LBF20406CV05 - Revision history

Editor at 10:37, 12 November 2010

2010-11-12T10:37:37Z

← Older revision		Revision as of 19:37, 12 November 2010
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	\|NOTE Spectra=CD lambda _{ext}(EtOH)( Delta epsilon )nm 248(+3.8),291(-5.0).[[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}}]]		\|NOTE Spectra=CD lambda _{ext}(EtOH)( Delta epsilon )nm 248(+3.8),291(-5.0).[[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}}]]		\|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 I 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: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}}]]		\|Chemical Synthesis=Clavulone I 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: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: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 clavulone 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}}]]		\|Metabolism=The biosynthesis of clavulone 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}}]]

Editor at 10:35, 12 November 2010

2010-11-12T10:35:21Z

← Older revision		Revision as of 19:35, 12 November 2010
Line 16:		Line 16:
	\|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}}]]		\|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 I 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: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}}]]		\|Chemical Synthesis=Clavulone I 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: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: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: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 clavulone 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}}]]		\|Metabolism=The biosynthesis of clavulone 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}}]]

Editor at 10:34, 12 November 2010

2010-11-12T10:34:03Z

← Older revision		Revision as of 19:34, 12 November 2010
Line 15:		Line 15:
	\|NOTE Spectra=CD lambda _{ext}(EtOH)( Delta epsilon )nm 248(+3.8),291(-5.0).[[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}}]]		\|NOTE Spectra=CD lambda _{ext}(EtOH)( Delta epsilon )nm 248(+3.8),291(-5.0).[[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}}]]		\|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 I 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: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}}]]		\|Chemical Synthesis=Clavulone I 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: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: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: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: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}}]]

Editor at 10:32, 12 November 2010

2010-11-12T10:32:59Z

← Older revision		Revision as of 19:32, 12 November 2010
Line 15:		Line 15:
	\|NOTE Spectra=CD lambda _{ext}(EtOH)( Delta epsilon )nm 248(+3.8),291(-5.0).[[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}}]]		\|NOTE Spectra=CD lambda _{ext}(EtOH)( Delta epsilon )nm 248(+3.8),291(-5.0).[[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}}]]		\|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 I 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: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}}]]		\|Chemical Synthesis=Clavulone I 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: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: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 clavulone 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}}]]		\|Metabolism=The biosynthesis of clavulone 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 I showed strong antiproliferative activity in the human myeloid leukemia (HL-60) cells (IC_{50} 0.2 mu g/ml). Clavulone arrests the cells in the G1-phase and inhibits the cell growth of HL-60 cells by inhibiting S-phase DNA synthesis.[[Reference:Honda_A:Yamamoto_Y:Mori_Y:Yamada_Y:Kikuchi_H:,Biochem. Biophys. Res. Commun.,1985,130,515\|{{RelationTable/GetFirstAuthor\|Reference:Honda_A:Yamamoto_Y:Mori_Y:Yamada_Y:Kikuchi_H:,Biochem. Biophys. Res. Commun.,1985,130,515}}]]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}}]]		\|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 I showed strong antiproliferative activity in the human myeloid leukemia (HL-60) cells (IC_{50} 0.2 mu g/ml). Clavulone arrests the cells in the G1-phase and inhibits the cell growth of HL-60 cells by inhibiting S-phase DNA synthesis.[[Reference:Honda_A:Yamamoto_Y:Mori_Y:Yamada_Y:Kikuchi_H:,Biochem. Biophys. Res. Commun.,1985,130,515\|{{RelationTable/GetFirstAuthor\|Reference:Honda_A:Yamamoto_Y:Mori_Y:Yamada_Y:Kikuchi_H:,Biochem. Biophys. Res. Commun.,1985,130,515}}]]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}}]]

Editor at 05:59, 21 October 2010

2010-10-21T05:59:07Z

← Older revision		Revision as of 14:59, 21 October 2010
Line 6:		Line 6:
	\|LipidBank=XPR8001		\|LipidBank=XPR8001
	\|LipidMaps=LMFA03120001		\|LipidMaps=LMFA03120001
	\|SysName=Methyl-4R- (~~trans~~-5,trans-7) -4-acetoxy-7- [ 2S-acetoxy-2- (cis-2-octenyl) -5-oxo-3-cyclopentenylidene] -5-heptenoic acid		\|SysName=Methyl-4R- (cis-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- (2Z-octenyl) -5-oxo-3-cyclopentenylidene] -5-heptenoic acid&&		\|Common Name=&&Clavulone I&&Claviridenone-d&&Methyl-4R- (5Z,7E) -4-acetoxy-7- [ 2S-acetoxy-2- (2Z-octenyl) -5-oxo-3-cyclopentenylidene] -5-heptenoic acid&&
	\|Optical=[ alpha ]_D -28.9°(C 0.36, 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 -28.9°(C 0.36, 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 at 05:58, 21 October 2010

2010-10-21T05:58:46Z

← Older revision		Revision as of 14:58, 21 October 2010
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	\|LipidBank=XPR8001		\|LipidBank=XPR8001
	\|LipidMaps=LMFA03120001		\|LipidMaps=LMFA03120001
	\|SysName=Methyl-4R- (~~cis~~-5,trans-7) -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 I&&Claviridenone-d&&Methyl-4R- (5Z,7E) -4-acetoxy-7- [ 2S-acetoxy-2- (2Z-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 -28.9°(C 0.36, 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 -28.9°(C 0.36, 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 at 05:58, 21 October 2010

2010-10-21T05:58:29Z

← Older revision		Revision as of 14:58, 21 October 2010
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	\|LipidBank=XPR8001		\|LipidBank=XPR8001
	\|LipidMaps=LMFA03120001		\|LipidMaps=LMFA03120001
	\|SysName=Methyl-4R- (cis-5,7~~-trans~~) -4-acetoxy-7- [ 2S-acetoxy-2- (cis-2-octenyl) -5-oxo-3-cyclopentenylidene] -5-heptenoic acid		\|SysName=Methyl-4R- (cis-5,trans-7) -4-acetoxy-7- [ 2S-acetoxy-2- (cis-2-octenyl) -5-oxo-3-cyclopentenylidene] -5-heptenoic acid
	\|Common Name=&&Clavulone I&&Claviridenone-d&&Methyl-4R- (5Z,7E) -4-acetoxy-7- [ 2S-acetoxy-2- (2Z-octenyl) -5-oxo-3-cyclopentenylidene] -5-heptenoic acid&&		\|Common Name=&&Clavulone I&&Claviridenone-d&&Methyl-4R- (5Z,7E) -4-acetoxy-7- [ 2S-acetoxy-2- (2Z-octenyl) -5-oxo-3-cyclopentenylidene] -5-heptenoic acid&&
	\|Optical=[ alpha ]_D -28.9°(C 0.36, 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 -28.9°(C 0.36, 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}}]]

Editor at 05:55, 21 October 2010

2010-10-21T05:55:20Z

← Older revision		Revision as of 14:55, 21 October 2010
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	\|LipidBank=XPR8001		\|LipidBank=XPR8001
	\|LipidMaps=LMFA03120001		\|LipidMaps=LMFA03120001
	\|SysName=Methyl-4R- (5~~-cis~~,7-trans) -4-acetoxy-7- [ 2S-acetoxy-2- [cis-2-octenyl] -5-oxo-3-cyclopentenylidene] -5-heptenoic acid		\|SysName=Methyl-4R- (cis-5,7-trans) -4-acetoxy-7- [ 2S-acetoxy-2- (cis-2-octenyl) -5-oxo-3-cyclopentenylidene] -5-heptenoic acid
	\|Common Name=&&Clavulone I&&Claviridenone-d&&Methyl-4R- (5Z,7E) -4-acetoxy-7- [ 2S-acetoxy-2- [(~~Z)-2~~-octenyl] -5-oxo-3-cyclopentenylidene] -5-heptenoic acid&&		\|Common Name=&&Clavulone I&&Claviridenone-d&&Methyl-4R- (5Z,7E) -4-acetoxy-7- [ 2S-acetoxy-2- (2Z-octenyl) -5-oxo-3-cyclopentenylidene] -5-heptenoic acid&&
	\|Optical=[ alpha ]_D -28.9°(C 0.36, 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 -28.9°(C 0.36, 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.

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{{Metabolite
|LipidBank=XPR8001
|LipidMaps=LMFA03120001
|SysName=Methyl-4R- (5-cis,7-trans) -4-acetoxy-7- [ 2S-acetoxy-2- [cis-2-octenyl] -5-oxo-3-cyclopentenylidene] -5-heptenoic acid
|Common Name=&&Clavulone I&&Claviridenone-d&&Methyl-4R- (5Z,7E) -4-acetoxy-7- [ 2S-acetoxy-2- [(Z)-2-octenyl] -5-oxo-3-cyclopentenylidene] -5-heptenoic acid&&
|Optical=[ alpha ]_D -28.9°(C 0.36, 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 13600),292 nm( epsilon 17300)[[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)1730,1700,1635,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=6.7Hz),2.03(3H,s),2.05(3H,s),2.38(2H,t,J=7.7Hz),2.66(1H,dd,J=7,14.5Hz),2.97(1H,dd,J=7,14.5Hz),3.70(3H,s),5.22(1H,dt,J=10.9,7Hz),5.45(1H,dt,J=10.9,8Hz),5.78(1H,m),5.86(1H,t,J=10Hz),6.42(1H,d,J=6.3Hz),6.59(1H,dd,J=10,12.5Hz),7.25(1H,d,J=12.5Hz),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),20.9(q),21.2(q),22.5(t),27.4(t),29.0(t),29.8(t),29.8(t),31.4(t),35.9(t),51.7(q),69.4(d),85.2(s),121.0(d),124.3(d),124.4(d),134.9(d),137.5(s),138.7(d),157.8(d),169.0(s),169.7(s),172.7(s),193.0(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 248(+3.8),291(-5.0).[[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 I 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: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 clavulone 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 I showed strong antiproliferative activity in the human myeloid leukemia (HL-60) cells (IC_{50} 0.2 mu g/ml). Clavulone arrests the cells in the G1-phase and inhibits the cell growth of HL-60 cells by inhibiting S-phase DNA synthesis.[[Reference:Honda_A:Yamamoto_Y:Mori_Y:Yamada_Y:Kikuchi_H:,Biochem. Biophys. Res. Commun.,1985,130,515|{{RelationTable/GetFirstAuthor|Reference:Honda_A:Yamamoto_Y:Mori_Y:Yamada_Y:Kikuchi_H:,Biochem. Biophys. Res. Commun.,1985,130,515}}]]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 248(+3.8),291(-5.0).[[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}}]]
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