Document Detail

Biosynthetic pathways of the sex pheromone components and substrate selectivity of the oxidation enzymes working in pheromone glands of the fall webworm, Hyphantria cunea.
MedLine Citation:
PMID:  21338674     Owner:  NLM     Status:  Publisher    
The fall webworm, Hyphantria cunea Drury (Lepidoptera: Arctiidae), is a harmful polyphagous defoliator. Female moths produce the following four pheromone components in a ratio of about 5:4:10:2; (9Z,12Z)-9,12-octadecadienal (I), (9Z,12Z,15Z)-9,12,15-octadecatrienal (II), cis-9,10-epoxy-(3Z,6Z)-3,6-henicosadiene (III), and cis-9,10-epoxy-(3Z,6Z)-1,3,6-henicosatriene (IV). Although (13)C-labeled linolenic acid was not converted into trienal II at the pheromone glands of H. cunea females, GC-MS analysis of an extract of the pheromone gland treated topically with (13)C-labeled linolenyl alcohol showed the aldehyde incorporating the isotope. Other C(18) and C(19) fatty alcohols were also oxidized to the corresponding aldehydes in the pheromone gland, indicating a biosynthetic pathway of IIvia linolenyl alcohol and low substrate selectivity of the alcohol oxidase in the pheromone gland. On the other hand, epoxydiene III was expected to be produced by specific 9,10-epoxidation of the corresponding C(21) trienyl hydrocarbon, which might be biosynthesized from dietary linolenic acid in oenocytes and transported to the pheromone gland. The final biosynthetic step in the pheromone gland was confirmed by an experiment using deuterated C(21) triene, which was synthesized by the chain elongation of linolenic acid and LiAlD(4) reduction as key reactions. When the labeled triene was administered to the female by topical application at the pheromone gland or injection into the abdomen, deuterated III was detected in a pheromone extract by GC-MS analysis. Furthermore, the substrate selectivity of epoxidase and selective incorporation by the pheromone glands were examined by treatments with mixtures of the deuterated precursor and other hydrocarbons such as C(19)-C(23) trienyl, C(21) dienyl, and C(21) monoenyl hydrocarbons. The 9,10-epoxy derivative of each alkene was produced, while the epoxidation of the C(21) monoene was poorer than those of the trienes and diene. The low selectivity indicated that the species-specific pheromone of the H. cunea female was mainly due to the critical formation of the precursor of each component.
Ryutaro Kiyota; Maki Arakawa; Rei Yamakawa; Abeda Yasmin; Tetsu Ando
Related Documents :
7582024 - Uptake of amino acids by the parasitic, flagellated protist trichomonas vaginalis.
2004114 - Functional reconstitution of the malate carrier of barley mesophyll vacuoles in liposomes.
9530094 - Cellular differentiation and i-fabp protein expression modulate fatty acid uptake and d...
8132234 - Characterisation of the routes of methionine transport in mouse mammary glands.
3059394 - Role of zinc in lipid and fatty acid metabolism and in membranes.
17923434 - Molecular evolution of fome lignosus laccase by ethyl methane sulfonate-based random mu...
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-2-18
Journal Detail:
Title:  Insect biochemistry and molecular biology     Volume:  -     ISSN:  1879-0240     ISO Abbreviation:  -     Publication Date:  2011 Feb 
Date Detail:
Created Date:  2011-2-22     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9207282     Medline TA:  Insect Biochem Mol Biol     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Copyright Information:
Copyright © 2011. Published by Elsevier Ltd.
Graduate School of Bio-Applications and Systems Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms

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

Previous Document:  Decline of sperm quality and testicular function in male mice during chronic low-dose exposure to mi...
Next Document:  Efficacy of hepatitis B sero-vaccination in newborns of African HBsAg positive mothers.