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标题：Characterization and biological effects of di-hydroxylated compounds deriving from the lipoxygenation of ALA
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作者：Miao Liu ; Ping Chen ; Evelyne Véricel 等
期刊名称：JLR Papers In Press
印刷版ISSN：0022-2275
电子版ISSN：1539-7262
出版年度：2013
卷号：54
期号：8
页码：2083-2094
DOI：10.1194/jlr.M035139
语种：English
出版社：American Society for Biochemistry and Molecular Biology
摘要：We have recently described a di-hydroxylated compound called protectin DX (PDX) which derives from docosahexaenoic acid (DHA) by double lipoxygenation. PDX exhibits anti-aggregatory and anti-inflammatory properties, that are also exhibited by similar molecules, called poxytrins, which possess the same E,Z,E conjugated triene geometry, and are synthesized from other polyunsaturated fatty acids with 22 or 20 carbons. Here we present new biological activities of di-hydroxylated metabolites deriving from α-linolenic acid (18:3n-3) treated by soybean 15-lipoxygenase (sLOX). We show that 18:3n-3 is converted by sLOX into mainly 13(S)-OH-18:3 after reduction of the hydroperoxide product. But surprisingly, and in contrast to DHA which is metabolized into only one di-hydroxylated compound, 18:3n-3 leads to four di-hydroxylated fatty acid isomers. We report here the complete characterization of these compounds using high field NMR and GC-MS techniques, and some of their biological activities. These compounds are: 9(R),16(S)-dihydroxy-10 E ,12 E ,14 E -octadecatrienoic acid, 9(S),16(S)-dihydroxy-10 E ,12 E ,14 E -octadecatrienoic acid, 9(S),16(S)-dihydroxy-10 E ,12 Z ,14 E -octadecatrienoic acid, and 9(R),16(S)-dihydroxy-10 E ,12 Z ,14 E -octadecatrienoic acid. They can also be synthesized by the human recombinant 15-lipoxygenase (type 2). Their inhibitory effect on blood platelet and anti-inflammatory properties were compared with those already reported for PDX.
关键词：octadecatrienoic acid ; 15-lipoxygenase ; platelet aggregation ; anti-inflammatory activity ; α-linolenic acid