Fatty Acid Amides, Previously Identified in Caterpillars, Found in the Cricket Teleogryllus taiwanemma and Fruit Fly Drosophila melanogaster Larvae

• Published in: Journal of chemical ecology Vol. 33; no. 7; pp. 1376 - 1381
• Main Authors: Yoshinaga, Naoko, Aboshi, Takako, Ishikawa, Chihiro, Fukui, Masao, Shimoda, Masami, Nishida, Ritsuo, Lait, Cameron G, Tumlinson, James H, Mori, Naoki
• Format: Journal Article
• Language: English
• Published: New York, NY New York : Springer-Verlag 01.07.2007; Springer; Springer Nature B.V
• Subjects: Amides; Amides - analysis; Animal and plant ecology; Animal, plant and microbial ecology; Animals; Autoecology; Biological and medical sciences; Caterpillars; chemical composition; Chromatography, Liquid; Conjugates; Crickets; Diptera; Drosophila melanogaster; Drosophilidae; Emma; Fatty acids; Fatty Acids - chemistry; Fruit flies; Fruits; Fundamental and applied biological sciences. Psychology; Glutamic acid; glutamic acid conjugates; Glutamine; Gryllidae; gut content analysis; Insects; Larva - chemistry; Larvae; Lepidoptera; Liquid chromatography; Mass Spectrometry; Mass spectroscopy; midgut; Orthoptera; plant elicitors; plant-insect relations; Protozoa. Invertebrata; Teleogryllus; Volatile compounds; Volicitin; Attractant; Larvae; Fatty amide; Insecta; Orthoptera; Gryllidae; Elicitor; Volicitin; Pest; Entomophagous; Host plant; Volatile compound; Drosophila; Gut; Elicitors; Fatty acids; Drosophilidae; Teleogryllus; Parasitoid; Larva; Animal plant relation; LCMS-IT-TOF, Fatty acid amides; Arthropoda; Adult animal; Lepidoptera; Invertebrata; Drosophila melanogaster; Diptera
• ISSN: 0098-0331; 1573-1561
• DOI: 10.1007/s10886-007-9321-2

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.