Document Detail

Hydroperoxide-dependent epoxidation of unsaturated fatty acids in the broad bean (Vicia faba L.).
MedLine Citation:
PMID:  2275553     Owner:  NLM     Status:  MEDLINE    
Incubation of linoleic acid with the 105,000g particle fraction of the homogenate of the broad bean (Vicia faba L.) led to the formation of the following products: 13(S)-hydroxy-9(Z),11(E)-octadecadienoic acid, 9,10-epoxy-12(Z)-octadecenoic acid (9(R),10(S)/9(S)/10(R), 80/20), 12,13-epoxy-9(Z)-octadecenoic acid (12(S),13(R)/12(R)/13(S), 64/36), and 9,10-epoxy-13(S)-hydroxy-11(E)-octadecenoic acid (9(S),10(R)/9(R),10(S), 91/9). Oleic acid incubated with the enzyme preparation in the presence of 13(S)-hydroperoxy-9(Z),11(E)-octadecadienoic acid or cumene hydroperoxide was converted into 9,10-epoxyoctadecanoic acid (9(R),10(S)/9(S),10(R), 79/21). Two enzyme activities were involved in the formation of the products, an omega 6-lipoxygenase and a hydroperoxide-dependent epoxygenase. The lipoxygenase, but not the epoxygenase, was inhibited by low concentrations of 5,8,11,14-eicosatetraynoic acid and nordihydroguaiaretic acid. In contrast, the epoxygenase, but not the lipoxygenase, was readily inactivated in the presence of 13(S)-hydroperoxy-9(Z),11(E)-octadecadienoic acid. Studies with 18O2-labeled 13(S)-hydroperoxy-9(Z),11(E)-octadecadienoic acid showed that the epoxide oxygens of 9,10-epoxyoctadecanoic acid and of 9,10-epoxy-13(S)-hydroxy-11(E)-octadecenoic acid were derived from hydroperoxide and not from molecular oxygen.
M Hamberg; G Hamberg
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Archives of biochemistry and biophysics     Volume:  283     ISSN:  0003-9861     ISO Abbreviation:  Arch. Biochem. Biophys.     Publication Date:  1990 Dec 
Date Detail:
Created Date:  1991-02-28     Completed Date:  1991-02-28     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0372430     Medline TA:  Arch Biochem Biophys     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  409-16     Citation Subset:  IM    
Department of Physiological Chemistry, Karolinska Institutet, Stockholm, Sweden.
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MeSH Terms
5,8,11,14-Eicosatetraynoic Acid / pharmacology
Chromatography, Thin Layer
Cytosol / metabolism
Epoxy Compounds / isolation & purification,  metabolism*
Fabaceae / metabolism*
Hydroxy Acids / isolation & purification,  metabolism*
Linoleic Acid
Linoleic Acids / metabolism*
Nordihydroguaiaretic Acid / pharmacology
Oleic Acid
Oleic Acids / metabolism*
Plants, Medicinal*
Reg. No./Substance:
0/Epoxy Compounds; 0/Hydroxy Acids; 0/Linoleic Acids; 0/Oleic Acids; 112-80-1/Oleic Acid; 1191-85-1/5,8,11,14-Eicosatetraynoic Acid; 2197-37-7/Linoleic Acid; 500-38-9/Nordihydroguaiaretic Acid

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