TY - JOUR
T1 - Identification and synthesis of volicitin and related components from beet armyworm oral secretions
AU - Alborn, H. T.
AU - Jones, T. H.
AU - Stenhagen, G. S.
AU - Tumlinson, J. H.
N1 - Funding Information:
Acknowledgments—This project was funded in part by a grant from the Swedish Natural Science Research Council. We are grateful to A. T. Proveaux, M. Appelgren, and H. Karlsson for assistance with mass spectrometric analysis of the natural product. We are also grateful to T. Spande and L. Pannell, NIDDK, NIH, for GC-FTIR and high-resolution mass spectral analysis of synthetic compounds. Special thanks to J. Lockerman and S. Sharp for oral secretion collection; to M. Brennan for technical assistance, and to J. G. Millar, A. Renwick, and K. Slessor for valuable comments on the manuscript.
PY - 2000
Y1 - 2000
N2 - Oral secretion of beet armyworm caterpillars (BAW), when applied to damaged tissues of corn seedlings, induces the seedlings to emit volatile compounds that attract the natural enemies of the caterpillars. The key elicitor present in BAW oral secretions is N-[17-hydroxylinolenoyl]-L- glutamine (volicitin). Analysis of the oral secretion showed that it also contained N-[17-hydroxyolinoleoyl]-L-glutamine, free 17-hydroxylinolenic, and 17-hydroxylinoleic 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.
AB - Oral secretion of beet armyworm caterpillars (BAW), when applied to damaged tissues of corn seedlings, induces the seedlings to emit volatile compounds that attract the natural enemies of the caterpillars. The key elicitor present in BAW oral secretions is N-[17-hydroxylinolenoyl]-L- glutamine (volicitin). Analysis of the oral secretion showed that it also contained N-[17-hydroxyolinoleoyl]-L-glutamine, free 17-hydroxylinolenic, and 17-hydroxylinoleic 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.
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U2 - 10.1023/A:1005401814122
DO - 10.1023/A:1005401814122
M3 - Article
AN - SCOPUS:0033962128
SN - 0098-0331
VL - 26
SP - 203
EP - 220
JO - Journal of Chemical Ecology
JF - Journal of Chemical Ecology
IS - 1
ER -