LBF20406CV16

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Upper classes: LB LBF



Bromovulone I
LBF20406CV16.png
Structural Information
Methyl- (cis-5,trans-7) -7- [ 4R-bromo-2- (cis-2-octenyl) -5-oxo-3-cyclopentenylidene ] -5-heptenoic acid
  • Bromovulone I
  • Methyl- (5Z,7E) -7- [ 4R-bromo-2- [ (2Z-octenyl) -5-oxo-3-cyclopentenylidene ] -5-heptenoic acid
Formula C21H29BrO4
Exact Mass 424.12492201599997
Average Mass 425.35655999999994
SMILES C(CC=CC[C@](O)(C(=CC=CCCCC(OC)=O)1)C=C(C1=O)Br)CCC
Physicochemical Information
[ α ]D +6.0°(C 0.05, MeOH)(Yamada Yasuji)
Bromovulone I is soluble in MeOH, EtOH, CHCl3, or hexane.
Bromovulone I was isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard. Iguchi_K et al.
Bromovulone I showed the strong antiproliferative and cytotoxic activities in himan promyelocytic leukemia (HL-60) ((IC_{50} 0.025 mu g/ml, cytotoxic effect >0.4 mu g/ml). Honda_A et al. Honda_A et al. Iguchi_K et al.
Spectral Information
Mass Spectra EIMS m/z 424 and 426 (1:1) IguchiKet al.
UV Spectra λ EtOH
max
     247 nm( ε 12000),312 nm( ε 12000) IguchiKet al.
IR Spectra ν max(CHCl3)3300,1730, 1700, and 1630cm-1 IguchiKet al.
NMR Spectra 1H-NMR(400MHz,CDCl3) δ ppm0.89(3H,t,J=7.2Hz),1.30(6H,m),1.80(2H,quint.,J=7.4Hz),1.98(2H,brq,J=7.0Hz),2.36(2H,t,J=7.4Hz),2.42(2H,m),2.66(1H,brdd,J=7.8,14.9Hz),2.81(1H,brdd,J=7.6,14.9Hz),3.69(3H,s),5.22(1H,brtd,J=7.8,11.0Hz),5.55(1H,brtd,J=7.0,11.0Hz),6.11(1H,brtd,J=7.3,10.9Hz),6.77(1H,brdd,J=10.9,12.6Hz),7.35(1H,d,J=12.6Hz),7.43(1H,d,J=0.5Hz). IguchiKet al.
Other Spectra CD λ ext(EtOH)( Δ ε )nm 235(+5.6),260(-3.0),360(+1.2). IguchiKet al.
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20406CV16 See above. Honda_A et al. 1987
n.a. LBF20406CV16 See above. Honda_A et al. 1988
n.a. LBF20406CV16 See above. Iguchi_K et al. 1986