ISOLATION AND IDENTIFICATION OF 5,6-EPOXYRETINOIC ACID - BIOLOGICALLY-ACTIVE METABOLITE OF RETINOIC ACID

被引:80
作者
MCCORMICK, AM [1 ]
NAPOLI, JL [1 ]
SCHNOES, HK [1 ]
DELUCA, HF [1 ]
机构
[1] UNIV WISCONSIN,COLL AGR & LIFE SCI,DEPT BIOCHEM,MADISON,WI 53706
关键词
D O I
10.1021/bi00612a033
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A highly biologically active metabolite of retinoic acid (8111) has been isolated in pure form from intestinal mucosa of vitamin A deficient rats given [3H] retinoic acid. This metabolite has been positively identified as 5,6-epoxyretinoic acid based on the ultraviolet absorption spectrum and mass spectrum of its methylated derivative. This identification was confirmed by cochromatography of the methylated metabolite and synthetic methyl 5,6-epoxyretinoate on reverse-phase and straight-phase high-pressure liquid chromatography. The 5,6-epoxyretinoic acid is a true in vivo generated metabolite of retinoic acid and not an artifact of the isolation procedure. In addition, 5,8-oxyretinoic acid previously isolated in this laboratory from intestinal mucosa was probably generated from 5,6-epoxyretinoic acid by the acidic conditions used in the extraction and isolation of the 5,8-oxyretinoic acid. © 1978, American Chemical Society. All rights reserved.
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页码:4085 / 4090
页数:6
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