| Title: | Metabolically blocked analogs of housefly sex pheromone: II. Metabolism studies |
| Author(s): | Guo L; Latli B; Prestwich GD; Blomquist GJ; |
| Address: | "Department of Biochemistry, University of Nevada, 89557-0014, Reno, Nevada" |
| ISSN/ISBN: | 0098-0331 (Print) 0098-0331 (Linking) |
| Abstract: | "Analogs of (Z)-9-tricosene (Z9-23: Hy) bearing methyl substituents, cyclopropyl groups, fluorine substituents, and additional double bonds were used to probe the substrate requirements for the monooxygenase system that converts Z9-23: Hy to the corresponding epoxide and ketone. Three of the seven analogs tested, 10-fluoro-(Z)-14-tricosene, 10,10-difluoro-(Z)-14-tricosene, and 14-methyl-(Z)-9-tricosene, were metabolized to the corresponding epoxide. Compounds with two methyl groups, a cyclopropane group, a hydroxy group, or an additional double bond at the 14 position were not epoxidized at the 9,10 position. This suggests that only minimal structural change at the 14-position of Z9-23: Hy is allowed with retention of metabolic activity. None of the analogs tested were hydroxylated at the position equivalent to the 14 position of Z9-23:Hy. Of the 13 analogs tested as inhibitors of Z9-23:Hy metabolism, the two compounds that were the most effective inhibitors in both male and female houseflies were (Z)-14-tricosen-10-one and 1-nonyl-1-[(Z)-4-tetradecen-1-yl]-cyclopropane. These data show that the poly substrate monooxy genase that metabolizes Z9-23: Hy in the housefly has very strict structural requirements for the substrate" |
| Notes: | "PubMed-not-MEDLINEGuo, L Latli, B Prestwich, G D Blomquist, G J eng 1991/09/01 J Chem Ecol. 1991 Sep; 17(9):1769-82. doi: 10.1007/BF00993727" |
