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Oxylipin metabolism in the red alga Gracilariopsis lemaneiformis: mechanism of formation of vicinal dihydroxy fatty acids.

Abstract：

:Conversion of arachidonic acid into the vicinal diol fatty acid 12R,13S-dihydroxy-5Z,8Z,10E,14Z-eicosatetraenoic acid using an acetone powder of the marine red alga, Gracilariopsis lemaneiformis, occurred via intermediate formation of 12S-hydroperoxy-5Z,8Z,10E,14Z-eicosatetraenoic acid. Incubations of the linoleic acid-derived 13S- and 13R-hydroperoxy-9Z,11E-octadecadienoic acids led to the formation of 13R,14S-dihydroxy-9Z,11E-octadecadienoic acid and 13S,14S-dihydroxy-9Z,11E-octadecadienoic acid, respectively, whereas incubation of 9S-hydroperoxy-10E,12Z-octadecadienoic acid resulted in the formation of 8S,9R-dihydroxy-10E,12Z-octadecadienoic acid. Experiments with 18O2-labeled 13S-hydroperoxyoctadecadienoic acid demonstrated that the oxygens of the two hydroxyl groups of 13R,14S-dihydroxy-9Z,11E-octadecadienoic acid originated in the hydroperoxy group of the substrate. Furthermore, experiments with mixtures of unlabeled and 18O2-labeled 13S-hydroperoxyoctadecadienoic acid showed that conversion into 13R,14S-dihydroxyoctadecadienoic acid occurred by a reaction involving an intramolecular hydroxylation at C-14 by the distal hydroperoxide oxygen. The existence of a hydroperoxide isomerase in G. lemaneiformis which catalyzes the conversion of fatty acid hydroperoxides into vicinal diol fatty acids is postulated.

journal_name

Arch Biochem Biophys

journal_title

Archives of biochemistry and biophysics

authors

Gerwick WH,Moghaddam M,Hamberg M

doi

10.1016/0003-9861(91)90563-x

subject

Has Abstract

pub_date

1991-11-01 00:00:00

pages

436-44

issue

2

eissn

0003-9861

issn

1096-0384

pii

0003-9861(91)90563-X

journal_volume

290

pub_type

杂志文章

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