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Pinoresinol: A lignol of plant origin serving for defense in a caterpillar
Frank C Schroeder1, Marta L del Campo, Jacqualine B Grant
1Department of Chemistry and Chemical Biology, Cornell University, Ithaca, NY 14853, USA.
Abstract:
Pinoresinol, a lignan of wide distribution in plants, is found to occur as a minor component in the defensive secretion produced by glandular hairs of caterpillars of the cabbage butterfly, Pieris rapae. The compound or a derivative is appropriated by the larva from its normal food plant (the cabbage, Brassica oleracea). Pinoresinol was shown to be absent from the secretion if the larva was given a cabbage-free diet but present in the effluent if that diet was supplemented with pinoresinol. Pinoresinol is shown to be a feeding deterrent to ants (Formica exsectoides), indicating that it can complement the defensive action of the primary components of the secretion, a set of previously reported lipids called mayolenes. In the test with F. exsectoides, pinoresinol proved to be more potent than concomitantly tested mayolene-16.
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The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.

