title: On agents favoring prostaglandin f formation during biosynthesis.
abstract: The microsomal fraction of bovine vesicular gland catalyzed the conversion of eicosapolyenoic acids exclusively to prostaglandin E in the presence of reduced glutathione, while hydrox fatty acids, prostaglandins D and F, decreased to a negligible level. After solubilizing the microsomal fraction with cutscum, the prostaglandin synthetase activity was purified 11-fold by batchwise absorption and elution of the enzyme activity from DEAE-cellulose. This partially purified enzyme fraction did not respond to reduced glutathione in promoting prostaglandin E formation at the expense of other products. A number of glutathione analogs were examined, but none of these was as effective as reduced glutathione. Dithiol complexes of Cu-2+, Ni-2+, and Zn-2+ exerted pronounced effects on relative amounts of the different prostaglandins biosynthesized. Both the Cu-2+-dithiothreitol (2:1) complex and stannous chloride markedly enhanced prostaglandin F synthesis at the expense of prostaglandin D and prostaglandin E. The following reagents chemically reduced the endoperoxide in ascaridole to p-menth-2-ene-cis-1,4-diol: Cu-2+0dithiothreitol, Cu-2+-epinephrine, and stannous chloride. It is concluded that the enhancement of prostaglandin F formation caused by copper-dithiols and L-epinephrine is due to nonenzymatic reduction of prostaglandin G or prostaglandin H.
mesh_terms: D015117:5,8,11,14-Eicosatetraynoic Acid / Q000378:metabolism; D015126:8,11,14-Eicosatrienoic Acid / Q000378:metabolism; D000818:Animals; D002417:Cattle; D055598:Chemical Phenomena; D002621:Chemistry; D003300:Copper / Q000494:pharmacology; D004229:Dithiothreitol / Q000494:pharmacology; D004837:Epinephrine / Q000494:pharmacology; D005978:Glutathione / Q000031:analogs & derivatives / Q000494:pharmacology; D008297:Male; D008670:Metals / Q000494:pharmacology; D008861:Microsomes / Q000201:enzymology; D008956:Models, Chemical; D010084:Oxidation-Reduction; D011451:Prostaglandin-Endoperoxide Synthases / Q000302:isolation & purification / Q000378:metabolism; D011453:Prostaglandins / Q000096:biosynthesis*; D011458:Prostaglandins E / Q000096:biosynthesis; D011460:Prostaglandins F / Q000096:biosynthesis; D012669:Seminal Vesicles / Q000201:enzymology; D014001:Tin / Q000031:analogs & derivatives
chemical_list: D008670:Metals; D011453:Prostaglandins; D011458:Prostaglandins E; D011460:Prostaglandins F; D015117:5,8,11,14-Eicosatetraynoic Acid; D014001:Tin; D003300:Copper; D011451:Prostaglandin-Endoperoxide Synthases; D015126:8,11,14-Eicosatrienoic Acid; D005978:Glutathione; D004229:Dithiothreitol; D004837:Epinephrine