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176 lines
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<document id="CD91AF3E97DD5E2D4B1BDB868D020882" ID-DOI="10.1016/j.phytochem.2020.112598" ID-ISSN="1873-3700" ID-Zenodo-Dep="8291902" IM.bibliography_approvedBy="felipe" IM.illustrations_approvedBy="juliana" IM.materialsCitations_approvedBy="juliana" IM.metadata_approvedBy="juliana" IM.tables_approvedBy="juliana" IM.taxonomicNames_approvedBy="juliana" IM.treatments_approvedBy="juliana" checkinTime="1693247058183" checkinUser="felipe" docAuthor="Eliwa, Duaa, Albadry, Mohamed A., Ibrahim, Abdel-Rahim S., Kabbash, Amal, Meepagala, Kumudini, Khan, Ikhlas A., El-Aasr, Mona & Ross, Samir A." docDate="2021" docId="03D387DCFFABFFC7CF0A8CAD473BCAF7" docLanguage="en" docName="Phytochemistry.183.112598.pdf" docOrigin="Phytochemistry (112598) 183" docSource="http://dx.doi.org/10.1016/j.phytochem.2020.112598" docStyle="DocumentStyle:F36D69FC8B198FBE91029DF9C24697D3.5:Phytochemistry.2020-.journal_article" docStyleId="F36D69FC8B198FBE91029DF9C24697D3" docStyleName="Phytochemistry.2020-.journal_article" docStyleVersion="5" docTitle="Aspergillus niger NRRL" docType="treatment" docVersion="1" lastPageNumber="7" masterDocId="FFEAFFA4FFAEFFC1CC388A394439CD4C" masterDocTitle="Biotransformation of papaverine and in silico docking studies of the metabolites on human phosphodiesterase 10 a" masterLastPageNumber="12" masterPageNumber="1" pageNumber="6" updateTime="1693407186317" updateUser="juliana">
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<mods:title id="73DB3494A1D9D0D89B2B6884EB23C081">Biotransformation of papaverine and in silico docking studies of the metabolites on human phosphodiesterase 10 a</mods:title>
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<mods:namePart id="4907E1C537931B2BF0057F4C8ECD5B9A">Eliwa, Duaa</mods:namePart>
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<mods:affiliation id="76DDCA041178960BC9D60762C679F038">* & National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, MS, 38677, USA & Department of Pharmacognosy, Faculty of Pharmacy, Tanta University, Tanta, 31527, Egypt</mods:affiliation>
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<mods:namePart id="5AD08B0AF2C258451F96EF743B76EF5D">Albadry, Mohamed A.</mods:namePart>
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<mods:affiliation id="AD7912E8C6EB60B020E9C7E8D4F15C02">* & National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, MS, 38677, USA</mods:affiliation>
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<mods:namePart id="D12A5258AE6FC2270EC2DF344EEE5F18">Ibrahim, Abdel-Rahim S.</mods:namePart>
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<mods:affiliation id="11BB55CE6CB0072388F4F63F3313B7A5">Department of Pharmacognosy, Faculty of Pharmacy, Tanta University, Tanta, 31527, Egypt</mods:affiliation>
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<mods:namePart id="105E41F64BEBFD23B38C74220F1981E4">Kabbash, Amal</mods:namePart>
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<mods:affiliation id="F68849C51F3C10F124347403D7A5DC00">Department of Pharmacognosy, Faculty of Pharmacy, Tanta University, Tanta, 31527, Egypt</mods:affiliation>
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<mods:namePart id="84FE6DE72146663626751A09FD694E53">Meepagala, Kumudini</mods:namePart>
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<mods:affiliation id="C602BB508803EC552F302975F3B68191">USDA-ARS, Natural Products Utilization Research Unit, University, MS, USA</mods:affiliation>
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<mods:namePart id="E3730D7DE9414BF19FFD6C65F09A7E9F">Khan, Ikhlas A.</mods:namePart>
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<mods:affiliation id="7DA57D5CCFFAC03D0C47469EDD3C4F32">* & National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, MS, 38677, USA & * & Division of Pharmacognosy, Department of Biomolecular Sciences, School of Pharmacy, University of Mississippi, MS, 38677, USA</mods:affiliation>
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<mods:namePart id="E0984E9B2B354DCFC8D88FE7DA0FC978">El-Aasr, Mona</mods:namePart>
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<mods:affiliation id="A0D2697D71E2DE6DC46DD89F8733B6A0">Department of Pharmacognosy, Faculty of Pharmacy, Tanta University, Tanta, 31527, Egypt</mods:affiliation>
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<mods:namePart id="010126D8104ECE89DC251164F6AFA210">Ross, Samir A.</mods:namePart>
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<mods:affiliation id="7CC347CE80DC10694DD060DB9A5983CB">* & National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, MS, 38677, USA & * & Division of Pharmacognosy, Department of Biomolecular Sciences, School of Pharmacy, University of Mississippi, MS, 38677, USA</mods:affiliation>
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<mods:title id="5EF51BFD479D3D2A414728AB5B7D7D47">Phytochemistry</mods:title>
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<mods:date id="18EE93C304025FEC1D4809B77B90F64D">2021</mods:date>
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<mods:title id="F09A964BAEB70EF5739FFCDCA8195253">112598</mods:title>
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<mods:number id="F2A13C29A4B38D51ACCE660860CD3D05">2021-03-31</mods:number>
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<mods:number id="ABC806EBCB86EFF6B1E392137C4D7968">183</mods:number>
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<mods:start id="6FC83632F157F2A77183F3839AD57EAF">1</mods:start>
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<mods:url id="E6D7BB8F18209DA900770A72E6A6E6D5">http://dx.doi.org/10.1016/j.phytochem.2020.112598</mods:url>
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<mods:classification id="EFAAF9C73EC9A77AA21E826E78D13671">journal article</mods:classification>
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<mods:identifier id="AB617D9535257BD6CCFE73F65E8AAABA" type="DOI">10.1016/j.phytochem.2020.112598</mods:identifier>
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<mods:identifier id="70AE3DA154176502D73A99DD02863B43" type="ISSN">1873-3700</mods:identifier>
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<mods:identifier id="3061A998407AB863561B49C85E8106FD" type="Zenodo-Dep">8291902</mods:identifier>
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<treatment id="03D387DCFFABFFC7CF0A8CAD473BCAF7" LSID="urn:lsid:plazi:treatment:03D387DCFFABFFC7CF0A8CAD473BCAF7" httpUri="http://treatment.plazi.org/id/03D387DCFFABFFC7CF0A8CAD473BCAF7" lastPageId="6" lastPageNumber="7" pageId="5" pageNumber="6">
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<subSubSection id="C3606541FFABFFC4CF0A8CAD414FCBEB" box="[818,1398,1683,1703]" pageId="5" pageNumber="6" type="nomenclature">
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<paragraph id="8BC536CAFFABFFC4CF0A8CAD414FCBEB" blockId="5.[818,1398,1683,1703]" box="[818,1398,1683,1703]" pageId="5" pageNumber="6">
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<emphasis id="B90EEAD8FFABFFC4CF0A8CAD414FCBEB" bold="true" box="[818,1398,1683,1703]" italics="true" pageId="5" pageNumber="6">
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3.5. Microbial transformation using
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<taxonomicName id="4C7A4D49FFABFFC4C8458CAA4136CBEB" authority="NRRL" authorityName="NRRL" box="[1149,1295,1683,1703]" class="Agaricomycetes" family="Fomitopsidaceae" genus="Aspergillus" kingdom="Fungi" order="Polyporales" pageId="5" pageNumber="6" phylum="Basidiomycota" rank="species" species="niger">Aspergillus niger</taxonomicName>
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NRRL 322
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</emphasis>
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</paragraph>
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</subSubSection>
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<subSubSection id="C3606541FFABFFC7CF698CF2473BCAF7" lastPageId="6" lastPageNumber="7" pageId="5" pageNumber="6" type="description">
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<paragraph id="8BC536CAFFABFFC7CF698CF245F9CA58" blockId="5.[818,1488,1739,1982]" lastBlockId="6.[100,770,1793,1981]" lastPageId="6" lastPageNumber="7" pageId="5" pageNumber="6">
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Biotransformation of papaverine using
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<taxonomicName id="4C7A4D49FFABFFC4C8F68CF2415BCB92" authority="NRRL" authorityName="NRRL" box="[1230,1378,1739,1758]" class="Agaricomycetes" family="Fomitopsidaceae" genus="Aspergillus" kingdom="Fungi" order="Polyporales" pageId="5" pageNumber="6" phylum="Basidiomycota" rank="species" species="niger">
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<emphasis id="B90EEAD8FFABFFC4C8F68CF2415BCB92" bold="true" box="[1230,1378,1739,1758]" italics="true" pageId="5" pageNumber="6">Aspergillus niger</emphasis>
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</taxonomicName>
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NRRL 322 afforded to two metabolites (2 and 3). The residue (1 gm) was dissolved in 50 ml of methanol/dichloromethane mixture (1:1) and adsorbed onto 1 gm Celite and dried. The adsorbed sample was placed onto a glass column (50 ×
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<quantity id="4C829B2FFFABFFC4CFF08D024036CA02" box="[968,1039,1851,1870]" metricMagnitude="-2" metricUnit="m" metricValue="2.5" pageId="5" pageNumber="6" unit="cm" value="2.5">2.5 cm</quantity>
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) packed with silica after making a slurry in dichloromethane. The column was isocratically eluted with dichloromethane: methanol (97.5:2.5) and 10 ml fractions were collected. Fractions 20–44 were pooled together to give mixture of
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<emphasis id="B90EEAD8FFABFFC4C95D8DB64148CAEE" bold="true" box="[1381,1393,1935,1954]" pageId="5" pageNumber="6">2</emphasis>
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and
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<emphasis id="B90EEAD8FFABFFC4C99E8DB6418BCAEE" bold="true" box="[1446,1458,1935,1954]" pageId="5" pageNumber="6">3</emphasis>
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as determined by TLC. The metabolites were obtained in the form of yellowish residue (
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<quantity id="4C829B2FFFA8FFC7CD2E8D38456CCA58" box="[278,341,1793,1812]" metricMagnitude="-5" metricUnit="kg" metricValue="8.0" pageId="6" pageNumber="7" unit="mg" value="80.0">80 mg</quantity>
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,
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<emphasis id="B90EEAD8FFA8FFC7CD678D384554CA58" bold="true" box="[351,365,1793,1812]" italics="true" pageId="6" pageNumber="7">
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<collectionCode id="ED6BAE0FFFA8FFC7CD678D384554CA58" box="[351,365,1793,1812]" country="Chile" name="Departamento de Geologia, Universidad de Chile" pageId="6" pageNumber="7">R</collectionCode>
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</emphasis>
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f
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<geoCoordinate id="EE4E500DFFA8FFC7CD428D384590CA58" box="[378,425,1793,1812]" degrees="0.3" direction="south" orientation="latitude" pageId="6" pageNumber="7" precision="5555" value="-0.3">0.3 S</geoCoordinate>
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<subScript id="17FE348FFFA8FFC7CD918D31458BCA5A" attach="left" box="[425,434,1800,1814]" fontSize="6" pageId="6" pageNumber="7">2</subScript>
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).
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</paragraph>
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<caption id="DF056642FFABFFC4CC8A8D2B44FECAF5" box="[178,199,1810,1977]" pageId="5" pageNumber="6" startId="5.[178,199,1810,1817]" targetBox="[202,672,148,1977]" targetPageId="5">
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<paragraph id="8BC536CAFFABFFC4CC8A8D2B44FECACD" blockId="5.[178,199,1810,1977]" box="[178,199,1810,1921]" pageId="5" pageNumber="6">
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)
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<emphasis id="B90EEAD8FFABFFC4CC8A8D2544FECA26" bold="true" box="[178,199,1820,1898]" italics="true" pageId="5" pageNumber="6">continued</emphasis>
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(
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<emphasis id="B90EEAD8FFABFFC4CC8A8D4F44FECACD" bold="true" box="[178,199,1910,1921]" pageId="5" pageNumber="6">4</emphasis>
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</paragraph>
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<paragraph id="8BC536CAFFABFFC4CC8A8DBE44FECAF5" blockId="5.[178,199,1810,1977]" box="[178,199,1927,1977]" pageId="5" pageNumber="6">
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<emphasis id="B90EEAD8FFABFFC4CC8A8DBE44FECAF5" bold="true" box="[178,199,1927,1977]" pageId="5" pageNumber="6">Table</emphasis>
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</paragraph>
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</caption>
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<caption id="DF056642FFA8FFC7CC5C889445ECCFBD" ID-DOI="http://doi.org/10.5281/zenodo.8291906" ID-Zenodo-Dep="8291906" httpUri="https://zenodo.org/record/8291906/files/figure.png" pageId="6" pageNumber="7" startId="6.[100,130,685,702]" targetBox="[340,1248,149,657]" targetPageId="6" targetType="figure">
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<paragraph id="8BC536CAFFA8FFC7CC5C889445ECCFBD" blockId="6.[100,1487,685,753]" pageId="6" pageNumber="7">
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<emphasis id="B90EEAD8FFA8FFC7CC5C889444A6CFF2" bold="true" box="[100,159,685,702]" pageId="6" pageNumber="7">Fig. 2.</emphasis>
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Docked poses of the five papaverine-based biotransformation products with better docking scores than the native ligand in the Human PDE-10 A crystal structure, PDB: 2WEY; 4 (red), 1 (yellow), 6 (blue), 3 (blum), 5 (faded orange). (For interpretation of the references to colour in this figure legend, the reader is referred to the Web version of this article.)
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</paragraph>
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</caption>
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<caption id="DF056642FFA8FFC7CDDF8CFE4077CB94" ID-DOI="http://doi.org/10.5281/zenodo.8291908" ID-Zenodo-Dep="8291908" box="[487,1102,1735,1752]" httpUri="https://zenodo.org/record/8291908/files/figure.png" pageId="6" pageNumber="7" startId="6.[487,517,1735,1752]" targetBox="[226,1361,802,1706]" targetPageId="6" targetType="figure">
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<paragraph id="8BC536CAFFA8FFC7CDDF8CFE4077CB94" blockId="6.[487,1102,1735,1752]" box="[487,1102,1735,1752]" pageId="6" pageNumber="7">
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<emphasis id="B90EEAD8FFA8FFC7CDDF8CFE4619CB94" bold="true" box="[487,544,1735,1752]" pageId="6" pageNumber="7">Fig. 3.</emphasis>
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Structure of papaverine and its metabolite from different Fungi.
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</paragraph>
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</caption>
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<paragraph id="8BC536CAFFA8FFC7CCBC8D24473BCAF7" blockId="6.[100,770,1793,1981]" pageId="6" pageNumber="7">
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The mixture was loaded in silica biotage column (18 ×
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<quantity id="4C829B2FFFA8FFC7CE478D2446E9CA7C" box="[639,720,1821,1840]" metricMagnitude="-1" metricUnit="m" metricValue="1.5" pageId="6" pageNumber="7" unit="mm" value="150.0">150 mm</quantity>
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). The column was gradiently eluted with dichloromethane 100% then dichloromethane:2-propanol (98:2, 97:3,95:5) and 20 ml fractions were collected. Fractions 27–31 were pooled together to give pure
|
|||
|
|
<emphasis id="B90EEAD8FFA8FFC7CE898D494684CACF" bold="true" box="[689,701,1904,1923]" pageId="6" pageNumber="7">2</emphasis>
|
|||
|
|
, in the form of white powder (
|
|||
|
|
<quantity id="4C829B2FFFA8FFC7CD798DB5454DCAEC" box="[321,372,1932,1952]" metricMagnitude="-6" metricUnit="kg" metricValue="7.0" pageId="6" pageNumber="7" unit="mg" value="7.0">7 mg</quantity>
|
|||
|
|
,
|
|||
|
|
<emphasis id="B90EEAD8FFA8FFC7CD468DB545A9CAED" bold="true" box="[382,400,1932,1953]" italics="true" pageId="6" pageNumber="7">
|
|||
|
|
<subScript id="17FE348FFFA8FFC7CD468DB545A9CAED" attach="left" box="[382,400,1932,1953]" fontSize="6" pageId="6" pageNumber="7">Rf</subScript>
|
|||
|
|
</emphasis>
|
|||
|
|
<geoCoordinate id="EE4E500DFFA8FFC7CDAF8DB545EBCAD3" box="[407,466,1932,1951]" degrees="0.70" direction="south" orientation="latitude" pageId="6" pageNumber="7" precision="555" value="-0.7">0.70 S</geoCoordinate>
|
|||
|
|
<subScript id="17FE348FFFA8FFC7CDEB8DAD45E5CAEE" attach="right" box="[467,476,1940,1954]" fontSize="6" pageId="6" pageNumber="7">1</subScript>
|
|||
|
|
). Fractions 65–85 were pooled together to give pure
|
|||
|
|
<emphasis id="B90EEAD8FFA8FFC7CD138D91450ECAF7" bold="true" box="[299,311,1960,1979]" pageId="6" pageNumber="7">3</emphasis>
|
|||
|
|
, in the form of white powder (
|
|||
|
|
<quantity id="4C829B2FFFA8FFC7CE6A8D9146A9CAF0" box="[594,656,1960,1980]" metricMagnitude="-5" metricUnit="kg" metricValue="3.0" pageId="6" pageNumber="7" unit="mg" value="30.0">30 mg</quantity>
|
|||
|
|
,
|
|||
|
|
<emphasis id="B90EEAD8FFA8FFC7CEA08D91469FCAF7" bold="true" box="[664,678,1960,1979]" italics="true" pageId="6" pageNumber="7">
|
|||
|
|
<collectionCode id="ED6BAE0FFFA8FFC7CEA08D91469FCAF7" box="[664,678,1960,1979]" country="Chile" name="Departamento de Geologia, Universidad de Chile" pageId="6" pageNumber="7">R</collectionCode>
|
|||
|
|
</emphasis>
|
|||
|
|
f
|
|||
|
|
<geoCoordinate id="EE4E500DFFA8FFC7CE898D9146D2CAF7" box="[689,747,1960,1979]" degrees="0.61" direction="south" orientation="latitude" pageId="6" pageNumber="7" precision="555" value="-0.61">0.61 S</geoCoordinate>
|
|||
|
|
<subScript id="17FE348FFFA8FFC7CED38D9646CDCAF1" attach="left" box="[747,756,1967,1981]" fontSize="6" pageId="6" pageNumber="7">1</subScript>
|
|||
|
|
).
|
|||
|
|
</paragraph>
|
|||
|
|
</subSubSection>
|
|||
|
|
</treatment>
|
|||
|
|
</document>
|