Bostrycin
Identifieur interne : 001402 ( Pmc/Checkpoint ); précédent : 001401; suivant : 001403Bostrycin
Auteurs : Shao-Yuan Chen [République populaire de Chine] ; Chao Huang [République populaire de Chine] ; Chu-Long Zhang [République populaire de Chine] ; Yu-Zhe Chen [République populaire de Chine] ; Fu-Cheng Lin [République populaire de Chine]Source :
- Acta Crystallographica Section E: Structure Reports Online [ 1600-5368 ] ; 2008.
Abstract
The title compound, C16H16O8, is a potent nonspecific phytotoxin. The crystal structure is the average of two tautomers, 5,6,7,9,10-pentahydroxy-2-methoxy-7-methyl-1,4,5,6,7,8-hexahydroanthracene-1,4-dione and 1,4,5,6,7-pentahydroxy-2-methoxy-7-methyl-5,6,7,8,9,10-hexahydroanthracene-9,10-dione. The cyclohexene rings in both tautomers display a half-chair conformation. An extensive O—H⋯O hydrogen-bonding network is present in the crystal structure.
Url:
DOI: 10.1107/S1600536808032030
PubMed: 21581081
PubMed Central: 2959567
Affiliations:
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<author><name sortKey="Chen, Shao Yuan" sort="Chen, Shao Yuan" uniqKey="Chen S" first="Shao-Yuan" last="Chen">Shao-Yuan Chen</name>
<affiliation wicri:level="1"><nlm:aff id="a">State Key Laboratory for Rice Biology, Institute of Biotechnology, Zhejiang University,<country>People’s Republic of China</country>
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<country xml:lang="fr">République populaire de Chine</country>
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<author><name sortKey="Huang, Chao" sort="Huang, Chao" uniqKey="Huang C" first="Chao" last="Huang">Chao Huang</name>
<affiliation wicri:level="1"><nlm:aff id="a">State Key Laboratory for Rice Biology, Institute of Biotechnology, Zhejiang University,<country>People’s Republic of China</country>
</nlm:aff>
<country xml:lang="fr">République populaire de Chine</country>
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<author><name sortKey="Zhang, Chu Long" sort="Zhang, Chu Long" uniqKey="Zhang C" first="Chu-Long" last="Zhang">Chu-Long Zhang</name>
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<country xml:lang="fr">République populaire de Chine</country>
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<author><name sortKey="Chen, Yu Zhe" sort="Chen, Yu Zhe" uniqKey="Chen Y" first="Yu-Zhe" last="Chen">Yu-Zhe Chen</name>
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</nlm:aff>
<country xml:lang="fr">République populaire de Chine</country>
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<author><name sortKey="Lin, Fu Cheng" sort="Lin, Fu Cheng" uniqKey="Lin F" first="Fu-Cheng" last="Lin">Fu-Cheng Lin</name>
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<author><name sortKey="Chen, Shao Yuan" sort="Chen, Shao Yuan" uniqKey="Chen S" first="Shao-Yuan" last="Chen">Shao-Yuan Chen</name>
<affiliation wicri:level="1"><nlm:aff id="a">State Key Laboratory for Rice Biology, Institute of Biotechnology, Zhejiang University,<country>People’s Republic of China</country>
</nlm:aff>
<country xml:lang="fr">République populaire de Chine</country>
<wicri:regionArea># see nlm:aff country strict</wicri:regionArea>
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<author><name sortKey="Huang, Chao" sort="Huang, Chao" uniqKey="Huang C" first="Chao" last="Huang">Chao Huang</name>
<affiliation wicri:level="1"><nlm:aff id="a">State Key Laboratory for Rice Biology, Institute of Biotechnology, Zhejiang University,<country>People’s Republic of China</country>
</nlm:aff>
<country xml:lang="fr">République populaire de Chine</country>
<wicri:regionArea># see nlm:aff country strict</wicri:regionArea>
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<author><name sortKey="Zhang, Chu Long" sort="Zhang, Chu Long" uniqKey="Zhang C" first="Chu-Long" last="Zhang">Chu-Long Zhang</name>
<affiliation wicri:level="1"><nlm:aff id="a">State Key Laboratory for Rice Biology, Institute of Biotechnology, Zhejiang University,<country>People’s Republic of China</country>
</nlm:aff>
<country xml:lang="fr">République populaire de Chine</country>
<wicri:regionArea># see nlm:aff country strict</wicri:regionArea>
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<author><name sortKey="Chen, Yu Zhe" sort="Chen, Yu Zhe" uniqKey="Chen Y" first="Yu-Zhe" last="Chen">Yu-Zhe Chen</name>
<affiliation wicri:level="1"><nlm:aff id="b">College of Pharmaceutical Sicence, Zhejiang University,<country>People’s Republic of China</country>
</nlm:aff>
<country xml:lang="fr">République populaire de Chine</country>
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<author><name sortKey="Lin, Fu Cheng" sort="Lin, Fu Cheng" uniqKey="Lin F" first="Fu-Cheng" last="Lin">Fu-Cheng Lin</name>
<affiliation wicri:level="1"><nlm:aff id="a">State Key Laboratory for Rice Biology, Institute of Biotechnology, Zhejiang University,<country>People’s Republic of China</country>
</nlm:aff>
<country xml:lang="fr">République populaire de Chine</country>
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<series><title level="j">Acta Crystallographica Section E: Structure Reports Online</title>
<idno type="eISSN">1600-5368</idno>
<imprint><date when="2008">2008</date>
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<front><div type="abstract" xml:lang="en"><p>The title compound, C<sub>16</sub>
H<sub>16</sub>
O<sub>8</sub>
, is a potent nonspecific phytotoxin. The crystal structure is the average of two tautomers, 5,6,7,9,10-pentahydroxy-2-methoxy-7-methyl-1,4,5,6,7,8-hexahydroanthracene-1,4-dione and 1,4,5,6,7-pentahydroxy-2-methoxy-7-methyl-5,6,7,8,9,10-hexahydroanthracene-9,10-dione. The cyclohexene rings in both tautomers display a half-chair conformation. An extensive O—H⋯O hydrogen-bonding network is present in the crystal structure.</p>
</div>
</front>
<back><div1 type="bibliography"><listBibl><biblStruct></biblStruct>
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<biblStruct></biblStruct>
<biblStruct></biblStruct>
<biblStruct></biblStruct>
<biblStruct></biblStruct>
<biblStruct></biblStruct>
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<pmc article-type="research-article"><pmc-dir>properties open_access</pmc-dir>
<front><journal-meta><journal-id journal-id-type="nlm-ta">Acta Crystallogr Sect E Struct Rep Online</journal-id>
<journal-id journal-id-type="publisher-id">Acta Cryst. E</journal-id>
<journal-title-group><journal-title>Acta Crystallographica Section E: Structure Reports Online</journal-title>
</journal-title-group>
<issn pub-type="epub">1600-5368</issn>
<publisher><publisher-name>International Union of Crystallography</publisher-name>
</publisher>
</journal-meta>
<article-meta><article-id pub-id-type="pmid">21581081</article-id>
<article-id pub-id-type="pmc">2959567</article-id>
<article-id pub-id-type="publisher-id">xu2453</article-id>
<article-id pub-id-type="doi">10.1107/S1600536808032030</article-id>
<article-id pub-id-type="coden">ACSEBH</article-id>
<article-id pub-id-type="pii">S1600536808032030</article-id>
<article-categories><subj-group subj-group-type="heading"><subject>Organic Papers</subject>
</subj-group>
</article-categories>
<title-group><article-title>Bostrycin</article-title>
<alt-title><italic>C<sub>16</sub>
H<sub>16</sub>
O<sub>8</sub>
</italic>
</alt-title>
</title-group>
<contrib-group><contrib contrib-type="author"><name><surname>Chen</surname>
<given-names>Shao-Yuan</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
<xref ref-type="corresp" rid="cor">*</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Huang</surname>
<given-names>Chao</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Zhang</surname>
<given-names>Chu-Long</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Chen</surname>
<given-names>Yu-Zhe</given-names>
</name>
<xref ref-type="aff" rid="b">b</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Lin</surname>
<given-names>Fu-Cheng</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
</contrib>
<aff id="a"><label>a</label>
State Key Laboratory for Rice Biology, Institute of Biotechnology, Zhejiang University,<country>People’s Republic of China</country>
</aff>
<aff id="b"><label>b</label>
College of Pharmaceutical Sicence, Zhejiang University,<country>People’s Republic of China</country>
</aff>
</contrib-group>
<author-notes><corresp id="cor">Correspondence e-mail: <email>fuchenglin@zju.edu.cn</email>
</corresp>
</author-notes>
<pub-date pub-type="collection"><day>01</day>
<month>11</month>
<year>2008</year>
</pub-date>
<pub-date pub-type="epub"><day>31</day>
<month>10</month>
<year>2008</year>
</pub-date>
<pub-date pub-type="pmc-release"><day>31</day>
<month>10</month>
<year>2008</year>
</pub-date>
<pmc-comment> PMC Release delay is 0 months and 0 days and was based on the
. </pmc-comment>
<volume>64</volume>
<issue>Pt 11</issue>
<issue-id pub-id-type="publisher-id">e081100</issue-id>
<fpage>o2226</fpage>
<lpage>o2226</lpage>
<history><date date-type="received"><day>06</day>
<month>9</month>
<year>2008</year>
</date>
<date date-type="accepted"><day>06</day>
<month>10</month>
<year>2008</year>
</date>
</history>
<permissions><copyright-statement>© Chen et al. 2008</copyright-statement>
<copyright-year>2008</copyright-year>
<license license-type="open-access" xlink:href="http://creativecommons.org/licenses/by/2.0/uk/"><license-p>This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.</license-p>
</license>
</permissions>
<self-uri xlink:type="simple" xlink:href="http://dx.doi.org/10.1107/S1600536808032030">A full version of this article is available from Crystallography Journals Online.</self-uri>
<abstract><p>The title compound, C<sub>16</sub>
H<sub>16</sub>
O<sub>8</sub>
, is a potent nonspecific phytotoxin. The crystal structure is the average of two tautomers, 5,6,7,9,10-pentahydroxy-2-methoxy-7-methyl-1,4,5,6,7,8-hexahydroanthracene-1,4-dione and 1,4,5,6,7-pentahydroxy-2-methoxy-7-methyl-5,6,7,8,9,10-hexahydroanthracene-9,10-dione. The cyclohexene rings in both tautomers display a half-chair conformation. An extensive O—H⋯O hydrogen-bonding network is present in the crystal structure.</p>
</abstract>
</article-meta>
</front>
<floats-group><table-wrap id="table1" position="float"><label>Table 1</label>
<caption><title>Hydrogen-bond geometry (Å, °)</title>
</caption>
<table frame="hsides" rules="groups"><thead valign="bottom"><tr><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom">H⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H⋯<italic>A</italic>
</th>
</tr>
</thead>
<tbody valign="top"><tr><td style="" rowspan="1" colspan="1" align="left" valign="top">O1—H1<italic>A</italic>
⋯O3<sup>i</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.85</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.55</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">3.229 (3)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">137</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">O3—H3<italic>A</italic>
⋯O8<sup>ii</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.84</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.40</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.808 (3)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">111</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">O4—H4<italic>A</italic>
⋯O8<sup>ii</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.90</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.54</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">3.223 (3)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">132</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">O5—H5<italic>A</italic>
⋯O4</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.92</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">1.85</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.687 (3)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">152</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">O6—H6<italic>A</italic>
⋯O7<sup>iii</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.97</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">1.92</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.821 (3)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">154</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">O7—H7<italic>A</italic>
⋯O1<sup>iv</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.90</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.11</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.966 (3)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">159</td>
</tr>
<tr><td style="" rowspan="1" colspan="1" align="left" valign="top">O7—H7<italic>A</italic>
⋯O2<sup>iv</sup>
</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">0.90</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">2.40</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">3.066 (3)</td>
<td style="" rowspan="1" colspan="1" align="left" valign="top">131</td>
</tr>
</tbody>
</table>
<table-wrap-foot><p>Symmetry codes: (i) <inline-formula><inline-graphic xlink:href="e-64-o2226-efi2.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
; (ii) <inline-formula><inline-graphic xlink:href="e-64-o2226-efi3.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
; (iii) <inline-formula><inline-graphic xlink:href="e-64-o2226-efi4.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
; (iv) <inline-formula><inline-graphic xlink:href="e-64-o2226-efi5.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
.</p>
</table-wrap-foot>
</table-wrap>
</floats-group>
</pmc>
<affiliations><list><country><li>République populaire de Chine</li>
</country>
</list>
<tree><country name="République populaire de Chine"><noRegion><name sortKey="Chen, Shao Yuan" sort="Chen, Shao Yuan" uniqKey="Chen S" first="Shao-Yuan" last="Chen">Shao-Yuan Chen</name>
</noRegion>
<name sortKey="Chen, Yu Zhe" sort="Chen, Yu Zhe" uniqKey="Chen Y" first="Yu-Zhe" last="Chen">Yu-Zhe Chen</name>
<name sortKey="Huang, Chao" sort="Huang, Chao" uniqKey="Huang C" first="Chao" last="Huang">Chao Huang</name>
<name sortKey="Lin, Fu Cheng" sort="Lin, Fu Cheng" uniqKey="Lin F" first="Fu-Cheng" last="Lin">Fu-Cheng Lin</name>
<name sortKey="Zhang, Chu Long" sort="Zhang, Chu Long" uniqKey="Zhang C" first="Chu-Long" last="Zhang">Chu-Long Zhang</name>
</country>
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