Identification and synthesis of volicitin and related components from beetarmyworm oral secretions

Oral secretion of beet armyworm caterpillars (BAW), when applied to damaged tissues of corn seedlings, induces the seedlings to emit volatile compound s that attract the natural enemies of the caterpillars. The key elicitor pr esent in BAW oral secretions is N-[17-hydroxylinolenoyl]-L-glutamine (volic itin). Analysis of the oral secretion showed that it also contained N-[17-h ydroxyolinoleoyl]-L-glutamine, free 17-hydroxylinolenic, and 17-hydroxylino leic acid, the glutamine conjugates of linolenic and linoleic acid as well as free linolenic and linoleic acid. Here we present the identification and synthesis of the hydroxy acids and of glutamine conjugates.