Editor at 05:59, 21 October 2010

2010-10-21T05:59:44Z

← Older revision		Revision as of 14:59, 21 October 2010
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	\|LipidBank=XPR8002		\|LipidBank=XPR8002
	\|LipidMaps=LMFA03120002		\|LipidMaps=LMFA03120002
	\|SysName=Methyl-4R- (5-~~trans,~~7~~-trans~~) -4-acetoxy-7- [ 2S-acetoxy-2- [cis-2-octenyl] -5-oxo-3-cyclopentenylidene] -5-heptenoic acid		\|SysName=Methyl-4R- (trans-5,trans-7) -4-acetoxy-7- [ 2S-acetoxy-2- (cis-2-octenyl) -5-oxo-3-cyclopentenylidene] -5-heptenoic acid
	\|Common Name=&&Clavulone II&&Claviridenone-c&&Methyl-4R- (5E,7E) -4-acetoxy-7- [ 2S-acetoxy-2- [(~~Z)-2~~-octenyl] -5-oxo-3-cyclopentenylidene] -5-heptenoic acid&&		\|Common Name=&&Clavulone II&&Claviridenone-c&&Methyl-4R- (5E,7E) -4-acetoxy-7- [ 2S-acetoxy-2- (2Z-octenyl) -5-oxo-3-cyclopentenylidene] -5-heptenoic acid&&
	\|Optical=[ alpha ]_D +10.9°(C 0.35, CHCl_3 )[[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}}]]		\|Optical=[ alpha ]_D +10.9°(C 0.35, CHCl_3 )[[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}}]]
	\|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=XPR8002 |LipidMaps=LMFA03120002 |SysName=Methyl-4R- (5-trans,7-trans) -4-acetoxy-7- [ 2S-acetoxy-2- [cis-2-octenyl] -5...

2010-09-16T08:57:35Z

New page: {{Lipid/Header}} {{Hierarchy|{{PAGENAME}}}} {{Metabolite |LipidBank=XPR8002 |LipidMaps=LMFA03120002 |SysName=Methyl-4R- (5-trans,7-trans) -4-acetoxy-7- [ 2S-acetoxy-2- [cis-2-octenyl] -5...

New page

{{Lipid/Header}}

{{Hierarchy|{{PAGENAME}}}}

{{Metabolite
|LipidBank=XPR8002
|LipidMaps=LMFA03120002
|SysName=Methyl-4R- (5-trans,7-trans) -4-acetoxy-7- [ 2S-acetoxy-2- [cis-2-octenyl] -5-oxo-3-cyclopentenylidene] -5-heptenoic acid
|Common Name=&&Clavulone II&&Claviridenone-c&&Methyl-4R- (5E,7E) -4-acetoxy-7- [ 2S-acetoxy-2- [(Z)-2-octenyl] -5-oxo-3-cyclopentenylidene] -5-heptenoic acid&&
|Optical=[ alpha ]_D +10.9°(C 0.35, CHCl_3 )[[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}}]]
|Solubility=Clavulones are soluble in MeOH, EtOH, CHCl_3 , or hexane.
|UV Spectra= lambda _{max}(EtOH) 230 nm( epsilon 14500),292 nm( epsilon 19300) [[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}}]]
|IR Spectra= nu _{max}(film)1730,1700,1640,and 1230cm^{-1}[[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}}]]
|NMR Spectra=^1 H-NMR(270MHz,CDCl_3 ) delta ppm0.88(3H,t,J=6.9Hz),2.07(3H,s),2.08(3H,s),2.38(2H,t,J=7.5Hz),2.69(1H,dd,J=8,14.5Hz),2.88(1H,dd,J=7,14.5Hz),3.68(3H,s),5.22(1H,m),5.52(1H,dt,J=10.9,8Hz),5.42(1H,q,J=7Hz),6.02(1H,dd,J=7,14.5Hz),6.41(1H,d,J=6.3Hz),6.75(1H,dd,J=11.6,14.5Hz),6.87(1H,d,J=11.6Hz),7.47(1H,d,J=6.3Hz).[[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}}]]^{13}C-NMR(67.8MHz,CDCl_3 ) delta ppm14.0(q),21.0(q),21.2(q),22.5(t),27.4(t),29.1(t),29.1(t),29.6(t),31.5(t),36.0(t),51.8(q),72.8(d),85.1(s),121.1(d),126.9(d),129.3(d),135.0(d),137.0(s),141.3(d),158.1(d),169.5(s),169.9(s),172.9(s),193.4(s).[[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}}]]
|NOTE Spectra=CD lambda _{ext}(EtOH)( Delta epsilon )nm 250(+4.2),293(-3.4).[[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.,1982,23,5171|{{RelationTable/GetFirstAuthor|Reference:Kikuchi_H:Tsukitani_Y:Iguchi_K:Yamada_Y:,Tetrahedron Lett.,1982,23,5171}}]][[Reference:Kobayashi_M:Yasuzawa_T:Yoshihara_M:Akutsu_H:Kyogoku_Y:Kitagawa_I:,Tetrahedron Lett.,1982,23,5331|{{RelationTable/GetFirstAuthor|Reference:Kobayashi_M:Yasuzawa_T:Yoshihara_M:Akutsu_H:Kyogoku_Y:Kitagawa_I:,Tetrahedron Lett.,1982,23,5331}}]][[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}}]]
|Chemical Synthesis=Clavulone II was synthesized from cyclopentadiene and methyl 3-chloroformylpropionate as a racemic form.[[Reference:Corey_EJ:Mehrotra_MM:,J. Am. Chem. Soc.,1984,106,3384|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Mehrotra_MM:,J. Am. Chem. Soc.,1984,106,3384}}]]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:Hashimoto_S:Arai_Y:Hamanaka_N:,Tetrahedron Lett.,1985,26,2679|{{RelationTable/GetFirstAuthor|Reference:Hashimoto_S:Arai_Y:Hamanaka_N:,Tetrahedron Lett.,1985,26,2679}}]][[Reference:Shibasaki_M:Ogawa_Y:,Tetrahedron Lett.,1985,26,3841|{{RelationTable/GetFirstAuthor|Reference:Shibasaki_M:Ogawa_Y:,Tetrahedron Lett.,1985,26,3841}}]][[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}}]][[Reference:Takeda_K:Nakajima_A:Yoshii_E:,Synlett,1997,,2554|{{RelationTable/GetFirstAuthor|Reference:Takeda_K:Nakajima_A:Yoshii_E:,Synlett,1997,,255}}]]
|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}}]]Clavulone II showed strong antiproliferative activity in the human myeloid leukemia (HL-60) cells (IC_{50} 0.2 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}}]]Clavulone II was entrapped into lipid microspheres of 0.2 mu m diameter to lipo-drug. Daily treatment with lipo-clavulone II (12.5 mg/kg/day, i.p.) on days 1 through 5 markedly prolonged the survival time (73% ILS) of mice inoculated with sarcoma 180 as compared with that of corresponding dose of respective free clavulone II.[[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 250(+4.2),293(-3.4).[[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}}

LBF20406CV06 - Revision history

Editor at 05:59, 21 October 2010

Editor: New page: {{Lipid/Header}} {{Hierarchy|{{PAGENAME}}}} {{Metabolite |LipidBank=XPR8002 |LipidMaps=LMFA03120002 |SysName=Methyl-4R- (5-trans,7-trans) -4-acetoxy-7- [ 2S-acetoxy-2- [cis-2-octenyl] -5...