Document Detail

Efficient and Specific Conversion of 9-Lipoxygenase Hydroperoxides in the Beetroot. Formation of Pinellic Acid.
MedLine Citation:
PMID:  21744276     Owner:  NLM     Status:  Publisher    
The linoleate 9-lipoxygenase product 9(S)-hydroperoxy-10(E),12(Z)-octadecadienoic acid was stirred with a crude enzyme preparation from the beetroot (Beta vulgaris ssp. vulgaris var. vulgaris) to afford a product consisting of 95% of 9(S),12(S),13(S)-trihydroxy-10(E)-octadecenoic acid (pinellic acid). The linolenic acid-derived hydroperoxide 9(S)-hydroperoxy-10(E),12(Z),15(Z)-octadecatrienoic acid was converted in an analogous way into 9(S),12(S),13(S)-trihydroxy-10(E),15(Z)-octadecadienoic acid (fulgidic acid). On the other hand, the 13-lipoxygenase-generated hydroperoxides of linoleic or linolenic acids failed to produce significant amounts of trihydroxy acids. Short-time incubation of 9(S)-hydroperoxy-10(E),12(Z)-octadecadienoic acid afforded the epoxy alcohol 12(R),13(S)-epoxy-9(S)-hydroxy-10(E)-octadecenoic acid as the main product indicating the sequence 9-hydroperoxide → epoxy alcohol → trihydroxy acid catalyzed by epoxy alcohol synthase and epoxide hydrolase activities, respectively. The high capacity of the enzyme system detected in beetroot combined with a simple isolation protocol made possible by the low amounts of endogenous lipids in the enzyme preparation offered an easy access to pinellic and fulgidic acids for use in biological and medical studies.
Mats Hamberg; Ulrika Olsson
Related Documents :
3170826 - Lipid synthesis and deposition by adult richardson's ground squirrels in the natural en...
16556926 - Nutrition modulation of cachexia/proteolysis.
3762326 - Distribution of hexadecenoic, octadecenoic and octadecadienoic acid isomers in human ti...
16662426 - Metabolism of 2,4-dichlorophenoxyacetic acid in 2,4-dichlorophenoxyacetic acid-resistan...
3828316 - Biosynthesis of lasalocid a: biochemical mechanism for assembly of the carbon framework.
8088366 - Structural requirements for the binding of fatty acids to 5-lipoxygenase-activating pro...
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-7-10
Journal Detail:
Title:  Lipids     Volume:  -     ISSN:  1558-9307     ISO Abbreviation:  -     Publication Date:  2011 Jul 
Date Detail:
Created Date:  2011-7-11     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0060450     Medline TA:  Lipids     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Division of Physiological Chemistry II, Department of Medical Biochemistry and Biophysics, Karolinska Institutet, Stockholm, Sweden,
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms

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

Previous Document:  Bio-oxidation of H(2)S by Sulfolobus metallicus.
Next Document:  2-Polyunsaturated Acyl Lysophosphatidylethanolamine Attenuates Inflammatory Response in Zymosan A-In...