Document Detail

Products of linoleic hydroperoxide-decomposing enzyme of alfalfa seed.
MedLine Citation:
PMID:  4208994     Owner:  NLM     Status:  MEDLINE    
Alfalfa seeds and seedlings contain an enzyme that catalyzes a reaction with the 13- and 9-hydroperoxides of linoleic acid to form 13-hydroxy-10-oxo-trans-octadecenoic acid and 9-hydroxy-12-oxo-trans-10-octadecenoic acid, respectively. When commercial lipoxygenase is used to generate the hydroperoxides, the above acids appear in about 2:1 proportions, respectively. The products of the action of the enzyme on the hydroperoxides were stabilized for analysis by reduction with H(2) and LiAIH(4). Trimethylsilyl derivatives of reduced products were analyzed by combined gas-liquid chromatography-mass spectrometry. Specific deuterium labeling permitted definite location of the oxo functions. (18)O(2) labeling experiments showed that the oxygens of both the oxo and the hydroxyl functions were derived from the hydroperoxide. Retention of both oxygens suggests that the reaction proceeds through a cyclic epiperoxide followed by a ketohydroxy-forming rearrangement. No products of hydroperoxide isomerase were found in reactions catalyzed by the crude enzyme from alfalfa seeds.
W J Esselman; C O Clagett
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Journal of lipid research     Volume:  15     ISSN:  0022-2275     ISO Abbreviation:  J. Lipid Res.     Publication Date:  1974 Mar 
Date Detail:
Created Date:  1974-08-02     Completed Date:  1974-08-02     Revised Date:  2007-03-22    
Medline Journal Info:
Nlm Unique ID:  0376606     Medline TA:  J Lipid Res     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  173-8     Citation Subset:  IM    
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MeSH Terms
Linoleic Acids
Mass Spectrometry
Medicago sativa / enzymology*
Oxygen Isotopes
Peroxidases / metabolism*
Pseudomonas aeruginosa / analysis
Seeds / enzymology
Spectrophotometry, Infrared
Spectrophotometry, Ultraviolet
Reg. No./Substance:
0/Linoleic Acids; 0/Oxygen Isotopes; 0/Peroxides; 7429-90-5/Aluminum; 7439-93-2/Lithium; 7782-39-0/Deuterium; EC 1.11.1.-/Peroxidases

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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