LBF20406CV17

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Upper classes: LB LBF



Iodovulone I
LBF20406CV17.png
Structural Information
Systematic Name Methyl- (cis-5,trans-7) -7- [ 4R-4-iodoo-2-hydroxy-2- (cis-2-octenyl) -5-oxo-3-cyclopentenylidene ] -5-heptenoic acid
Common Name
  • Iodovulone I
  • Methyl- (5Z,7E) -7- [ 4R-4-iodoo-2-hydroxy-2- (2Z-octenyl) -5-oxo-3-cyclopentenylidene ] -5-heptenoic acid
Symbol
Formula C21H29IO4
Exact Mass 472.111052416
Average Mass 472.35732999999993
SMILES C(C(=CC=CCCCC(OC)=O)1)(C(=C[C@@](O)1CC=CCCCCC)I)=O
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation [ α ]D +15.2°(C 0.07, MeOH)(Yamada Yasuji)
Refractive Index
Solubility Iodovulone I is soluble in MeOH, EtOH, CHCl3, or hexane.
Source Iodovulone I was isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard. Iguchi_K et al.
Chemical Synthesis
Metabolism
Biological Activity Iodovulone I showed the strong antiproliferative and cytotoxic activities in himan promyelocytic leukemia (HL-60) ((IC^{50} 0.06 mu g/ml, cytotoxic effect >0.4 mu g/ml). Honda_A et al. Honda_A et al. Iguchi_K et al.
Genetic Information
Note
Spectral Information
Mass Spectra CIMS m/z 473 (M+1) IguchiKet al.
UV Spectra λ max(EtOH) 240 nm( ε 22000),313 nm( ε 19500) IguchiKet al.
IR Spectra ν max(CHCl3)3300,1720, 1690, and 1620cm-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),1.97(2H,brq,J=7.7Hz),2.36(2H,t,J=7.4Hz),2.42(2H,m),2.65(1H,brdd,J=7.7,14.3Hz),2.78(1H,brdd,J=7.4,14.3Hz),3.69(3H,s),5.21(1H,brtd,J=7.7,11.0Hz),5.55(1H,brtd,J=7.4,11.0Hz),6.10(1H,tdd,J=7.9,0.9,10.9Hz),6.77(1H,brdd,J=10.9,12.6Hz),7.34(1H,d,J=12.6Hz),7.69(1H,d,J=0.5Hz). IguchiKet al.
Other Spectra CD λ ext(EtOH)( Δ ε )nm 235(+11.4),260(-5.3),365(+2.7). IguchiKet al.
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20406CV17 See above. Honda_A et al. 1987
n.a. LBF20406CV17 See above. Honda_A et al. 1988
n.a. LBF20406CV17 See above. Iguchi_K et al. 1986


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