Back to HOME

Eicosanoid


DATA No : XPR8004 INFORMANT : Yasuji Yamada

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

COMMON NAME: clavulone IV(Ref. 8022)/claviridenone-a(Ref. 8002/8006)
SYMBOL:
FORMULA: C25H34O7 MOL.WT (average) : 446.533


Download ChemDraw structure data
BIOLOGICAL ACTIVITY
Clavulones showed a significant anti-inflammatory effect at 30 mg/ml by the fertile egg test.(Ref. 8001)Clavulone showed positive chronotropic action on the cultured myocardial cells.(Ref. 8014)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D -80.0deg(CHCl3)(Ref. 8022)

DENSITY:

SOLUBILITY:Clavulones are soluble in MeOH, EtOH, CHCl3, or hexane.
SPECTRAL DATA
UV SPECTRA:lmax(EtOH) 230 nm(e10600),295 nm(e9900)(Ref. 8022)

IR SPECTRA:nmax(film)1730,1695,1640,and 1240cm-1(Ref. 8022)

NMR SPECTRA:1H-NMR(270MHz,CDCl3)dppm0.88(3H,t,J=6.9Hz),2.03(3H,s),2.07(3H,s),2.36(2H,t,J=7.5Hz),2.65(1H,dd,J=7.3,14.2Hz),2.83(1H,dd,J=8,14.2Hz),3.68(3H,s),5.27(1H,m),5.52(1H,m),5.73(1H,t,J=10.6Hz),5.83(1H,m),6.39(1H,d,J=5.9Hz),7.02(1H,d,J=12.5Hz),7.49(1H,d,J=5.9Hz),7.61(1H,t,J=11.5Hz).(Yamada Yasuji)13C-NMR(67.8MHz,CDCl3)dppm14.0(q),21.1(q),21.6(q),22.5(t),27.4(t),29.1(t),29.6(t),29.8(t),31.5(t),36.1(t),51.7(q),68.1(d),85.0(s),121.5(d),126.0(d),127.9(d),134.8(d),136.5(d),136.6(d),137.0(s),156.7(d),169.9(s),170.1(s),172.9(s),194.2(s).(Yasuji Yamada)

MASS SPECTRA:

OTHER SPECTRA:CDlext(EtOH)(De)nm 245(+1.2),290(-1.4).(Ref. 8022)
CHROMATOGRAM DATA

SOURCE
Clavulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard.(Ref. 8003/8006/8022)
CHEMICAL SYNTHESIS
Clavulones were synthesized from L-(+)-diethyl tartarate and D-mannitol as a natural form.(Ref. 8008)Other synthesis of clavulone.(Ref. 8015/8016/8017)
METABOLISM
The biosynthesis of clavulones is suggested to proceed from arachidonic acid via 8(R)-HEPETE and pre-clavulone A.(Ref. 8004/8005/8012/8013)
GENETIC INFORMATION

NOTE

REFERENCES
[8001]
AUTHOR:Kikuchi,H., Tsukitani,Y., Iguchi,K., and Yamada,Y.
TITLE:Clavulones, New Type of Prostanoids from the Stolonifer Clavularia viridis Quoy and Gaimard.
JOURNAL:Tetrahedron Lett.
VOL:23 PAGE : 5171 -5174 (1982)
[TOP]

[8002]
AUTHOR:Kobayashi,M., Yasuzawa,T., Yoshihara,M., Akutsu,H., Kyogoku,Y., and Kitagawa,I.
TITLE:Four New Prostanoids: Claviridenone-a, -b, -c, and -d from the Okinawan Soft Coral Clavularia viridis.
JOURNAL:Tetrahedron Lett.
VOL:23 PAGE : 5331 -5334 (1982)
[TOP]

[8003]
AUTHOR:Kikuchi,H., Tsukitani,Y., Iguchi,K., and Yamada,Y.
TITLE:Absolute Stereochemistry of New Prostanoids Clavulone I, II, and III, from Clavularia viridis Quoy and Gaimard.
JOURNAL:Tetrahedron Lett.
VOL:24 PAGE : 1549 -1552 (1983)
[TOP]

[8004]
AUTHOR:Corey,E.J.
TITLE:A Proposal for the Biosynthesis of the Clavulones, a New Family of Eicosanoids.
JOURNAL:Experientia
VOL:39 PAGE : 1084 -1085 (1983)
[TOP]

[8005]
AUTHOR:Corey,E.J., Schmidt,G., and Shimoji,K.
TITLE:Formation of a, b-epoxy Systems from b-epoxy Carbon Free Radicals.
JOURNAL:Tetrahedron Lett.
VOL:24 PAGE : 3169 -3170 (1983)
[TOP]

[8006]
AUTHOR:Kobayashi,M., Yasuzawa,T., Yoshihara,M., Son,B.W., Kyogoku,Y., and Kitagawa,I.
TITLE:Absolute Stereostructures of Claviridenone-a,b,c, and -d Four Prostanoids from the Okinawan Soft Coral Clavuraria viridis.
JOURNAL:Chem.Pharm.Bull.
VOL:31 PAGE : 1440 -1443 (1983)
[TOP]

[8008]
AUTHOR:Nagaoka,H., Miyakoshi,T., and Yamada,Y.
TITLE:Total Synthesis of Marine Prostanoids: Clavulones.
JOURNAL:Tetrahedron Lett.
VOL:25 PAGE : 3621 -3624 (1984)
[TOP]

[8012]
AUTHOR:Corey,E.J., Lansbury,Jr.,P.T., and Yamada,Y.
TITLE:Identification of a New Eicosanoid from in vitro Biosynthetic Experiments with Clavularia viridis. Implications for the biosynthesis of Clavulones.
JOURNAL:Tetrahedron Lett.
VOL:26 PAGE : 4171 -4174 (1985)
[TOP]

[8013]
AUTHOR:Corey,E.J., D'Alarcao,M., Matsuda,S., Lansbury,P.T.Jr., and Yamada,Y.
TITLE:Intermediacy of 8-(R)-HPETE in the Conversion of Arachidonic Acid to Pre-clavulone a by Clavularia viridis. Implications for the Biosynthesis of Marine Prostanoids.
JOURNAL:J. Am. Chem. Soc.
VOL:109 PAGE : 289 -290 (1987)
[TOP]

[8014]
AUTHOR:Honda, A., Hong, S., Yamada, Y., and Mori, Y.
TITLE:Effect of marine coral prostanoids, clavulones, on spontaneous beating rate of cultured myocardial cells from fetal mouse hearts PubMed ID:1719591
JOURNAL:Res Commun Chem Pathol Pharmacol.
VOL:72 PAGE : 363-366 (1991)
[TOP]

[8015]
AUTHOR:Klunder,A.J.H., Zwanenburg,B., and Liu,Z.Y.
TITLE:A Stereospecific Formal Synthesis of Clavulones from tricyclo[5.2.1.02.6]decadienone Epoxides.
JOURNAL:Tetrahedron Lett.
VOL:32 PAGE : 3131 -3132 (1991)
[TOP]

[8016]
AUTHOR:Takemoto,M., Koshida.,A., Miyazima,K., Suzuki,K., and Achiwa,K.
TITLE:Prostanoids and Related Compounds. IV. Total Synthesis of Clavulones.
JOURNAL:Chem.Pharm.Bull.
VOL:39 PAGE : 1106 -1111 (1991)
[TOP]

[8017]
AUTHOR:Zhu,J., Yang,J.-Y., Klunder,A.J.H., Liu,Z.-Y., and Zwanenburg,B.
TITLE:A Stereo- and Enantioselective Approach to Clavulones from Tricyclodecadienone using Flash Vacum Thermolysis.
JOURNAL:Tetrahedron
VOL:51 PAGE : 5847 -5870 (1995)
[TOP]

[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)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.