LBF20406CV05

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Upper classes: LB LBF



Clavulone I
LBF20406CV05.png
Structural Information
Systematic Name 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
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 -28.9°(C 0.36, 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 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.

Metabolism 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.
Biological Activity 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.
Genetic Information
Note
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


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