Editor at 06:02, 21 October 2010

2010-10-21T06:02:34Z

← Older revision		Revision as of 15:02, 21 October 2010
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	\|LipidBank=XPR8008		\|LipidBank=XPR8008
	\|LipidMaps=LMFA03120008		\|LipidMaps=LMFA03120008
	\|SysName=Methyl- (5-~~cis,~~7~~-trans~~) -7- [ 4R-chloro-2-hydroxy-2- [cis-2-octenyl] -5-oxo-3-cyclopentenylidene ] -5-heptenoic acid		\|SysName=Methyl- (cis-5,trans-7) -7- [ 4R-chloro-2-hydroxy-2- (cis-2-octenyl) -5-oxo-3-cyclopentenylidene ] -5-heptenoic acid
	\|Common Name=&&Chlorovulone I&&Methyl- (5Z,7E) -7- [ 4R-chloro-2-hydroxy-2- [(~~Z)-2~~-octenyl] -5-oxo-3-cyclopentenylidene ] -5-heptenoic acid&&		\|Common Name=&&Chlorovulone I&&Methyl- (5Z,7E) -7- [4R-chloro-2-hydroxy-2- [(2Z-octenyl) -5-oxo-3-cyclopentenylidene] -5-heptenoic acid&&
	\|Optical=[ alpha ]_D -1.2°(C 0.17, 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}}]]		\|Optical=[ alpha ]_D -1.2°(C 0.17, 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}}]]
	\|Solubility=Chlorovulones are soluble in MeOH, EtOH, CHCl_3 , or hexane.		\|Solubility=Chlorovulones are soluble in MeOH, EtOH, CHCl_3 , or hexane.

Editor: New page: {{Lipid/Header}} {{Hierarchy|{{PAGENAME}}}} {{Metabolite |LipidBank=XPR8008 |LipidMaps=LMFA03120008 |SysName=Methyl- (5-cis,7-trans) -7- [ 4R-chloro-2-hydroxy-2- [cis-2-octenyl] -5-oxo-3...

2010-09-16T09:09:02Z

New page: {{Lipid/Header}} {{Hierarchy|{{PAGENAME}}}} {{Metabolite |LipidBank=XPR8008 |LipidMaps=LMFA03120008 |SysName=Methyl- (5-cis,7-trans) -7- [ 4R-chloro-2-hydroxy-2- [cis-2-octenyl] -5-oxo-3...

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{{Lipid/Header}}

{{Hierarchy|{{PAGENAME}}}}

{{Metabolite
|LipidBank=XPR8008
|LipidMaps=LMFA03120008
|SysName=Methyl- (5-cis,7-trans) -7- [ 4R-chloro-2-hydroxy-2- [cis-2-octenyl] -5-oxo-3-cyclopentenylidene ] -5-heptenoic acid
|Common Name=&&Chlorovulone I&&Methyl- (5Z,7E) -7- [ 4R-chloro-2-hydroxy-2- [(Z)-2-octenyl] -5-oxo-3-cyclopentenylidene ] -5-heptenoic acid&&
|Optical=[ alpha ]_D -1.2°(C 0.17, 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}}]]
|Solubility=Chlorovulones are soluble in MeOH, EtOH, CHCl_3 , or hexane.
|UV Spectra= lambda _{max}(EtOH) 243 nm( epsilon 14600),315 nm( epsilon 15100)[[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}}]]
|IR Spectra= nu _{max}(CHCl_3 )1705cm^{-1}[[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}}]]
|NMR Spectra=^1 H-NMR(400MHz,CDCl_3 ) delta ppm0.88(3H,t,J=7.2Hz),1.30(6H,m),1.80(2H,quint.,J=7.4Hz),1.97(2H,brq,J=7.0Hz),2.35(2H,t,J=7.4Hz),2.42(2H,m),2.67(1H,ddd,J=0.5,7.8,14.2Hz),2.82(1H,ddd,J=0.5,7.5,14.2Hz),3.68(3H,s),5.22(1H,ttd,J=1.5,7.7,10.9Hz),5.54(1H,ttd,J=1.4,8.7,10.9Hz),6.11(1H,tdd,J=7.9,0.9,10.9Hz),6.77(1H,tdd,J=1.5,10.9,12.6Hz),7.21(1H,d,J=0.6Hz),7.33(1H,brd,J=12.6Hz).[[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}}]]^{13}C-NMR(100MHz,CDCl_3 ) delta ppm13.9(q),22.4(t),24.3(t),27.1(t),27.3(t),29.0(t),31.4(t),33.2(t),33.6(t),51.6(q),77.7(s),121.7(d),123.8(d),127.9(d),134.8(d),136.4(s),137.9(s),143.6(d),154.0(d),173.6(s),187.7(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}}]]
|NOTE Spectra=CD lambda _{ext}(EtOH)( Delta epsilon )nm 232(+7.6),265(-6.1),360(+3.1).[[Reference:Iguchi_K:Kaneta_S:Mori_K:Yamada_Y:Honda_A:Mori_Y:,J. Chem. Soc., Chem. Commun.,1986,,981|{{RelationTable/GetFirstAuthor|Reference:Iguchi_K:Kaneta_S:Mori_K:Yamada_Y:Honda_A:Mori_Y:,J. Chem. Soc., Chem. Commun.,1986,,981}}]]
|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}}]]
|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}}]]
|Metabolism=
|Biological Activity=Chlorovulone I showed the strong antiproliferative and cytotoxic activities in himan promyelocytic leukemia (HL-60) ((IC_{50} 0.01 mu g/ml, cytotoxic effect >0.1 mu g/ml).[[Reference:Honda_A:Mori_Y:Iguchi_K:Yamada_Y:,Prostaglandins,1988,36,621|{{RelationTable/GetFirstAuthor|Reference:Honda_A:Mori_Y:Iguchi_K:Yamada_Y:,Prostaglandins,1988,36,621}}]][[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}}]][[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}}]]Chlorovulone I was entrapped into lipid microspheres of 0.2 mu m diameter to lipo-drug. Daily treatment with lipo-chlorovulone I (1.6 mg/kg/day, i.p.) on days 1 through 5 markedly prolonged the survival time (135% ILS) of mice inoculated with sarcoma 180 as compared with that of corresponding dose of respective free chlorovulone I.[[Reference:Honda_A:Mori_Y:Yamada_Y:Nakaike_S:Hayashi_H:Otomo_S:,Res. Commun. Chem. Pathol. Pharmacol.,1988,61,413|{{RelationTable/GetFirstAuthor|Reference:Honda_A:Mori_Y:Yamada_Y:Nakaike_S:Hayashi_H:Otomo_S:,Res. Commun. Chem. Pathol. Pharmacol.,1988,61,413}}]]
|Other Spectra=CD lambda _{ext}(EtOH)( Delta epsilon )nm 232(+7.6),265(-6.1),360(+3.1).[[Reference:Iguchi_K:Kaneta_S:Mori_K:Yamada_Y:Honda_A:Mori_Y:,J. Chem. Soc., Chem. Commun.,1986,,981|{{RelationTable/GetFirstAuthor|Reference:Iguchi_K:Kaneta_S:Mori_K:Yamada_Y:Honda_A:Mori_Y:,J. Chem. Soc., Chem. Commun.,1986,,981}}]]
}}

{{Lipid/Footer}}

LBF20406CV12 - Revision history

Editor at 06:02, 21 October 2010

Editor: New page: {{Lipid/Header}} {{Hierarchy|{{PAGENAME}}}} {{Metabolite |LipidBank=XPR8008 |LipidMaps=LMFA03120008 |SysName=Methyl- (5-cis,7-trans) -7- [ 4R-chloro-2-hydroxy-2- [cis-2-octenyl] -5-oxo-3...