9-Deoxy-A9,A12-13,14
Proc. Natl. Acad. Sci. USA Vol. 81, pp. 1317-1321, March 1984 Biochemistry 9-Deoxy-A9,A12-13,14-dihydroprostaglandin D2, a metabolite of prostaglandin D2 formed in human plasma (dehydration product of prostaglandin D2/serum albumin/cell growth inhibition) YOSHIHARU KIKAWA*, SHUH NARUMIYA*, MASANORI FUKUSHIMAt, HIROHISA WAKATSUKAt, AND OSAMU HAYAISHI§ *Department of Medical Chemistry, Kyoto University Faculty of Medicine, Sakyo-ku, Kyoto 606, Japan; tDepartment of Internal Medicine and Laboratory of Chemotherapy, Aichi Cancer Center, Chikusa-ku, Nagoya 464, Japan; tResearch Institute, Ono Pharmaceutical Co., Shimamoto, Mishima, Osaka 618, Japan; and §Osaka Medical College, Daigaku-cho, Takatsuki, Osaka 569, Japan Contributed by Osamu Hayaishi, November 8, 1983 ABSTRACT Incubation of prostaglandin D2 (PGD2) with from Sigma. Dimethylisopropylsilyl (Me2iPrSi) imidazole human plasma yielded a product that has been identified as 9- and methoxyamine hydrochloride were from Tokyo Kasei deoxy-9,10-didehydro-12,13-cdidehydro-13,14-dihydro-PGD2 (Tokyo). Sep-pak silica and Sep-pak C18 cartridges were (9-deoxy-_9,9'2-13,14-dihydro-PGD2). The identification was from Waters Associates. Precoated silica gel plates [G60- based on mass spectrometry, UV spectrometry, mobilities and (F254)] with concentration zones and silica gel 60 for column retention time on TLC and HPLC, and NMR. The conversion chromatography were from Merck. Sephadex LH-20 was a of PGD2 to this product was dependent on the incubation time product of Pharmacia. Solvents used in the extraction of and the amount of plasma added to a reaction mixture and was PGD2 metabolites for identification were distilled before use. abolished by prior boiling.
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