Document Detail

Unusual mechanism of hydrocarbon formation in the housefly: cytochrome P450 converts aldehyde to the sex pheromone component (Z)-9-tricosene and CO2.
MedLine Citation:
PMID:  7937826     Owner:  NLM     Status:  MEDLINE    
An unusual mechanism for hydrocarbon biosynthesis is proposed from work examining the formation of (Z)-9-tricosene (Z9-23:Hy), the major sex pheromone component of the female housefly, Musca domestica. Incubation of (Z)-15-[1-14C]- and (Z)-15-[15,16-3H2]tetracosenoic acid (24:1 fatty acid) with microsomes from houseflies gave equal amounts of [3H]Z9-23:Hy and 14CO2. The formation of CO2 and not CO, as reported for hydrocarbon formation in plants, animals, and microorganisms [Dennis, M. & Kolattukudy, P. E. (1992) Proc. Natl. Acad. Sci. USA 89, 5306-5310], was verified by trapping agents and by radio-GLC analysis. Incubation of (Z)-15-[15,16-3H2]tetracosenoyl-CoA with microsomal preparations in the presence of NADPH and O2 gave almost equal amounts of (Z)-15-3H2]tetrasosenal (24:1 aldehyde) and Z9-23:Hy. Addition of increasing amounts of hydroxylamine (aldehyde trapping agent) caused a decrease in hydrocarbon formation with a concomitant increase in oxime (aldehyde derivative) formation. The 24:1 aldehyde was efficiently converted to (Z)-9-tricosene only in the presence of both NADPH and O2. Bubbling carbon monoxide (20:80 CO/O2) or including an antibody against housefly cytochrome P450 reductase inhibited the formation Z9-23:Hy from 24:1 aldehyde. These data demonstrate an unusual mechanism for hydrocarbon formation in insects in which the acyl-CoA is reduced to the corresponding aldehyde and then carbon-1 is removed as CO2. The requirement for NADPH and O2 and the inhibition by CO and the antibody to cytochrome P450 reductase strongly implicate the participation of a cytochrome P450 in this reaction.
J R Reed; D Vanderwel; S Choi; J G Pomonis; R C Reitz; G J Blomquist
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, Non-P.H.S.    
Journal Detail:
Title:  Proceedings of the National Academy of Sciences of the United States of America     Volume:  91     ISSN:  0027-8424     ISO Abbreviation:  Proc. Natl. Acad. Sci. U.S.A.     Publication Date:  1994 Oct 
Date Detail:
Created Date:  1994-11-10     Completed Date:  1994-11-10     Revised Date:  2009-11-18    
Medline Journal Info:
Nlm Unique ID:  7505876     Medline TA:  Proc Natl Acad Sci U S A     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  10000-4     Citation Subset:  IM    
Department of Biochemistry, University of Nevada, Reno 89557-0014.
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MeSH Terms
Aldehydes / metabolism
Alkenes / metabolism*
Carbon Dioxide / metabolism
Carbon Radioisotopes
Cytochrome P-450 Enzyme System / metabolism*
Fatty Acids, Monounsaturated / metabolism*
Houseflies / enzymology*
Hydrocarbons / metabolism
Microsomes / enzymology*
Pheromones / biosynthesis*
Radioisotope Dilution Technique
Reg. No./Substance:
0/Aldehydes; 0/Alkenes; 0/Carbon Radioisotopes; 0/Fatty Acids, Monounsaturated; 0/Hydrocarbons; 0/Pheromones; 10028-17-8/Tritium; 124-38-9/Carbon Dioxide; 26444-06-4/tetracosenoic acid; 52078-48-5/muscalure; 9035-51-2/Cytochrome P-450 Enzyme System

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

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