title: Fatty acid-amino acid conjugates diversification in lepidopteran caterpillars.
abstract: Fatty acid amino acid conjugates (FACs) have been found in noctuid as well as sphingid caterpillar oral secretions; in particular, volicitin [N-(17-hydroxylinolenoyl)-L-glutamine] and its biochemical precursor, N-linolenoyl-L-glutamine, are known elicitors of induced volatile emissions in corn plants. These induced volatiles, in turn, attract natural enemies of the caterpillars. In a previous study, we showed that N-linolenoyl-L-glutamine in larval Spodoptera litura plays an important role in nitrogen assimilation which might be an explanation for caterpillars synthesizing FACs despite an increased risk of attracting natural enemies. However, the presence of FACs in lepidopteran species outside these families of agricultural interest is not well known. We conducted FAC screening of 29 lepidopteran species, and found them in 19 of these species. Thus, FACs are commonly synthesized through a broad range of lepidopteran caterpillars. Since all FAC-containing species had N-linolenoyl-L-glutamine and/or N-linoleoyl-L-glutamine in common, and the evolutionarily earliest species among them had only these two FACs, these glutamine conjugates might be the evolutionarily older FACs. Furthermore, some species had glutamic acid conjugates, and some had hydroxylated FACs. Comparing the diversity of FACs with lepidopteran phylogeny indicates that glutamic acid conjugates can be synthesized by relatively primitive species, while hydroxylation of fatty acids is limited mostly to larger and more developed macrolepidopteran species.
authors.affiliation: Center for Chemical Ecology, Department of Entomology, The Pennsylvania State University, University Park, PA 16802, USA.
authors.forename: Naoko
authors.initials: N
authors.lastname: Yoshinaga
authors.forename: Hans T
authors.initials: HT
authors.lastname: Alborn
authors.forename: Tomoaki
authors.initials: T
authors.lastname: Nakanishi
authors.forename: David M
authors.initials: DM
authors.lastname: Suckling
authors.forename: Ritsuo
authors.initials: R
authors.lastname: Nishida
authors.forename: James H
authors.initials: JH
authors.lastname: Tumlinson
authors.forename: Naoki
authors.initials: N
authors.lastname: Mori
mesh_terms: D000596:Amino Acids / Q000737:chemistry* / Q000378:metabolism; D000818:Animals; D002851:Chromatography, High Pressure Liquid; D005227:Fatty Acids / Q000737:chemistry* / Q000378:metabolism; D005973:Glutamine / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification; D007814:Larva / Q000378:metabolism; D007915:Lepidoptera / Q000254:growth & development / Q000378:metabolism*; D008042:Linolenic Acids / Q000737:chemistry / Q000302:isolation & purification; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D000596:Amino Acids; D005227:Fatty Acids; D008042:Linolenic Acids; C475661:N-linolenoyl-L-glutamine; D005973:Glutamine