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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}}]][[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: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}}]]

Latest revision as of 10:37, 12 November 2010

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Upper classes: LB LBF



Clavulone I
LBF20406CV05.png
Structural Information
Methyl-4R- (cis-5,trans-7) -4-acetoxy-7- [ 2S-acetoxy-2- (cis-2-octenyl) -5-oxo-3-cyclopentenylidene] -5-heptenoic acid
  • Clavulone I
  • Claviridenone-d
  • Methyl-4R- (5Z,7E) -4-acetoxy-7- [ 2S-acetoxy-2- (2Z-octenyl) -5-oxo-3-cyclopentenylidene] -5-heptenoic acid
Formula C25H34O7
Exact Mass 446.230453442
Average Mass 446.53326000000004
SMILES O(C(C)=O)[C@@](C1=CC=C[C@@H](CCC(OC)=O)OC(C)=O)(CC=CCCCCC)C=CC1=O
Physicochemical Information
[ α ]D -28.9°(C 0.36, CHCl3) KikuchiHet al.
Clavulones are soluble in MeOH, EtOH, CHCl3 or hexane.
Clavulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard. Kikuchi_H et al. Kobayashi_M et al. Kikuchi_H et al. Kobayashi_M et al.
Clavulone I was synthesized from cyclopentadiene and methyl 3-chloroformylpropionate as a racemic form. Corey_EJ et al.Clavulones were synthesized from L-(+)-diethyl tartarate and D-mannitol as a natural form. Nagaoka_H et al. Other synthesis of clavulone. Klunder_AJH et al.

Takemoto M et al. Zhu_J et al.

The biosynthesis of clavulone is suggested to proceed from arachidonic acid via 8(R)-HEPETE and pre-clavulone A. Corey_EJ Corey_EJ et al. Corey_EJ et al. Corey_EJ et al.
Clavulones showed a significant anti-inflammatory effect at 30 mu g/ml by the fertile egg test. Kikuchi_H et al.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. Honda_A et al.Clavulone showed positive chronotropic action on the cultured myocardial cells. Honda_A et al.
Spectral Information
Mass Spectra
UV Spectra λ max(EtOH) 230 nm( ε 13600),292 nm( ε 17300) KikuchiHet al.
IR Spectra ν max(film)1730,1700,1635,and 1230cm-1 KikuchiHet al.
NMR Spectra 1H-NMR(270MHz,CDCl3) δ 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). KikuchiHet al.13C-NMR(67.8MHz,CDCl3) δ 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). KikuchiHet al.
Other Spectra CD λ ext(EtOH)( Δ ε )nm 248(+3.8),291(-5.0). KikuchiHet al.
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20406CV05 See above. Corey_EJ 1983
n.a. LBF20406CV05 See above. Corey_EJ et al. 1985
n.a. LBF20406CV05 See above. Corey_EJ et al. 1984
n.a. LBF20406CV05 See above. Corey_EJ et al. 1983
n.a. LBF20406CV05 See above. Corey_EJ et al. 1987
n.a. LBF20406CV05 See above. Honda_A et al. 1991
n.a. LBF20406CV05 See above. Honda_A et al. 1985
n.a. LBF20406CV05 See above. Kikuchi_H et al. 1983
n.a. LBF20406CV05 See above. Kikuchi_H et al. 1982
n.a. LBF20406CV05 See above. Kikuchi_H et al. 1983
n.a. LBF20406CV05 See above. Klunder_AJH et al. 1991
n.a. LBF20406CV05 See above. Kobayashi_M et al. 1982
n.a. LBF20406CV05 See above. Kobayashi_M et al. 1983
n.a. LBF20406CV05 See above. Nagaoka_H et al. 1984
n.a. LBF20406CV05 See above. Takemoto_M et al. 1991
n.a. LBF20406CV05 See above. Zhu_J et al. 1995