Eicosanoid

DATA No : XPR1501 INFORMANT : Shouzo Yamamoto

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

COMMON NAME	:	PROSTAGLANDIN F2a
SYMBOL	:	PGF2a
FORMULA	:	C₂₀H₃₄O₅ MOL.WT (average) : 354.481

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BIOLOGICAL ACTIVITY

Prostaglandin F2a exhibits various biological activities such as uterine contraction, gastrointestinal contraction, bronchoconstriction, luteolysis and vasoconstriction (Ref. 0002). Prostaglandin F2a is a ligand to a receptor (FP) present in the cell membrane (Ref. 0003).

PHYSICAL AND CHEMICAL PROPERTIES

MELTING POINT	:	25-35C (Ref. 1007)

BOILING POINT	:

REFRACTIVE INDEX	:

OPTICAL ROTATION	:	[a]=23.8 (C=1,THF) (Ref. 1001)

DENSITY	:

SOLUBILITY	:	ETHYL ACETATE, ACETONE, DIETHYLETHER (Ref. 1005). STABILITIES: to be stable under neutral and basic conditions (Ref. 1004)

SPECTRAL DATA

UV SPECTRA	:

IR SPECTRA	:	NEAT : 3320, 2640, 1710, 1295, 1260, 1245, 1120, 1080, 1055, 1025, 975cm^-¹ (Ref. 1005)

NMR SPECTRA	:	¹H-NMR(d₆-ACETONE) : d 5.48(m, 4H), 4.05(m, 3H), 0.9(t, 3H, 20-CH3) (Ref. 1005). ¹³C-NMR : 176.6(C1), 135.0(C14), 132.8(C5), 129.1(C13 or C6), 128.9(C6 or C13), 77.2(C11), 72.9(C15), 71.8(C9), 55.0(C12), 49.9(C8), 42,6(C10), 36.8(C16), 33.2(C2), 31,5(C18), 26.3(C4), 25.1(C7), 25.1(C17), 24.5 (Ref. 1008)

MASS SPECTRA	:	354(M⁺), 336, 318, 292, 274, 264(100), 247, 229, 191, 177, 165, 137, 99, 81, 67 (Ref. 1009)

OTHER SPECTRA	:

CHROMATOGRAM DATA

SOURCE

Prostaglandin F2a was found to be accummulating in human semen in an amount of about 2 microgram per ml (Ref. 0001). In most animal tissues prostanoids are synthesized enzymatically de novo upon physiological and pathological stimulations, and this is also the case of prostaglandin F2a.

CHEMICAL SYNTHESIS

(Ref. 1001)
[Table 0001]

METABOLISM

Prostaglandin F synthase reduces 9,11-endoperoxide of prostaglandin H2 requiring NADPH, and produces prostaglandin F2a. The same enzyme also reduces 9-keto group of prostaglandin D2 producing 11b-prostaglandin F2 (Ref. 0005).

GENETIC INFORMATION

cDNA for prostaglandin F synthase was cloned from bovine lung (Ref. 0005). cDNA for prostaglandin F2a receptor (FP) was cloned, and its 7ptransmembrane structure was reported (Ref. 0003).

NOTE

REFERENCES

[0001]

AUTHOR	:	Bergstrom, S.
TITLE	:	Prostaglandins: members of a new hormonal system. These physiologically very potent compounds of ubiquitous occurrence are formed from essential fatty acids PubMed ID:4291104
JOURNAL	:	Science.
VOL	:	157 PAGE : 382-391 (1967)

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[0002]

AUTHOR	:	Bergstrom, S., Carlson, L. A., and Weeks, J. R.
TITLE	:	The prostaglandins: a family of biologically active lipids PubMed ID:4873508
JOURNAL	:	Pharmacol Rev.
VOL	:	20 PAGE : 1-48 (1968)

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[0003]

AUTHOR	:	Negishi, M., Sugimoto, Y., and Ichikawa, A.
TITLE	:	Molecular mechanisms of diverse actions of prostanoid receptors PubMed ID:7492609
JOURNAL	:	Biochim Biophys Acta.
VOL	:	1259 PAGE : 109-119 (1995)

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[0005]

AUTHOR	:	Urade, Y., Watanabe, K., and Hayaishi, O.
TITLE	:	Prostaglandin D, E, and F synthases PubMed ID:8777570
JOURNAL	:	J Lipid Mediat Cell Signal.
VOL	:	12 PAGE : 257-273 (1995)

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[1001]

AUTHOR	:	Corey, E. J., Schaaf, T. K., Huber, W., Koelliker, U., and Weinshenker, N. M.
TITLE	:	Total synthesis of prostaglandins F2-alpha and E2 as the naturally occurring forms PubMed ID:5411057
JOURNAL	:	J Am Chem Soc.
VOL	:	92 PAGE : 397-398 (1970)

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[1004]

AUTHOR	:	Karim, S. M., Devlin, J., and Hillier, K.
TITLE	:	The stability of dilute solutions of prostaglandins E1, E2, F1-alpha and F2-alpha PubMed ID:5724918
JOURNAL	:	Eur J Pharmacol.
VOL	:	4 PAGE : 416-420 (1968)

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[1005]

AUTHOR	:	Pike, J.E., Lincoln,F.H., and Schneider,W.P.
TITLE	:	Prostanoic Acid Chemistry.
JOURNAL	:	J. Org. Chem.
VOL	:	34 PAGE : 3552 -3557 (1969)

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[1007]

AUTHOR	:	Bundy, G. L., Schneider, W. P., Lincoln, F. H., and Pike, J. E.
TITLE	:	The synthesis of prostaglandins E 2 and F 2a from (15R)- and (15S)-PGA 2 PubMed ID:5016033
JOURNAL	:	J Am Chem Soc.
VOL	:	94 PAGE : 2123-2124 (1972)

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[1008]

AUTHOR	:	Lukacs,G., Piriou,F., and Gero,S.D.
TITLE	:	Carbon-13 Nuclear Magnetic Resonance Spectroscopy of Naturally Occurring Substances. Prostaglandins.
JOURNAL	:	Tetrah. Lett.
VOL	:	PAGE : 515 -518 (1973)

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[1009]

AUTHOR	:	Horvath, G.
TITLE	:	Mass spectral studies on prostaglandins. IV--Prostaglandin F2alpha PubMed ID:990421
JOURNAL	:	Biomed Mass Spectrom.
VOL	:	3 PAGE : 127-136 (1976)

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