Eicosanoid

DATA No : XPR1601 INFORMANT : Shouzo Yamamoto

NAME : 7-[2(R)-(3(S)-Hydroperoxy-1(E)-octenyl)-1(R),4(S)-5,6-dioxabicyclo[2.2.1]-heptan-3(R)-yl]-5(Z)-heptenoic acid

COMMON NAME	:	PROSTAGLANDIN G2
SYMBOL	:	PGG2
FORMULA	:	C₂₀H₃₂O₆ MOL.WT (average) : 368.464

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BIOLOGICAL ACTIVITY

Prostaglandin G2 is a metabolic intermediate, but the compound as such has biological activities of bronchoconstriction and vasoconstriction (Ref. 0013/0020).

PHYSICAL AND CHEMICAL PROPERTIES

MELTING POINT	:

BOILING POINT	:

REFRACTIVE INDEX	:

OPTICAL ROTATION	:

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SPECTRAL DATA

UV SPECTRA	:

IR SPECTRA	:

NMR SPECTRA	:	¹³C-NMR : d 84.6(C15) (Ref. 1016)

MASS SPECTRA	:

OTHER SPECTRA	:

CHROMATOGRAM DATA

SOURCE

Prostaglandin G2 is produced by bis-dioxygenation and cyclization of arachidonic acid as an intermediate for the biosyntheses of various prostaglandins and thromboxanes. The responsible enzyme is prostaglandin endoperoxide synthase usually referred to as fatty acid cyclooxygenase, and distributed in various animal tissues (Ref. 0015/0019).

CHEMICAL SYNTHESIS

(Ref. 1016)
[Table 0001]

METABOLISM

Prostaglandin endoperoxide synthase is a bifunctional enzyme with an oxygenase activity (fatty acid cyclooxygenase) producing prostaglandin G2 from arachidonic acid and a peroxidase activity (prostagladnin hydroperoxidase) converting prostaglandin G2 to prostaglandin H2 (Ref. 0019). The enzyme is usually referred to briefly as cyclooxygenase. There are two isozymes of the enzyme. Cyclooxygenase-1 is a constitutive enzyme expressed in most mammalian cells, while cyclooxygenase-2 is a product of immediate early gene and is induced rapidly and transiently in certain types of cell by various bioactive compounds (Ref. 0004/0008).

GENETIC INFORMATION

cDNA and genomic DNA each for cyclooxygenas-1 and 2 were cloned (Ref. 0007).

NOTE

Stability:unstable in water around neutrality with a half life of about 5 min at 37

C and decomposes to PGE2, PGD2, PGF2 and 12L-hydroxy-5,8,10-heptadecatrienoic acid(Ref. 0068).

REFERENCES

[0004]

AUTHOR	:	Smith, W. L., Garavito, R. M., and DeWitt, D. L.
TITLE	:	Prostaglandin endoperoxide H synthases (cyclooxygenases)-1 and -2 PubMed ID:8969167
JOURNAL	:	J Biol Chem.
VOL	:	271 PAGE : 33157-33160 (1996)

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[0007]

AUTHOR	:	Funk, C.D.
TITLE	:	Molecular biology in the eicosanoid field . PubMed ID:8341804
JOURNAL	:	Progr. Nucleic Acid Res.
VOL	:	45 PAGE : 67 -98 (1993)

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[0008]

AUTHOR	:	Herschman, H.R.
TITLE	:	Prostaglandin synthase 2. PubMed ID:8341804
JOURNAL	:	Biochim. Biophys. Acta
VOL	:	1299 PAGE : 125 -140 (1996)

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[0013]

AUTHOR	:	Moncada, S., and Vane, J. R.
TITLE	:	Pharmacology and endogenous roles of prostaglandin endoperoxides, thromboxane A2, and prostacyclin PubMed ID:116251
JOURNAL	:	Pharmacol Rev.
VOL	:	30 PAGE : 293-331 (1978)

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[0015]

AUTHOR	:	Pace-Asciak,C.R., and Smith,W.L.
TITLE	:	Enzymes in the biosynthesis and catabolism of the eicosanoids: prostaglandins, thromboxanes, leukotrienes and hydroxy fatty acids.
JOURNAL	:	The Enzymes
VOL	:	16 PAGE : 543 -603 (1983)

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[0019]

AUTHOR	:	Yamamoto,S. (1983) Enzymes in the arachidonic acid cascade. in Prostaglandins and related substances (Pace-Asciak,C.R. and Granstroem,E., eds), pp171-202, Elsevier, Amsterdam
TITLE	:
JOURNAL	:
VOL	:	PAGE : - ()

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[0020]

AUTHOR	:	Chijimatsu, Y., Nguyen, T. V., and Said, S. I.
TITLE	:	Effects of prostaglandin endoperoxide analogs on contractile elements in lung and gastrointestinal tract PubMed ID:866698
JOURNAL	:	Prostaglandins.
VOL	:	13 PAGE : 909-916 (1977)

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[0068]

AUTHOR	:	Nugteren, D. H., and Hazelhof, E.
TITLE	:	Isolation and properties of intermediates in prostaglandin biosynthesis PubMed ID:4776443
JOURNAL	:	Biochim Biophys Acta.
VOL	:	326 PAGE : 448-461 (1973)

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[1016]

AUTHOR	:	Porter,N.A., Byers,J.D., Ali,A.E., and Eling,T.E.
TITLE	:	Prostaglandin G2.
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	102 PAGE : 1183 -1184 (1980)

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