Document Detail


Biogenesis of volatile aldehydes from fatty acid hydroperoxides: molecular cloning of a hydroperoxide lyase (CYP74C) with specificity for both the 9- and 13-hydroperoxides of linoleic and linolenic acids.
MedLine Citation:
PMID:  11368353     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
A novel member of the plant cytochrome P450 CYP74 family of fatty acid hydroperoxide metabolizing enzymes has been cloned from melon fruit (Cucumis melo). The cDNA is comprised of 1,446 nucleotides encoding a protein of 481 amino acids. The homology at the amino acid level to other members of the CYP74 family is 35-50%, the closest relatives being allene oxide synthases. The cDNA was expressed in Escherichia coli, and the corresponding protein was purified by affinity column chromatography. The native enzyme showed a main Soret band at 418 nm, indicative of a low spin ferric cytochrome P450, and a 447-nm peak appeared in the CO-difference spectrum. Using [U-14C]radiolabeled substrate, HPLC, UV, and GC-MS, the products of conversion of 9S-hydroperoxy-linoleic acid were identified as 9-oxo-nonanic acid and 3Z-nonenal. Kinetic analysis of this hydroperoxide lyase showed the highest rate of reaction with 9-hydroperoxy-linolenic acid followed by 9-hydroperoxy-linoleic acid and then the corresponding 13-hydroperoxides. Overall, the newly characterized cytochrome P450 enzyme is a fatty acid hydroperoxide lyase with a preference, but not absolute specificity for the 9-positional hydroperoxides of linoleic and linolenic acids.
Authors:
N Tijet; C Schneider; B L Muller; A R Brash
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Archives of biochemistry and biophysics     Volume:  386     ISSN:  0003-9861     ISO Abbreviation:  Arch. Biochem. Biophys.     Publication Date:  2001 Feb 
Date Detail:
Created Date:  2001-05-22     Completed Date:  2001-06-07     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:  281-9     Citation Subset:  IM    
Affiliation:
Department of Pharmacology, Vanderbilt University Medical School, Nashville, Tennessee 37232, USA.
Data Bank Information
Bank Name/Acc. No.:
GENBANK/AF081955
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MeSH Terms
Descriptor/Qualifier:
Aldehyde-Lyases / chemistry,  genetics*,  metabolism*
Aldehydes / metabolism*
Amino Acid Sequence
Base Sequence
Catalysis
Chromatography, High Pressure Liquid
Cloning, Molecular
Cucurbitaceae / enzymology*,  genetics
Cytochrome P-450 Enzyme System / chemistry,  genetics*,  metabolism*
Escherichia coli / genetics
Gas Chromatography-Mass Spectrometry
Hydrogen-Ion Concentration
Kinetics
Linoleic Acid / chemistry,  metabolism*
Lipid Peroxides / chemistry,  metabolism*
Molecular Sequence Data
Phylogeny
Recombinant Fusion Proteins / chemistry,  metabolism
Spectrum Analysis
Substrate Specificity
alpha-Linolenic Acid / chemistry,  metabolism*
Chemical
Reg. No./Substance:
0/Aldehydes; 0/Lipid Peroxides; 0/Recombinant Fusion Proteins; 2197-37-7/Linoleic Acid; 31823-43-5/3-nonenal; 463-40-1/alpha-Linolenic Acid; 9035-51-2/Cytochrome P-450 Enzyme System; EC 4.1.2.-/Aldehyde-Lyases; EC 4.1.2.-/hydroperoxide lyase

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


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