LBF20406CV07

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Fatty acid (脂肪酸)

Glycerolipid (グリセロ脂質)

Sphingolipid (スフィンゴ脂質)

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Upper classes: LB LBF

IDs and Links
LipidBank	XPR8003
LipidMaps	LMFA03120003
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}
mol	LBF20406CV07

Clavulone III
Structural Information
Systematic Name	Methyl-4R- (trans-5,cis-7) -4-acetoxy-7- [ 2S-acetoxy-2- (cis-2-octenyl) -5-oxo-3-cyclopentenylidene] -5-heptenoic acid
Common Name	Clavulone III Claviridenone-b Methyl-4R- (5E,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 +45.5°(C 0.22, 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. Kobayashi_M 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. Hashimoto_S et al. 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 17200),295 nm( ε 17600) KikuchiHet al.
IR Spectra	ν max(film)1735,1690,1640,and 1230cm-1 KikuchiHet al.
NMR Spectra	1H-NMR(270MHz,CDCl3) δ ppm0.88(3H,t,J=6.9Hz),2.04(3H,s),2.10(3H,s),2.39(2H,t,J=7.5Hz),2.66(1H,dd,J=7,14.5Hz),2.86(1H,dd,J=7,14.5Hz),3.67(3H,s),5.21(1H,dt,J=11,7Hz),5.52(1H,dt,J=11,8Hz),5.44(1H,q,J=6Hz),6.02(1H,dd,J=6,15.5Hz),6.36(1H,d,J=6.3Hz),6.52(1H,d,J=11.2Hz),7.50(1H,d,J=6.3Hz),7.74(1H,dd,J=11.2,15.5Hz). KikuchiHet al.13C-NMR(67.8MHz,CDCl3) δ ppm14.0(q),21.0(q),21.7(q),22.5(t),27.4(t),29.1(t),29.2(t),29.8(t),31.5(t),35.6(t),51.7(q),72.5(d),85.3(s),121.4(d),126.5(d),133.4(d),134.8(d),135.7(s),141.0(d),156.1(d),169.7(s),170.1(s),173.1(s),194.1(s). KikuchiHet al.
Other Spectra	CD λ ext(EtOH)( Δ ε )nm 245(+3.4),297(-0.6). KikuchiHet al.
Chromatograms

Reported Metabolites, References

Biospecies ID Compound Name Reference Comment n.a. LBF20406CV07 See above. Corey_EJ 1983 n.a. LBF20406CV07 See above. Corey_EJ et al. 1985 n.a. LBF20406CV07 See above. Corey_EJ et al. 1983 n.a. LBF20406CV07 See above. Corey_EJ et al. 1987 n.a. LBF20406CV07 See above. Hashimoto_S et al. 1985 n.a. LBF20406CV07 See above. Honda_A et al. 1991 n.a. LBF20406CV07 See above. Kikuchi_H et al. 1983 n.a. LBF20406CV07 See above. Kikuchi_H et al. 1982 n.a. LBF20406CV07 See above. Kikuchi_H et al. 1983 n.a. LBF20406CV07 See above. Klunder_AJH et al. 1991 n.a. LBF20406CV07 See above. Kobayashi_M et al. 1982 n.a. LBF20406CV07 See above. Kobayashi_M et al. 1983 n.a. LBF20406CV07 See above. Nagaoka_H et al. 1984 n.a. LBF20406CV07 See above. Takeda_K et al. 1997 n.a. LBF20406CV07 See above. Takemoto_M et al. 1991 n.a. LBF20406CV07 See above. Zhu_J et al. 1995