10030. Volicitin
Nomenclature
CAS number: 191670-18-5
N2-[(9Z,12Z,15Z)-17-Hydroxy-1-oxo-9,12,15-octadecatrienyl]-l-glutamine; N-(17-hydroxylinolenoyl)-l-glutamine. C23H38N2O5; mol wt 422.56.
C 65.37%, H 9.06%, N 6.63%, O 18.93%.
Description and references
Key component in plant recognition of damage from insect herbivory. Isolated from the oral secretions of the beet armyworm caterpillar, it acts as a chemical signal to corn seedlings to produce volatile compounds to attract the caterpillar predator, parasitic wasps. Isolation and structure elucidation: H. T. Alborn et al., Science 276, 945 (1997). Biosynthesis: P. W. Paré et al., Proc. Natl. Acad. Sci. USA 95, 13971 (1998). Stereoselective synthesis: G. Phonert et al., Chem. Commun. 1999, 1087.
