https://lipidbank.jp/mediawiki/index.php?action=history&feed=atom&title=LBF20406CV13 2026-04-30T20:09:49Z Revision history for this page on the wiki MediaWiki 1.43.0 https://lipidbank.jp/mediawiki/index.php?title=LBF20406CV13&diff=55205&oldid=prev 2010-10-21T06:02:55Z

<p></p> <table style="background-color: #fff; color: #202122;" data-mw="interface"> <col class="diff-marker" /> <col class="diff-content" /> <col class="diff-marker" /> <col class="diff-content" /> <tr class="diff-title" lang="en"> <td colspan="2" style="background-color: #fff; color: #202122; text-align: center;">← Older revision</td> <td colspan="2" style="background-color: #fff; color: #202122; text-align: center;">Revision as of 15:02, 21 October 2010</td> </tr><tr><td colspan="2" class="diff-lineno" id="mw-diff-left-l6">Line 6:</td> <td colspan="2" class="diff-lineno">Line 6:</td></tr> <tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|LipidBank=XPR8009</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|LipidBank=XPR8009</div></td></tr> <tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|LipidMaps=LMFA03120009</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|LipidMaps=LMFA03120009</div></td></tr> <tr><td class="diff-marker" data-marker="−"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #ffe49c; vertical-align: top; white-space: pre-wrap;"><div>|SysName=Methyl- (5-<del style="font-weight: bold; text-decoration: none;">trans,</del>7<del style="font-weight: bold; text-decoration: none;">-trans</del>) -7- [ 4R-chloro-2-hydroxy-2- <del style="font-weight: bold; text-decoration: none;">[</del>cis-2-octenyl<del style="font-weight: bold; text-decoration: none;">] </del>-5-oxo-3-cyclopentenylidene ] -5-heptenoic acid</div></td><td class="diff-marker" data-marker="+"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #a3d3ff; vertical-align: top; white-space: pre-wrap;"><div>|SysName=Methyl- (<ins style="font-weight: bold; text-decoration: none;">trans-</ins>5<ins style="font-weight: bold; text-decoration: none;">,trans</ins>-7) -7- [ 4R-chloro-2-hydroxy-2- <ins style="font-weight: bold; text-decoration: none;"> (</ins>cis-2-octenyl<ins style="font-weight: bold; text-decoration: none;">) </ins>-5-oxo-3-cyclopentenylidene ] -5-heptenoic acid</div></td></tr> <tr><td class="diff-marker" data-marker="−"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #ffe49c; vertical-align: top; white-space: pre-wrap;"><div>|Common Name=&amp;&amp;Chlorovulone II&amp;&amp;Methyl- (5E,7E) -7- [ 4R-chloro-2-hydroxy-2- [(<del style="font-weight: bold; text-decoration: none;">Z)-2</del>-octenyl<del style="font-weight: bold; text-decoration: none;">] </del>-5-oxo-3-cyclopentenylidene ] -5-heptenoic acid&amp;&amp;</div></td><td class="diff-marker" data-marker="+"></td><td style="color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #a3d3ff; vertical-align: top; white-space: pre-wrap;"><div>|Common Name=&amp;&amp;Chlorovulone II&amp;&amp;Methyl- (5E,7E) -7- [ 4R-chloro-2-hydroxy-2- [(<ins style="font-weight: bold; text-decoration: none;">2Z</ins>-octenyl<ins style="font-weight: bold; text-decoration: none;">) </ins>-5-oxo-3-cyclopentenylidene ] -5-heptenoic acid&amp;&amp;</div></td></tr> <tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Optical=[ alpha ]_D  +22.7°(C 0.075, CHCl_3 )[[Reference:Iguchi_K:Kaneta_S:Mori_K:Yamada_Y:Honda_A:Mori_Y:,Tetrahedron Lett.,1985,26,5787|{{RelationTable/GetFirstAuthor|Reference:Iguchi_K:Kaneta_S:Mori_K:Yamada_Y:Honda_A:Mori_Y:,Tetrahedron Lett.,1985,26,5787}}]]</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Optical=[ alpha ]_D  +22.7°(C 0.075, CHCl_3 )[[Reference:Iguchi_K:Kaneta_S:Mori_K:Yamada_Y:Honda_A:Mori_Y:,Tetrahedron Lett.,1985,26,5787|{{RelationTable/GetFirstAuthor|Reference:Iguchi_K:Kaneta_S:Mori_K:Yamada_Y:Honda_A:Mori_Y:,Tetrahedron Lett.,1985,26,5787}}]]</div></td></tr> <tr><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Solubility=Chlorovulones are soluble in MeOH, EtOH, CHCl_3 , or hexane.</div></td><td class="diff-marker"></td><td style="background-color: #f8f9fa; color: #202122; font-size: 88%; border-style: solid; border-width: 1px 1px 1px 4px; border-radius: 0.33em; border-color: #eaecf0; vertical-align: top; white-space: pre-wrap;"><div>|Solubility=Chlorovulones are soluble in MeOH, EtOH, CHCl_3 , or hexane.</div></td></tr> </table>

Editor https://lipidbank.jp/mediawiki/index.php?title=LBF20406CV13&diff=55204&oldid=prev 2010-09-16T09:10:56Z

<p>New page: {{Lipid/Header}} {{Hierarchy|{{PAGENAME}}}} {{Metabolite |LipidBank=XPR8009 |LipidMaps=LMFA03120009 |SysName=Methyl- (5-trans,7-trans) -7- [ 4R-chloro-2-hydroxy-2- [cis-2-octenyl] -5-oxo...</p> <p><b>New page</b></p><div>{{Lipid/Header}}<br /> <br /> {{Hierarchy|{{PAGENAME}}}}<br /> <br /> {{Metabolite<br /> |LipidBank=XPR8009<br /> |LipidMaps=LMFA03120009<br /> |SysName=Methyl- (5-trans,7-trans) -7- [ 4R-chloro-2-hydroxy-2- [cis-2-octenyl] -5-oxo-3-cyclopentenylidene ] -5-heptenoic acid<br /> |Common Name=&amp;&amp;Chlorovulone II&amp;&amp;Methyl- (5E,7E) -7- [ 4R-chloro-2-hydroxy-2- [(Z)-2-octenyl] -5-oxo-3-cyclopentenylidene ] -5-heptenoic acid&amp;&amp;<br /> |Optical=[ alpha ]_D +22.7°(C 0.075, CHCl_3 )[[Reference:Iguchi_K:Kaneta_S:Mori_K:Yamada_Y:Honda_A:Mori_Y:,Tetrahedron Lett.,1985,26,5787|{{RelationTable/GetFirstAuthor|Reference:Iguchi_K:Kaneta_S:Mori_K:Yamada_Y:Honda_A:Mori_Y:,Tetrahedron Lett.,1985,26,5787}}]]<br /> |Solubility=Chlorovulones are soluble in MeOH, EtOH, CHCl_3 , or hexane.<br /> |UV Spectra= lambda _{max}(EtOH) 237 nm( epsilon 10000),312 nm( epsilon 10100)[[Reference:Iguchi_K:Kaneta_S:Mori_K:Yamada_Y:Honda_A:Mori_Y:,Tetrahedron Lett.,1985,26,5787|{{RelationTable/GetFirstAuthor|Reference:Iguchi_K:Kaneta_S:Mori_K:Yamada_Y:Honda_A:Mori_Y:,Tetrahedron Lett.,1985,26,5787}}]]<br /> |IR Spectra= nu _{max}(CHCl_3 )3560,3300,1730,1705, and 1635cm^{-1}(Yamada Yasuji)<br /> |NMR Spectra=^1 H-NMR(400MHz,CDCl_3 ) delta ppm0.88(3H,t,J=7.1Hz),1.30(6H,m),1.82(2H,quint.,J=7.4Hz),1.96(2H,brq,J=7.5Hz),2.30(2H,t,J=7.5Hz),2.35(2H,t,J=7.4Hz),2.68(1H,brdd,J=7.9,14.3Hz),2.81(1H,brdd,J=7.5,14.3Hz),3.67(3H,s),5.23(1H,ttd,J=1.4,7.7,10.9Hz),5.55(1H,brtd,J=7.5,10.9Hz),6.28(1H,td,J=7.4,15.1Hz),6.77(1H,tdd,J=1.3,11.9,15.1Hz),7.03(1H,d,J=11.9Hz),7.20(1H,s).[[Reference:Iguchi_K:Kaneta_S:Mori_K:Yamada_Y:Honda_A:Mori_Y:,Tetrahedron Lett.,1985,26,5787|{{RelationTable/GetFirstAuthor|Reference:Iguchi_K:Kaneta_S:Mori_K:Yamada_Y:Honda_A:Mori_Y:,Tetrahedron Lett.,1985,26,5787}}]]<br /> |Source=Chlorovulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.[[Reference:Iguchi_K:Kaneta_S:Mori_K:Yamada_Y:Honda_A:Mori_Y:,Tetrahedron Lett.,1985,26,5787|{{RelationTable/GetFirstAuthor|Reference:Iguchi_K:Kaneta_S:Mori_K:Yamada_Y:Honda_A:Mori_Y:,Tetrahedron Lett.,1985,26,5787}}]][[Reference:Nagaoka_H:Iguchi_K:Miyakoshi_T:Yamada_N:Yamada_Y:,Tetrahedron Lett.,1986,27,223|{{RelationTable/GetFirstAuthor|Reference:Nagaoka_H:Iguchi_K:Miyakoshi_T:Yamada_N:Yamada_Y:,Tetrahedron Lett.,1986,27,223}}]]<br /> |Chemical Synthesis=Photoisomerization of chlorovulone I (fluoresent lamp, benzene, 40 hr) gave a mixture of chlorovulones I, II and III.[[Reference:Iguchi_K:Kaneta_S:Mori_K:Yamada_Y:Honda_A:Mori_Y:,Tetrahedron Lett.,1985,26,5787|{{RelationTable/GetFirstAuthor|Reference:Iguchi_K:Kaneta_S:Mori_K:Yamada_Y:Honda_A:Mori_Y:,Tetrahedron Lett.,1985,26,5787}}]](-)-Cholovulone II was synthesized from D-(-)-diethyl tartarate.[[Reference:Nagaoka_H:Iguchi_K:Miyakoshi_T:Yamada_N:Yamada_Y:,Tetrahedron Lett.,1986,27,223|{{RelationTable/GetFirstAuthor|Reference:Nagaoka_H:Iguchi_K:Miyakoshi_T:Yamada_N:Yamada_Y:,Tetrahedron Lett.,1986,27,223}}]]<br /> |Metabolism=<br /> |Biological Activity=(-)-Chlorovulone II showed the strong antiproliferative and cytotoxic activities in himan promyelocytic leukemia (HL-60) ((IC_{50} 0.01 mu g/ml, cytotoxic effect &gt;0.1 mu g/ml).[[Reference:Honda_A:Mori_Y:Iguchi_K:Yamada_Y:,Mol. Pharmacol.,1987,32,530|{{RelationTable/GetFirstAuthor|Reference:Honda_A:Mori_Y:Iguchi_K:Yamada_Y:,Mol. Pharmacol.,1987,32,530}}]]<br /> }}<br /> <br /> {{Lipid/Footer}}</div>

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