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Eicosanoid


DATA No : XPR1511 INFORMANT : Shouzo Yamamoto

NAME : 7-[3(R),5(S)-Dihydroxy-2(R)-(3-oxo-1(E)-octenyl)cyclopentan-1(R)-yl]-5(Z)-heptenoic acid

COMMON NAME: 15-KETOPROSTAGLANDIN F2a
SYMBOL: 15-KETO-PGF2a
FORMULA: C20H32O5 MOL.WT (average) : 352.465


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BIOLOGICAL ACTIVITY
It is well known that the biological activities of various prostaglandins are reduced upon their dehydrogenation at carbon-15 by the catalysis of 15-hydroxyprostaglandin dehydrogenase (Ref. 0044).
PHYSICAL AND CHEMICAL PROPERTIES
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CHROMATOGRAM DATA

SOURCE
15-Keto-prostaglandin F2a is the oxidized product of prostaglandin F2a by 15-hydroxyprostaglandin dehydrogenase, which is present in lung, kidney, placenta and other tissues and catalyzes the NAD- or NADP-dependent dehydrogenation of 15-dydroxyl group (Ref. 0006).
CHEMICAL SYNTHESIS

METABOLISM
15-Keto-prostaglandin F2a is further metabolized by its D13-reduction, b-oxidation and w oxidation. The ultimate metabolite is 5a,7a-dihydroxy-11-keto-tetranorprosta-1,16-dioic acid, and excreted in urine (Ref. 0047).
GENETIC INFORMATION
cDNA for placental 15-hydroxyprostaglandin dehydrogenase was cloned (Ref. 0046).
NOTE

REFERENCES
[0006]
AUTHOR:Hansen, H. S.
TITLE:15-hydroxyprostaglandin dehydrogenase. A review PubMed ID:184496
JOURNAL:Prostaglandins.
VOL:12 PAGE : 647-679 (1976)
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[0044]
AUTHOR:Anggard, E.
TITLE:The biological activities of three metabolites of prostaglandin E 1 PubMed ID:5951401
JOURNAL:Acta Physiol Scand.
VOL:66 PAGE : 509-510 (1966)
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[0046]
AUTHOR:Ensor, C. M., and Tai, H. H.
TITLE:15-Hydroxyprostaglandin dehydrogenase PubMed ID:8777575
JOURNAL:J Lipid Mediat Cell Signal.
VOL:12 PAGE : 313-319 (1995)
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[0047]
AUTHOR:Granstrom, E., and Samuelsson, B.
TITLE:On the metabolism of prostaglandin F-2-alpha in female subjects PubMed ID:5125749
JOURNAL:J Biol Chem.
VOL:246 PAGE : 5254-5263 (1971)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.