LBF20406CV08

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(脂肪酸)
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Upper classes: LB LBF



Clavulone IV
LBF20406CV08.png
Structural Information
Systematic Name 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- (2Z-octenyl) -5-oxo-3-cyclopentenylidene] -5-heptenoic acid
Symbol
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
Melting Point
Boiling Point
Density
Optical Rotation [ α ]D -80.0°(CHCl3) KikuchiHet al.
Refractive Index
Solubility Clavulones are soluble in MeOH, EtOH, CHCl3, or hexane.
Source 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.
Chemical Synthesis 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.
Metabolism The biosynthesis of clavulones 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.
Biological Activity Clavulones showed a significant anti-inflammatory effect at 30 mu g/ml by the fertile egg test. Kikuchi_H et al.Clavulone showed positive chronotropic action on the cultured myocardial cells. Honda_A et al.
Genetic Information
Note
Spectral Information
Mass Spectra
UV Spectra λ max(EtOH) 230 nm( ε 10600),295 nm( ε 9900) KikuchiHet al.
IR Spectra ν max(film)1730,1695,1640,and 1240cm-1 KikuchiHet al.
NMR Spectra 1H-NMR(270MHz,CDCl3) δ 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)13C-NMR(67.8MHz,CDCl3) δ 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)
Other Spectra CD λ ext(EtOH)( Δ ε )nm 245(+1.2),290(-1.4). KikuchiHet al.
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20406CV08 See above. Corey_EJ 1983
n.a. LBF20406CV08 See above. Corey_EJ et al. 1985
n.a. LBF20406CV08 See above. Corey_EJ et al. 1983
n.a. LBF20406CV08 See above. Corey_EJ et al. 1987
n.a. LBF20406CV08 See above. Honda_A et al. 1991
n.a. LBF20406CV08 See above. Kikuchi_H et al. 1983
n.a. LBF20406CV08 See above. Kikuchi_H et al. 1982
n.a. LBF20406CV08 See above. Kikuchi_H et al. 1983
n.a. LBF20406CV08 See above. Klunder_AJH et al. 1991
n.a. LBF20406CV08 See above. Kobayashi_M et al. 1982
n.a. LBF20406CV08 See above. Kobayashi_M et al. 1983
n.a. LBF20406CV08 See above. Nagaoka_H et al. 1984
n.a. LBF20406CV08 See above. Takemoto_M et al. 1991
n.a. LBF20406CV08 See above. Zhu_J et al. 1995


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