Isolation and chemical conversion of two novel prostaglandin endoperoxides: 5(6)-epoxy-PGG1 and 5(6)-epoxy-PGH1.
5(6)-Epoxy-PGG1 and 5(6)-epoxy-PGH1 were isolated after incubation of microsomes of RSV with 3H-labelled 5(6)-epoxy-C20:3 for 45 s at 37 degrees C. The endoperoxides were methylated and characterized by conversion to prostaglandins. In buffer, the endoperoxides were converted to methyl-5(6)-epoxy-PGE1 and methyl-5(6)-epoxy-15-hydroperoxy-PGE1, while treatment with SnCl2 reduced the endoperoxides to methyl-5-hydroxy-PGI1 alpha and methyl-5-hydroxy-PGI1 beta. Significant amounts of methyl-5(6)-epoxy-HHD were also formed. The endoperoxides could be separated by silicic acid chromatography and when 1 mM phenol was present in the incubation, 5(6)-epoxy-PGH1 was obtained as the main product.
D000818:Animals; D002845:Chromatography; D004852:Epoxy Compounds / Q000302:isolation & purification / Q000378:metabolism; D008401:Gas Chromatography-Mass Spectrometry; D008297:Male; D008745:Methylation; D008861:Microsomes / Q000378:metabolism*; D011449:Prostaglandin Endoperoxides / Q000378:metabolism*; D011458:Prostaglandins E / Q000302:isolation & purification / Q000378:metabolism*; D011462:Prostaglandins G / Q000302:isolation & purification / Q000378:metabolism*; D011463:Prostaglandins H / Q000302:isolation & purification / Q000378:metabolism*; D012669:Seminal Vesicles / Q000378:metabolism*; D012756:Sheep
D004852:Epoxy Compounds; D011449:Prostaglandin Endoperoxides; D011458:Prostaglandins E; D011462:Prostaglandins G; D011463:Prostaglandins H