LBF20406CV06

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Upper classes: LB LBF



Clavulone II
LBF20406CV06.png
Structural Information
Systematic Name 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 II
  • Claviridenone-c
  • Methyl-4R- (5E,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 +10.9°(C 0.35, 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 II 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. Hashimoto_S et al. Shibasaki_M et al. Klunder_AJH et al. Takemoto M et al. Zhu_J et al. Takeda_K 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.Clavulone II showed strong antiproliferative activity in the human myeloid leukemia (HL-60) cells (IC_{50} 0.2 mu g/ml). Honda_A et al.Clavulone II was entrapped into lipid microspheres of 0.2 mu m diameter to lipo-drug. Daily treatment with lipo-clavulone II (12.5 mg/kg/day, i.p.) on days 1 through 5 markedly prolonged the survival time (73% ILS) of mice inoculated with sarcoma 180 as compared with that of corresponding dose of respective free clavulone II. Honda_A et al.
Genetic Information
Note
Spectral Information
Mass Spectra
UV Spectra λ max(EtOH) 230 nm( ε 14500),292 nm( ε 19300) KikuchiHet al.
IR Spectra ν max(film)1730,1700,1640,and 1230cm-1 KikuchiHet al.
NMR Spectra 1H-NMR(270MHz,CDCl3) δ ppm0.88(3H,t,J=6.9Hz),2.07(3H,s),2.08(3H,s),2.38(2H,t,J=7.5Hz),2.69(1H,dd,J=8,14.5Hz),2.88(1H,dd,J=7,14.5Hz),3.68(3H,s),5.22(1H,m),5.52(1H,dt,J=10.9,8Hz),5.42(1H,q,J=7Hz),6.02(1H,dd,J=7,14.5Hz),6.41(1H,d,J=6.3Hz),6.75(1H,dd,J=11.6,14.5Hz),6.87(1H,d,J=11.6Hz),7.47(1H,d,J=6.3Hz). KikuchiHet al.13C-NMR(67.8MHz,CDCl3) δ ppm14.0(q),21.0(q),21.2(q),22.5(t),27.4(t),29.1(t),29.1(t),29.6(t),31.5(t),36.0(t),51.8(q),72.8(d),85.1(s),121.1(d),126.9(d),129.3(d),135.0(d),137.0(s),141.3(d),158.1(d),169.5(s),169.9(s),172.9(s),193.4(s). KikuchiHet al.
Other Spectra CD λ ext(EtOH)( Δ ε )nm 250(+4.2),293(-3.4). KikuchiHet al.
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20406CV06 See above. Corey_EJ 1983
n.a. LBF20406CV06 See above. Corey_EJ et al. 1985
n.a. LBF20406CV06 See above. Corey_EJ et al. 1984
n.a. LBF20406CV06 See above. Corey_EJ et al. 1983
n.a. LBF20406CV06 See above. Corey_EJ et al. 1987
n.a. LBF20406CV06 See above. Hashimoto_S et al. 1985
n.a. LBF20406CV06 See above. Honda_A et al. 1991
n.a. LBF20406CV06 See above. Honda_A et al. 1988
n.a. LBF20406CV06 See above. Honda_A et al. 1988
n.a. LBF20406CV06 See above. Kikuchi_H et al. 1983
n.a. LBF20406CV06 See above. Kikuchi_H et al. 1982
n.a. LBF20406CV06 See above. Kikuchi_H et al. 1983
n.a. LBF20406CV06 See above. Klunder_AJH et al. 1991
n.a. LBF20406CV06 See above. Kobayashi_M et al. 1982
n.a. LBF20406CV06 See above. Kobayashi_M et al. 1983
n.a. LBF20406CV06 See above. Nagaoka_H et al. 1984
n.a. LBF20406CV06 See above. Shibasaki_M et al. 1985
n.a. LBF20406CV06 See above. Takeda_K et al. 1997
n.a. LBF20406CV06 See above. Takemoto_M et al. 1991
n.a. LBF20406CV06 See above. Zhu_J et al. 1995


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