METABOLISM OF 6,9,12-OCTADECATRIENOIC ACID IN THE RED ALGA LITHOTHAMNION-CORALLIOIDES - MECHANISM OF FORMATION OF A CONJUGATED TETRAENE FATTY-ACID

被引:28
作者
HAMBERG, M
机构
[1] Department of Physiological Chemistry, Karolinska Institutet
关键词
D O I
10.1016/0006-291X(92)91361-S
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Incubation of [1-14C]6(Z),9(Z),12(Z)-octadecatrienoic acid with an enzyme preparation from the red alga Lithothamnion corallioides Crouan led to the formation of two new compounds, i.e. the conjugated tetraene 6(Z),8(E),10(E),12(Z)-octadecatetraenoic acid and the bis-allylic hydroxy acid 11(R)-hydroxy-6(Z),9(Z),12(Z)-octadecatrienoic acid. These two compounds were formed by independent pathways and were not interconvertible by the enzyme preparation. Experiments with stereospecifically deuteriated 6,9,12-octadecatrienoic acids demonstrated that formation of 6,8,10,12-octadecatetraenoic acid was accompanied by loss of the pro-S and pro-R hydrogens from C-8 and C-11, respectively, whereas formation of 11-hydroxy-6,9,12-octadecatrienoic acid proceeded with loss of the pro-S hydrogen from C-11. Biosynthesis of 6,8,10,12-octadecatetraenoic acid was dioxygen-dependent and was accompanied by production of hydrogen peroxide. A number of artificial electron acceptors supported formation of 6,8,10,12-octadecatetraenoic acid under anaerobic conditions. The existence in Lithothamnion corallioides of a fatty acid oxidase that catalyzes the oxidation of certain poly-unsaturated fatty acids into conjugated tetraene fatty acids is postulated. © 1992.
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页码:1220 / 1227
页数:8
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