Document Detail

Fatty acid amides, previously identified in caterpillars, found in the cricket Teleogryllus taiwanemma and fruit fly Drosophila melanogaster larvae.
MedLine Citation:
PMID:  17566833     Owner:  NLM     Status:  MEDLINE    
Fatty acid amides (FAAs) are known elicitors that induce plants to release volatile compounds that, in turn, attract foraging parasitoids. Since the discovery of volicitin [N-(17-hydroxylinolenoyl)-L-glutamine] in the regurgitant of larval Spodoptera exigua, a series of related FAAs have been identified in several other species of lepidopteran caterpillars. We screened 13 non-lepidopteran insects for the presence of FAAs and found that these compounds were present in adults of two closely related cricket species, Teleogryllus taiwanemma and T. emma (Orthoptera: Gryllidae), and larvae of the fruit fly, Drosophila melanogaster (Diptera: Drosophilidae). When analyzed by liquid chromatography/mass spectrometry-ion trap-time-of-flight (LCMS-IT-TOF), the gut contents of both crickets had nearly identical FAA composition, the major FAAs comprising N-linolenoyl-L-glutamic acid and N-linoleoyl-L-glutamic acid. There were also two previously uncharacterized FAAs that were thought to be hydroxylated derivatives of these glutamic acid conjugates, based on their observed fragmentation patterns. In addition to these four FAAs containing glutamic acid, N-linolenoyl-L-glutamine and a small amount of volicitin were detected. In D. melanogaster, N-linolenoyl-L-glutamic acid and N-linoleoyl-L-glutamic acid were the major FAAs found in larval extracts, while hydroxylated glutamic acid conjugates, volicitin and N-linolenoyl-L-glutamine, were detected as trace components. Although these FAAs were not found in ten of the insects studied here, their identification in two additional orders of insects suggests that FAAs are more common than previously reported and may have physiological roles in a wide range of insects besides caterpillars.
Naoko Yoshinaga; Takako Aboshi; Chihiro Ishikawa; Masao Fukui; Masami Shimoda; Ritsuo Nishida; Cameron G Lait; James H Tumlinson; Naoki Mori
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Journal of chemical ecology     Volume:  33     ISSN:  0098-0331     ISO Abbreviation:  J. Chem. Ecol.     Publication Date:  2007 Jul 
Date Detail:
Created Date:  2007-11-16     Completed Date:  2008-01-29     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  7505563     Medline TA:  J Chem Ecol     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1376-81     Citation Subset:  IM    
Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Sakyo, Kyoto 606-8502, Japan.
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MeSH Terms
Amides / analysis*
Chromatography, Liquid
Drosophila melanogaster
Fatty Acids / chemistry*
Larva / chemistry*
Mass Spectrometry
Reg. No./Substance:
0/Amides; 0/Fatty Acids

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