Document Detail

Conversion of linoleic acid into novel oxylipins by the mushroom Agaricus bisporus.
MedLine Citation:
PMID:  16459929     Owner:  NLM     Status:  MEDLINE    
Oxylipins are associated with important processes of the fungal life cycle, such as spore formation. Here, we report the formation of FA metabolites in Agaricus bisporus. Incubation of a crude extract of lamellae with linoleic acid (18:2) led to the extensive formation of two oxylipins. They were identified as 8(R)-hydroxy-9Z,12Z-octadecadienoic acid (8-HOD) and 8(R),11 (S)-dihydroxy-9Z,12Z-octadecadienoic acid (8,11-diHOD) by using RP-HPLC, GC-MS, IR, GC-MS analysis of diastereomeric derivatives, and 1H NMR and 13C NMR spectroscopy. Neither compound has been reported before in A. bisporus. Oleic (18:1), alpha-linolenic (18:3n-3), and gamma-linolenic (18:3n-6) acids were converted into their 8-hydroxy derivatives as well, and 18:3n-3 was further metabolized to its 8,11-diol derivative. Reactions with [U-13C]18:2 demonstrated that the compounds 8-HOD and 8,11-diHOD were formed from exogenously supplied 18:2. When [U-13C]8-HOD was supplied, it was not converted into 8,11-diHOD, indicating that it was not an intermediate in the formation of 8,11-diHOD. When a crude extract of A. bisporus was incubated under an atmosphere of 16O2/18O2, the two hydroxyl groups of 8,11-diHOD contained either two 180 atoms or two 60 atoms. Species that contained one of each isotope could not be detected. We propose that the formation of the 8,11-dihydroxy compounds occurs through either an 8,11-endoperoxy, an 8-peroxo free radical, or an 8-hydroperoxy intermediate. In the latter case, the reaction should be catalyzed by dioxygenase with novel specificity.
Mayken W Wadman; Guus van Zadelhoff; Mats Hamberg; Tom Visser; Gerrit A Veldink; Johannes F G Vliegenthart
Related Documents :
10493789 - Nature of hydrogen transfer in soybean lipoxygenase 1: separation of primary and second...
19571159 - Hepatomegaly induced by trans-10,cis-12 conjugated linoleic acid in adult hamsters fed ...
25309529 - L,l-diaminopimelate aminotransferase (dapl): a putative target for the development of n...
24454759 - Olives and olive oil are sources of electrophilic fatty acid nitroalkenes.
18457679 - The mechanism of oleic acid nitration by *no(2).
21636269 - Thermo-mechanical extrusion pretreatment for conversion of soybean hulls to fermentable...
16069 - Mechanism by which neutral phosphate infusion elevates urine pco2.
24862279 - Analysis of hypoxia-induced metabolic reprogramming.
23193999 - Pd(ii)-catalyzed regio-, enantio-, and diastereoselective 1,4-addition of azlactones fo...
Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Lipids     Volume:  40     ISSN:  0024-4201     ISO Abbreviation:  Lipids     Publication Date:  2005 Nov 
Date Detail:
Created Date:  2006-02-07     Completed Date:  2006-06-06     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0060450     Medline TA:  Lipids     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1163-70     Citation Subset:  IM    
Department of Bio-organic Chemistry, Utrecht University, 3584-CH, Utrecht, The Netherlands.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Agaricus / enzymology,  metabolism*
Chromatography, High Pressure Liquid
Fatty Acids, Unsaturated / biosynthesis*,  chemistry
Gas Chromatography-Mass Spectrometry
Linoleic Acid / metabolism*
Magnetic Resonance Spectroscopy
Spectrophotometry, Infrared
Reg. No./Substance:
0/Fatty Acids, Unsaturated; 2197-37-7/Linoleic Acid; 26764-25-0/octadecadienoic acid

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

Previous Document:  Synthesis of dihydroperoxides of linoleic and linolenic acids and studies on their transformation to...
Next Document:  Inhibition of 12- and 15-lipoxygenase activities and protection of human and tilapia low density lip...