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Eicosanoid


DATA No : XPR8005 INFORMANT : Yasuji Yamada

NAME : methyl (4R,5Z,7E)-4-acetoxy-7-[(S)-2-acetoxy-2-[(Z)-7-acetoxy-2-octenyl]-5-oxo-3-cyclopentenylidene]-5-heptenoate

COMMON NAME: 20-acetoxyclavulone I (Ref. 8024)
SYMBOL:
FORMULA: C27H36O9 MOL.WT (average) : 504.569


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BIOLOGICAL ACTIVITY
20-Acetoxyclavulones showed a significant anti-inflammatory effect at 30 mg/ml by the fertile egg test.(Ref. 8022)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D -31.1deg(C 0.09, CHCl3)(Ref. 8024)

DENSITY:

SOLUBILITY:20-Acetoxyclavulones are soluble in MeOH, EtOH, CHCl3, or hexane.
SPECTRAL DATA
UV SPECTRA:lmax(EtOH) 230 nm(e10900),288 nm(e13700)(Ref. 8024)

IR SPECTRA:nmax(film)1735,1705,1640,and 1235cm-1(Ref. 8024)

NMR SPECTRA:1H-NMR(270MHz,CDCl3)dppm2.03(3H,s),2.05(6H,s),2.38(2H,t,J=7.5Hz),2.66(1H,dd,J=8,14.5Hz),3.00(1H,dd,J=7,14.5Hz),3.70(3H,s),4.04(2H,t,J=6.6Hz),5.22(1H,m),5.47(1H,m),5.79(1H,m),5.79(1H,m),5.84(1H,t,J=10.2Hz),6.42(1H,d,J=6.3Hz),6.58(1H,dd,J=10.2,12.5Hz),7.27(1H,d,J=12.5Hz), 7.47(1H,d,J=6.3Hz).(Ref. 8024)13C-NMR(67.8MHz,CDCl3)dppm21.0(q,2C),21.3(q),25.6(t),27.3(t),28.5(t),29.0(t),29.8(t,2C),35.8(t),51.8(q),64.5(t),69.4(d),85.1(s),121.5(d),124.2(d),124.6(d),134.5(d),135.2(d),137.4(s),138.9(d),157.8(d),169.1(s),169.9(s),171.2(s),172.9(s),193.1(s).(Ref. 8024)

MASS SPECTRA:

OTHER SPECTRA:CDlext(EtOH)(De)nm 247(+2.6),290(-3.6).(Ref. 8022/8024)
CHROMATOGRAM DATA

SOURCE
20-Acetoxyclavulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8024)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[8022]
AUTHOR:Kikuchi,H., Tsukitani,Y., Iguchi,K., and Yamada,Y.
TITLE:Isolation and Structure Elucidation of New Type of Prostanoids Clavulone I, II, III, IV and Their Congeners, from the Okinawan Marine Animal Clavularia viridis Quoy and Gaimard.
JOURNAL:Tennen Yuki Kagoubutsu Toronkai Koen Yoshishu 26th
VOL:26 PAGE : 220 -227 (1983)
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[8024]
AUTHOR:Iguchi,K., Yamada,Y., Kikuchi,H., and Tsukitani,Y.
TITLE:Novel C-20-oxygenated Prostanoids, 20-Acetoxyclavulones, from the Stolonifer Clavularia viridis Quoy and Gaimard.
JOURNAL:Tetrahedron Lett.
VOL:24 PAGE : 4433 -4434 (1983)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.