Document Detail

Steric analysis of epoxyalcohol and trihydroxy derivatives of 9-hydroperoxy-linoleic acid from hematin and enzymatic synthesis.
MedLine Citation:
PMID:  23352713     Owner:  NLM     Status:  MEDLINE    
We characterize the allylic epoxyalcohols and their trihydroxy hydrolysis products generated from 9R- and 9S-hydroperoxy-octadecenoic acid (HPODE) under non-enzymatic conditions, reaction with hematin and subsequent acid hydrolysis, and enzymatic conditions, incubation with Beta vulgaris containing a hydroperoxide isomerase and epoxide hydrolase. The products were resolved by HPLC and the regio and stereo-chemistry of the transformations were determined through a combination of (1)H NMR and GC-MS analysis of dimethoxypropane derivatives. Four trihydroxy isomers were identified upon mild acid hydrolysis of 9S,10S-trans-epoxy-11E-13S-hydroxyoctadecenoate: 9S,10R,13S, 9S,12R,13S, 9S,10S,13S and 9S,12S,13S-trihydroxy-octadecenoic acids, in the ratio 40:26:22:12. We also identified a prominent δ-ketol rearrangement product from the hydrolysis as mainly the 9-hydroxy-10E-13-oxo isomer. Short incubation (5 min) of 9R- and 9S-HPODE with B. vulgaris extract yielded the 9R- and 9S-hydroxy-10E-12R,13S-cis-epoxy products respectively. Longer incubation (60 min) gave one specific hydrolysis product via epoxide hydrolase, the 9R/S,12S,13S-trihydroxyoctadecenoate. These studies provide a practical approach for the isolation and characterization of allylic epoxy alcohol and trihydroxy products using a combination of HPLC, GC-MS and (1)H NMR.
Christopher P Thomas; William E Boeglin; Yoel Garcia-Diaz; Valerie B O'Donnell; Alan R Brash
Related Documents :
24301983 - Biosynthesis of wax esters in tissues of sinapis alba l. seeds.
25088313 - Thin-layer chromatography - an image processing method for the determination of acidic ...
17827763 - Synthesis of gamma-hydroxybutenolides applying crossed aldol condensation in the presen...
Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't     Date:  2013-01-23
Journal Detail:
Title:  Chemistry and physics of lipids     Volume:  167-168     ISSN:  1873-2941     ISO Abbreviation:  Chem. Phys. Lipids     Publication Date:    2013 Feb-Mar
Date Detail:
Created Date:  2013-04-02     Completed Date:  2013-09-09     Revised Date:  2014-02-04    
Medline Journal Info:
Nlm Unique ID:  0067206     Medline TA:  Chem Phys Lipids     Country:  Ireland    
Other Details:
Languages:  eng     Pagination:  21-32     Citation Subset:  IM    
Copyright Information:
Copyright © 2013 Elsevier Ireland Ltd. All rights reserved.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Beta vulgaris / chemistry,  enzymology*,  metabolism
Chromatography, High Pressure Liquid
Epoxide Hydrolases / metabolism
Epoxy Compounds / chemistry*,  metabolism
Gas Chromatography-Mass Spectrometry
Hemin / analogs & derivatives*,  metabolism
Intramolecular Oxidoreductases / metabolism
Linoleic Acid / chemistry*,  metabolism
Magnetic Resonance Spectroscopy
Oleic Acids / chemistry*,  metabolism
Propanols / chemistry*,  metabolism
Grant Support
Reg. No./Substance:
0/10-hydroperoxy-8-octadecenoic acid; 0/Epoxy Compounds; 0/Oleic Acids; 0/Propanols; 3W678R12M0/allyl alcohol; 743LRP9S7N/Hemin; 9KJL21T0QJ/Linoleic Acid; EC 3.3.2.-/Epoxide Hydrolases; EC 5.3.-/Intramolecular Oxidoreductases; EC isomerase

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

Previous Document:  Wormian bones in a general paediatric population.
Next Document:  Image analysis is driving a renaissance in growth measurement.