Transformation of arachidonic acid in leukocytes. isolation and structural analysis of a novel dihydroxy derivative

Prostaglandins and medicine Pub Date : 1981-06-01 DOI:10.1016/0161-4630(81)90117-8

Pierre Borgeat , Serge Picard, Pierre Vallerand, Pierre Sirois

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引用次数: 118

Abstract

A suspension of mixed peripheral blood leukocytes was incubated with arachidonic acid. After ether extraction and silicic acid fractionation of the products, the fraction containing the mono- and dihydroxy derivatives of arachidonic acid was further analyzed by high pressure liquid chromatography on silica gel and octadecyl silica (reversed-phase) columns. A previously undescribed metabolite was detected and isolated in pure form. The compound co-chromatographed with leukotriene B₄ on octadecyl silica but was eluted earlier than leukotriene B₄ from silica gel columns. Ultraviolet spectrophotometry, gas chromatography-mass spectrometry, ozonolysis and steric analysis indicated that the new metabolite was the 5S,12S-dihydroxy-6,8,10,14-icosatetraenoic acid. The yield of the novel dihydroxy acid was 1 to 4% of the added substrate. The new metabolite showed less than 1% of the myotropic activity of leukotriene B4 on the guinea pig lung parenchymal strip.

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花生四烯酸在白细胞中的转化。一种新型二羟基衍生物的分离与结构分析

混合外周血白细胞悬液与花生四烯酸孵育。产品经醚萃取和硅酸分馏后，采用硅胶柱和十八烷基硅(反相)柱的高压液相色谱法对花生四烯酸单羟基和二羟基衍生物进行进一步分析。先前未描述的代谢物被检测并以纯形式分离。该化合物与白三烯B4在十八烷基二氧化硅上共层，但比白三烯B4更早从硅胶柱中洗脱。紫外分光光度法、气相色谱-质谱法、臭氧分解和空间位联分析表明，新代谢产物为5S, 12s -二羟基-6,8,10,14-二十碳四烯酸。新型二羟基酸的产率为添加底物的1 ~ 4%。新代谢产物在豚鼠肺实质条上的促肌活性低于白三烯B4的1%。

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Prostaglandins and medicine

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