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Insect Biochem Mol Biol

Title:		CYPs in different families are involved in the divergent regio-specific epoxidation of alkenyl sex pheromone precursors in moths
Author(s):		Rong Y; Fujii T; Ishikawa Y;
Address:		"Graduate School of Agricultural and Life Sciences, The University of Tokyo, Tokyo, 113-8657, Japan. Electronic address: honour_scau@yahoo.co.jp. Graduate School of Agricultural and Life Sciences, The University of Tokyo, Tokyo, 113-8657, Japan"
Journal Title:		Insect Biochem Mol Biol
Year:		2019
Volume:		20190308
Issue:
Page Number:		9 - 15
DOI:		10.1016/j.ibmb.2019.03.002
ISSN/ISBN:		1879-0240 (Electronic) 0965-1748 (Linking)
Abstract:		"In moth species that utilize alkenyl sex pheromones, the epoxidation of alkenes confers further diversity on the chemical structures of pheromone components. Hc_epo1 (CYP341B14), the first pheromone gland (PG)-specific epoxidase identified from the fall webworm Hyphantria cunea (Erebidae), specifically epoxidizes the Z9 double bond in the triene precursor, (3Z,6Z,9Z)-3,6,9-henicosatriene (Z3,Z6,Z9-21:H). In the present study, we identified a novel PG-specific epoxidase, As_epo1, from the Japanese giant looper Ascotis selenaria (Geometridae), which secretes cis-3,4-epoxy-(6Z,9Z)-6,9-nonadecadiene (epo3,Z6,Z9-19:H) as the main sex pheromone component. A functional assay using the Sf9 insect cell line-baculovirus expression system showed that As_epo1 specifically epoxidizes the Z3 double bond in the pheromone precursor triene, (3Z,6Z,9Z)-3,6,9-nonadecatriene (Z3,Z6,Z9-19:H). As_epo1 also Z3-specifically epoxidized a triene with a longer carbon chain, Z3,Z6,Z9-21:H, which does not occur in this species. A phylogenetic analysis indicated that As_epo1 belonged to the CYP340 family, not the CYP341 family to which Hc_epo1 belongs. These results suggest that moth PG-specific epoxidases with divergent regio-specificities have evolved independently"
Keywords:		Animals Baculoviridae Cytochrome P-450 Enzyme System/*metabolism Female Insect Proteins/chemistry/metabolism Moths/classification/*enzymology/metabolism Oxidoreductases/metabolism Phylogeny Sex Attractants/biosynthesis/chemistry/*metabolism Sf9 Cells Spod;
Notes:		"MedlineRong, Yu Fujii, Takeshi Ishikawa, Yukio eng Research Support, Non-U.S. Gov't England 2019/03/13 Insect Biochem Mol Biol. 2019 May; 108:9-15. doi: 10.1016/j.ibmb.2019.03.002. Epub 2019 Mar 8"