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Eicosanoid


DATA No : XPR8035 INFORMANT : Yasuji Yamada

NAME : (R)-4-{(1E,3E)-3-[(S)-2-acetoxy-2-[(Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-1-propenyl}-4-butanolide

COMMON NAME: clavulolactone II (Ref. 8039)
SYMBOL:
FORMULA: C22H28O5 MOL.WT (average) : 372.455


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D -25.6deg(C 0.26, CHCl3)(Ref. 8039)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lEtOHmax 292 nm(e16500),231 nm(e12500)(Ref. 8039)

IR SPECTRA:nfilmmax1778,1745, 1704, 1644, and 1231cm-1(Ref. 8039)

NMR SPECTRA:1H-NMR(400MHz,CDCl3)dppm0.87(3H,t,J=7.2Hz),1.20-1.34(6H,m),1.94(2H,brq,J=6.3Hz),2.02(3H,s),2.04(1H,m),2.52(1H,m),2.55(2H,m),2.71(1H,brdd,J=8.1,14.2Hz),2.91(1H,brdd,J=7.1,14.2Hz),5.15(1H,m),5.15(1H,m),5.52(1H,m),6.17(1H,dd,J=4.9,14.7Hz),6.42(1H,d,J=6.1Hz),6.82(1H,ddd,J=1.5,12.0,14.7Hz),6.91(1H,brd,J=12.0Hz),7.50(1H,brd,J=6.1Hz).(Ref. 8039) 13C-NMR(100MHz,CDCl3)dppm14.0,21.2,22.5,27.4,27.7,28.2,29.0,31.5,35.8,78.6,85.2,121.0,124.9,128.9,135.06,135.14,137.2,140.8,158.0,169.3,176.2,193.3.(Ref. 8039)

MASS SPECTRA:EIMS m/z 372 (M+). HREIMS m/z 372.1920 for C22H28O5, calcd 372.1937.(Ref. 8039)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Clavulolactones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8038/8039)
CHEMICAL SYNTHESIS
Clavulolactone II was converted from clavulone II.(Ref. 8039)
METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[8038]
AUTHOR:Iwashima, M., Okamoto, K., Konno, F., and Iguchi, K.
TITLE:New marine prostanoids from the okinawan soft coral, clavularia viridis PubMed ID:10075785
JOURNAL:J Nat Prod.
VOL:62 PAGE : 352-354 (1999)
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[8039]
AUTHOR:Iguchi, K., Iwashima, M., and Watanabe, K.
TITLE:Clavulolactones, New Marine Prostanoids with g-Lactonic Moiety in the a-Side-Chain from the Okinawan Soft Coral, Clavularia viridis.
JOURNAL:J. Nat. Prod.
VOL:58 PAGE : 790 -793 (1995)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.