N-(17-Acyloxy-acyl)-glutamines: novel surfactants from oral secretions of lepidopteran larvae.
N-(17-Acyloxy-acyl)-glutamine conjugates such as N-(17-linolenoyloxy-linolenoyl)-glutamine (6), N-(17-linolenoyloxy-linoleoyl)-glutamine (7), N-(17-linoleoyloxy-linolenoyl)-glutamine (8), and N-(17-linoleoyloxy-linoleoyl)-glutamine (9) were identified as novel surfactants in the oral secretion of several lepidopteran larvae (S. exigua, S. littoralis, S. frugiperda, and H. virescens) by LC-MS/MS and chemical degradation. Authentic reference compounds were synthesized via a dissymmetric bis-Wittig approach and confirmed the assigned structures.
Spiteller
Dieter
D
Department of Bioorganic Chemistry, Max Planck Institute for Chemical Ecology, Winzerlaer Strasse 10, D-07745 Jena, Germany.
Boland
Wilhelm
W
D000818:Animals; D005973:Glutamine / Q000031:analogs & derivatives / Q000378:metabolism*; D007915:Lepidoptera / Q000145:classification; D009055:Mouth / Q000378:metabolism*; D019906:Nuclear Magnetic Resonance, Biomolecular; D013045:Species Specificity; D013501:Surface-Active Agents / Q000378:metabolism*
D013501:Surface-Active Agents; D005973:Glutamine