Editor at 06:00, 21 October 2010

2010-10-21T06:00:37Z

← Older revision		Revision as of 15:00, 21 October 2010
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	\|LipidBank=XPR8004		\|LipidBank=XPR8004
	\|LipidMaps=LMFA03120004		\|LipidMaps=LMFA03120004
	\|SysName=Methyl-4R- (5-~~cis,~~7~~-cis~~) -4-acetoxy-7- [ 2S-acetoxy-2- [cis-2-octenyl] -5-oxo-3-cyclopentenylidene] -5-heptenoic acid		\|SysName=Methyl-4R- (cis-5,cis-7) -4-acetoxy-7- [ 2S-acetoxy-2- (cis-2-octenyl) -5-oxo-3-cyclopentenylidene] -5-heptenoic acid
	\|Common Name=&&Clavulone IV&&Claviridenone-a&&Methyl-4R- (5Z,7Z) -4-acetoxy-7- [ 2S-acetoxy-2- [(~~Z)-2~~-octenyl] -5-oxo-3-cyclopentenylidene] -5-heptenoic acid&&		\|Common Name=&&Clavulone IV&&Claviridenone-a&&Methyl-4R- (5Z,7Z) -4-acetoxy-7- [ 2S-acetoxy-2- (2Z-octenyl) -5-oxo-3-cyclopentenylidene] -5-heptenoic acid&&
	\|Optical=[ alpha ]_D -80.0°(CHCl_3 )[[Reference:Kikuchi_H:Tsukitani_Y:Iguchi_K:Yamada_Y:,Tennen Yuki Kagoubutsu Toronkai Koen Yoshishu 26th,1983,26,220\|{{RelationTable/GetFirstAuthor\|Reference:Kikuchi_H:Tsukitani_Y:Iguchi_K:Yamada_Y:,Tennen Yuki Kagoubutsu Toronkai Koen Yoshishu 26th,1983,26,220}}]]		\|Optical=[ alpha ]_D -80.0°(CHCl_3 )[[Reference:Kikuchi_H:Tsukitani_Y:Iguchi_K:Yamada_Y:,Tennen Yuki Kagoubutsu Toronkai Koen Yoshishu 26th,1983,26,220\|{{RelationTable/GetFirstAuthor\|Reference:Kikuchi_H:Tsukitani_Y:Iguchi_K:Yamada_Y:,Tennen Yuki Kagoubutsu Toronkai Koen Yoshishu 26th,1983,26,220}}]]
	\|Solubility=Clavulones are soluble in MeOH, EtOH, CHCl_3 , or hexane.		\|Solubility=Clavulones are soluble in MeOH, EtOH, CHCl_3 , or hexane.

Editor: New page: {{Lipid/Header}} {{Hierarchy|{{PAGENAME}}}} {{Metabolite |LipidBank=XPR8004 |LipidMaps=LMFA03120004 |SysName=Methyl-4R- (5-cis,7-cis) -4-acetoxy-7- [ 2S-acetoxy-2- [cis-2-octenyl] -5-oxo...

2010-09-16T09:02:00Z

New page: {{Lipid/Header}} {{Hierarchy|{{PAGENAME}}}} {{Metabolite |LipidBank=XPR8004 |LipidMaps=LMFA03120004 |SysName=Methyl-4R- (5-cis,7-cis) -4-acetoxy-7- [ 2S-acetoxy-2- [cis-2-octenyl] -5-oxo...

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{{Lipid/Header}}

{{Hierarchy|{{PAGENAME}}}}

{{Metabolite
|LipidBank=XPR8004
|LipidMaps=LMFA03120004
|SysName=Methyl-4R- (5-cis,7-cis) -4-acetoxy-7- [ 2S-acetoxy-2- [cis-2-octenyl] -5-oxo-3-cyclopentenylidene] -5-heptenoic acid
|Common Name=&&Clavulone IV&&Claviridenone-a&&Methyl-4R- (5Z,7Z) -4-acetoxy-7- [ 2S-acetoxy-2- [(Z)-2-octenyl] -5-oxo-3-cyclopentenylidene] -5-heptenoic acid&&
|Optical=[ alpha ]_D -80.0°(CHCl_3 )[[Reference:Kikuchi_H:Tsukitani_Y:Iguchi_K:Yamada_Y:,Tennen Yuki Kagoubutsu Toronkai Koen Yoshishu 26th,1983,26,220|{{RelationTable/GetFirstAuthor|Reference:Kikuchi_H:Tsukitani_Y:Iguchi_K:Yamada_Y:,Tennen Yuki Kagoubutsu Toronkai Koen Yoshishu 26th,1983,26,220}}]]
|Solubility=Clavulones are soluble in MeOH, EtOH, CHCl_3 , or hexane.
|UV Spectra= lambda _{max}(EtOH) 230 nm( epsilon 10600),295 nm( epsilon 9900)[[Reference:Kikuchi_H:Tsukitani_Y:Iguchi_K:Yamada_Y:,Tennen Yuki Kagoubutsu Toronkai Koen Yoshishu 26th,1983,26,220|{{RelationTable/GetFirstAuthor|Reference:Kikuchi_H:Tsukitani_Y:Iguchi_K:Yamada_Y:,Tennen Yuki Kagoubutsu Toronkai Koen Yoshishu 26th,1983,26,220}}]]
|IR Spectra= nu _{max}(film)1730,1695,1640,and 1240cm^{-1}[[Reference:Kikuchi_H:Tsukitani_Y:Iguchi_K:Yamada_Y:,Tennen Yuki Kagoubutsu Toronkai Koen Yoshishu 26th,1983,26,220|{{RelationTable/GetFirstAuthor|Reference:Kikuchi_H:Tsukitani_Y:Iguchi_K:Yamada_Y:,Tennen Yuki Kagoubutsu Toronkai Koen Yoshishu 26th,1983,26,220}}]]
|NMR Spectra=^1 H-NMR(270MHz,CDCl_3 ) delta ppm0.88(3H,t,J=6.9Hz),2.03(3H,s),2.07(3H,s),2.36(2H,t,J=7.5Hz),2.65(1H,dd,J=7.3,14.2Hz),2.83(1H,dd,J=8,14.2Hz),3.68(3H,s),5.27(1H,m),5.52(1H,m),5.73(1H,t,J=10.6Hz),5.83(1H,m),6.39(1H,d,J=5.9Hz),7.02(1H,d,J=12.5Hz),7.49(1H,d,J=5.9Hz),7.61(1H,t,J=11.5Hz).(Yamada Yasuji)^{13}C-NMR(67.8MHz,CDCl_3 ) delta ppm14.0(q),21.1(q),21.6(q),22.5(t),27.4(t),29.1(t),29.6(t),29.8(t),31.5(t),36.1(t),51.7(q),68.1(d),85.0(s),121.5(d),126.0(d),127.9(d),134.8(d),136.5(d),136.6(d),137.0(s),156.7(d),169.9(s),170.1(s),172.9(s),194.2(s).(Yasuji Yamada)
|NOTE Spectra=CD lambda _{ext}(EtOH)( Delta epsilon )nm 245(+1.2),290(-1.4).[[Reference:Kikuchi_H:Tsukitani_Y:Iguchi_K:Yamada_Y:,Tennen Yuki Kagoubutsu Toronkai Koen Yoshishu 26th,1983,26,220|{{RelationTable/GetFirstAuthor|Reference:Kikuchi_H:Tsukitani_Y:Iguchi_K:Yamada_Y:,Tennen Yuki Kagoubutsu Toronkai Koen Yoshishu 26th,1983,26,220}}]]
|Source=Clavulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.[[Reference:Kikuchi_H:Tsukitani_Y:Iguchi_K:Yamada_Y:,Tetrahedron Lett.,1983,24,1549|{{RelationTable/GetFirstAuthor|Reference:Kikuchi_H:Tsukitani_Y:Iguchi_K:Yamada_Y:,Tetrahedron Lett.,1983,24,1549}}]][[Reference:Kobayashi_M:Yasuzawa_T:Yoshihara_M:Son_BW:Kyogoku_Y:Kitagawa_I:,Chem. Pharm. Bull. (Tokyo),1983,31,1440|{{RelationTable/GetFirstAuthor|Reference:Kobayashi_M:Yasuzawa_T:Yoshihara_M:Son_BW:Kyogoku_Y:Kitagawa_I:,Chem. Pharm. Bull. (Tokyo),1983,31,1440}}]][[Reference:Kikuchi_H:Tsukitani_Y:Iguchi_K:Yamada_Y:,Tennen Yuki Kagoubutsu Toronkai Koen Yoshishu 26th,1983,26,220|{{RelationTable/GetFirstAuthor|Reference:Kikuchi_H:Tsukitani_Y:Iguchi_K:Yamada_Y:,Tennen Yuki Kagoubutsu Toronkai Koen Yoshishu 26th,1983,26,220}}]]
|Chemical Synthesis=Clavulones were synthesized from L-(+)-diethyl tartarate and D-mannitol as a natural form.[[Reference:Nagaoka_H:Miyakoshi_T:Yamada_Y:,Tetrahedron Lett.,1984,25,3621|{{RelationTable/GetFirstAuthor|Reference:Nagaoka_H:Miyakoshi_T:Yamada_Y:,Tetrahedron Lett.,1984,25,3621}}]]Other synthesis of clavulone.[[Reference:Klunder_AJH:Zwanenburg_B:Liu_ZY:,Tetrahedron Lett.,1991,32,3131|{{RelationTable/GetFirstAuthor|Reference:Klunder_AJH:Zwanenburg_B:Liu_ZY:,Tetrahedron Lett.,1991,32,3131}}]][[Reference:Takemoto_M:Koshida_A:Miyazima_K:Suzuki_K:Achiwa_K:,Chem. Pharm. Bull. (Tokyo),1991,39,1106|{{RelationTable/GetFirstAuthor|Reference:Takemoto_M:Koshida_A:Miyazima_K:Suzuki_K:Achiwa_K:,Chem. Pharm. Bull. (Tokyo),1991,39,1106}}]][[Reference:Zhu_J:Yang_JY:Klunder_AJH:Liu_ZY:Zwanenburg_B:,Tetrahedron,1995,51,5847|{{RelationTable/GetFirstAuthor|Reference:Zhu_J:Yang_JY:Klunder_AJH:Liu_ZY:Zwanenburg_B:,Tetrahedron,1995,51,5847}}]]
|Metabolism=The biosynthesis of clavulones is suggested to proceed from arachidonic acid via 8(R)-HEPETE and pre-clavulone A.[[Reference:Corey_EJ:,Experientia,1983,39,1084|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:,Experientia,1983,39,1084}}]][[Reference:Corey_EJ:Schmidt_G:Shimoji_K:,Tetrahedron Lett.,1983,24,3169|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Schmidt_G:Shimoji_K:,Tetrahedron Lett.,1983,24,3169}}]][[Reference:Corey_EJ:Lansbury_PT_Jr:Yamada_Y:,Tetrahedron Lett.,1985,26,4171|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Lansbury_PT_Jr:Yamada_Y:,Tetrahedron Lett.,1985,26,4171}}]][[Reference:Corey_EJ:dAlarcao_M:Matsuda_SPT:Lansbury_PT_Jr:Yamada_Y:,J. Am. Chem. Soc.,1987,109,289|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:dAlarcao_M:Matsuda_SPT:Lansbury_PT_Jr:Yamada_Y:,J. Am. Chem. Soc.,1987,109,289}}]]
|Biological Activity=Clavulones showed a significant anti-inflammatory effect at 30 mu g/ml by the fertile egg test.[[Reference:Kikuchi_H:Tsukitani_Y:Iguchi_K:Yamada_Y:,Tetrahedron Lett.,1982,23,5171|{{RelationTable/GetFirstAuthor|Reference:Kikuchi_H:Tsukitani_Y:Iguchi_K:Yamada_Y:,Tetrahedron Lett.,1982,23,5171}}]]Clavulone showed positive chronotropic action on the cultured myocardial cells.[[Reference:Honda_A:Hong_S:Yamada_Y:Mori_Y:,Res. Commun. Chem. Pathol. Pharmacol.,1991,72,363|{{RelationTable/GetFirstAuthor|Reference:Honda_A:Hong_S:Yamada_Y:Mori_Y:,Res. Commun. Chem. Pathol. Pharmacol.,1991,72,363}}]]
|Other Spectra=CD lambda _{ext}(EtOH)( Delta epsilon )nm 245(+1.2),290(-1.4).[[Reference:Kikuchi_H:Tsukitani_Y:Iguchi_K:Yamada_Y:,Tennen Yuki Kagoubutsu Toronkai Koen Yoshishu 26th,1983,26,220|{{RelationTable/GetFirstAuthor|Reference:Kikuchi_H:Tsukitani_Y:Iguchi_K:Yamada_Y:,Tennen Yuki Kagoubutsu Toronkai Koen Yoshishu 26th,1983,26,220}}]]
}}

{{Lipid/Footer}}

LBF20406CV08 - Revision history

Editor at 06:00, 21 October 2010

Editor: New page: {{Lipid/Header}} {{Hierarchy|{{PAGENAME}}}} {{Metabolite |LipidBank=XPR8004 |LipidMaps=LMFA03120004 |SysName=Methyl-4R- (5-cis,7-cis) -4-acetoxy-7- [ 2S-acetoxy-2- [cis-2-octenyl] -5-oxo...