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<document id="87B75D2E3DC32CC51E94D32C32E49E30" ID-DOI="10.1016/j.phytochem.2018.12.022" ID-ISSN="1873-3700" ID-Zenodo-Dep="10481924" IM.bibliography_approvedBy="felipe" IM.illustrations_approvedBy="felipe" IM.materialsCitations_approvedBy="felipe" IM.metadata_approvedBy="felipe" IM.tables_requiresApprovalFor="GgImagineBatch" IM.taxonomicNames_approvedBy="karina" IM.treatments_approvedBy="karina" checkinTime="1704928502977" checkinUser="felipe" docAuthor="Nawrot, Joanna, Budzianowski, Jaromir &amp; Nowak, Gerard" docDate="2019" docId="038587F2FFB3FFC22933F929FC02FB9D" docLanguage="en" docName="Phytochemistry.159.172-178.pdf" docOrigin="Phytochemistry 159" docSource="http://dx.doi.org/10.1016/j.phytochem.2018.12.022" docStyle="DocumentStyle:9E596C34F4E94307D29315B03ACE1007.6:Phytochemistry.2014-2019.journal_article" docStyleId="9E596C34F4E94307D29315B03ACE1007" docStyleName="Phytochemistry.2014-2019.journal_article" docStyleVersion="6" docTitle="Stizolophus balsamita subsp. leaves" docType="treatment" docVersion="1" lastPageNumber="177" masterDocId="FFBCFF8AFFB7FFC72A01FFD8FFA3FFEF" masterDocTitle="Phytochemical profiles of the leaves of Stizolophus balsamita and Psephellus sibiricus and their chemotaxonomic implications" masterLastPageNumber="178" masterPageNumber="172" pageNumber="176" updateTime="1706406631498" updateUser="karina">
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<mods:title id="E24D635F2384EAB57287579FEFA6288E">Phytochemical profiles of the leaves of Stizolophus balsamita and Psephellus sibiricus and their chemotaxonomic implications</mods:title>
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<mods:namePart id="480FDC16D0F19D01B3EF5F546121DA66">Nawrot, Joanna</mods:namePart>
<mods:affiliation id="BECA2B8AFD91024A32E1E81CBC1F104B"> &amp; Department of Medicinal and Cosmetic Natural Products, Poznan University of Medical Sciences, Mazowiecka Str. 33, 60 - 623 Poznan, Poland</mods:affiliation>
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<mods:namePart id="7662B3538A4421788377B88F68946432">Budzianowski, Jaromir</mods:namePart>
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<treatment id="038587F2FFB3FFC22933F929FC02FB9D" LSID="urn:lsid:plazi:treatment:038587F2FFB3FFC22933F929FC02FB9D" httpUri="http://treatment.plazi.org/id/038587F2FFB3FFC22933F929FC02FB9D" lastPageId="5" lastPageNumber="177" pageId="4" pageNumber="176">
<subSubSection id="C336656FFFB3FFC32933F929FA38F8EB" box="[818,1435,1777,1796]" pageId="4" pageNumber="176" type="nomenclature">
<paragraph id="8B9336E4FFB3FFC32933F929FA38F8EB" blockId="4.[818,1435,1777,1796]" box="[818,1435,1777,1796]" pageId="4" pageNumber="176">
<heading id="D0DB8188FFB3FFC32933F929FA38F8EB" bold="true" box="[818,1435,1777,1796]" fontSize="36" level="1" pageId="4" pageNumber="176" reason="1">
<emphasis id="B958EAF6FFB3FFC32933F929FA38F8EB" bold="true" box="[818,1435,1777,1796]" italics="true" pageId="4" pageNumber="176">
3.3. Extraction and isolation of compounds from
<taxonomicName id="4C2C4D67FFB3FFC32EF0F929FAC3F8EB" box="[1265,1376,1777,1796]" class="Magnoliopsida" family="Asteraceae" genus="Stizolophus" kingdom="Plantae" order="Asterales" pageId="4" pageNumber="176" phylum="Tracheophyta" rank="subSpecies" species="balsamita" subSpecies="leaves">S. balsamita</taxonomicName>
leaves
</emphasis>
</heading>
</paragraph>
</subSubSection>
<subSubSection id="C336656FFFB3FFC22952F8F1FC02FB9D" lastPageId="5" lastPageNumber="177" pageId="4" pageNumber="176" type="description">
<paragraph id="8B9336E4FFB3FFC32952F8F1FCC6F827" blockId="4.[818,1489,1833,1992]" pageId="4" pageNumber="176">
The dried leaves of
<taxonomicName id="4C2C4D67FFB3FFC32E0DF8F1FBD9F8D3" box="[1036,1146,1833,1852]" class="Magnoliopsida" family="Asteraceae" genus="Stizolophus" kingdom="Plantae" order="Asterales" pageId="4" pageNumber="176" phylum="Tracheophyta" rank="species" species="balsamita">
<emphasis id="B958EAF6FFB3FFC32E0DF8F1FBB4F8D3" bold="true" box="[1036,1047,1833,1852]" italics="true" pageId="4" pageNumber="176">S</emphasis>
.
<emphasis id="B958EAF6FFB3FFC32E25F8F1FBD9F8D3" bold="true" box="[1060,1146,1833,1852]" italics="true" pageId="4" pageNumber="176">balsamita</emphasis>
</taxonomicName>
(
<quantity id="4CD49B01FFB3FFC32E87F8F1FB1FF8D3" box="[1158,1212,1833,1852]" metricMagnitude="-1" metricUnit="kg" metricValue="6.3" pageId="4" pageNumber="176" unit="g" value="630.0">630 g</quantity>
) were crushed and soaked in MeOH. The MeOH extract was evapd, and the residue was dissolved in H
<subScript id="17A834A1FFB3FFC32940F8B2FCE9F899" attach="both" box="[833,842,1898,1910]" fontSize="5" pageId="4" pageNumber="176">2</subScript>
O. The aq. soln was re-extracted with
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<subScript id="17A834A1FFB3FFC32ED5F8B2FB7EF899" attach="both" box="[1236,1245,1898,1910]" fontSize="5" pageId="4" pageNumber="176">2</subScript>
Cl
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and then with AcOEt. The
<collectingCountry id="F33B7674FFB3FFC3295DF8A5FCDAF87F" box="[860,889,1917,1936]" name="Switzerland" pageId="4" pageNumber="176">CH</collectingCountry>
<subScript id="17A834A1FFB3FFC3297BF85EFC20F87D" attach="right" box="[890,899,1926,1938]" fontSize="5" pageId="4" pageNumber="176">2</subScript>
Cl
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extract which was dried with Na
<subScript id="17A834A1FFB3FFC32EDEF85EFB4BF87D" attach="both" box="[1247,1256,1926,1938]" fontSize="5" pageId="4" pageNumber="176">2</subScript>
SO
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, filtrated and evapd gave a residue (
<quantity id="4CD49B01FFB3FFC329CCF840FBA9F843" box="[973,1034,1944,1964]" metricMagnitude="-2" metricUnit="kg" metricValue="1.55" pageId="4" pageNumber="176" unit="g" value="15.5">15.5 g</quantity>
). The AcOEt extract evapd and gave a residue
<quantity id="4CD49B01FFB3FFC32933F86CFCC1F827" box="[818,866,1972,1992]" metricMagnitude="-3" metricUnit="kg" metricValue="4.6" pageId="4" pageNumber="176" unit="g" value="4.6">4.6 g</quantity>
.
</paragraph>
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<paragraph id="8B9336E4FFB2FFC22A65FF79FDB3FF24" blockId="5.[100,528,161,205]" pageId="5" pageNumber="177">
<emphasis id="B958EAF6FFB2FFC22A65FF79FF0BFF5D" bold="true" box="[100,168,161,178]" pageId="5" pageNumber="177">Table 6</emphasis>
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H and
<superScript id="7C599BACFFB2FFC22AA1FF6EFF13FF2D" attach="both" box="[160,176,182,194]" fontSize="5" pageId="5" pageNumber="177">13</superScript>
C NMR data of compound 8 (in CD OD).
</paragraph>
</caption>
<caption id="DF53666CFFB2FFC22933FF79FA92FF24" pageId="5" pageNumber="177" startId="5.[818,868,161,177]" targetType="table">
<paragraph id="8B9336E4FFB2FFC22933FF79FA92FF24" blockId="5.[818,1329,161,203]" pageId="5" pageNumber="177">
<emphasis id="B958EAF6FFB2FFC22933FF79FCD6FF5D" bold="true" box="[818,885,161,178]" pageId="5" pageNumber="177">Table 8</emphasis>
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H and
<superScript id="7C599BACFFB2FFC2296FFF6EFCDDFF2D" attach="right" box="[878,894,182,194]" fontSize="5" pageId="5" pageNumber="177">13</superScript>
C NMR data of compounds 12 and 13 in DMSO-d6
</paragraph>
</caption>
<paragraph id="8B9336E4FFB2FFC22BDFFF19FE45FF22" blockId="5.[100,528,161,205]" box="[478,486,193,205]" pageId="5" pageNumber="177">
<subScript id="17A834A1FFB2FFC22BDFFF19FE45FF22" attach="both" box="[478,486,193,205]" fontSize="5" pageId="5" pageNumber="177">3</subScript>
</paragraph>
<paragraph id="8B9336E4FFB2FFC22A75FF3BFD95FCAE" pageId="5" pageNumber="177">
<table id="F92CC444FFB200382A75FF3AFD51FCAE" box="[116,754,226,833]" gridcols="5" gridrows="26" pageId="5" pageNumber="177">
<tr id="351C34A6FFB200382A75FF3AFD51FF1C" box="[116,754,226,243]" gridrow="0" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382A75FF3AFF39FF1C" box="[116,154,226,243]" gridcol="0" gridrow="0" pageId="5" pageNumber="177">atom</th>
<th id="76CD5DDAFFB200382ABCFF3AFF4BFF1C" box="[189,232,226,243]" gridcol="1" gridrow="0" pageId="5" pageNumber="177">δC</th>
<th id="76CD5DDAFFB200382B0BFF3AFE1BFF1C" box="[266,440,226,243]" gridcol="2" gridrow="0" pageId="5" pageNumber="177">δH</th>
<th id="76CD5DDAFFB200382BDAFF3AFDF2FF1C" box="[475,593,226,243]" gridcol="3" gridrow="0" pageId="5" pageNumber="177">HMBC (H → C)</th>
<th id="76CD5DDAFFB200382875FF3AFD51FF1C" box="[628,754,226,243]" gridcol="4" gridrow="0" pageId="5" pageNumber="177">NOESY (H → H)</th>
</tr>
<tr id="351C34A6FFB200382A75FED6FD51FEF3" box="[116,754,270,284]" gridrow="1" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382A75FED6FD51FEF3" box="[116,754,270,284]" colspan="5" colspanRight="4" gridcol="0" gridrow="1" pageId="5" pageNumber="177">aglycon</th>
</tr>
<tr id="351C34A6FFB200382A75FEFDFD51FEDC" box="[116,754,293,307]" gridrow="2" pageId="5" pageNumber="177" rowspan-3="1" rowspan-4="1">
<th id="76CD5DDAFFB200382A75FEFDFF39FEDC" box="[116,154,293,307]" gridcol="0" gridrow="2" pageId="5" pageNumber="177">1</th>
<td id="76CD5DDAFFB200382ABCFEFDFF4BFEDC" box="[189,232,293,307]" gridcol="1" gridrow="2" pageId="5" pageNumber="177">134.5</td>
<td id="76CD5DDAFFB200382B0BFEFDFE1BFEDC" box="[266,440,293,307]" gridcol="2" gridrow="2" pageId="5" pageNumber="177"></td>
</tr>
<tr id="351C34A6FFB200382A75FEE3FD51FEA5" box="[116,754,315,330]" gridrow="3" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382A75FEE3FF39FEA5" box="[116,154,315,330]" gridcol="0" gridrow="3" pageId="5" pageNumber="177">2</th>
<td id="76CD5DDAFFB200382ABCFEE3FF4BFEA5" box="[189,232,315,330]" gridcol="1" gridrow="3" pageId="5" pageNumber="177">119.0</td>
<td id="76CD5DDAFFB200382B0BFEE3FE1BFEA5" box="[266,440,315,330]" gridcol="2" gridrow="3" pageId="5" pageNumber="177">7.04 d (1.5)</td>
<td id="76CD5DDAFFB200382BDAFEE3FDF2FEA5" box="[475,593,315,330]" gridcol="3" gridrow="3" pageId="5" pageNumber="177">1,3,4,6,7</td>
<td id="76CD5DDAFFB200382875FEE3FD51FEA5" box="[628,754,315,330]" gridcol="4" gridrow="3" pageId="5" pageNumber="177">7, 8, 1</td>
</tr>
<tr id="351C34A6FFB200382A75FE8BFD51FE8E" box="[116,754,339,353]" gridrow="4" pageId="5" pageNumber="177" rowspan-3="1" rowspan-4="1">
<th id="76CD5DDAFFB200382A75FE8BFF39FE8E" box="[116,154,339,353]" gridcol="0" gridrow="4" pageId="5" pageNumber="177">3</th>
<td id="76CD5DDAFFB200382ABCFE8BFF4BFE8E" box="[189,232,339,353]" gridcol="1" gridrow="4" pageId="5" pageNumber="177">146.6</td>
<td id="76CD5DDAFFB200382B0BFE8BFE1BFE8E" box="[266,440,339,353]" gridcol="2" gridrow="4" pageId="5" pageNumber="177"></td>
</tr>
<tr id="351C34A6FFB200382A75FEB2FD51FE97" box="[116,754,362,376]" gridrow="5" pageId="5" pageNumber="177" rowspan-3="1" rowspan-4="1">
<th id="76CD5DDAFFB200382A75FEB2FF39FE97" box="[116,154,362,376]" gridcol="0" gridrow="5" pageId="5" pageNumber="177">4</th>
<td id="76CD5DDAFFB200382ABCFEB2FF4BFE97" box="[189,232,362,376]" gridcol="1" gridrow="5" pageId="5" pageNumber="177">146.7</td>
<td id="76CD5DDAFFB200382B0BFEB2FE1BFE97" box="[266,440,362,376]" gridcol="2" gridrow="5" pageId="5" pageNumber="177"></td>
</tr>
<tr id="351C34A6FFB200382A75FE58FD51FE60" box="[116,754,384,399]" gridrow="6" pageId="5" pageNumber="177" rowspan-4="1">
<th id="76CD5DDAFFB200382A75FE58FF39FE60" box="[116,154,384,399]" gridcol="0" gridrow="6" pageId="5" pageNumber="177">5</th>
<td id="76CD5DDAFFB200382ABCFE58FF4BFE60" box="[189,232,384,399]" gridcol="1" gridrow="6" pageId="5" pageNumber="177">117.0</td>
<td id="76CD5DDAFFB200382B0BFE58FE1BFE60" box="[266,440,384,399]" gridcol="2" gridrow="6" pageId="5" pageNumber="177">6.75 d (8.1)</td>
<td id="76CD5DDAFFB200382BDAFE58FDF2FE60" box="[475,593,384,399]" gridcol="3" gridrow="6" pageId="5" pageNumber="177">1,3,4</td>
</tr>
<tr id="351C34A6FFB200382A75FE4FFD51FE49" box="[116,754,407,422]" gridrow="7" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382A75FE4FFF39FE49" box="[116,154,407,422]" gridcol="0" gridrow="7" pageId="5" pageNumber="177">6</th>
<td id="76CD5DDAFFB200382ABCFE4FFF4BFE49" box="[189,232,407,422]" gridcol="1" gridrow="7" pageId="5" pageNumber="177">124.6</td>
<td id="76CD5DDAFFB200382B0BFE4FFE1BFE49" box="[266,440,407,422]" gridcol="2" gridrow="7" pageId="5" pageNumber="177">6.74 dd (1.5, 8.2)</td>
<td id="76CD5DDAFFB200382BDAFE4FFDF2FE49" box="[475,593,407,422]" gridcol="3" gridrow="7" pageId="5" pageNumber="177">1,4,7</td>
<td id="76CD5DDAFFB200382875FE4FFD51FE49" box="[628,754,407,422]" gridcol="4" gridrow="7" pageId="5" pageNumber="177">7</td>
</tr>
<tr id="351C34A6FFB200382A75FE76FD51FE53" box="[116,754,430,444]" gridrow="8" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382A75FE76FF39FE53" box="[116,154,430,444]" gridcol="0" gridrow="8" pageId="5" pageNumber="177">7</th>
<td id="76CD5DDAFFB200382ABCFE76FF4BFE53" box="[189,232,430,444]" gridcol="1" gridrow="8" pageId="5" pageNumber="177">32.5</td>
<td id="76CD5DDAFFB200382B0BFE76FE1BFE53" box="[266,440,430,444]" gridcol="2" gridrow="8" pageId="5" pageNumber="177">2.60 t (7.5)</td>
<td id="76CD5DDAFFB200382BDAFE76FDF2FE53" box="[475,593,430,444]" gridcol="3" gridrow="8" pageId="5" pageNumber="177">1,2,6,8,9</td>
<td id="76CD5DDAFFB200382875FE76FD51FE53" box="[628,754,430,444]" gridcol="4" gridrow="8" pageId="5" pageNumber="177">6</td>
</tr>
<tr id="351C34A6FFB200382A75FE1DFD51FE3C" box="[116,754,453,467]" gridrow="9" pageId="5" pageNumber="177" rowspan-4="1">
<th id="76CD5DDAFFB200382A75FE1DFF39FE3C" box="[116,154,453,467]" gridcol="0" gridrow="9" pageId="5" pageNumber="177">8</th>
<td id="76CD5DDAFFB200382ABCFE1DFF4BFE3C" box="[189,232,453,467]" gridcol="1" gridrow="9" pageId="5" pageNumber="177">31.6</td>
<td id="76CD5DDAFFB200382B0BFE1DFE1BFE3C" box="[266,440,453,467]" gridcol="2" gridrow="9" pageId="5" pageNumber="177">1.92 ddt (6.5, 6.5, 7.5)</td>
<td id="76CD5DDAFFB200382BDAFE1DFDF2FE3C" box="[475,593,453,467]" gridcol="3" gridrow="9" pageId="5" pageNumber="177">1,7,9</td>
</tr>
<tr id="351C34A6FFB200382A75FE03FD51FE05" box="[116,754,475,490]" gridrow="10" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382A75FE03FF39FE05" box="[116,154,475,490]" gridcol="0" gridrow="10" pageId="5" pageNumber="177">9</th>
<td id="76CD5DDAFFB200382ABCFE03FF4BFE05" box="[189,232,475,490]" gridcol="1" gridrow="10" pageId="5" pageNumber="177">64.0</td>
<td id="76CD5DDAFFB200382B0BFE03FE1BFE05" box="[266,440,475,490]" gridcol="2" gridrow="10" pageId="5" pageNumber="177">4.06 dt (13.2, 6.5)</td>
<td id="76CD5DDAFFB200382BDAFE03FDF2FE05" box="[475,593,475,490]" gridcol="3" gridrow="10" pageId="5" pageNumber="177">7, 1</td>
<td id="76CD5DDAFFB200382875FE03FD51FE05" box="[628,754,475,490]" gridcol="4" gridrow="10" pageId="5" pageNumber="177">8</td>
</tr>
<tr id="351C34A6FFB200382A75FE2AFD51FDEE" box="[116,754,498,513]" gridrow="11" pageId="5" pageNumber="177" rowspan-0="1" rowspan-1="1">
<td id="76CD5DDAFFB200382B0BFE2AFE1BFDEE" box="[266,440,498,513]" gridcol="2" gridrow="11" pageId="5" pageNumber="177">4.04 dt (13.2, 6.5)</td>
<td id="76CD5DDAFFB200382BDAFE2AFDF2FDEE" box="[475,593,498,513]" gridcol="3" gridrow="11" pageId="5" pageNumber="177">7, 1</td>
<td id="76CD5DDAFFB200382875FE2AFD51FDEE" box="[628,754,498,513]" gridcol="4" gridrow="11" pageId="5" pageNumber="177">8</td>
</tr>
<tr id="351C34A6FFB200382A75FDD2FD51FDF7" box="[116,754,522,536]" gridrow="12" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382A75FDD2FD51FDF7" box="[116,754,522,536]" colspan="5" colspanRight="4" gridcol="0" gridrow="12" pageId="5" pageNumber="177">glucosyl</th>
</tr>
<tr id="351C34A6FFB200382A75FDF8FD51FDC0" box="[116,754,544,559]" gridrow="13" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382A75FDF8FF39FDC0" box="[116,154,544,559]" gridcol="0" gridrow="13" pageId="5" pageNumber="177">1</th>
<td id="76CD5DDAFFB200382ABCFDF8FF4BFDC0" box="[189,232,544,559]" gridcol="1" gridrow="13" pageId="5" pageNumber="177">104.5</td>
<td id="76CD5DDAFFB200382B0BFDF8FE1BFDC0" box="[266,440,544,559]" gridcol="2" gridrow="13" pageId="5" pageNumber="177">4.74 d (7.4)</td>
<td id="76CD5DDAFFB200382BDAFDF8FDF2FDC0" box="[475,593,544,559]" gridcol="3" gridrow="13" pageId="5" pageNumber="177">3</td>
<td id="76CD5DDAFFB200382875FDF8FD51FDC0" box="[628,754,544,559]" gridcol="4" gridrow="13" pageId="5" pageNumber="177">2, 3, 5</td>
</tr>
<tr id="351C34A6FFB200382A75FDEEFD51FDAA" box="[116,754,566,581]" gridrow="14" pageId="5" pageNumber="177" rowspan-3="1" rowspan-4="1">
<th id="76CD5DDAFFB200382A75FDEEFF39FDAA" box="[116,154,566,581]" gridcol="0" gridrow="14" pageId="5" pageNumber="177">2</th>
<td id="76CD5DDAFFB200382ABCFDEEFF4BFDAA" box="[189,232,566,581]" gridcol="1" gridrow="14" pageId="5" pageNumber="177">75.0</td>
<td id="76CD5DDAFFB200382B0BFDEEFE1BFDAA" box="[266,440,566,581]" gridcol="2" gridrow="14" pageId="5" pageNumber="177">3.49 dd (7.4, 9.1)</td>
</tr>
<tr id="351C34A6FFB200382A75FD95FD51FDB3" box="[116,754,589,604]" gridrow="15" pageId="5" pageNumber="177" rowspan-3="1" rowspan-4="1">
<th id="76CD5DDAFFB200382A75FD95FF39FDB3" box="[116,154,589,604]" gridcol="0" gridrow="15" pageId="5" pageNumber="177">3</th>
<td id="76CD5DDAFFB200382ABCFD95FF4BFDB3" box="[189,232,589,604]" gridcol="1" gridrow="15" pageId="5" pageNumber="177">77.7</td>
<td id="76CD5DDAFFB200382B0BFD95FE1BFDB3" box="[266,440,589,604]" gridcol="2" gridrow="15" pageId="5" pageNumber="177">3.46 t (9.1)</td>
</tr>
<tr id="351C34A6FFB200382A75FDBCFD51FD9C" box="[116,754,612,627]" gridrow="16" pageId="5" pageNumber="177" rowspan-3="1" rowspan-4="1">
<th id="76CD5DDAFFB200382A75FDBCFF39FD9C" box="[116,154,612,627]" gridcol="0" gridrow="16" pageId="5" pageNumber="177">4</th>
<td id="76CD5DDAFFB200382ABCFDBCFF4BFD9C" box="[189,232,612,627]" gridcol="1" gridrow="16" pageId="5" pageNumber="177">71.4</td>
<td id="76CD5DDAFFB200382B0BFDBCFE1BFD9C" box="[266,440,612,627]" gridcol="2" gridrow="16" pageId="5" pageNumber="177">3.39 t (9.1)</td>
</tr>
<tr id="351C34A6FFB200382A75FDA3FD51FD65" box="[116,754,635,650]" gridrow="17" pageId="5" pageNumber="177" rowspan-3="1" rowspan-4="1">
<th id="76CD5DDAFFB200382A75FDA3FF39FD65" box="[116,154,635,650]" gridcol="0" gridrow="17" pageId="5" pageNumber="177">5</th>
<td id="76CD5DDAFFB200382ABCFDA3FF4BFD65" box="[189,232,635,650]" gridcol="1" gridrow="17" pageId="5" pageNumber="177">78.3</td>
<td id="76CD5DDAFFB200382B0BFDA3FE1BFD65" box="[266,440,635,650]" gridcol="2" gridrow="17" pageId="5" pageNumber="177">3.41 m</td>
</tr>
<tr id="351C34A6FFB200382A75FD4AFD51FD4E" box="[116,754,658,673]" gridrow="18" pageId="5" pageNumber="177" rowspan-3="1" rowspan-4="1">
<th id="76CD5DDAFFB200382A75FD4AFF39FD4E" box="[116,154,658,673]" gridcol="0" gridrow="18" pageId="5" pageNumber="177">6</th>
<td id="76CD5DDAFFB200382ABCFD4AFF4BFD4E" box="[189,232,658,673]" gridcol="1" gridrow="18" pageId="5" pageNumber="177">62.5</td>
<td id="76CD5DDAFFB200382B0BFD4AFE1BFD4E" box="[266,440,658,673]" gridcol="2" gridrow="18" pageId="5" pageNumber="177">3.89 dd (1.7, 12.1)</td>
</tr>
<tr id="351C34A6FFB200382A75FD71FD51FD57" box="[116,754,681,696]" gridrow="19" pageId="5" pageNumber="177" rowspan-0="1" rowspan-1="1" rowspan-3="1" rowspan-4="1">
<td id="76CD5DDAFFB200382B0BFD71FE1BFD57" box="[266,440,681,696]" gridcol="2" gridrow="19" pageId="5" pageNumber="177">3.71 dd (5.2, 12.1)</td>
</tr>
<tr id="351C34A6FFB200382A75FD18FD51FD21" box="[116,754,704,718]" gridrow="20" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382A75FD18FD51FD21" box="[116,754,704,718]" colspan="5" colspanRight="4" gridcol="0" gridrow="20" pageId="5" pageNumber="177">acyl</th>
</tr>
<tr id="351C34A6FFB200382A75FD0EFD51FD0A" box="[116,754,726,741]" gridrow="21" pageId="5" pageNumber="177" rowspan-3="1" rowspan-4="1">
<th id="76CD5DDAFFB200382A75FD0EFF39FD0A" box="[116,154,726,741]" gridcol="0" gridrow="21" pageId="5" pageNumber="177">1″</th>
<td id="76CD5DDAFFB200382ABCFD0EFF4BFD0A" box="[189,232,726,741]" gridcol="1" gridrow="21" pageId="5" pageNumber="177">168.4</td>
<td id="76CD5DDAFFB200382B0BFD0EFE1BFD0A" box="[266,440,726,741]" gridcol="2" gridrow="21" pageId="5" pageNumber="177"></td>
</tr>
<tr id="351C34A6FFB200382A75FD35FD51FD13" box="[116,754,749,764]" gridrow="22" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382A75FD35FF39FD13" box="[116,154,749,764]" gridcol="0" gridrow="22" pageId="5" pageNumber="177">2″</th>
<td id="76CD5DDAFFB200382ABCFD35FF4BFD13" box="[189,232,749,764]" gridcol="1" gridrow="22" pageId="5" pageNumber="177">116.9</td>
<td id="76CD5DDAFFB200382B0BFD35FE1BFD13" box="[266,440,749,764]" gridcol="2" gridrow="22" pageId="5" pageNumber="177">5.69 qq (1.3)</td>
<td id="76CD5DDAFFB200382BDAFD35FDF2FD13" box="[475,593,749,764]" gridcol="3" gridrow="22" pageId="5" pageNumber="177">1,4,5″</td>
<td id="76CD5DDAFFB200382875FD35FD51FD13" box="[628,754,749,764]" gridcol="4" gridrow="22" pageId="5" pageNumber="177">4″</td>
</tr>
<tr id="351C34A6FFB200382A75FCDCFD51FCFC" box="[116,754,772,787]" gridrow="23" pageId="5" pageNumber="177" rowspan-3="1" rowspan-4="1">
<th id="76CD5DDAFFB200382A75FCDCFF39FCFC" box="[116,154,772,787]" gridcol="0" gridrow="23" pageId="5" pageNumber="177">3″</th>
<td id="76CD5DDAFFB200382ABCFCDCFF4BFCFC" box="[189,232,772,787]" gridcol="1" gridrow="23" pageId="5" pageNumber="177">158.4</td>
<td id="76CD5DDAFFB200382B0BFCDCFE1BFCFC" box="[266,440,772,787]" gridcol="2" gridrow="23" pageId="5" pageNumber="177"></td>
</tr>
<tr id="351C34A6FFB200382A75FCC3FD51FCC5" box="[116,754,795,810]" gridrow="24" pageId="5" pageNumber="177" rowspan-4="1">
<th id="76CD5DDAFFB200382A75FCC3FF39FCC5" box="[116,154,795,810]" gridcol="0" gridrow="24" pageId="5" pageNumber="177">4″</th>
<td id="76CD5DDAFFB200382ABCFCC3FF4BFCC5" box="[189,232,795,810]" gridcol="1" gridrow="24" pageId="5" pageNumber="177">27.5</td>
<td id="76CD5DDAFFB200382B0BFCC3FE1BFCC5" box="[266,440,795,810]" gridcol="2" gridrow="24" pageId="5" pageNumber="177">1.91 d (1.3)</td>
<td id="76CD5DDAFFB200382BDAFCC3FDF2FCC5" box="[475,593,795,810]" gridcol="3" gridrow="24" pageId="5" pageNumber="177">2,3,5″</td>
</tr>
<tr id="351C34A6FFB200382A75FCEAFD51FCAE" box="[116,754,818,833]" gridrow="25" pageId="5" pageNumber="177" rowspan-4="1">
<th id="76CD5DDAFFB200382A75FCEAFF39FCAE" box="[116,154,818,833]" gridcol="0" gridrow="25" pageId="5" pageNumber="177">5″</th>
<td id="76CD5DDAFFB200382ABCFCEAFF4BFCAE" box="[189,232,818,833]" gridcol="1" gridrow="25" pageId="5" pageNumber="177">20.4</td>
<td id="76CD5DDAFFB200382B0BFCEAFE1BFCAE" box="[266,440,818,833]" gridcol="2" gridrow="25" pageId="5" pageNumber="177">2.15 d (1.3)</td>
<td id="76CD5DDAFFB200382BDAFCEAFDF2FCAE" box="[475,593,818,833]" gridcol="3" gridrow="25" pageId="5" pageNumber="177">1,2,3, 4″</td>
</tr>
</table>
</paragraph>
<paragraph id="8B9336E4FFB2FFC22943FF3BFA87FC5C" pageId="5" pageNumber="177">
<table id="F92CC444FFB200382943FF3AFA1CFC5C" box="[834,1471,226,947]" gridcols="5" gridrows="31" pageId="5" pageNumber="177">
<tr id="351C34A6FFB200382943FF3AFA1CFF1E" box="[834,1471,226,241]" gridrow="0" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382943FF3AFCD6FF1E" box="[834,885,226,241]" gridcol="0" gridrow="0" pageId="5" pageNumber="177">Pos.</th>
<th id="76CD5DDAFFB2003829ABFF3AFB98FF1E" box="[938,1083,226,241]" gridcol="1" gridrow="0" pageId="5" pageNumber="177">12</th>
<th id="76CD5DDAFFB200382E6EFF3AFB39FF1E" box="[1135,1178,226,241]" gridcol="2" gridrow="0" pageId="5" pageNumber="177">12</th>
<th id="76CD5DDAFFB200382ECEFF3AFAC3FF1E" box="[1231,1376,226,241]" gridcol="3" gridrow="0" pageId="5" pageNumber="177">13</th>
<th id="76CD5DDAFFB200382F95FF3AFA1CFF1E" box="[1428,1471,226,241]" gridcol="4" gridrow="0" pageId="5" pageNumber="177">13</th>
</tr>
<tr id="351C34A6FFB200382943FF21FA1CFEE5" box="[834,1471,249,266]" gridrow="1" pageId="5" pageNumber="177" rowspan-0="1">
<td id="76CD5DDAFFB2003829ABFF21FB98FEE5" box="[938,1083,249,266]" gridcol="1" gridrow="1" pageId="5" pageNumber="177">δΗ</td>
<td id="76CD5DDAFFB200382E6EFF21FB39FEE5" box="[1135,1178,249,266]" gridcol="2" gridrow="1" pageId="5" pageNumber="177">δC</td>
<td id="76CD5DDAFFB200382ECEFF21FAC3FEE5" box="[1231,1376,249,266]" gridcol="3" gridrow="1" pageId="5" pageNumber="177">δΗ</td>
<td id="76CD5DDAFFB200382F95FF21FA1CFEE5" box="[1428,1471,249,266]" gridcol="4" gridrow="1" pageId="5" pageNumber="177">δC</td>
</tr>
<tr id="351C34A6FFB200382943FEFDFA1CFEDC" box="[834,1471,293,307]" gridrow="2" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382943FEFDFCD6FEDC" box="[834,885,293,307]" gridcol="0" gridrow="2" pageId="5" pageNumber="177">1</th>
<td id="76CD5DDAFFB2003829ABFEFDFB98FEDC" box="[938,1083,293,307]" gridcol="1" gridrow="2" pageId="5" pageNumber="177">2.90 m</td>
<td id="76CD5DDAFFB200382E6EFEFDFB39FEDC" box="[1135,1178,293,307]" gridcol="2" gridrow="2" pageId="5" pageNumber="177">44.0</td>
<td id="76CD5DDAFFB200382ECEFEFDFAC3FEDC" box="[1231,1376,293,307]" gridcol="3" gridrow="2" pageId="5" pageNumber="177">2.90 m</td>
<td id="76CD5DDAFFB200382F95FEFDFA1CFEDC" box="[1428,1471,293,307]" gridcol="4" gridrow="2" pageId="5" pageNumber="177">44.0</td>
</tr>
<tr id="351C34A6FFB200382943FEE4FA1CFEA5" box="[834,1471,316,330]" gridrow="3" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382943FEE4FCD6FEA5" box="[834,885,316,330]" gridcol="0" gridrow="3" pageId="5" pageNumber="177">2a</th>
<td id="76CD5DDAFFB2003829ABFEE4FB98FEA5" box="[938,1083,316,330]" gridcol="1" gridrow="3" pageId="5" pageNumber="177">1.90 m</td>
<td id="76CD5DDAFFB200382E6EFEE4FB39FEA5" box="[1135,1178,316,330]" gridcol="2" gridrow="3" pageId="5" pageNumber="177">39.5</td>
<td id="76CD5DDAFFB200382ECEFEE4FAC3FEA5" box="[1231,1376,316,330]" gridcol="3" gridrow="3" pageId="5" pageNumber="177">1.91 m</td>
<td id="76CD5DDAFFB200382F95FEE4FA1CFEA5" box="[1428,1471,316,330]" gridcol="4" gridrow="3" pageId="5" pageNumber="177">38.6</td>
</tr>
<tr id="351C34A6FFB200382943FE8BFA1CFE8E" box="[834,1471,339,353]" gridrow="4" pageId="5" pageNumber="177" rowspan-2="1" rowspan-4="1">
<th id="76CD5DDAFFB200382943FE8BFCD6FE8E" box="[834,885,339,353]" gridcol="0" gridrow="4" pageId="5" pageNumber="177">2b</th>
<td id="76CD5DDAFFB2003829ABFE8BFB98FE8E" box="[938,1083,339,353]" gridcol="1" gridrow="4" pageId="5" pageNumber="177">1.62 m</td>
<td id="76CD5DDAFFB200382ECEFE8BFAC3FE8E" box="[1231,1376,339,353]" gridcol="3" gridrow="4" pageId="5" pageNumber="177">1.63 m</td>
</tr>
<tr id="351C34A6FFB200382943FEB2FA1CFE97" box="[834,1471,362,376]" gridrow="5" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382943FEB2FCD6FE97" box="[834,885,362,376]" gridcol="0" gridrow="5" pageId="5" pageNumber="177">3</th>
<td id="76CD5DDAFFB2003829ABFEB2FB98FE97" box="[938,1083,362,376]" gridcol="1" gridrow="5" pageId="5" pageNumber="177">4.35 m</td>
<td id="76CD5DDAFFB200382E6EFEB2FB39FE97" box="[1135,1178,362,376]" gridcol="2" gridrow="5" pageId="5" pageNumber="177">72.0</td>
<td id="76CD5DDAFFB200382ECEFEB2FAC3FE97" box="[1231,1376,362,376]" gridcol="3" gridrow="5" pageId="5" pageNumber="177">4.37 m</td>
<td id="76CD5DDAFFB200382F95FEB2FA1CFE97" box="[1428,1471,362,376]" gridcol="4" gridrow="5" pageId="5" pageNumber="177">72.0</td>
</tr>
<tr id="351C34A6FFB200382943FE58FA1CFE60" box="[834,1471,384,399]" gridrow="6" pageId="5" pageNumber="177" rowspan-1="1" rowspan-3="1">
<th id="76CD5DDAFFB200382943FE58FCD6FE60" box="[834,885,384,399]" gridcol="0" gridrow="6" pageId="5" pageNumber="177">4</th>
<td id="76CD5DDAFFB200382E6EFE58FB39FE60" box="[1135,1178,384,399]" gridcol="2" gridrow="6" pageId="5" pageNumber="177">153.7</td>
<td id="76CD5DDAFFB200382F95FE58FA1CFE60" box="[1428,1471,384,399]" gridcol="4" gridrow="6" pageId="5" pageNumber="177">153.7</td>
</tr>
<tr id="351C34A6FFB200382943FE4FFA1CFE49" box="[834,1471,407,422]" gridrow="7" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382943FE4FFCD6FE49" box="[834,885,407,422]" gridcol="0" gridrow="7" pageId="5" pageNumber="177">5</th>
<td id="76CD5DDAFFB2003829ABFE4FFB98FE49" box="[938,1083,407,422]" gridcol="1" gridrow="7" pageId="5" pageNumber="177">2.90 m</td>
<td id="76CD5DDAFFB200382E6EFE4FFB39FE49" box="[1135,1178,407,422]" gridcol="2" gridrow="7" pageId="5" pageNumber="177">51.6</td>
<td id="76CD5DDAFFB200382ECEFE4FFAC3FE49" box="[1231,1376,407,422]" gridcol="3" gridrow="7" pageId="5" pageNumber="177">2.90 m</td>
<td id="76CD5DDAFFB200382F95FE4FFA1CFE49" box="[1428,1471,407,422]" gridcol="4" gridrow="7" pageId="5" pageNumber="177">49.6</td>
</tr>
<tr id="351C34A6FFB200382943FE76FA1CFE53" box="[834,1471,430,444]" gridrow="8" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382943FE76FCD6FE53" box="[834,885,430,444]" gridcol="0" gridrow="8" pageId="5" pageNumber="177">6</th>
<td id="76CD5DDAFFB2003829ABFE76FB98FE53" box="[938,1083,430,444]" gridcol="1" gridrow="8" pageId="5" pageNumber="177">4.38 dd (10.1; 8.7)</td>
<td id="76CD5DDAFFB200382E6EFE76FB39FE53" box="[1135,1178,430,444]" gridcol="2" gridrow="8" pageId="5" pageNumber="177">78.1</td>
<td id="76CD5DDAFFB200382ECEFE76FAC3FE53" box="[1231,1376,430,444]" gridcol="3" gridrow="8" pageId="5" pageNumber="177">4.38 dd (10.1; 8.7)</td>
<td id="76CD5DDAFFB200382F95FE76FA1CFE53" box="[1428,1471,430,444]" gridcol="4" gridrow="8" pageId="5" pageNumber="177">78.2</td>
</tr>
<tr id="351C34A6FFB200382943FE1DFA1CFE3C" box="[834,1471,453,467]" gridrow="9" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382943FE1DFCD6FE3C" box="[834,885,453,467]" gridcol="0" gridrow="9" pageId="5" pageNumber="177">7</th>
<td id="76CD5DDAFFB2003829ABFE1DFB98FE3C" box="[938,1083,453,467]" gridcol="1" gridrow="9" pageId="5" pageNumber="177">3.22 m</td>
<td id="76CD5DDAFFB200382E6EFE1DFB39FE3C" box="[1135,1178,453,467]" gridcol="2" gridrow="9" pageId="5" pageNumber="177">46.3</td>
<td id="76CD5DDAFFB200382ECEFE1DFAC3FE3C" box="[1231,1376,453,467]" gridcol="3" gridrow="9" pageId="5" pageNumber="177">3.23 m</td>
<td id="76CD5DDAFFB200382F95FE1DFA1CFE3C" box="[1428,1471,453,467]" gridcol="4" gridrow="9" pageId="5" pageNumber="177">46.4</td>
</tr>
<tr id="351C34A6FFB200382943FE04FA1CFE05" box="[834,1471,476,490]" gridrow="10" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382943FE04FCD6FE05" box="[834,885,476,490]" gridcol="0" gridrow="10" pageId="5" pageNumber="177">8</th>
<td id="76CD5DDAFFB2003829ABFE04FB98FE05" box="[938,1083,476,490]" gridcol="1" gridrow="10" pageId="5" pageNumber="177">5.16 m</td>
<td id="76CD5DDAFFB200382E6EFE04FB39FE05" box="[1135,1178,476,490]" gridcol="2" gridrow="10" pageId="5" pageNumber="177">73.6</td>
<td id="76CD5DDAFFB200382ECEFE04FAC3FE05" box="[1231,1376,476,490]" gridcol="3" gridrow="10" pageId="5" pageNumber="177">5.08 m</td>
<td id="76CD5DDAFFB200382F95FE04FA1CFE05" box="[1428,1471,476,490]" gridcol="4" gridrow="10" pageId="5" pageNumber="177">73.7</td>
</tr>
<tr id="351C34A6FFB200382943FE2BFA1CFDEE" box="[834,1471,499,513]" gridrow="11" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382943FE2BFCD6FDEE" box="[834,885,499,513]" gridcol="0" gridrow="11" pageId="5" pageNumber="177">9a</th>
<td id="76CD5DDAFFB2003829ABFE2BFB98FDEE" box="[938,1083,499,513]" gridcol="1" gridrow="11" pageId="5" pageNumber="177">2.23 dd (3.4;14.4)</td>
<td id="76CD5DDAFFB200382E6EFE2BFB39FDEE" box="[1135,1178,499,513]" gridcol="2" gridrow="11" pageId="5" pageNumber="177">36.3</td>
<td id="76CD5DDAFFB200382ECEFE2BFAC3FDEE" box="[1231,1376,499,513]" gridcol="3" gridrow="11" pageId="5" pageNumber="177">2.23 dd (3.4;14.4)</td>
<td id="76CD5DDAFFB200382F95FE2BFA1CFDEE" box="[1428,1471,499,513]" gridcol="4" gridrow="11" pageId="5" pageNumber="177">36.5</td>
</tr>
<tr id="351C34A6FFB200382943FDD1FA1CFDF7" box="[834,1471,521,536]" gridrow="12" pageId="5" pageNumber="177" rowspan-2="1" rowspan-4="1">
<th id="76CD5DDAFFB200382943FDD1FCD6FDF7" box="[834,885,521,536]" gridcol="0" gridrow="12" pageId="5" pageNumber="177">9b</th>
<td id="76CD5DDAFFB2003829ABFDD1FB98FDF7" box="[938,1083,521,536]" gridcol="1" gridrow="12" pageId="5" pageNumber="177">2.65 dd (5.1;14.4)</td>
<td id="76CD5DDAFFB200382ECEFDD1FAC3FDF7" box="[1231,1376,521,536]" gridcol="3" gridrow="12" pageId="5" pageNumber="177">2.65 dd (5.1;14.4)</td>
</tr>
<tr id="351C34A6FFB200382943FDF8FA1CFDC1" box="[834,1471,544,558]" gridrow="13" pageId="5" pageNumber="177" rowspan-1="1" rowspan-3="1">
<th id="76CD5DDAFFB200382943FDF8FCD6FDC1" box="[834,885,544,558]" gridcol="0" gridrow="13" pageId="5" pageNumber="177">10</th>
<td id="76CD5DDAFFB200382E6EFDF8FB39FDC1" box="[1135,1178,544,558]" gridcol="2" gridrow="13" pageId="5" pageNumber="177">140.9</td>
<td id="76CD5DDAFFB200382F95FDF8FA1CFDC1" box="[1428,1471,544,558]" gridcol="4" gridrow="13" pageId="5" pageNumber="177">143.7</td>
</tr>
<tr id="351C34A6FFB200382943FDEFFA1CFDAA" box="[834,1471,567,581]" gridrow="14" pageId="5" pageNumber="177" rowspan-1="1" rowspan-3="1">
<th id="76CD5DDAFFB200382943FDEFFCD6FDAA" box="[834,885,567,581]" gridcol="0" gridrow="14" pageId="5" pageNumber="177">11</th>
<td id="76CD5DDAFFB200382E6EFDEFFB39FDAA" box="[1135,1178,567,581]" gridcol="2" gridrow="14" pageId="5" pageNumber="177">138.4</td>
<td id="76CD5DDAFFB200382F95FDEFFA1CFDAA" box="[1428,1471,567,581]" gridcol="4" gridrow="14" pageId="5" pageNumber="177">138.5</td>
</tr>
<tr id="351C34A6FFB200382943FD96FA1CFDB3" box="[834,1471,590,604]" gridrow="15" pageId="5" pageNumber="177" rowspan-1="1" rowspan-3="1">
<th id="76CD5DDAFFB200382943FD96FCD6FDB3" box="[834,885,590,604]" gridcol="0" gridrow="15" pageId="5" pageNumber="177">12</th>
<td id="76CD5DDAFFB200382E6EFD96FB39FDB3" box="[1135,1178,590,604]" gridcol="2" gridrow="15" pageId="5" pageNumber="177">168.8</td>
<td id="76CD5DDAFFB200382F95FD96FA1CFDB3" box="[1428,1471,590,604]" gridcol="4" gridrow="15" pageId="5" pageNumber="177">168.9</td>
</tr>
<tr id="351C34A6FFB200382943FDBDFA1CFD9C" box="[834,1471,613,627]" gridrow="16" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382943FDBDFCD6FD9C" box="[834,885,613,627]" gridcol="0" gridrow="16" pageId="5" pageNumber="177">13a</th>
<td id="76CD5DDAFFB2003829ABFDBDFB98FD9C" box="[938,1083,613,627]" gridcol="1" gridrow="16" pageId="5" pageNumber="177">6.01 d (3.4)</td>
<td id="76CD5DDAFFB200382E6EFDBDFB39FD9C" box="[1135,1178,613,627]" gridcol="2" gridrow="16" pageId="5" pageNumber="177">120.8</td>
<td id="76CD5DDAFFB200382ECEFDBDFAC3FD9C" box="[1231,1376,613,627]" gridcol="3" gridrow="16" pageId="5" pageNumber="177">6.00 d (3.4)</td>
<td id="76CD5DDAFFB200382F95FDBDFA1CFD9C" box="[1428,1471,613,627]" gridcol="4" gridrow="16" pageId="5" pageNumber="177">120.7</td>
</tr>
<tr id="351C34A6FFB200382943FDA4FA1CFD65" box="[834,1471,636,650]" gridrow="17" pageId="5" pageNumber="177" rowspan-2="1" rowspan-4="1">
<th id="76CD5DDAFFB200382943FDA4FCD6FD65" box="[834,885,636,650]" gridcol="0" gridrow="17" pageId="5" pageNumber="177">13b</th>
<td id="76CD5DDAFFB2003829ABFDA4FB98FD65" box="[938,1083,636,650]" gridcol="1" gridrow="17" pageId="5" pageNumber="177">5.51 d (3.0)</td>
<td id="76CD5DDAFFB200382ECEFDA4FAC3FD65" box="[1231,1376,636,650]" gridcol="3" gridrow="17" pageId="5" pageNumber="177">5.44 d (3.0)</td>
</tr>
<tr id="351C34A6FFB200382943FD4BFA1CFD4E" box="[834,1471,659,673]" gridrow="18" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382943FD4BFCD6FD4E" box="[834,885,659,673]" gridcol="0" gridrow="18" pageId="5" pageNumber="177">14a</th>
<td id="76CD5DDAFFB2003829ABFD4BFB98FD4E" box="[938,1083,659,673]" gridcol="1" gridrow="18" pageId="5" pageNumber="177">5.09 d (2.7)</td>
<td id="76CD5DDAFFB200382E6EFD4BFB39FD4E" box="[1135,1178,659,673]" gridcol="2" gridrow="18" pageId="5" pageNumber="177">117.0</td>
<td id="76CD5DDAFFB200382ECEFD4BFAC3FD4E" box="[1231,1376,659,673]" gridcol="3" gridrow="18" pageId="5" pageNumber="177">5.09 d (2.6)</td>
<td id="76CD5DDAFFB200382F95FD4BFA1CFD4E" box="[1428,1471,659,673]" gridcol="4" gridrow="18" pageId="5" pageNumber="177">116.9</td>
</tr>
<tr id="351C34A6FFB200382943FD71FA1CFD57" box="[834,1471,681,696]" gridrow="19" pageId="5" pageNumber="177" rowspan-2="1" rowspan-4="1">
<th id="76CD5DDAFFB200382943FD71FCD6FD57" box="[834,885,681,696]" gridcol="0" gridrow="19" pageId="5" pageNumber="177">14b</th>
<td id="76CD5DDAFFB2003829ABFD71FB98FD57" box="[938,1083,681,696]" gridcol="1" gridrow="19" pageId="5" pageNumber="177">4.83 d (2.0)</td>
<td id="76CD5DDAFFB200382ECEFD71FAC3FD57" box="[1231,1376,681,696]" gridcol="3" gridrow="19" pageId="5" pageNumber="177">4.82 d (2.1)</td>
</tr>
<tr id="351C34A6FFB200382943FD18FA1CFD21" box="[834,1471,704,718]" gridrow="20" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382943FD18FCD6FD21" box="[834,885,704,718]" gridcol="0" gridrow="20" pageId="5" pageNumber="177">15a</th>
<td id="76CD5DDAFFB2003829ABFD18FB98FD21" box="[938,1083,704,718]" gridcol="1" gridrow="20" pageId="5" pageNumber="177">5.24 d (2.1)</td>
<td id="76CD5DDAFFB200382E6EFD18FB39FD21" box="[1135,1178,704,718]" gridcol="2" gridrow="20" pageId="5" pageNumber="177">110.3</td>
<td id="76CD5DDAFFB200382ECEFD18FAC3FD21" box="[1231,1376,704,718]" gridcol="3" gridrow="20" pageId="5" pageNumber="177">5.24 d (2.1)</td>
<td id="76CD5DDAFFB200382F95FD18FA1CFD21" box="[1428,1471,704,718]" gridcol="4" gridrow="20" pageId="5" pageNumber="177">110.4</td>
</tr>
<tr id="351C34A6FFB200382943FD0FFA1CFD0A" box="[834,1471,727,741]" gridrow="21" pageId="5" pageNumber="177" rowspan-2="1" rowspan-4="1">
<th id="76CD5DDAFFB200382943FD0FFCD6FD0A" box="[834,885,727,741]" gridcol="0" gridrow="21" pageId="5" pageNumber="177">15b</th>
<td id="76CD5DDAFFB2003829ABFD0FFB98FD0A" box="[938,1083,727,741]" gridcol="1" gridrow="21" pageId="5" pageNumber="177">5.21 d (1.8)</td>
<td id="76CD5DDAFFB200382ECEFD0FFAC3FD0A" box="[1231,1376,727,741]" gridcol="3" gridrow="21" pageId="5" pageNumber="177">5.21 d (1.9)</td>
</tr>
<tr id="351C34A6FFB200382943FD36FA1CFD13" box="[834,1471,750,764]" gridrow="22" pageId="5" pageNumber="177" rowspan-2="1" rowspan-4="1">
<th id="76CD5DDAFFB200382943FD36FCD6FD13" box="[834,885,750,764]" gridcol="0" gridrow="22" pageId="5" pageNumber="177">3-OH</th>
<td id="76CD5DDAFFB2003829ABFD36FB98FD13" box="[938,1083,750,764]" gridcol="1" gridrow="22" pageId="5" pageNumber="177">5.18 d (5.5)</td>
<td id="76CD5DDAFFB200382ECEFD36FAC3FD13" box="[1231,1376,750,764]" gridcol="3" gridrow="22" pageId="5" pageNumber="177">5.18 d (5.4)</td>
</tr>
<tr id="351C34A6FFB200382943FCDCFA1CFCFC" box="[834,1471,772,787]" gridrow="23" pageId="5" pageNumber="177" rowspan-1="1" rowspan-3="1">
<th id="76CD5DDAFFB200382943FCDCFCD6FCFC" box="[834,885,772,787]" gridcol="0" gridrow="23" pageId="5" pageNumber="177">1</th>
<td id="76CD5DDAFFB200382E6EFCDCFB39FCFC" box="[1135,1178,772,787]" gridcol="2" gridrow="23" pageId="5" pageNumber="177">164.9</td>
<td id="76CD5DDAFFB200382F95FCDCFA1CFCFC" box="[1428,1471,772,787]" gridcol="4" gridrow="23" pageId="5" pageNumber="177">166.2</td>
</tr>
<tr id="351C34A6FFB200382943FCC3FA1CFCC5" box="[834,1471,795,810]" gridrow="24" pageId="5" pageNumber="177" rowspan-3="1">
<th id="76CD5DDAFFB200382943FCC3FCD6FCC5" box="[834,885,795,810]" gridcol="0" gridrow="24" pageId="5" pageNumber="177">2</th>
<td id="76CD5DDAFFB2003829ABFCC3FB98FCC5" box="[938,1083,795,810]" gridcol="1" gridrow="24" pageId="5" pageNumber="177"></td>
<td id="76CD5DDAFFB200382E6EFCC3FB39FCC5" box="[1135,1178,795,810]" gridcol="2" gridrow="24" pageId="5" pageNumber="177">140.7</td>
<td id="76CD5DDAFFB200382F95FCC3FA1CFCC5" box="[1428,1471,795,810]" gridcol="4" gridrow="24" pageId="5" pageNumber="177">126.5</td>
</tr>
<tr id="351C34A6FFB200382943FCEAFA1CFCAE" box="[834,1471,818,833]" gridrow="25" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382943FCEAFCD6FCAE" box="[834,885,818,833]" gridcol="0" gridrow="25" pageId="5" pageNumber="177">3</th>
<td id="76CD5DDAFFB2003829ABFCEAFB98FCAE" box="[938,1083,818,833]" gridcol="1" gridrow="25" pageId="5" pageNumber="177">4.17 brs</td>
<td id="76CD5DDAFFB200382E6EFCEAFB39FCAE" box="[1135,1178,818,833]" gridcol="2" gridrow="25" pageId="5" pageNumber="177">59.5</td>
<td id="76CD5DDAFFB200382ECEFCEAFAC3FCAE" box="[1231,1376,818,833]" gridcol="3" gridrow="25" pageId="5" pageNumber="177">6.77 tq (1.2;?)</td>
<td id="76CD5DDAFFB200382F95FCEAFA1CFCAE" box="[1428,1471,818,833]" gridcol="4" gridrow="25" pageId="5" pageNumber="177">143.1</td>
</tr>
<tr id="351C34A6FFB200382943FC91FA1CFCB7" box="[834,1471,841,856]" gridrow="26" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382943FC91FCD6FCB7" box="[834,885,841,856]" gridcol="0" gridrow="26" pageId="5" pageNumber="177">4</th>
<td id="76CD5DDAFFB2003829ABFC91FB98FCB7" box="[938,1083,841,856]" gridcol="1" gridrow="26" pageId="5" pageNumber="177">6.17 d (1.6)</td>
<td id="76CD5DDAFFB200382E6EFC91FB39FCB7" box="[1135,1178,841,856]" gridcol="2" gridrow="26" pageId="5" pageNumber="177">124.2</td>
<td id="76CD5DDAFFB200382ECEFC91FAC3FCB7" box="[1231,1376,841,856]" gridcol="3" gridrow="26" pageId="5" pageNumber="177">4.18 brs</td>
<td id="76CD5DDAFFB200382F95FC91FA1CFCB7" box="[1428,1471,841,856]" gridcol="4" gridrow="26" pageId="5" pageNumber="177">58.2</td>
</tr>
<tr id="351C34A6FFB200382943FCB8FA1CFC81" box="[834,1471,864,878]" gridrow="27" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382943FCB8FA1CFC81" box="[834,1471,864,878]" colspan="5" colspanRight="4" gridcol="0" gridrow="27" pageId="5" pageNumber="177">5.91 d (1.7)</th>
</tr>
<tr id="351C34A6FFB200382943FCAEFA1CFC6A" box="[834,1471,886,901]" gridrow="28" pageId="5" pageNumber="177" rowspan-1="1" rowspan-2="1">
<th id="76CD5DDAFFB200382943FCAEFCD6FC6A" box="[834,885,886,901]" gridcol="0" gridrow="28" pageId="5" pageNumber="177">5</th>
<td id="76CD5DDAFFB200382ECEFCAEFAC3FC6A" box="[1231,1376,886,901]" gridcol="3" gridrow="28" pageId="5" pageNumber="177">1.79 q</td>
<td id="76CD5DDAFFB200382F95FCAEFA1CFC6A" box="[1428,1471,886,901]" gridcol="4" gridrow="28" pageId="5" pageNumber="177">12.4</td>
</tr>
<tr id="351C34A6FFB200382943FC55FA1CFC73" box="[834,1471,909,924]" gridrow="29" pageId="5" pageNumber="177" rowspan-2="1" rowspan-3="1" rowspan-4="1">
<th id="76CD5DDAFFB200382943FC55FCD6FC73" box="[834,885,909,924]" gridcol="0" gridrow="29" pageId="5" pageNumber="177">3eOH</th>
<td id="76CD5DDAFFB2003829ABFC55FB98FC73" box="[938,1083,909,924]" gridcol="1" gridrow="29" pageId="5" pageNumber="177">5.15 t (5.2)</td>
</tr>
<tr id="351C34A6FFB200382943FC7CFA1CFC5C" box="[834,1471,932,947]" gridrow="30" pageId="5" pageNumber="177" rowspan-1="1" rowspan-2="1" rowspan-4="1">
<th id="76CD5DDAFFB200382943FC7CFCD6FC5C" box="[834,885,932,947]" gridcol="0" gridrow="30" pageId="5" pageNumber="177">4eOH</th>
<td id="76CD5DDAFFB200382ECEFC7CFAC3FC5C" box="[1231,1376,932,947]" gridcol="3" gridrow="30" pageId="5" pageNumber="177">5.03 t (5.2)</td>
</tr>
</table>
</paragraph>
<caption id="DF53666CFFB2FFC22A65FC59FE69FC44" pageId="5" pageNumber="177" startId="5.[100,150,897,913]" targetType="table">
<paragraph id="8B9336E4FFB2FFC22A65FC59FE69FC44" blockId="5.[100,458,897,939]" pageId="5" pageNumber="177">
<emphasis id="B958EAF6FFB2FFC22A65FC59FF0BFC7E" bold="true" box="[100,168,897,913]" pageId="5" pageNumber="177">Table 7</emphasis>
<superScript id="7C599BACFFB2FFC22A65FC4EFFCFFC4D" attach="right" box="[100,108,918,930]" fontSize="5" pageId="5" pageNumber="177">1</superScript>
H and
<superScript id="7C599BACFFB2FFC22AA1FC4EFF13FC4D" attach="both" box="[160,176,918,930]" fontSize="5" pageId="5" pageNumber="177">13</superScript>
C NMR data of compounds 9-11.
</paragraph>
</caption>
<paragraph id="8B9336E4FFB2FFC22A75FC1BFD73FAE1" pageId="5" pageNumber="177">
<table id="F92CC444FFB200382A75FC66FD51FAFF" box="[116,754,958,1296]" gridcols="7" gridrows="13" pageId="5" pageNumber="177">
<tr id="351C34A6FFB200382A75FC66FD51FC3E" box="[116,754,958,977]" gridrow="0" pageId="5" pageNumber="177" rowspan-2="1" rowspan-4="1" rowspan-6="1">
<th id="76CD5DDAFFB200382A75FC66FF0DFC3E" box="[116,174,958,977]" gridcol="0" gridrow="0" pageId="5" pageNumber="177">Pos.</th>
<th id="76CD5DDAFFB200382AC4FC66FEBDFC3E" box="[197,286,958,977]" gridcol="1" gridrow="0" pageId="5" pageNumber="177">9a</th>
<th id="76CD5DDAFFB200382B76FC66FE73FC3E" box="[375,464,958,977]" gridcol="3" gridrow="0" pageId="5" pageNumber="177">10b</th>
<th id="76CD5DDAFFB200382828FC66FD13FC3E" box="[553,688,958,977]" gridcol="5" gridrow="0" pageId="5" pageNumber="177">11a</th>
</tr>
<tr id="351C34A6FFB200382A75FC28FD51FBEF" box="[116,754,1008,1024]" gridrow="1" pageId="5" pageNumber="177" rowspan-0="1">
<td id="76CD5DDAFFB200382AC4FC28FEBDFBEF" box="[197,286,1008,1024]" gridcol="1" gridrow="1" pageId="5" pageNumber="177">δH</td>
<td id="76CD5DDAFFB200382B34FC28FEC3FBEF" box="[309,352,1008,1024]" gridcol="2" gridrow="1" pageId="5" pageNumber="177">δC</td>
<td id="76CD5DDAFFB200382B76FC28FE73FBEF" box="[375,464,1008,1024]" gridcol="3" gridrow="1" pageId="5" pageNumber="177">δH</td>
<td id="76CD5DDAFFB200382BE6FC28FDB1FBEF" box="[487,530,1008,1024]" gridcol="4" gridrow="1" pageId="5" pageNumber="177">δC</td>
<td id="76CD5DDAFFB200382828FC28FD13FBEF" box="[553,688,1008,1024]" gridcol="5" gridrow="1" pageId="5" pageNumber="177">δH</td>
<td id="76CD5DDAFFB2003828C6FC28FD51FBEF" box="[711,754,1008,1024]" gridcol="6" gridrow="1" pageId="5" pageNumber="177">δC</td>
</tr>
<tr id="351C34A6FFB200382A75FBC3FD51FBC5" box="[116,754,1051,1066]" gridrow="2" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382A75FBC3FF0DFBC5" box="[116,174,1051,1066]" gridcol="0" gridrow="2" pageId="5" pageNumber="177">2</th>
<td id="76CD5DDAFFB200382AC4FBC3FEBDFBC5" box="[197,286,1051,1066]" gridcol="1" gridrow="2" pageId="5" pageNumber="177"></td>
<td id="76CD5DDAFFB200382B34FBC3FEC3FBC5" box="[309,352,1051,1066]" gridcol="2" gridrow="2" pageId="5" pageNumber="177">161.4</td>
<td id="76CD5DDAFFB200382B76FBC3FE73FBC5" box="[375,464,1051,1066]" gridcol="3" gridrow="2" pageId="5" pageNumber="177"></td>
<td id="76CD5DDAFFB200382BE6FBC3FDB1FBC5" box="[487,530,1051,1066]" gridcol="4" gridrow="2" pageId="5" pageNumber="177">160.1</td>
<td id="76CD5DDAFFB200382828FBC3FD13FBC5" box="[553,688,1051,1066]" gridcol="5" gridrow="2" pageId="5" pageNumber="177"></td>
<td id="76CD5DDAFFB2003828C6FBC3FD51FBC5" box="[711,754,1051,1066]" gridcol="6" gridrow="2" pageId="5" pageNumber="177">161.8</td>
</tr>
<tr id="351C34A6FFB200382A75FBEAFD51FBAF" box="[116,754,1074,1088]" gridrow="3" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382A75FBEAFF0DFBAF" box="[116,174,1074,1088]" gridcol="0" gridrow="3" pageId="5" pageNumber="177">3</th>
<td id="76CD5DDAFFB200382AC4FBEAFEBDFBAF" box="[197,286,1074,1088]" gridcol="1" gridrow="3" pageId="5" pageNumber="177">6.29 d (9.5)</td>
<td id="76CD5DDAFFB200382B34FBEAFEC3FBAF" box="[309,352,1074,1088]" gridcol="2" gridrow="3" pageId="5" pageNumber="177">111.5</td>
<td id="76CD5DDAFFB200382B76FBEAFE73FBAF" box="[375,464,1074,1088]" gridcol="3" gridrow="3" pageId="5" pageNumber="177">6.22 d (9.4)</td>
<td id="76CD5DDAFFB200382BE6FBEAFDB1FBAF" box="[487,530,1074,1088]" gridcol="4" gridrow="3" pageId="5" pageNumber="177">111.7</td>
<td id="76CD5DDAFFB200382828FBEAFD13FBAF" box="[553,688,1074,1088]" gridcol="5" gridrow="3" pageId="5" pageNumber="177">6.22 d (9.4)</td>
<td id="76CD5DDAFFB2003828C6FBEAFD51FBAF" box="[711,754,1074,1088]" gridcol="6" gridrow="3" pageId="5" pageNumber="177">112.3</td>
</tr>
<tr id="351C34A6FFB200382A75FB91FD51FBB8" box="[116,754,1097,1111]" gridrow="4" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382A75FB91FF0DFBB8" box="[116,174,1097,1111]" gridcol="0" gridrow="4" pageId="5" pageNumber="177">4</th>
<td id="76CD5DDAFFB200382AC4FB91FEBDFBB8" box="[197,286,1097,1111]" gridcol="1" gridrow="4" pageId="5" pageNumber="177">7.62 d (9.5)</td>
<td id="76CD5DDAFFB200382B34FB91FEC3FBB8" box="[309,352,1097,1111]" gridcol="2" gridrow="4" pageId="5" pageNumber="177">143.3</td>
<td id="76CD5DDAFFB200382B76FB91FE73FBB8" box="[375,464,1097,1111]" gridcol="3" gridrow="4" pageId="5" pageNumber="177">7.91 d (9.4)</td>
<td id="76CD5DDAFFB200382BE6FB91FDB1FBB8" box="[487,530,1097,1111]" gridcol="4" gridrow="4" pageId="5" pageNumber="177">144.4</td>
<td id="76CD5DDAFFB200382828FB91FD13FBB8" box="[553,688,1097,1111]" gridcol="5" gridrow="4" pageId="5" pageNumber="177">7.64 d (9.4)</td>
<td id="76CD5DDAFFB2003828C6FB91FD51FBB8" box="[711,754,1097,1111]" gridcol="6" gridrow="4" pageId="5" pageNumber="177">143.9</td>
</tr>
<tr id="351C34A6FFB200382A75FBB8FD51FB81" box="[116,754,1120,1134]" gridrow="5" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382A75FBB8FF0DFB81" box="[116,174,1120,1134]" gridcol="0" gridrow="5" pageId="5" pageNumber="177">5</th>
<td id="76CD5DDAFFB200382AC4FBB8FEBDFB81" box="[197,286,1120,1134]" gridcol="1" gridrow="5" pageId="5" pageNumber="177">6.85 s</td>
<td id="76CD5DDAFFB200382B34FBB8FEC3FB81" box="[309,352,1120,1134]" gridcol="2" gridrow="5" pageId="5" pageNumber="177">108.0</td>
<td id="76CD5DDAFFB200382B76FBB8FE73FB81" box="[375,464,1120,1134]" gridcol="3" gridrow="5" pageId="5" pageNumber="177">7.22 s</td>
<td id="76CD5DDAFFB200382BE6FBB8FDB1FB81" box="[487,530,1120,1134]" gridcol="4" gridrow="5" pageId="5" pageNumber="177">109.6</td>
<td id="76CD5DDAFFB200382828FBB8FD13FB81" box="[553,688,1120,1134]" gridcol="5" gridrow="5" pageId="5" pageNumber="177">7.33 d (8.4)</td>
<td id="76CD5DDAFFB2003828C6FBB8FD51FB81" box="[711,754,1120,1134]" gridcol="6" gridrow="5" pageId="5" pageNumber="177">129.1</td>
</tr>
<tr id="351C34A6FFB200382A75FBAFFD51FB6A" box="[116,754,1143,1157]" gridrow="6" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382A75FBAFFF0DFB6A" box="[116,174,1143,1157]" gridcol="0" gridrow="6" pageId="5" pageNumber="177">6</th>
<td id="76CD5DDAFFB200382AC4FBAFFEBDFB6A" box="[197,286,1143,1157]" gridcol="1" gridrow="6" pageId="5" pageNumber="177"></td>
<td id="76CD5DDAFFB200382B34FBAFFEC3FB6A" box="[309,352,1143,1157]" gridcol="2" gridrow="6" pageId="5" pageNumber="177">150.1</td>
<td id="76CD5DDAFFB200382B76FBAFFE73FB6A" box="[375,464,1143,1157]" gridcol="3" gridrow="6" pageId="5" pageNumber="177"></td>
<td id="76CD5DDAFFB200382BE6FBAFFDB1FB6A" box="[487,530,1143,1157]" gridcol="4" gridrow="6" pageId="5" pageNumber="177">145.2</td>
<td id="76CD5DDAFFB200382828FBAFFD13FB6A" box="[553,688,1143,1157]" gridcol="5" gridrow="6" pageId="5" pageNumber="177">6.79 dd (8.4, 2.3)</td>
<td id="76CD5DDAFFB2003828C6FBAFFD51FB6A" box="[711,754,1143,1157]" gridcol="6" gridrow="6" pageId="5" pageNumber="177">113.4</td>
</tr>
<tr id="351C34A6FFB200382A75FB55FD51FB73" box="[116,754,1165,1180]" gridrow="7" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382A75FB55FF0DFB73" box="[116,174,1165,1180]" gridcol="0" gridrow="7" pageId="5" pageNumber="177">7</th>
<td id="76CD5DDAFFB200382AC4FB55FEBDFB73" box="[197,286,1165,1180]" gridcol="1" gridrow="7" pageId="5" pageNumber="177"></td>
<td id="76CD5DDAFFB200382B34FB55FEC3FB73" box="[309,352,1165,1180]" gridcol="2" gridrow="7" pageId="5" pageNumber="177">152.1</td>
<td id="76CD5DDAFFB200382B76FB55FE73FB73" box="[375,464,1165,1180]" gridcol="3" gridrow="7" pageId="5" pageNumber="177"></td>
<td id="76CD5DDAFFB200382BE6FB55FDB1FB73" box="[487,530,1165,1180]" gridcol="4" gridrow="7" pageId="5" pageNumber="177">151.1</td>
<td id="76CD5DDAFFB200382828FB55FD13FB73" box="[553,688,1165,1180]" gridcol="5" gridrow="7" pageId="5" pageNumber="177"></td>
<td id="76CD5DDAFFB2003828C6FB55FD51FB73" box="[711,754,1165,1180]" gridcol="6" gridrow="7" pageId="5" pageNumber="177">160.5</td>
</tr>
<tr id="351C34A6FFB200382A75FB7CFD51FB5C" box="[116,754,1188,1203]" gridrow="8" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382A75FB7CFF0DFB5C" box="[116,174,1188,1203]" gridcol="0" gridrow="8" pageId="5" pageNumber="177">8</th>
<td id="76CD5DDAFFB200382AC4FB7CFEBDFB5C" box="[197,286,1188,1203]" gridcol="1" gridrow="8" pageId="5" pageNumber="177">6.84 s</td>
<td id="76CD5DDAFFB200382B34FB7CFEC3FB5C" box="[309,352,1188,1203]" gridcol="2" gridrow="8" pageId="5" pageNumber="177">100.1</td>
<td id="76CD5DDAFFB200382B76FB7CFE73FB5C" box="[375,464,1188,1203]" gridcol="3" gridrow="8" pageId="5" pageNumber="177">6.78 s</td>
<td id="76CD5DDAFFB200382BE6FB7CFDB1FB5C" box="[487,530,1188,1203]" gridcol="4" gridrow="8" pageId="5" pageNumber="177">102.7</td>
<td id="76CD5DDAFFB200382828FB7CFD13FB5C" box="[553,688,1188,1203]" gridcol="5" gridrow="8" pageId="5" pageNumber="177">6.81 d (2.3)</td>
<td id="76CD5DDAFFB2003828C6FB7CFD51FB5C" box="[711,754,1188,1203]" gridcol="6" gridrow="8" pageId="5" pageNumber="177">103.1</td>
</tr>
<tr id="351C34A6FFB200382A75FB63FD51FB25" box="[116,754,1211,1226]" gridrow="9" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382A75FB63FF0DFB25" box="[116,174,1211,1226]" gridcol="0" gridrow="9" pageId="5" pageNumber="177">9</th>
<td id="76CD5DDAFFB200382AC4FB63FEBDFB25" box="[197,286,1211,1226]" gridcol="1" gridrow="9" pageId="5" pageNumber="177"></td>
<td id="76CD5DDAFFB200382B34FB63FEC3FB25" box="[309,352,1211,1226]" gridcol="2" gridrow="9" pageId="5" pageNumber="177">146.4</td>
<td id="76CD5DDAFFB200382B76FB63FE73FB25" box="[375,464,1211,1226]" gridcol="3" gridrow="9" pageId="5" pageNumber="177"></td>
<td id="76CD5DDAFFB200382BE6FB63FDB1FB25" box="[487,530,1211,1226]" gridcol="4" gridrow="9" pageId="5" pageNumber="177">149.5</td>
<td id="76CD5DDAFFB200382828FB63FD13FB25" box="[553,688,1211,1226]" gridcol="5" gridrow="9" pageId="5" pageNumber="177"></td>
<td id="76CD5DDAFFB2003828C6FB63FD51FB25" box="[711,754,1211,1226]" gridcol="6" gridrow="9" pageId="5" pageNumber="177">112.1</td>
</tr>
<tr id="351C34A6FFB200382A75FB0AFD51FB0E" box="[116,754,1234,1249]" gridrow="10" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382A75FB0AFF0DFB0E" box="[116,174,1234,1249]" gridcol="0" gridrow="10" pageId="5" pageNumber="177">10</th>
<td id="76CD5DDAFFB200382AC4FB0AFEBDFB0E" box="[197,286,1234,1249]" gridcol="1" gridrow="10" pageId="5" pageNumber="177"></td>
<td id="76CD5DDAFFB200382B34FB0AFEC3FB0E" box="[309,352,1234,1249]" gridcol="2" gridrow="10" pageId="5" pageNumber="177">113.6</td>
<td id="76CD5DDAFFB200382B76FB0AFE73FB0E" box="[375,464,1234,1249]" gridcol="3" gridrow="10" pageId="5" pageNumber="177"></td>
<td id="76CD5DDAFFB200382BE6FB0AFDB1FB0E" box="[487,530,1234,1249]" gridcol="4" gridrow="10" pageId="5" pageNumber="177">110.5</td>
<td id="76CD5DDAFFB200382828FB0AFD13FB0E" box="[553,688,1234,1249]" gridcol="5" gridrow="10" pageId="5" pageNumber="177"></td>
<td id="76CD5DDAFFB2003828C6FB0AFD51FB0E" box="[711,754,1234,1249]" gridcol="6" gridrow="10" pageId="5" pageNumber="177">155.6</td>
</tr>
<tr id="351C34A6FFB200382A75FB31FD51FB16" box="[116,754,1257,1273]" gridrow="11" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382A75FB31FF0DFB16" box="[116,174,1257,1273]" gridcol="0" gridrow="11" pageId="5" pageNumber="177">6-OCH3</th>
<td id="76CD5DDAFFB200382AC4FB31FEBDFB16" box="[197,286,1257,1273]" gridcol="1" gridrow="11" pageId="5" pageNumber="177">3.95 s</td>
<td id="76CD5DDAFFB200382B34FB31FEC3FB16" box="[309,352,1257,1273]" gridcol="2" gridrow="11" pageId="5" pageNumber="177">56.4</td>
<td id="76CD5DDAFFB200382B76FB31FE73FB16" box="[375,464,1257,1273]" gridcol="3" gridrow="11" pageId="5" pageNumber="177">3.82 s</td>
<td id="76CD5DDAFFB200382BE6FB31FDB1FB16" box="[487,530,1257,1273]" gridcol="4" gridrow="11" pageId="5" pageNumber="177">56.0</td>
<td id="76CD5DDAFFB200382828FB31FD13FB16" box="[553,688,1257,1273]" gridcol="5" gridrow="11" pageId="5" pageNumber="177"></td>
<td id="76CD5DDAFFB2003828C6FB31FD51FB16" box="[711,754,1257,1273]" gridcol="6" gridrow="11" pageId="5" pageNumber="177"></td>
</tr>
<tr id="351C34A6FFB200382A75FAD8FD51FAFF" box="[116,754,1280,1296]" gridrow="12" pageId="5" pageNumber="177">
<th id="76CD5DDAFFB200382A75FAD8FF0DFAFF" box="[116,174,1280,1296]" gridcol="0" gridrow="12" pageId="5" pageNumber="177">7-OCH3</th>
<td id="76CD5DDAFFB200382AC4FAD8FEBDFAFF" box="[197,286,1280,1296]" gridcol="1" gridrow="12" pageId="5" pageNumber="177">3.92 s</td>
<td id="76CD5DDAFFB200382B34FAD8FEC3FAFF" box="[309,352,1280,1296]" gridcol="2" gridrow="12" pageId="5" pageNumber="177">56.4</td>
<td id="76CD5DDAFFB200382B76FAD8FE73FAFF" box="[375,464,1280,1296]" gridcol="3" gridrow="12" pageId="5" pageNumber="177"></td>
<td id="76CD5DDAFFB200382BE6FAD8FDB1FAFF" box="[487,530,1280,1296]" gridcol="4" gridrow="12" pageId="5" pageNumber="177"></td>
<td id="76CD5DDAFFB200382828FAD8FD13FAFF" box="[553,688,1280,1296]" gridcol="5" gridrow="12" pageId="5" pageNumber="177"></td>
<td id="76CD5DDAFFB2003828C6FAD8FD51FAFF" box="[711,754,1280,1296]" gridcol="6" gridrow="12" pageId="5" pageNumber="177"></td>
</tr>
</table>
</paragraph>
<paragraph id="8B9336E4FFB2FFC22A76FAF1FF50FAB7" blockId="5.[119,243,1321,1368]" pageId="5" pageNumber="177">
<tableNote id="76CA376AFFB2FFC22A76FAF1FF50FAB7" pageId="5" pageNumber="177" targetBox="[116,754,958,1296]" targetPageId="5">
<superScript id="7C599BACFFB2FFC22A76FAF1FFDDFADA" attach="left" box="[119,126,1321,1333]" fontSize="5" pageId="5" pageNumber="177">a</superScript>
In CDCl.
<subScript id="17A834A1FFB2FFC22ACAFAEDFF70FAAE" attach="left" box="[203,211,1333,1345]" fontSize="5" pageId="5" pageNumber="177">3</subScript>
<superScript id="7C599BACFFB2FFC22A76FA9AFFDCFAA1" attach="left" box="[119,127,1346,1358]" fontSize="5" pageId="5" pageNumber="177">b</superScript>
In DMSO-d6
</tableNote>
</paragraph>
<paragraph id="8B9336E4FFB2FFC22A84FAA5FDDAF92C" blockId="5.[100,771,1405,1982]" pageId="5" pageNumber="177">
The
<collectingCountry id="F33B7674FFB2FFC22AB1FAA5FF6EFA7F" box="[176,205,1405,1424]" name="Switzerland" pageId="5" pageNumber="177">CH</collectingCountry>
<subScript id="17A834A1FFB2FFC22ACCFA5EFF75FA7D" attach="both" box="[205,214,1414,1426]" fontSize="5" pageId="5" pageNumber="177">2</subScript>
Cl
<subScript id="17A834A1FFB2FFC22AEBFA5EFF50FA7D" attach="left" box="[234,243,1414,1426]" fontSize="5" pageId="5" pageNumber="177">2</subScript>
extract was chromatographed on silica gel with a mixtures of
<collectingCountry id="F33B7674FFB2FFC22AB5FA41FF72FA43" box="[180,209,1433,1452]" name="Switzerland" pageId="5" pageNumber="177">CH</collectingCountry>
<subScript id="17A834A1FFB2FFC22AD0FA7AFF79FA41" attach="both" box="[209,218,1442,1454]" fontSize="5" pageId="5" pageNumber="177">2</subScript>
Cl
<subScript id="17A834A1FFB2FFC22AEFFA7AFF54FA41" attach="left" box="[238,247,1442,1454]" fontSize="5" pageId="5" pageNumber="177">2</subScript>
and (
<collectingCountry id="F33B7674FFB2FFC22B2FFA41FEEEFA43" box="[302,333,1433,1452]" name="Switzerland" pageId="5" pageNumber="177">CH</collectingCountry>
<subScript id="17A834A1FFB2FFC22B4CFA7AFEF5FA41" attach="left" box="[333,342,1442,1454]" fontSize="5" pageId="5" pageNumber="177">3</subScript>
)
<subScript id="17A834A1FFB2FFC22B5FFA7AFEC4FA41" attach="right" box="[350,359,1442,1454]" fontSize="5" pageId="5" pageNumber="177">2</subScript>
CO (ratio 15:1) as eluent. The polarity was gradually increased with added (
<collectingCountry id="F33B7674FFB2FFC22BADFA6DFE68FA27" box="[428,459,1461,1480]" name="Switzerland" pageId="5" pageNumber="177">CH</collectingCountry>
<subScript id="17A834A1FFB2FFC22BCAFA66FE77FA25" attach="left" box="[459,468,1470,1482]" fontSize="5" pageId="5" pageNumber="177">3</subScript>
)
<subScript id="17A834A1FFB2FFC22BDDFA66FE46FA25" attach="right" box="[476,485,1470,1482]" fontSize="5" pageId="5" pageNumber="177">2</subScript>
CO. Some collected fractions needed purifying and were rechromatographed on silica gel with mixture of n-hexane and (
<collectingCountry id="F33B7674FFB2FFC22B30FA35FEF3F9EF" box="[305,336,1517,1536]" name="Switzerland" pageId="5" pageNumber="177">CH</collectingCountry>
<subScript id="17A834A1FFB2FFC22B50FA2EFEF9F9ED" attach="right" box="[337,346,1526,1538]" fontSize="5" pageId="5" pageNumber="177">3</subScript>
)
<subScript id="17A834A1FFB2FFC22B60FA2EFEC9F9ED" attach="right" box="[353,362,1526,1538]" fontSize="5" pageId="5" pageNumber="177">2</subScript>
CO (ratio1:3 or 1:8) or n-hexane and AcOEt (ratio1:3). The result was the isolation of the following compounds: balsamin (
<emphasis id="B958EAF6FFB2FFC22AC8F9FCFF76F9D8" bold="true" box="[201,213,1572,1591]" pageId="5" pageNumber="177">1</emphasis>
) (
<quantity id="4CD49B01FFB2FFC22AEAF9FCFE98F9D7" box="[235,315,1572,1592]" metricMagnitude="-5" metricUnit="kg" metricValue="3.56" pageId="5" pageNumber="177" unit="mg" value="35.6">35.6 mg</quantity>
, m.p. 225228 °C), izospiciformin (
<emphasis id="B958EAF6FFB2FFC2288CF9FCFD3AF9D8" bold="true" box="[653,665,1572,1591]" pageId="5" pageNumber="177">2</emphasis>
) (
<quantity id="4CD49B01FFB2FFC228AEF9FDFD5CF9D7" box="[687,767,1573,1592]" metricMagnitude="-5" metricUnit="kg" metricValue="9.89" pageId="5" pageNumber="177" unit="mg" value="98.9">98.9 mg</quantity>
, m.p. 192195 °C), stizolin (
<emphasis id="B958EAF6FFB2FFC22B70F998FEDEF9BC" bold="true" box="[369,381,1600,1619]" pageId="5" pageNumber="177">3</emphasis>
) (
<quantity id="4CD49B01FFB2FFC22B97F998FE7CF9BB" box="[406,479,1600,1620]" metricMagnitude="-4" metricUnit="kg" metricValue="1.76" pageId="5" pageNumber="177" unit="mg" value="176.0">176 mg</quantity>
, m.p. 183188 °C), 9α-hydroxyparthenolide (
<emphasis id="B958EAF6FFB2FFC22B02F984FEACF980" bold="true" box="[259,271,1628,1647]" pageId="5" pageNumber="177">4</emphasis>
) (
<quantity id="4CD49B01FFB2FFC22B29F984FED4F99F" box="[296,375,1628,1648]" metricMagnitude="-5" metricUnit="kg" metricValue="1.53" pageId="5" pageNumber="177" unit="mg" value="15.3">15.3 mg</quantity>
, m.p. 140142 °C), 8α-
<emphasis id="B958EAF6FFB2FFC22858F985FDCFF99F" bold="true" box="[601,620,1629,1648]" italics="true" pageId="5" pageNumber="177">E-</emphasis>
(4-hydroxy)-senecioyloxy-9α-hydroxyparthenolide (
<emphasis id="B958EAF6FFB2FFC22BCAF9A0FE74F964" bold="true" box="[459,471,1656,1675]" pageId="5" pageNumber="177">5</emphasis>
) (
<quantity id="4CD49B01FFB2FFC22BF2F9A0FDE1F963" box="[499,578,1656,1676]" metricMagnitude="-5" metricUnit="kg" metricValue="2.41" pageId="5" pageNumber="177" unit="mg" value="24.1">24.1 mg</quantity>
, m.p. 188190 °C), 11βH,13-dihydrostizolicin (
<emphasis id="B958EAF6FFB2FFC22B6BF94CFED5F948" bold="true" box="[362,374,1684,1703]" pageId="5" pageNumber="177">6</emphasis>
) (
<quantity id="4CD49B01FFB2FFC22B8DF94CFE6CF947" box="[396,463,1684,1704]" metricMagnitude="-6" metricUnit="kg" metricValue="5.3" pageId="5" pageNumber="177" unit="mg" value="5.3">5.3 mg</quantity>
, amorphous solid) and stizolicin (
<emphasis id="B958EAF6FFB2FFC22A6DF968FFDBF92C" bold="true" box="[108,120,1712,1731]" pageId="5" pageNumber="177">7</emphasis>
) (
<quantity id="4CD49B01FFB2FFC22A8FF968FF7BF92C" box="[142,216,1712,1731]" metricMagnitude="-4" metricUnit="kg" metricValue="3.42" pageId="5" pageNumber="177" unit="mg" value="342.0">342 mg</quantity>
, m.p. 143144 °C). NMR data in
<tableCitation id="C6AE035FFFB2FFC22812F968FDDAF92C" box="[531,633,1712,1731]" captionStart-0="Table 2" captionStart-1="Table 3" captionStart-2="Table 4" captionStartId-0="2.[100,150,161,177]" captionStartId-1="2.[100,150,905,921]" captionStartId-2="3.[100,150,161,177]" captionText-0="Table 2 1H NMR (600 MHz) spectroscopic data (δin ppm, mult; J in Hz) of compounds 14, 6 and 7. H" captionText-1="Table 3 13C NMR data of compounds 14, 6 and 7." captionText-2="Table 4 NMR data for compound 5." pageId="5" pageNumber="177">Tables 24</tableCitation>
</paragraph>
<paragraph id="8B9336E4FFB2FFC22A84F914FCA1F851" blockId="5.[100,771,1405,1982]" pageId="5" pageNumber="177">
The purified AcOEt extract (
<quantity id="4CD49B01FFB2FFC22B96F914FE64F930" box="[407,455,1740,1759]" metricMagnitude="-3" metricUnit="kg" metricValue="4.6" pageId="5" pageNumber="177" unit="g" value="4.6">4.6 g</quantity>
) was chromatographed on silica gel. A mixture of
<collectingCountry id="F33B7674FFB2FFC22B0DF930FE8AF914" box="[268,297,1768,1787]" name="Switzerland" pageId="5" pageNumber="177">CH</collectingCountry>
<subScript id="17A834A1FFB2FFC22B28F929FE91F912" attach="both" box="[297,306,1777,1789]" fontSize="5" pageId="5" pageNumber="177">2</subScript>
Cl
<subScript id="17A834A1FFB2FFC22B47F929FEECF912" attach="left" box="[326,335,1777,1789]" fontSize="5" pageId="5" pageNumber="177">2</subScript>
and (
<collectingCountry id="F33B7674FFB2FFC22B87F930FE06F914" box="[390,421,1768,1787]" name="Switzerland" pageId="5" pageNumber="177">CH</collectingCountry>
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)
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CO (ratio 4:1) was used as eluent, and the polarity was gradually increased with added (
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)
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CO. The collected fractions with the dominating compound needed purifying, so it was rechromatographed on silica gel with a mixture of
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Cl
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and
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OH (ratio 25:1 then 20:1 and 15:1). The result was a white amorphous solid (
<quantity id="4CD49B01FFB2FFC22AE1F8ABFE8CF869" box="[224,303,1907,1926]" metricMagnitude="-5" metricUnit="kg" metricValue="4.04" pageId="5" pageNumber="177" unit="mg" value="40.4">40.4 mg</quantity>
) identified as 3-(3,4-dihydroxyphenyl)propyl senecioate 3-
<emphasis id="B958EAF6FFB2FFC22AD4F857FF47F84D" bold="true" box="[213,228,1935,1954]" italics="true" pageId="5" pageNumber="177">O</emphasis>
-β-glucopyranoside = [(3-(3,4- dihydroxyphenyl)propyl- 3-methylbut-2-enoate- 3-
<emphasis id="B958EAF6FFB2FFC22B52F873FEC1F851" bold="true" box="[339,354,1963,1982]" italics="true" pageId="5" pageNumber="177">O</emphasis>
-β-glucopyranoside)] (
<emphasis id="B958EAF6FFB2FFC22839F873FDE7F851" bold="true" box="[568,580,1963,1982]" pageId="5" pageNumber="177">8</emphasis>
).
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H and
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C NMR
</paragraph>
<paragraph id="8B9336E4FFB2FFC22933FC37FC06FB9D" blockId="5.[818,1487,1003,1138]" pageId="5" pageNumber="177">
data in
<tableCitation id="C6AE035FFFB2FFC2297AFC37FC61FBED" box="[891,962,1007,1026]" captionStart="Table 6" captionStartId="5.[100,150,161,177]" captionText="Table 6 1H and13C NMR data of compound 8 (in CD OD)." pageId="5" pageNumber="177">Table 6</tableCitation>
. HR-ESI-MS (positive mode):
<emphasis id="B958EAF6FFB2FFC22EDEFC37FAA7FBED" bold="true" box="[1247,1284,1007,1026]" italics="true" pageId="5" pageNumber="177">m/z</emphasis>
435.1631 [M+Na]
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(calcd for C
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H
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O
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+Na, 435.1625), 413.1812 [M+H]
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(calcd for C
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H
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O
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+H, 413.1806); LR-ESI-MS (negative mode):
<emphasis id="B958EAF6FFB2FFC22F37FBFFFAF9FBD5" bold="true" box="[1334,1370,1063,1082]" italics="true" pageId="5" pageNumber="177">m/z</emphasis>
411 [M-H]
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, 249 [M-H-162]
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; LR-EI-MS (70 eV)
<emphasis id="B958EAF6FFB2FFC22E84FB9AFB09FBBA" bold="true" box="[1157,1194,1090,1109]" italics="true" pageId="5" pageNumber="177">m/z</emphasis>
250.2 [M-163 + H]
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, 168.0, 150.0, 83.0.
</paragraph>
</subSubSection>
</treatment>
</document>