5,6-环氧维甲酸的分离与鉴定：维甲酸的一种生物活性代谢产物

Isolation and identification of 5, 6-epoxyretinoic acid: a biologically active metabolite of retinoic acid.

作者信息

McCormick A M, Napoli J L, Schnoes H K, DeLuca H F

出版信息

Biochemistry. 1978 Sep 19;17(19):4085-90. doi: 10.1021/bi00612a033.

Abstract

A highly biologically active metabolite of retinoic acid (8III) 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.

摘要

从给予[³H]视黄酸的维生素A缺乏大鼠的肠粘膜中，已以纯形式分离出一种具有高生物活性的视黄酸代谢物（8III）。基于其甲基化衍生物的紫外吸收光谱和质谱，该代谢物已被明确鉴定为5,6-环氧视黄酸。通过甲基化代谢物与合成的5,6-环氧视黄酸甲酯在反相和正相高压液相色谱上的共色谱分析，证实了这一鉴定结果。5,6-环氧视黄酸是视黄酸真正在体内生成的代谢物，而非分离过程中的人为产物。此外，此前在本实验室从肠粘膜中分离出的5,8-氧代视黄酸，可能是在提取和分离5,8-氧代视黄酸时所使用的酸性条件下，由5,6-环氧视黄酸生成的。