Biosynthesis and chemistry of 9α, 15(S)-dihydroxy-11-oxo-13-trans-prostenoic acid

Foss, Paul; Sih, Charles J.; Takeguchi, C.; Schnoes, Heinrich K.

doi:10.1021/bi00762a010

Cited by 36 publications

(14 citation statements)

References 9 publications

(10 reference statements)

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“…Preparation and enzymatic properties of an acetone pentane powder of the sheep vesicular gland enzyme have been descfibed (34 Bovine seminal vesicle micro somes were reportea to possess a prostaglandin synthetase, whose activity was apparent when a heat labile, nondialyzable inhibitor present in the supernatant fraction was removed (3). L-Epinephrine enhanced fo rmation of PGF 1., whereas serotonin favored formation of PGD1 (35, 36). L-Epinephrine enhanced fo rmation of PGF 1., whereas serotonin favored formation of PGD1 (35, 36).…”

Section: Enzymes and Cofactorsmentioning

confidence: 99%

Prostaglandins

Samuelsson¹,

Granström²,

Green³

et al. 1975

Annu. Rev. Biochem.

567

170

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Section: Enzymes and Cofactorsmentioning

confidence: 99%

Prostaglandins

Samuelsson¹,

Granström²,

Green³

et al. 1975

Annu. Rev. Biochem.

567

170

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“…The stimulation was reflected in the synthesis of all three prostaglandins. This is in contrast with the seminal-vesicular system, in which GSH stimulates the synthesis of prostaglandin E at the expense of other products (Foss et al, 1972;Lands et al, 1971). A variety of phenolic compounds stimulated the synthesis of prostaglandins in the kidney-medulla system similarly to that in seminalvesicular systems.…”

Section: Discussionmentioning

confidence: 80%

“…Since borohydride reduction of prostaglandin D, (9a,15a-dihydroxy-1 1-oxoprost-13-trans-enoic acid) afforded predominantly. prostagla.ndin Fl,6 (Foss "et al, 1972), the same treatment of the third polar product yielded a major component which had a mobility identical with that of the prostaglandin F2,, t.l.c. plate developed in solvent system I as shown in Fig.…”

Section: Subeellular Localization Ofprostaglandin Synthasementioning

confidence: 89%

“…However, the third product, prostaglandin D2, which was consistently detected under our assay conditions, has not been reported by other workers. Prostaglandin D2 has been well established as one of the reaction products of the prostaglandin synthase system from seminal vesicles (Granstrom et al, 1968;Foss et al, 1972). Failure to detect this product in the kidney-medulla system by other laboratories was probably due to the poor enzyme activity of the crude homogenates used.…”

Section: Discussionmentioning

confidence: 99%

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Biosynthesis of prostaglandins in rabbit kidney medulla. Properties of prostaglandin synthase

Tai

Hollander

1976

Biochemical Journal

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A simple radioactive-substrate assay for prostaglandin synthase (EC 1.14.99.1), which uses t.l.c. to measure simultaneously different prostaglandins synthesized from one precursor substrate, was developed. Rabbit kidney-medulla prostaglandin synthase catalyses the formation of prostaglandin E2, prostaglandin F2alpha and prostaglandin D2 from arachidonic acid. Fractionation of crude homogenates indicated that the microsomal fraction possessed the highest specific activity of prostaglandin synthase, whereas the soluble fraction exhibited little enzyme activity but rather contained a heat-labile inhibitory macromolecular factor(s), which might be attributed to the serum albumin present in this fraction. The microsomal fraction possessed low intrinsic enzyme activity, but the actvity could be fully stimulated by the presence of both GSH (reduced glutathione) and a phenolic cofactor. Only cysteine could partially replace GSH, whereas other thiols were inactive and some were even inhibitory. A variety of phenolic compounds, including catecholamines, dopamine (3,4-dihydroxyphenethylamine), 5-hydroxytryptamine and quinol, were active in stimulating prostaglandin synthase. In all cases, the stimulation was reflected in the synthesis of all three prostaglandins with ratios not significantly altered by different phenolic cofactors. The synthesis of each of the different prostaglandins appeared to have similar pH optima. The enzyme system was not inhibited by thiol-group inhibitors or a variety of metal chelators except for cyanide and 8-hydroxyquinoline. Characterization of the kidney-medulla prostaglandin synthase system indicated that it exhibited properties similar to those of the enzyme system present in seminal vesicles.

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“…Procedures used for the structural analysis of oxidized lipids include the reduction with KI (1,2), SnC12 (3)(4)(5), triphenylphosphine (6-8), NaBH4 (9)(10)(11)(12), and LiAIH4 (13,14), as well as catalytic hydrogenation (15,16). NaBH 4 reduction is one of the most widely used methods since it is simple and quantitative, and the reaction is relatively free of by-products.…”

Section: Lipids 25 578-580 (1990)mentioning

confidence: 99%

Inevitable generation of primary alcohols during reduction of oxidized lipids with sodium borohydride

Nakamura

Maeda

Takahashi

et al. 1990

Lipids

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This report deals with the fluorometric determination of fatty alcohols generated by the reduction of the ester linkage of lipids with NaBH4, and with the limitations of the reduction method for assaying oxidized lipids. Optimum conditions for the fluorometric analysis of primary and secondary alcohols using 1-anthroyl nitrile were obtained. After reduction with NaBH4 in MeOH or in MeOH/benzene (8∶2, v/v), the formation of 1-hexadecanol from a variety of palmitic acid esters was measured fluorometrically by reverse-phase high-performance liquid chromatography (HPLC): From glycerides and methyl palmitate, 1-3% (w/w) 1-hexadecanol was produced and a trace was produced from cholesteryl palmitate (10 min, 21°C). 1-Hexadecanol was never generated from palmitic acid. Although considerable improvement occurred with the choice of the solvent for the NaBH4 reduction, the generation of primary alcohols from ester lipids usually seems inevitable.

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Biosynthesis and chemistry of 9α, 15(S)-dihydroxy-11-oxo-13-trans-prostenoic acid

Cited by 36 publications

References 9 publications

Prostaglandins

Prostaglandins

Biosynthesis of prostaglandins in rabbit kidney medulla. Properties of prostaglandin synthase

Inevitable generation of primary alcohols during reduction of oxidized lipids with sodium borohydride

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