title: Absolute configuration of volicitin from the regurgitant of lepidopteran caterpillars and biological activity of volicitin-related compounds.
abstract: Volicitin [N-(17-hydroxylinolenoyl)-L-glutamine] and N-linolenoyl-L-glutamine are known as insect-produced plant volatile elicitors. The absolute configuration of the hydroxylinolenoyl moiety of volicitin from three noctuid species, Helicoverpa armigera, Mythimna separata and Spodoptera litura, was determined to be all 17S in high enantiomeric excess. When treated with 30 pmol of (17S)- and (17R)-volicitin, corn seedlings were induced to release volatiles, there being no significant difference in the amount released between the two isomers. On the other hand, N-linolenoyl-L-glutamine was only about 30% as active as volicitin. Among several synthesized N-linolenoylamino acid conjugates, only the L-glutamine conjugate induced the emission of volatile organic compounds. These results show that the L-glutamine moiety of volicitin played a more critical role than the hydroxyl moiety, although both moieties affected the elicitor activity inducing the release of volatiles.
authors.affiliation: Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Sakyo, Kyoto, Japan.
authors.forename: Yoshitsugu
authors.initials: Y
authors.lastname: Sawada
authors.forename: Naoko
authors.initials: N
authors.lastname: Yoshinaga
authors.forename: Kenji
authors.initials: K
authors.lastname: Fujisaki
authors.forename: Ritsuo
authors.initials: R
authors.lastname: Nishida
authors.forename: Yasumasa
authors.initials: Y
authors.lastname: Kuwahara
authors.forename: Naoki
authors.initials: N
authors.lastname: Mori
mesh_terms: D000818:Animals; D008401:Gas Chromatography-Mass Spectrometry; D005973:Glutamine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D007915:Lepidoptera / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D036226:Seedlings / Q000187:drug effects / Q000378:metabolism; D013329:Structure-Activity Relationship; D013729:Terpenes / Q000378:metabolism; D003313:Zea mays / Q000187:drug effects / Q000378:metabolism; D017962:alpha-Linolenic Acid / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D013729:Terpenes; C419781:volicitin; D017962:alpha-Linolenic Acid; D005973:Glutamine