« Previous AbstractFunctional expression of a bark beetle cytochrome P450 that hydroxylates myrcene to ipsdienol    Next AbstractIdentification and Characterization of Geranic Acid as a Unique Flavor Compound of Hops ( Humulus lupulus L.) Variety Sorachi Ace »

J Chem Ecol

Title:		Myrcene hydroxylases do not determine enantiomeric composition of pheromonal ipsdienol in Ips spp
Author(s):		Sandstrom P; Ginzel MD; Bearfield JC; Welch WH; Blomquist GJ; Tittiger C;
Address:		"Department of Biochemistry and Molecular Biology, University of Nevada, Reno, Reno, NV 89557, USA"
Journal Title:		J Chem Ecol
Year:		2008
Volume:		20081126
Issue:		12
Page Number:		1584 - 1592
DOI:		10.1007/s10886-008-9563-7
ISSN/ISBN:		0098-0331 (Print) 0098-0331 (Linking)
Abstract:		"Myrcene (7-methyl-3-methylene-1,6-octadiene) hydroxylation is likely one of the final reactions involved in the production of the Ips spp. (Coleoptera: Scolytidae) aggregation pheromone components, ipsdienol (2-methyl-6-methylene-2,7-octadien-4-ol) and ipsenol (2-methyl-6-methylene-7-octen-4-ol). To gain insight into the evolution of pheromone production, we isolated a full-length cDNA from the pinyon ips, Ips confusus (LeConte), that encodes a pheromone-biosynthetic cytochrome P450, I. confusus CYP9T1 (IcCYP9T1). The recovered cDNA is 1.70 kb, and the open reading frame encodes a 532 amino acid protein. IcCYP9T1 is 94% identical to the pine engraver, Ips pini (Say), CYP9T2 ortholog that hydroxylates myrcene. Quantitative real-time PCR experiments showed that IcCYP9T1, as does CYP9T2, has an expression pattern similar to other pheromone-biosynthetic genes in I. pini. Basal expression levels were higher in males than females, and expression was significantly induced in male, but not in female, anterior midguts by feeding on host phloem. Microsomes, prepared from Sf9 cells co-expressing baculoviral-mediated recombinant IcCYP9T1 and house fly (Musca domestica) NADPH-cytochrome P450 reductase, converted myrcene to ~85%-(R)-(-)-ipsdienol. These results are consistent with IcCYP9T1 encoding a myrcene hydroxylase that functions near the end of the pheromone-biosynthetic pathway. Since the I. confusus pheromone blend contains >90%-(S)-(+)-ipsdienol, these results confirm further that Ips spp. myrcene hydroxylases do not control the final ipsdienol enantiomeric blend. Other enzymes are required following myrcene hydroxylation to achieve the critical quantity and enantiomeric composition of pheromonal ipsenol and ipsdienol used by different Ips spp"
Keywords:		"Acyclic Monoterpenes Alkenes/*metabolism Amino Acid Sequence Animals Coleoptera/*enzymology/genetics DNA, Complementary/genetics Gene Expression Regulation, Enzymologic Hydroxylation Male Mixed Function Oxygenases/chemistry/genetics/isolation & purificati;"
Notes:		"MedlineSandstrom, Pamela Ginzel, Matthew D Bearfield, Jeremy C Welch, William H Blomquist, Gary J Tittiger, Claus eng Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, Non-P.H.S. 2008/11/27 J Chem Ecol. 2008 Dec; 34(12):1584-92. doi: 10.1007/s10886-008-9563-7. Epub 2008 Nov 26"