| Title: | Absolute configuration of volicitin from the regurgitant of lepidopteran caterpillars and biological activity of volicitin-related compounds |
| Author(s): | Sawada Y; Yoshinaga N; Fujisaki K; Nishida R; Kuwahara Y; Mori N; |
| Address: | "Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Sakyo, Kyoto, Japan" |
| Journal Title: | Biosci Biotechnol Biochem |
| ISSN/ISBN: | 0916-8451 (Print) 0916-8451 (Linking) |
| 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" |
| Keywords: | Animals Gas Chromatography-Mass Spectrometry Glutamine/*analogs & derivatives/chemistry/pharmacology Lepidoptera/*metabolism Magnetic Resonance Spectroscopy Molecular Conformation Seedlings/drug effects/metabolism Structure-Activity Relationship Terpenes/; |
| Notes: | "MedlineSawada, Yoshitsugu Yoshinaga, Naoko Fujisaki, Kenji Nishida, Ritsuo Kuwahara, Yasumasa Mori, Naoki eng Research Support, Non-U.S. Gov't England 2006/09/09 Biosci Biotechnol Biochem. 2006 Sep; 70(9):2185-90. doi: 10.1271/bbb.60133. Epub 2006 Sep 7" |
