LBF20406CV13

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Upper classes: LB LBF



Chlorovulone II
LBF20406CV13.png
Structural Information
Systematic Name Methyl- (trans-5,trans-7) -7- [ 4R-chloro-2-hydroxy-2- (cis-2-octenyl) -5-oxo-3-cyclopentenylidene ] -5-heptenoic acid
Common Name
  • Chlorovulone II
  • Methyl- (5E,7E) -7- [ 4R-chloro-2-hydroxy-2- [(2Z-octenyl) -5-oxo-3-cyclopentenylidene ] -5-heptenoic acid
Symbol
Formula C21H29ClO4
Exact Mass 380.175437126
Average Mass 380.90525999999994
SMILES C(C(=O)1)(Cl)=C[C@](CC=CCCCCC)(C(=CC=CCCCC(OC)=O)1)O
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation [ α ]D +22.7°(C 0.075, CHCl3) IguchiKet al.
Refractive Index
Solubility Chlorovulones are soluble in MeOH, EtOH, CHCl3, or hexane.
Source Chlorovulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard. Iguchi_K et al. Nagaoka_H et al.
Chemical Synthesis Photoisomerization of chlorovulone I (fluoresent lamp, benzene, 40 hr) gave a mixture of chlorovulones I, II and III. Iguchi_K et al.(-)-Cholovulone II was synthesized from D-(-)-diethyl tartarate. Nagaoka_H et al.
Metabolism
Biological Activity (-)-Chlorovulone II showed the strong antiproliferative and cytotoxic activities in himan promyelocytic leukemia (HL-60) ((IC_{50} 0.01 mu g/ml, cytotoxic effect >0.1 mu g/ml). Honda_A et al.
Genetic Information
Note
Spectral Information
Mass Spectra
UV Spectra λ max(EtOH) 237 nm( ε 10000),312 nm( ε 10100) IguchiKet al.
IR Spectra ν max(CHCl3)3560,3300,1730,1705, and 1635cm-1(Yamada Yasuji)
NMR Spectra 1H-NMR(400MHz,CDCl3) δ ppm0.88(3H,t,J=7.1Hz),1.30(6H,m),1.82(2H,quint.,J=7.4Hz),1.96(2H,brq,J=7.5Hz),2.30(2H,t,J=7.5Hz),2.35(2H,t,J=7.4Hz),2.68(1H,brdd,J=7.9,14.3Hz),2.81(1H,brdd,J=7.5,14.3Hz),3.67(3H,s),5.23(1H,ttd,J=1.4,7.7,10.9Hz),5.55(1H,brtd,J=7.5,10.9Hz),6.28(1H,td,J=7.4,15.1Hz),6.77(1H,tdd,J=1.3,11.9,15.1Hz),7.03(1H,d,J=11.9Hz),7.20(1H,s). IguchiKet al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20406CV13 See above. Honda_A et al. 1987
n.a. LBF20406CV13 See above. Iguchi_K et al. 1985
n.a. LBF20406CV13 See above. Nagaoka_H et al. 1986


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