="julia" IM.taxonomicNames_approvedBy="julia" IM.treatments_approvedBy="julia" checkinTime="1704944120295" checkinUser="felipe" docAuthor="Stevenson, Philip C., Green, Paul W. C., Veitch, Nigel C., Farrell, Iain W., Kusolwa, Paul & Belmain, Steven R." docDate="2016" docId="03C0879E2B160A47FFC64CF1FBF91525" docLanguage="en" docName="Phytochemistry.123.25-32.pdf" docOrigin="Phytochemistry 123" docSource="http://dx.doi.org/10.1016/j.phytochem.2016.01.008" docStyle="DocumentStyle:9E596C34F4E94307D29315B03ACE1007.6:Phytochemistry.2014-2019.journal_article" docStyleId="9E596C34F4E94307D29315B03ACE1007" docStyleName="Phytochemistry.2014-2019.journal_article" docStyleVersion="6" docTitle="Zanha africana" docType="treatment" docVersion="4" lastPageNumber="26" masterDocId="FFF9FFE62B170A46FF914D41FFBF1319" masterDocTitle="Nor-hopanes from Zanha africana root bark with toxicity to bruchid beetles" masterLastPageNumber="32" masterPageNumber="25" pageNumber="26" updateTime="1705352687479" updateUser="ExternalLinkService">
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<mods:title id="DFA6BF7ABF82551B32D9BD754E15619B">Nor-hopanes from Zanha africana root bark with toxicity to bruchid beetles</mods:title>
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<mods:namePart id="FB86A71F5EC4A8D611AB552DE1A6439D">Stevenson, Philip C.</mods:namePart>
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<mods:affiliation id="81F177E409B62153F47EDD7ABE1C4C59">Natural Resources Institute, University of Greenwich, Central Avenue, Chatham Maritime, Kent ME 4 4 TB, UK & Royal Botanic Gardens, Kew, Richmond, Surrey TW 9 3 AB, UK</mods:affiliation>
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<mods:namePart id="51C9ECBF9D43AA7C597942B6AD27E3DB">Green, Paul W. C.</mods:namePart>
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<mods:affiliation id="C80A4F8E3F52D3B7C2B55B741A2628A0">Royal Botanic Gardens, Kew, Richmond, Surrey TW 9 3 AB, UK</mods:affiliation>
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<mods:namePart id="D6EC60B793B5DAFFD3EE1877208C725F">Veitch, Nigel C.</mods:namePart>
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<mods:affiliation id="6F7B1B4B24EA06F432B0F604551663EF">Royal Botanic Gardens, Kew, Richmond, Surrey TW 9 3 AB, UK</mods:affiliation>
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<mods:namePart id="843BCE4615FA2B520D94A7B90471F770">Farrell, Iain W.</mods:namePart>
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<mods:affiliation id="ADD6ADCD5D422703137ACA881057B393">Royal Botanic Gardens, Kew, Richmond, Surrey TW 9 3 AB, UK</mods:affiliation>
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<mods:namePart id="6D79FA22B9EE109D05C84D85A3A10EB1">Kusolwa, Paul</mods:namePart>
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<mods:affiliation id="D8C708D6964F135A0D4CFD57BB8E4964">Faculty of Agriculture, Sokoine University of Agriculture, Box 3005, Morogoro, Tanzania</mods:affiliation>
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<mods:namePart id="C0F7D1F5FFCEC17DA09EC239F4DDB185">Belmain, Steven R.</mods:namePart>
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<mods:affiliation id="4934A289767483F5F539B03D0D756FE6">Natural Resources Institute, University of Greenwich, Central Avenue, Chatham Maritime, Kent ME 4 4 TB, UK</mods:affiliation>
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<mods:title id="E8B5D16FE416F9BC0BA607411392BF10">Phytochemistry</mods:title>
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<mods:date id="A9CAE019728872DE805B102F2D6398A6">2016</mods:date>
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<mods:classification id="B6A22D1617F15D9D64B8F54993641FDE">journal article</mods:classification>
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<mods:identifier id="0A8188FB335A5013A475C04DDBC8A733" type="DOI">10.1016/j.phytochem.2016.01.008</mods:identifier>
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<treatment id="03C0879E2B160A47FFC64CF1FBF91525" ID-DOI="http://doi.org/10.5281/zenodo.10515255" ID-GBIF-Taxon="220753479" ID-Zenodo-Dep="10515255" LSID="urn:lsid:plazi:treatment:03C0879E2B160A47FFC64CF1FBF91525" httpUri="http://treatment.plazi.org/id/03C0879E2B160A47FFC64CF1FBF91525" lastPageNumber="26" pageId="1" pageNumber="26">
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<subSubSection id="C37365032B160A47FFC64CF1FDA012DD" box="[87,543,432,452]" pageId="1" pageNumber="26" type="nomenclature">
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<heading id="D09E81E42B160A47FFC64CF1FDA012DD" box="[87,543,432,452]" fontSize="36" level="2" pageId="1" pageNumber="26" reason="3">
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<emphasis id="B91DEA9A2B160A47FFC64CF1FDA012DD" box="[87,543,432,452]" italics="true" pageId="1" pageNumber="26">
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2.1. Identification of nor-hopanes in
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<taxonomicName id="4C694D0B2B160A47FE284CF1FDA012DD" ID-CoL="5CW39" authority="Radlk" box="[441,543,432,452]" class="Magnoliopsida" family="Sapindaceae" genus="Zanha" kingdom="Plantae" order="Sapindales" pageId="1" pageNumber="26" phylum="Tracheophyta" rank="species" species="africana">Z. africana</taxonomicName>
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</emphasis>
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</heading>
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</paragraph>
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<paragraph id="8BD636882B160A47FFE74CA8FDEC11BD" blockId="1.[87,758,488,2015]" pageId="1" pageNumber="26">
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The chloroform extract of
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<taxonomicName id="4C694D0B2B160A47FEEF4CA9FE5D12E5" box="[382,482,488,508]" class="Magnoliopsida" family="Sapindaceae" genus="Zanha" kingdom="Plantae" order="Sapindales" pageId="1" pageNumber="26" phylum="Tracheophyta" rank="species" species="africana">
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<emphasis id="B91DEA9A2B160A47FEEF4CA9FE5D12E5" box="[382,482,488,508]" italics="true" pageId="1" pageNumber="26">Z. africana</emphasis>
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</taxonomicName>
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root bark was shown to be toxic to a bruchid beetle,
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<taxonomicName id="4C694D0B2B160A47FEC54F45FDF31101" baseAuthorityName="Fabricius" baseAuthorityYear="1775" box="[340,588,516,536]" class="Insecta" family="Chrysomelidae" genus="Callosobruchus" kingdom="Animalia" order="Coleoptera" pageId="1" pageNumber="26" phylum="Arthropoda" rank="species" species="maculatus">
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<emphasis id="B91DEA9A2B160A47FEC54F45FDF31101" box="[340,588,516,536]" italics="true" pageId="1" pageNumber="26">Callosobruchus maculatus</emphasis>
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</taxonomicName>
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(L.), in bioassays described in detail below (Sections 2.2 and 3.1). This extract was analysed using LC-UV-MS/MS and indicated the presence of numerous non-polar peaks with similar UV spectra. Seven compounds,
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<emphasis id="B91DEA9A2B160A47FF214F35FF69119E" bold="true" box="[176,214,628,647]" pageId="1" pageNumber="26">1–7</emphasis>
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(
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<figureCitation id="13522A0D2B160A47FF764F34FE9E1191" box="[231,289,629,648]" captionStart="Fig" captionStartId="2.[485,511,1277,1291]" captionTargetBox="[197,1407,186,1244]" captionTargetPageId="2" captionText="Fig. 1. Nor-hopanes isolated from Zanha africana root-bark (see text for detail)." figureDoi="http://doi.org/10.5281/zenodo.10515717" httpUri="https://zenodo.org/record/10515717/files/figure.png" pageId="1" pageNumber="26">Fig. 1</figureCitation>
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), were isolated using semi-preparative HPLC and characterized using spectroscopic techniques.
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</paragraph>
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<paragraph id="8BD636882B160A47FFE74FEDFDC317F4" blockId="1.[87,758,488,2015]" pageId="1" pageNumber="26">
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Full assignment of the
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H and
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<superScript id="7C1C9BC02B160A47FE304FE8FE0B11AC" attach="right" box="[417,436,681,693]" fontSize="5" pageId="1" pageNumber="26">13</superScript>
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C NMR spectra of
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<quantity id="4C919B6D2B160A47FDF24FEDFD3611A6" box="[611,649,684,703]" metricMagnitude="-2" metricUnit="m" metricValue="2.54" pageId="1" pageNumber="26" unit="in" value="1.0">
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<emphasis id="B91DEA9A2B160A47FDF24FEDFDCF11A6" bold="true" box="[611,624,684,703]" pageId="1" pageNumber="26">1</emphasis>
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in
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</quantity>
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CDCl
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<subScript id="17ED34CD2B160A47FD2E4FF4FD7711D8" attach="left" box="[703,712,693,705]" fontSize="5" pageId="1" pageNumber="26">3</subScript>
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was obtained using COSY, HSQC and HMBC data (
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<tableCitation id="C6EB03332B160A47FDB74F89FDC411C2" box="[550,635,712,731]" captionStart="Table 1" captionStartId="3.[87,131,183,197]" captionTargetBox="[110,1434,241,1053]" captionText="Table 1 1H NMR spectroscopic data (δ 1H, J in Hz) for 1–4 in ‡ CDCl or MeOD. 3" httpUri="http://table.plazi.org/id/DF1666002B140A45FFC64DF6FD8E13C7" pageId="1" pageNumber="26" tableUuid="DF1666002B140A45FFC64DF6FD8E13C7">Tables 1</tableCitation>
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and
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<tableCitation id="C6EB03332B160A47FD3E4F89FD0311C2" box="[687,700,712,731]" captionStart="Table 2" captionStartId="4.[114,158,183,197]" captionTargetBox="[136,1478,241,1304]" captionText="Table 2 13C NMR spectroscopic data for 1–7 in ‡ CDCl or MeOD. 3" httpUri="http://table.plazi.org/id/DF1666002B130A42FFE34DF6FE6213C7" pageId="1" pageNumber="26" tableUuid="DF1666002B130A42FFE34DF6FE6213C7">2</tableCitation>
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). The
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C NMR assignments of
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<emphasis id="B91DEA9A2B160A47FECC4FA5FED511EE" bold="true" box="[349,362,740,759]" pageId="1" pageNumber="26">1</emphasis>
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showed a good match with those for 3β,6β- dihydroxy-7β-[(4-hydroxybenzoyl)oxy]-21oi
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<emphasis id="B91DEA9A2B160A47FDC54FBEFDDB100A" box="[596,612,767,787]" italics="true" pageId="1" pageNumber="26">H</emphasis>
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-24-norhopa-4(23),22(29)-diene (
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<bibRefCitation id="EFF84B792B160A47FEB54E5DFE5F1036" author="Chavez, J. P. & David, J. M. & Yang, S. W. & Cordell, G. A." box="[292,480,796,815]" pageId="1" pageNumber="26" pagination="909 - 911" refId="ref7911" refString="Chavez, J. P., David, J. M., Yang, S. W., Cordell, G. A., 1997. 24 - norhopene derivatives from Diatenopteryx sorbifolia. J. Nat. Prod. 60, 909 - 911." type="journal article" year="1997">Chávez et al., 1997</bibRefCitation>
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). Good agreement was also found between the
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<superScript id="7C1C9BC02B160A47FEBD4E75FE8A1059" attach="right" box="[300,309,820,832]" fontSize="5" pageId="1" pageNumber="26">1</superScript>
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H NMR assignments and a partial dataset given by the latter authors, with the exception of the assignments of H-9 and H-13 which required revision (
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<tableCitation id="C6EB03332B160A47FD954E31FDF1109A" box="[516,590,880,899]" captionStart="Table 1" captionStartId="3.[87,131,183,197]" captionTargetBox="[110,1434,241,1053]" captionText="Table 1 1H NMR spectroscopic data (δ 1H, J in Hz) for 1–4 in ‡ CDCl or MeOD. 3" httpUri="http://table.plazi.org/id/DF1666002B140A45FFC64DF6FD8E13C7" pageId="1" pageNumber="26" tableUuid="DF1666002B140A45FFC64DF6FD8E13C7">Table 1</tableCitation>
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). A second NMR dataset for
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<emphasis id="B91DEA9A2B160A47FF5F4ECAFF641087" bold="true" box="[206,219,907,926]" pageId="1" pageNumber="26">1</emphasis>
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was acquired in MeOH-
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<emphasis id="B91DEA9A2B160A47FE494ECBFE5B1087" box="[472,484,906,926]" italics="true" pageId="1" pageNumber="26">d</emphasis>
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||
<subScript id="17ED34CD2B160A47FE754ED4FE5210B8" attach="left" box="[484,493,917,929]" fontSize="5" pageId="1" pageNumber="26">4</subScript>
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because of the improved resolution of the multiplet structure of several key resonances including H-3 and H-6. A series of 1D site selective ROE experiments indicated that
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<emphasis id="B91DEA9A2B160A47FEA34E9EFE8010EB" bold="true" box="[306,319,991,1010]" pageId="1" pageNumber="26">1</emphasis>
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had the same relative configuration as the published structure (
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<figureCitation id="13522A0D2B160A47FEA34EBAFED41717" box="[306,363,1019,1038]" captionStart="Fig" captionStartId="2.[485,511,1277,1291]" captionTargetBox="[197,1407,186,1244]" captionTargetPageId="2" captionText="Fig. 1. Nor-hopanes isolated from Zanha africana root-bark (see text for detail)." figureDoi="http://doi.org/10.5281/zenodo.10515717" httpUri="https://zenodo.org/record/10515717/files/figure.png" pageId="1" pageNumber="26">Fig. 1</figureCitation>
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). In particular, the oi- configuration of H-21 was confirmed by an ROE correlation with 28-Me. Other key ROE correlations were between 28-Me and 27-Me, 27-Me and H-7 (confirming the β- configuration of the 7-(4-hydroxybenzoyl)oxy group), H-7 and H-5, H-6 and H-5 (confirming the β- configuration of the 6-OH group), H-5 and H-3 (confirming the β- configuration of the 3-OH group) and 25-Me and 26-Me. The optical rotation for
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<emphasis id="B91DEA9A2B160A47FED049FFFEF117C8" bold="true" box="[321,334,1214,1233]" pageId="1" pageNumber="26">1</emphasis>
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of
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||
<emphasis id="B91DEA9A2B160A47FEFD49FCFEC617CB" bold="true" box="[364,377,1213,1234]" italics="true" pageId="1" pageNumber="26">u</emphasis>
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<subScript id="17ED34CD2B160A47FEE84989FE3B17CD" attach="right" box="[377,388,1224,1236]" fontSize="5" pageId="1" pageNumber="26">D</subScript>
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= +45.7 (
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<emphasis id="B91DEA9A2B160A47FE4E49FCFE5617C8" box="[479,489,1213,1233]" italics="true" pageId="1" pageNumber="26">c</emphasis>
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||
0.54, MeOH) had the same sign as the literature value of
|
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<emphasis id="B91DEA9A2B160A47FE184998FE2917F7" bold="true" box="[393,406,1241,1262]" italics="true" pageId="1" pageNumber="26">u</emphasis>
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<subScript id="17ED34CD2B160A47FE0749A5FE1E17E9" attach="right" box="[406,417,1252,1264]" fontSize="5" pageId="1" pageNumber="26">D</subScript>
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||
= +10 (
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<emphasis id="B91DEA9A2B160A47FE7C4998FE4817F4" box="[493,503,1241,1261]" italics="true" pageId="1" pageNumber="26">c</emphasis>
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||
0.79, CHCl
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||
).
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</paragraph>
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<paragraph id="8BD636882B160A47FFE749B7FF2C15FA" blockId="1.[87,758,488,2015]" pageId="1" pageNumber="26">
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||
The molecular formula of
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<emphasis id="B91DEA9A2B160A47FEE949B7FE3A1610" bold="true" box="[376,389,1270,1289]" pageId="1" pageNumber="26">2</emphasis>
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established by HRESIMS as C
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<subScript id="17ED34CD2B160A47FD3649BEFD051612" attach="right" box="[679,698,1279,1291]" fontSize="5" pageId="1" pageNumber="26">36</subScript>
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H
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<subScript id="17ED34CD2B160A47FD5849BEFD641612" attach="both" box="[713,731,1279,1291]" fontSize="5" pageId="1" pageNumber="26">50</subScript>
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O
|
||
<subScript id="17ED34CD2B160A47FD7A49BEFD4B1612" attach="left" box="[747,756,1279,1291]" fontSize="5" pageId="1" pageNumber="26">6</subScript>
|
||
differed from that of
|
||
<emphasis id="B91DEA9A2B160A47FEA24853FEFF163C" bold="true" box="[307,320,1298,1317]" pageId="1" pageNumber="26">1</emphasis>
|
||
by the inclusion of one additional oxygen atom. Full assignment of the
|
||
<superScript id="7C1C9BC02B160A47FEEA486BFE3B162F" attach="right" box="[379,388,1322,1334]" fontSize="5" pageId="1" pageNumber="26">1</superScript>
|
||
H and
|
||
<superScript id="7C1C9BC02B160A47FE56486BFE65162F" attach="right" box="[455,474,1322,1334]" fontSize="5" pageId="1" pageNumber="26">13</superScript>
|
||
C NMR spectra of
|
||
<emphasis id="B91DEA9A2B160A47FD1C486FFD251658" bold="true" box="[653,666,1326,1345]" pageId="1" pageNumber="26">2</emphasis>
|
||
was carried out in both CDCl
|
||
<subScript id="17ED34CD2B160A47FEBB4812FE8C1646" attach="left" box="[298,307,1363,1375]" fontSize="5" pageId="1" pageNumber="26">3</subScript>
|
||
and MeOH-
|
||
<emphasis id="B91DEA9A2B160A47FE3D4808FE071644" box="[428,440,1353,1373]" italics="true" pageId="1" pageNumber="26">d</emphasis>
|
||
<subScript id="17ED34CD2B160A47FE294812FE7E1646" attach="left" box="[440,449,1363,1375]" fontSize="5" pageId="1" pageNumber="26">4</subScript>
|
||
. Comparison of the latter with the analogous assignments for
|
||
<emphasis id="B91DEA9A2B160A47FE334827FE101660" bold="true" box="[418,431,1382,1401]" pageId="1" pageNumber="26">1</emphasis>
|
||
indicated that
|
||
<emphasis id="B91DEA9A2B160A47FDC74827FDDC1660" bold="true" box="[598,611,1382,1401]" pageId="1" pageNumber="26">2</emphasis>
|
||
possessed an oxygenated methine in place of a methylene group. In the COSY spectrum (CDCl
|
||
<subScript id="17ED34CD2B160A47FF6B48E6FEBC16AA" attach="left" box="[250,259,1447,1459]" fontSize="5" pageId="1" pageNumber="26">3</subScript>
|
||
), the oxygenated methine (
|
||
<emphasis id="B91DEA9A2B160A47FDBF48DCFD8616A8" bold="true" box="[558,569,1437,1457]" italics="true" pageId="1" pageNumber="26">δ</emphasis>
|
||
<subScript id="17ED34CD2B160A47FDA848E6FDFA16AA" attach="left" box="[569,581,1447,1459]" fontSize="5" pageId="1" pageNumber="26">H</subScript>
|
||
4.30) correlated with H-9 (
|
||
<emphasis id="B91DEA9A2B160A47FF5948F8FF6C16D4" bold="true" box="[200,211,1465,1485]" italics="true" pageId="1" pageNumber="26">δ</emphasis>
|
||
<subScript id="17ED34CD2B160A47FF424882FF6016D6" attach="left" box="[211,223,1475,1487]" fontSize="5" pageId="1" pageNumber="26">H</subScript>
|
||
1.65) and 12-
|
||
<collectingCountry id="F37E76182B160A47FEE348F8FE2A16D5" box="[370,405,1465,1484]" name="Switzerland" pageId="1" pageNumber="26">CH</collectingCountry>
|
||
<subScript id="17ED34CD2B160A47FE044882FE2116D6" attach="left" box="[405,414,1475,1487]" fontSize="5" pageId="1" pageNumber="26">2</subScript>
|
||
(
|
||
<emphasis id="B91DEA9A2B160A47FE2148F8FE0416D4" bold="true" box="[432,443,1465,1485]" italics="true" pageId="1" pageNumber="26">δ</emphasis>
|
||
<subScript id="17ED34CD2B160A47FE2A4882FE7816D6" attach="left" box="[443,455,1475,1487]" fontSize="5" pageId="1" pageNumber="26">H</subScript>
|
||
1.81 and 1.59). Similarly, in the HMBC spectrum acquired in CDCl
|
||
<subScript id="17ED34CD2B160A47FE41489FFE6616F3" attach="left" box="[464,473,1502,1514]" fontSize="5" pageId="1" pageNumber="26">3</subScript>
|
||
, correlations were observed from
|
||
<emphasis id="B91DEA9A2B160A47FF1F48B0FF26151C" bold="true" box="[142,153,1521,1541]" italics="true" pageId="1" pageNumber="26">δ</emphasis>
|
||
<subScript id="17ED34CD2B160A47FF0848BBFF1A151F" attach="left" box="[153,165,1530,1542]" fontSize="5" pageId="1" pageNumber="26">H</subScript>
|
||
4.30 to C-8 (
|
||
<emphasis id="B91DEA9A2B160A47FEB848B0FE8B151C" bold="true" box="[297,308,1521,1541]" italics="true" pageId="1" pageNumber="26">δ</emphasis>
|
||
<subScript id="17ED34CD2B160A47FEA548BBFE81151F" attach="left" box="[308,318,1530,1542]" fontSize="5" pageId="1" pageNumber="26">C</subScript>
|
||
48.4), C-9 (
|
||
<emphasis id="B91DEA9A2B160A47FE2248B0FE01151C" bold="true" box="[435,446,1521,1541]" italics="true" pageId="1" pageNumber="26">δ</emphasis>
|
||
<subScript id="17ED34CD2B160A47FE2F48BBFE77151F" attach="left" box="[446,456,1530,1542]" fontSize="5" pageId="1" pageNumber="26">C</subScript>
|
||
54.2), and C-10 (
|
||
<emphasis id="B91DEA9A2B160A47FDE748B0FD3E151C" bold="true" box="[630,641,1521,1541]" italics="true" pageId="1" pageNumber="26">δ</emphasis>
|
||
<subScript id="17ED34CD2B160A47FD1048BBFD34151F" attach="left" box="[641,651,1530,1542]" fontSize="5" pageId="1" pageNumber="26">C</subScript>
|
||
39.8). The additional hydroxyl group was therefore located at C-11. NOE connectivities observed between both 25-Me and 26-Me with H-11 indicated that this hydrogen atom was β- oriented. The significant downfield shift (Δ
|
||
<emphasis id="B91DEA9A2B160A47FE844B21FE9F156D" bold="true" box="[277,288,1632,1652]" italics="true" pageId="1" pageNumber="26">δ</emphasis>
|
||
+ 1.06 ppm) experienced by H-1β (
|
||
<emphasis id="B91DEA9A2B160A47FD1C4B21FD27156D" bold="true" box="[653,664,1632,1652]" italics="true" pageId="1" pageNumber="26">δ</emphasis>
|
||
<subScript id="17ED34CD2B160A47FD094B2BFD1B156F" attach="left" box="[664,676,1642,1654]" fontSize="5" pageId="1" pageNumber="26">H</subScript>
|
||
<quantity id="4C919B6D2B160A47FD3C4B20FD4A156D" box="[685,757,1633,1652]" metricMagnitude="-2" metricUnit="m" metricValue="7.3406" pageId="1" pageNumber="26" unit="in" value="2.89">2.89 in</quantity>
|
||
CDCl
|
||
<subScript id="17ED34CD2B160A47FF194BC7FF2E158B" attach="left" box="[136,145,1670,1682]" fontSize="5" pageId="1" pageNumber="26">3</subScript>
|
||
) was also consistent with an oi- configuration for 11-OH (
|
||
<bibRefCitation id="EFF84B792B160A47FFCE4BD8FEAD15B5" author="Isaka, M. & Palasarn, S. & Supothina, S. & Komwijit, S." box="[95,274,1689,1708]" pageId="1" pageNumber="26" pagination="782 - 789" refId="ref8213" refString="Isaka, M., Palasarn, S., Supothina, S., Komwijit, S., Luangsa-ard, J. J., 2011. Bioactive compounds from the scale insect pathogenic fungus Conoideocrella tenuis BCC 18627. J. Nat. Prod. 74, 782 - 789." type="journal article" year="2011">Isaka et al., 2011</bibRefCitation>
|
||
). Compound
|
||
<emphasis id="B91DEA9A2B160A47FE304BD8FE1115B5" bold="true" box="[417,430,1689,1708]" pageId="1" pageNumber="26">2</emphasis>
|
||
was therefore 3β,6β,11oi- trihydroxy-7β-[(4-hydroxybenzoyl)oxy]-21oi
|
||
<emphasis id="B91DEA9A2B160A47FE4F4BF2FE5215DE" box="[478,493,1715,1735]" italics="true" pageId="1" pageNumber="26">H</emphasis>
|
||
-24-norhopa-4(23),22(29)- diene.
|
||
</paragraph>
|
||
<paragraph id="8BD636882B160A47FFE74BADFCDE1218" blockId="1.[87,758,488,2015]" lastBlockId="1.[805,1475,180,1596]" pageId="1" pageNumber="26">
|
||
The
|
||
<superScript id="7C1C9BC02B160A47FF354BA9FF1215ED" attach="right" box="[164,173,1768,1780]" fontSize="5" pageId="1" pageNumber="26">1</superScript>
|
||
H NMR spectrum of
|
||
<emphasis id="B91DEA9A2B160A47FE174BADFE2C15E6" bold="true" box="[390,403,1772,1791]" pageId="1" pageNumber="26">3</emphasis>
|
||
was similar to that of
|
||
<emphasis id="B91DEA9A2B160A47FD164BADFD2B15E6" bold="true" box="[647,660,1772,1791]" pageId="1" pageNumber="26">2</emphasis>
|
||
with the exception that H-11 (
|
||
<emphasis id="B91DEA9A2B160A47FEAA4A49FEF91405" bold="true" box="[315,326,1800,1820]" italics="true" pageId="1" pageNumber="26">δ</emphasis>
|
||
<subScript id="17ED34CD2B160A47FED74A50FEED1404" attach="left" box="[326,338,1809,1821]" fontSize="5" pageId="1" pageNumber="26">H</subScript>
|
||
<quantity id="4C919B6D2B160A47FECD4A49FE1A1402" box="[348,421,1800,1819]" metricMagnitude="-1" metricUnit="m" metricValue="1.39192" pageId="1" pageNumber="26" unit="in" value="5.48">5.48 in</quantity>
|
||
MeOH-
|
||
<emphasis id="B91DEA9A2B160A47FE664A46FDBC1402" box="[503,515,1799,1819]" italics="true" pageId="1" pageNumber="26">d</emphasis>
|
||
<subScript id="17ED34CD2B160A47FD954A50FDB21404" attach="right" box="[516,525,1809,1821]" fontSize="5" pageId="1" pageNumber="26">4</subScript>
|
||
) showed a significant downfield shift (Δ
|
||
<emphasis id="B91DEA9A2B160A47FE844A62FE9F142E" bold="true" box="[277,288,1827,1847]" italics="true" pageId="1" pageNumber="26">δ</emphasis>
|
||
+ 1.28 ppm) and a 3H singlet at
|
||
<emphasis id="B91DEA9A2B160A47FDE84A62FD3B142E" bold="true" box="[633,644,1827,1847]" italics="true" pageId="1" pageNumber="26">δ</emphasis>
|
||
<subScript id="17ED34CD2B160A47FD154A6CFD2F1420" attach="left" box="[644,656,1837,1849]" fontSize="5" pageId="1" pageNumber="26">H</subScript>
|
||
2.03 was observed corresponding to an acetyl group (
|
||
<emphasis id="B91DEA9A2B160A47FD8B4A7EFD9A144A" bold="true" box="[538,549,1855,1875]" italics="true" pageId="1" pageNumber="26">δ</emphasis>
|
||
<subScript id="17ED34CD2B160A47FDB54A08FD91144C" attach="left" box="[548,558,1865,1877]" fontSize="5" pageId="1" pageNumber="26">C</subScript>
|
||
172.1 and 22.1). In the HMBC spectrum, H-11 correlated with the acetyl carbonyl group at
|
||
<emphasis id="B91DEA9A2B160A47FF214A36FF041492" bold="true" box="[176,187,1911,1931]" italics="true" pageId="1" pageNumber="26">δ</emphasis>
|
||
<subScript id="17ED34CD2B160A47FF2A4AC0FF7A1494" attach="left" box="[187,197,1921,1933]" fontSize="5" pageId="1" pageNumber="26">C</subScript>
|
||
172.1 and also with C-9 (
|
||
<emphasis id="B91DEA9A2B160A47FE504A36FE731492" bold="true" box="[449,460,1911,1931]" italics="true" pageId="1" pageNumber="26">δ</emphasis>
|
||
<subScript id="17ED34CD2B160A47FE5D4AC0FE691494" attach="left" box="[460,470,1921,1933]" fontSize="5" pageId="1" pageNumber="26">C</subScript>
|
||
52.9). In the COSY spectrum, H-11 correlated with both H-9 and 12-
|
||
<collectingCountry id="F37E76182B160A47FE4E4AD5FDBD14BE" box="[479,514,1940,1959]" name="Switzerland" pageId="1" pageNumber="26">CH</collectingCountry>
|
||
<subScript id="17ED34CD2B160A47FD934ADCFDB414B0" attach="left" box="[514,523,1949,1961]" fontSize="5" pageId="1" pageNumber="26">2</subScript>
|
||
as expected. The magnitude of the coupling constant
|
||
<emphasis id="B91DEA9A2B160A47FE0E4AEEFE1914DA" box="[415,422,1967,1987]" italics="true" pageId="1" pageNumber="26">J</emphasis>
|
||
<subScript id="17ED34CD2B160A47FE344AF8FE7B14DC" attach="left" box="[421,452,1977,1989]" fontSize="5" pageId="1" pageNumber="26">9,11</subScript>
|
||
of 11.3 Hz indicated a diaxial relationship between these hydrogen atoms such that H-11 was β- oriented. Compound
|
||
<emphasis id="B91DEA9A2B160A47FB874DF7FB9C13D0" bold="true" box="[1046,1059,182,201]" pageId="1" pageNumber="26">3</emphasis>
|
||
was therefore 11oi- acetoxy-3β,6β- dihydroxy-7β-[(4-hydroxybenzoyl)oxy]-21oi
|
||
<emphasis id="B91DEA9A2B160A47FB3A4D90FB0513FC" box="[1195,1210,209,229]" italics="true" pageId="1" pageNumber="26">H</emphasis>
|
||
-24-norhopa-4(23),22(29)- diene.
|
||
</paragraph>
|
||
<paragraph id="8BD636882B160A47FCD54C4BFC131175" blockId="1.[805,1475,180,1596]" pageId="1" pageNumber="26">
|
||
The main difference between the
|
||
<superScript id="7C1C9BC02B160A47FB004C47FB25120B" attach="right" box="[1169,1178,262,274]" fontSize="5" pageId="1" pageNumber="26">1</superScript>
|
||
H NMR spectra of
|
||
<emphasis id="B91DEA9A2B160A47FADC4C4BFAE51204" bold="true" box="[1357,1370,266,285]" pageId="1" pageNumber="26">4</emphasis>
|
||
and
|
||
<emphasis id="B91DEA9A2B160A47FA184C4BFA291204" bold="true" box="[1417,1430,266,285]" pageId="1" pageNumber="26">2</emphasis>
|
||
was that the former contained resonances corresponding to two 4- hydroxybenzoyl groups rather than one. The first set of resonances was assigned to the 4-hydroxybenzoyl group at 7-OH. The second was placed at 11-OH on the basis of the large downfield shift (Δ
|
||
<emphasis id="B91DEA9A2B160A47FA234C38FA021294" bold="true" box="[1458,1469,377,397]" italics="true" pageId="1" pageNumber="26">δ</emphasis>
|
||
+ 1.56 ppm) experienced by H-11 (
|
||
<emphasis id="B91DEA9A2B160A47FB114CD4FB3412B0" bold="true" box="[1152,1163,405,425]" italics="true" pageId="1" pageNumber="26">δ</emphasis>
|
||
<subScript id="17ED34CD2B160A47FB1A4CDEFB2812B2" attach="left" box="[1163,1175,415,427]" fontSize="5" pageId="1" pageNumber="26">H</subScript>
|
||
5.76) and the long-range correlation between this proton and the remaining 4-hydroxybenzoyl carbonyl at
|
||
<emphasis id="B91DEA9A2B160A47FC304C8CFC1312F8" bold="true" box="[929,940,461,481]" italics="true" pageId="1" pageNumber="26">δ</emphasis>
|
||
<subScript id="17ED34CD2B160A47FC3D4C97FC0912FB" attach="left" box="[940,950,470,482]" fontSize="5" pageId="1" pageNumber="26">C</subScript>
|
||
167.3. As expected, H-11 correlated with H-9 and 12-
|
||
<collectingCountry id="F37E76182B160A47FCD34CA8FCDA12E5" box="[834,869,489,508]" name="Switzerland" pageId="1" pageNumber="26">CH</collectingCountry>
|
||
<quantity id="4C919B6D2B160A47FCF54CB3FC3512E5" box="[868,906,489,510]" metricMagnitude="-2" metricUnit="m" metricValue="5.08" pageId="1" pageNumber="26" unit="in" value="2.0">
|
||
<subScript id="17ED34CD2B160A47FCF54CB3FCD212E7" attach="left" box="[868,877,498,510]" fontSize="5" pageId="1" pageNumber="26">2</subScript>
|
||
in
|
||
</quantity>
|
||
the COSY spectrum. In common with
|
||
<emphasis id="B91DEA9A2B160A47FA884CA8FA9912E5" bold="true" box="[1305,1318,489,508]" pageId="1" pageNumber="26">3</emphasis>
|
||
,
|
||
<emphasis id="B91DEA9A2B160A47FAA34CA9FA8612E5" box="[1330,1337,488,508]" italics="true" pageId="1" pageNumber="26">J</emphasis>
|
||
<subScript id="17ED34CD2B160A47FAA84CB3FAE712E7" attach="left" box="[1337,1368,498,510]" fontSize="5" pageId="1" pageNumber="26">9,11</subScript>
|
||
for
|
||
<emphasis id="B91DEA9A2B160A47FA144CA8FA2D12E5" bold="true" box="[1413,1426,489,508]" pageId="1" pageNumber="26">4</emphasis>
|
||
was also 11.3 Hz, confirming a diaxial relationship between H-9 and H-11 with the latter β- oriented. Thus compound
|
||
<emphasis id="B91DEA9A2B160A47FA9F4F60FAA4112D" bold="true" box="[1294,1307,545,564]" pageId="1" pageNumber="26">4</emphasis>
|
||
was 3β,6β- dihydroxy-7β,11oi- di[(4-hydroxybenzoyl)oxy]-21oi
|
||
<emphasis id="B91DEA9A2B160A47FB604F7DFABF1149" box="[1265,1280,572,592]" italics="true" pageId="1" pageNumber="26">H</emphasis>
|
||
-24-norhopa-4(23), 22(29)-diene.
|
||
</paragraph>
|
||
<paragraph id="8BD636882B160A47FCD54F34FB4B10A3" blockId="1.[805,1475,180,1596]" pageId="1" pageNumber="26">
|
||
A full set of
|
||
<superScript id="7C1C9BC02B160A47FC484F30FC5D1164" attach="right" box="[985,994,625,637]" fontSize="5" pageId="1" pageNumber="26">1</superScript>
|
||
H and
|
||
<superScript id="7C1C9BC02B160A47FBA34F30FBFB1164" attach="right" box="[1074,1092,625,637]" fontSize="5" pageId="1" pageNumber="26">13</superScript>
|
||
C NMR resonance assignments was obtained for
|
||
<emphasis id="B91DEA9A2B160A47FC3C4FD0FC0511BD" bold="true" box="[941,954,657,676]" pageId="1" pageNumber="26">5</emphasis>
|
||
using COSY, HSQC and HMBC data. Compound
|
||
<emphasis id="B91DEA9A2B160A47FA244FD0FA7D11BD" bold="true" box="[1461,1474,657,676]" pageId="1" pageNumber="26">5</emphasis>
|
||
was isomeric with
|
||
<emphasis id="B91DEA9A2B160A47FC674FEDFBBC11A6" bold="true" box="[1014,1027,684,703]" pageId="1" pageNumber="26">1</emphasis>
|
||
and could be readily identified as a 24- norhopadiene derivative. The difference between the two compounds resided in the structure of the E-ring. In the case of
|
||
<emphasis id="B91DEA9A2B160A47FA194FA5FA2A11EE" bold="true" box="[1416,1429,740,759]" pageId="1" pageNumber="26">5</emphasis>
|
||
, the E-ring was a fused cyclopentene with an isopropyl group at C-21, whereas
|
||
<emphasis id="B91DEA9A2B160A47FC134E5DFC301036" bold="true" box="[898,911,796,815]" pageId="1" pageNumber="26">1</emphasis>
|
||
featured an isopropylidene group attached to C-21 of a fused cyclopentane moiety. The multiplet structure and
|
||
<emphasis id="B91DEA9A2B160A47FAE24E76FAC51052" box="[1395,1402,823,843]" italics="true" pageId="1" pageNumber="26">J</emphasis>
|
||
-values for H-3, H-6, and H-7 (MeOH-
|
||
<emphasis id="B91DEA9A2B160A47FBC54E12FBDF107E" box="[1108,1120,851,871]" italics="true" pageId="1" pageNumber="26">d</emphasis>
|
||
<subScript id="17ED34CD2B160A47FBF14E1CFBD61070" attach="left" box="[1120,1129,861,873]" fontSize="5" pageId="1" pageNumber="26">4</subScript>
|
||
) were similar for
|
||
<emphasis id="B91DEA9A2B160A47FAB04E15FA91107E" bold="true" box="[1313,1326,852,871]" pageId="1" pageNumber="26">5</emphasis>
|
||
and
|
||
<emphasis id="B91DEA9A2B160A47FAF04E15FAD1107E" bold="true" box="[1377,1390,852,871]" pageId="1" pageNumber="26">1</emphasis>
|
||
indicating that the configurations of these atoms were conserved between the two compounds. Thus
|
||
<emphasis id="B91DEA9A2B160A47FBBE4ECDFB831086" bold="true" box="[1071,1084,908,927]" pageId="1" pageNumber="26">5</emphasis>
|
||
was 3β,6β- dihydroxy-7β-[(4-hydroxybenzoyl)oxy]-24-norhopa-4(23),17(21)-diene.
|
||
</paragraph>
|
||
<paragraph id="8BD636882B160A47FCD54E82FCDD163C" blockId="1.[805,1475,180,1596]" pageId="1" pageNumber="26">
|
||
The molecular formula of compound
|
||
<emphasis id="B91DEA9A2B160A47FB274E82FB7C10CF" bold="true" box="[1206,1219,963,982]" pageId="1" pageNumber="26">6</emphasis>
|
||
differed from that of
|
||
<emphasis id="B91DEA9A2B160A47FA064E82FA1B10CF" bold="true" box="[1431,1444,963,982]" pageId="1" pageNumber="26">5</emphasis>
|
||
by the inclusion of one additional oxygen atom, and it was also isomeric with
|
||
<emphasis id="B91DEA9A2B160A47FC094EBAFC1A1717" bold="true" box="[920,933,1019,1038]" pageId="1" pageNumber="26">2</emphasis>
|
||
. Analysis of its
|
||
<superScript id="7C1C9BC02B160A47FBD14EB6FBF6171A" attach="right" box="[1088,1097,1015,1027]" fontSize="5" pageId="1" pageNumber="26">1</superScript>
|
||
H and
|
||
<superScript id="7C1C9BC02B160A47FB1B4EB6FB22171A" attach="right" box="[1162,1181,1015,1027]" fontSize="5" pageId="1" pageNumber="26">13</superScript>
|
||
C NMR spectra indicated that
|
||
<emphasis id="B91DEA9A2B160A47FCB44956FC8D1733" bold="true" box="[805,818,1047,1066]" pageId="1" pageNumber="26">6</emphasis>
|
||
was the 11oi- hydroxyl derivative of
|
||
<emphasis id="B91DEA9A2B160A47FB3F4956FB041733" bold="true" box="[1198,1211,1047,1066]" pageId="1" pageNumber="26">5</emphasis>
|
||
. Thus in the HMBC spectrum acquired in CDCl
|
||
<subScript id="17ED34CD2B160A47FB83497DFBA41751" attach="left" box="[1042,1051,1084,1096]" fontSize="5" pageId="1" pageNumber="26">3</subScript>
|
||
, H-11 (
|
||
<emphasis id="B91DEA9A2B160A47FBE14973FBC4175F" bold="true" box="[1136,1147,1074,1094]" italics="true" pageId="1" pageNumber="26">δ</emphasis>
|
||
<subScript id="17ED34CD2B160A47FBEA497DFB381751" attach="left" box="[1147,1159,1084,1096]" fontSize="5" pageId="1" pageNumber="26">H</subScript>
|
||
4.25) correlated with C-8 (
|
||
<emphasis id="B91DEA9A2B160A47FA3C4973FA07175F" bold="true" box="[1453,1464,1074,1094]" italics="true" pageId="1" pageNumber="26">δ</emphasis>
|
||
<subScript id="17ED34CD2B160A47FA29497DFA7D1751" attach="left" box="[1464,1474,1084,1096]" fontSize="5" pageId="1" pageNumber="26">C</subScript>
|
||
48.5), C-9 (
|
||
<emphasis id="B91DEA9A2B160A47FC07490FFC1E177B" bold="true" box="[918,929,1102,1122]" italics="true" pageId="1" pageNumber="26">δ</emphasis>
|
||
<subScript id="17ED34CD2B160A47FC304919FC14177D" attach="left" box="[929,939,1112,1124]" fontSize="5" pageId="1" pageNumber="26">C</subScript>
|
||
54.5), C-10 (
|
||
<emphasis id="B91DEA9A2B160A47FBA1490FFB84177B" bold="true" box="[1072,1083,1102,1122]" italics="true" pageId="1" pageNumber="26">δ</emphasis>
|
||
<subScript id="17ED34CD2B160A47FBAA4919FBFA177D" attach="left" box="[1083,1093,1112,1124]" fontSize="5" pageId="1" pageNumber="26">C</subScript>
|
||
39.8) and C-12 (
|
||
<emphasis id="B91DEA9A2B160A47FB63490FFB42177B" bold="true" box="[1266,1277,1102,1122]" italics="true" pageId="1" pageNumber="26">δ</emphasis>
|
||
<subScript id="17ED34CD2B160A47FB6D4919FAB9177D" attach="left" box="[1276,1286,1112,1124]" fontSize="5" pageId="1" pageNumber="26">C</subScript>
|
||
36.6). Similarly in the COSY spectrum, H-11 correlated with H-9 and 12-
|
||
<collectingCountry id="F37E76182B160A47FAF9492AFA3A1767" box="[1384,1413,1131,1150]" name="Switzerland" pageId="1" pageNumber="26">CH</collectingCountry>
|
||
<subScript id="17ED34CD2B160A47FA144935FA311799" attach="left" box="[1413,1422,1140,1152]" fontSize="5" pageId="1" pageNumber="26">2</subScript>
|
||
. The relative configuration of
|
||
<emphasis id="B91DEA9A2B160A47FBBB49C7FB881780" bold="true" box="[1066,1079,1158,1177]" pageId="1" pageNumber="26">6</emphasis>
|
||
was examined in a series of 1D site selective ROE experiments (
|
||
<figureCitation id="13522A0D2B160A47FBD449E3FBC117AF" box="[1093,1150,1186,1206]" captionStart="Fig" captionStartId="4.[113,139,1947,1961]" captionTargetBox="[348,1256,1425,1918]" captionTargetId="figure-405@4.[348,1256,1425,1919]" captionTargetPageId="4" captionText="Fig. 2. Relationship between bruchid mortality and number of eggs laid per female when exposed for six days to crude extracts and isolated nor-hopane compounds from Zanha africana root bark and a positive control (rotenone)." figureDoi="http://doi.org/10.5281/zenodo.10485293" httpUri="https://zenodo.org/record/10485293/files/figure.png" pageId="1" pageNumber="26">Fig. 2</figureCitation>
|
||
). In particular, H-11 correlated with both 25-Me and 26-Me, as was also found with the isomeric
|
||
<emphasis id="B91DEA9A2B160A47FCB4499BFC8D17F4" bold="true" box="[805,818,1242,1261]" pageId="1" pageNumber="26">2</emphasis>
|
||
, allowing the β- orientation to be assigned. Thus
|
||
<emphasis id="B91DEA9A2B160A47FA86499BFA9B17F4" bold="true" box="[1303,1316,1242,1261]" pageId="1" pageNumber="26">6</emphasis>
|
||
was 3β,6β,11oitrihydroxy-7β-[(4-hydroxybenzoyl)oxy]-24-norhopa-4(23),17(21)- diene.
|
||
</paragraph>
|
||
<paragraph id="8BD636882B160A47FCD5486FFBF91525" blockId="1.[805,1475,180,1596]" pageId="1" pageNumber="26">
|
||
Comparison of the
|
||
<superScript id="7C1C9BC02B160A47FB93486BFBB4162F" attach="right" box="[1026,1035,1322,1334]" fontSize="5" pageId="1" pageNumber="26">1</superScript>
|
||
H NMR spectra of
|
||
<emphasis id="B91DEA9A2B160A47FB50486FFB711658" bold="true" box="[1217,1230,1326,1345]" pageId="1" pageNumber="26">7</emphasis>
|
||
with
|
||
<emphasis id="B91DEA9A2B160A47FA99486FFAAA1658" bold="true" box="[1288,1301,1326,1345]" pageId="1" pageNumber="26">6</emphasis>
|
||
indicated that 2-
|
||
<collectingCountry id="F37E76182B160A47FCB4480BFCFD1644" box="[805,834,1354,1373]" name="Switzerland" pageId="1" pageNumber="26">CH</collectingCountry>
|
||
<subScript id="17ED34CD2B160A47FCD34812FCF41646" attach="left" box="[834,843,1363,1375]" fontSize="5" pageId="1" pageNumber="26">2</subScript>
|
||
, H-5 and 23-
|
||
<collectingCountry id="F37E76182B160A47FC5B480BFC531644" box="[970,1004,1354,1373]" name="Switzerland" pageId="1" pageNumber="26">CH</collectingCountry>
|
||
<subScript id="17ED34CD2B160A47FC7D4812FC4A1646" attach="left" box="[1004,1013,1363,1375]" fontSize="5" pageId="1" pageNumber="26">2</subScript>
|
||
were all downfield shifted, and the doublet of doublets resonance of H-3 was lacking. In the
|
||
<superScript id="7C1C9BC02B160A47FB6F4823FAAE1677" attach="right" box="[1278,1297,1378,1390]" fontSize="5" pageId="1" pageNumber="26">13</superScript>
|
||
C NMR spectrum, there were 3 rather than 4 resonances attributable to oxygenated methines and a new resonance at
|
||
<emphasis id="B91DEA9A2B160A47FB1248DCFB3116A8" bold="true" box="[1155,1166,1437,1457]" italics="true" pageId="1" pageNumber="26">δ</emphasis>
|
||
<subScript id="17ED34CD2B160A47FB1F48E6FB2716AA" attach="left" box="[1166,1176,1447,1459]" fontSize="5" pageId="1" pageNumber="26">C</subScript>
|
||
204.8 assigned to a carbonyl group. The location of the latter was readily established as C-3 from HMBC data, with correlations from 1-
|
||
<collectingCountry id="F37E76182B160A47FB734894FAB816F1" box="[1250,1287,1493,1512]" name="Switzerland" pageId="1" pageNumber="26">CH</collectingCountry>
|
||
<subScript id="17ED34CD2B160A47FA97489FFAB016F3" attach="left" box="[1286,1295,1502,1514]" fontSize="5" pageId="1" pageNumber="26">2</subScript>
|
||
, 2-
|
||
<collectingCountry id="F37E76182B160A47FABE4894FAEE16F1" box="[1327,1361,1493,1512]" name="Switzerland" pageId="1" pageNumber="26">CH</collectingCountry>
|
||
<subScript id="17ED34CD2B160A47FAC0489FFAE516F3" attach="left" box="[1361,1370,1502,1514]" fontSize="5" pageId="1" pageNumber="26">2</subScript>
|
||
, H-5, and 23-
|
||
<collectingCountry id="F37E76182B160A47FCD348B0FCDB151D" box="[834,868,1521,1540]" name="Switzerland" pageId="1" pageNumber="26">CH</collectingCountry>
|
||
<subScript id="17ED34CD2B160A47FCF548BBFCD2151F" attach="left" box="[868,877,1530,1542]" fontSize="5" pageId="1" pageNumber="26">2</subScript>
|
||
to
|
||
<emphasis id="B91DEA9A2B160A47FC0748B0FC1E151C" bold="true" box="[918,929,1521,1541]" italics="true" pageId="1" pageNumber="26">δ</emphasis>
|
||
<subScript id="17ED34CD2B160A47FC3048BBFC14151F" attach="left" box="[929,939,1530,1542]" fontSize="5" pageId="1" pageNumber="26">C</subScript>
|
||
204.8 detected in the spectrum. Compound
|
||
<emphasis id="B91DEA9A2B160A47FA1548B0FA2E151D" bold="true" box="[1412,1425,1521,1540]" pageId="1" pageNumber="26">7</emphasis>
|
||
was thus 6β,11oi- dihydroxy-7β-[(4-hydroxybenzoyl)oxy]-3-oxo-24- norhopa-4(23),17(21)-diene.
|
||
</paragraph>
|
||
</subSubSection>
|
||
</treatment>
|
||
</document> |