Eicosanoid

DATA No : XPR1430 INFORMANT : Shouzo Yamamoto

NAME : 7-[3(R)-Hydroxy-2(R)-(3(S)-hydroxy-1(E)-octenyl)-5-oxocyclopentan-1(R)-yl]-6-oxoheptanoic acid

COMMON NAME	:	6-KETO-PROSTAGLANDIN E1
SYMBOL	:	6-KETO-PGE1
FORMULA	:	C₂₀H₃₂O₆ MOL.WT (average) : 368.464

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BIOLOGICAL ACTIVITY

6-Keto-prostaglandin E1 is a stable metabolite. The compound inhibits platelet aggregation with activity comparable or greater than prostaglandin D2 although less potent than prostaglandin I2. Its vasodilatory and hypotensive activities, bronchodilatory property, and inhibition of gastric acid secretion were reported (Ref. 0054).

PHYSICAL AND CHEMICAL PROPERTIES

MELTING POINT	:	65C (Ref. 1053)

BOILING POINT	:

REFRACTIVE INDEX	:

OPTICAL ROTATION	:	[a]=-50(C=1.55, METHANOL) (Ref. 1053)

DENSITY	:

SOLUBILITY	:	METHANOL, CHLOROFORM (Ref. 1053)

SPECTRAL DATA

UV SPECTRA	:

IR SPECTRA	:	KBr: n 3400, 1740, 1720, 1710, 1245, 1160, 1075, 970 cm^-¹ (Ref. 1053)

NMR SPECTRA	:	¹H-NMR(CDCl₃) : d 5.58(m, 2H, 13,14-CH), 4.09(m, 1H, 11-CH), 4.02(m, 1H, 15-CH), 2.7(2H, 7-CH), 2.69(IH, 10b-CH), 2.45-2.47(m, 3H, 5,8,12-CH), 2.29(1H, 10a-CH), 2.28(2H, 2-CH), 1.58 - 1.32(12H), 0.91(t, 3H, 20-CH₃) (Ref. 1069). METHYL ESTER ; ¹³C-NMR(CDCl₃) : 216.6, 208.4, 173.8, 138.0, 126.5, 72.3, 51.5, 44.6, 45.7, 42.4, 37.6, 33.8, 31.8, 25.2, 24.5, 23.4, 22.6, 14.0 (Ref. 1053)

MASS SPECTRA	:	DIRECT EXPOSURE AMMONIA CI, POSITIVE : 386(M⁺+18), 368(M+), 351, 350, 244, 136. NEGATIVE : 368(M⁺) ,350, 338, 332 (Ref. 1054)

OTHER SPECTRA	:

CHROMATOGRAM DATA

SOURCE

There were reports of prolonged biological activity of chemically unstable prostaglandin I2, which suggested a possible transformation of prostaglandin I2 to a more stable metabolite with potent bioactivity (Ref. 0053). Futher investigations led to the discovery of 6-keto-prostaglandin E1.

CHEMICAL SYNTHESIS

(Ref. 1053)
[Table 0001]

METABOLISM

A potential role of 9-hydroxyprostaglandin dehydrogenase was demonstrated in the transformation of prostaglandin I2 to 6-keto-prostaglandin E1 (Ref. 0053).

GENETIC INFORMATION

NOTE

REFERENCES

[0053]

AUTHOR	:	Wong, P. Y., Lee, W. H., Chao, P. H., Reiss, R. F., and McGiff, J. C.
TITLE	:	Metabolism of prostacyclin by 9-hydroxyprostaglandin dehydrogenase in human platelets. Formation of a potent inhibitor of platelet aggregation and enzyme purification PubMed ID:6997309
JOURNAL	:	J Biol Chem.
VOL	:	255 PAGE : 9021-9024 (1980)

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[0054]

AUTHOR	:	Moore, P. K., and Griffiths, R. J.
TITLE	:	Review: 6 keto-prostaglandin-E1 PubMed ID:6361908
JOURNAL	:	Prostaglandins.
VOL	:	26 PAGE : 509-517 (1983)

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[1053]

AUTHOR	:	Tanaka,T., Hazato,A., Bannai,K., Okamura,N., Sugiura,S., Manabe,K., Toru,T., Kurozumi,S., Suzuki,M., Kawagishi,T., et al
TITLE	:	Nitro-Olefin Trapping Reaction of Enolates In Situ Generated by Conjugate Addition Reaction: Short Synthesis of PGE1, 6-Oxo-PGE1, 6-Oxo-PGF1a, and PGI2.
JOURNAL	:	Tetrahedron
VOL	:	43 PAGE : 813 -824 (1987)

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[1054]

AUTHOR	:	Cepa, S. R., Hall, E. R., and Venton, D. L.
TITLE	:	Positive-negative, chemical-ionization, direct exposure mass spectrometry of underivatized prostaglandins PubMed ID:6547237
JOURNAL	:	Prostaglandins.
VOL	:	27 PAGE : 645-652 (1984)

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[1069]

AUTHOR	:	Kotovych,G. and Aarts,G.H.M.
TITLE	:	Homonuclear One- and Two-Dimentional Nuclear Overhauser Effect Experiments and Spin-Echo Correlated Spectroscopy. Application to Prostaglandin E1 and 6-Keto-Prostaglandin E1.
JOURNAL	:	Can. J. Chem.
VOL	:	60 PAGE : 2617 -2624 (1982)

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