| Title: | Direct inhibition of (Z)-9 desaturation of (E)-11-tetradecenoic acid by methylenehexadecenoic acids in the biosynthesis of Spodoptera littoralis sex pheromone |
| Author(s): | Fabrias G; Gosalbo L; Quintana J; Camps F; |
| Address: | "Department of Biological Organic Chemistry, CID-CSIC, Barcelona, Spain" |
| ISSN/ISBN: | 0022-2275 (Print) 0022-2275 (Linking) |
| Abstract: | "Analysis by gas chromatography coupled to mass spectrometry demonstrated that 11,12-methylenehexadec-11-enoic acid and 12,13-methylenehexadec-12-enoic acid are beta-oxidized in Spodoptera littoralis sex pheromone gland to 9, 10-methylenetetradec-10-enoic acid and 10,11-methylenetetradec-10-enoic acid, respectively. This result supported our previous hypothesis that inhibition of the (Z)-9 desaturation of (E)-11-tetradecenoic acid by those C-16 fatty acids is actually caused by their corresponding beta-oxidation products. However, although (2,2,3,3-2H4)-11,12-methylenehexadec-11-enoic acid was not chain-shortened to the C-14 derivative, its activity as inhibitor of the (Z)-9 desaturation reaction was similar to that exhibited by 11,12-methylenehexadec-11-enoic acid. Therefore, the C-16 cyclopropene fatty acids may inhibit the (Z)-9 desaturation enzyme by themselves, probably through interaction of the cyclopropene ring with a binding site of the enzyme with the substrate double bond" |
| Keywords: | "Animals Fatty Acids, Unsaturated/*metabolism Gas Chromatography-Mass Spectrometry Sex Attractants/*biosynthesis Spodoptera/*metabolism;" |
| Notes: | "MedlineFabrias, G Gosalbo, L Quintana, J Camps, F eng Research Support, Non-U.S. Gov't 1996/07/01 J Lipid Res. 1996 Jul; 37(7):1503-9" |
