顺式和反式十氢化萘的代谢
The metabolism of cis- and trans-decalin.
作者信息
Elliott T H, Robertson J S, Williams R T
出版信息
Biochem J. 1966 Aug;100(2):403-6. doi: 10.1042/bj1000403.
Abstract
- The metabolism of cis- and trans-decalin in the rabbit has been investigated. 2. Both hydrocarbons were oxidized to racemic secondary alcohols and excreted as ether glucuronides in amounts equal to about 60% of the dose administered. The principal glucuronides were isolated as triacetyl methyl esters and as sodium salts. 3. cis-Decalin gave rise mainly to (+/-)-cis-cis-2-decalol, together with a little cis-trans-2-decalol, and trans-decalin mainly to (+/-)-trans-cis-2-decalol and a small amount of trans-trans-2-decalol. 4. These results suggest that biological oxidation of the decalins does not occur via a free-radical mechanism. An attempt is made to explain why racemic alcohols are obtained, rather than the more typical optically active products of enzymic reaction, and a mechanism is proposed. It is suggested that enzymes similar to steroid hydroxylases are involved.
摘要
- 已对家兔体内顺式和反式十氢化萘的代谢进行了研究。2. 两种烃类均被氧化为外消旋仲醇，并以醚葡糖醛酸苷的形式排泄，排泄量约为给药剂量的60%。主要的葡糖醛酸苷被分离为三乙酰甲酯和钠盐。3. 顺式十氢化萘主要生成(±)-顺式-顺式-2-十氢萘醇，同时伴有少量顺式-反式-2-十氢萘醇，而反式十氢化萘主要生成(±)-反式-顺式-2-十氢萘醇和少量反式-反式-2-十氢萘醇。4. 这些结果表明，十氢化萘的生物氧化并非通过自由基机制发生。尝试解释为何得到的是外消旋醇，而非酶促反应中更典型的旋光性产物，并提出了一种机制。研究表明，参与其中的是类似于甾体羟化酶的酶。
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