Phenolic compounds on the pod-surface of pigeonpea, Cajanus cajan, mediate feeding behavior of Helicoverpa armigera larvae

• Published in: Journal of chemical ecology 2003-04, Vol.29 (4), p.811-821
• Main Authors: GREEN, Paul W. C, STEVENSON, Philip C, SIMMONDS, Monique S. J, SHARMA, Hari C
• Format: Article
• Language: English
• Subjects: Animal and plant ecology; Animal, plant and microbial ecology; Animals; Autoecology; Bioassays; Biological and medical sciences; Cajanus - chemistry; Carboxylic acids; Crop improvement; Cultivars; Feeding Behavior; Fundamental and applied biological sciences. Psychology; Larva; Larvae; Liquid chromatography; Mass spectrometry; Moths; Phenols; Phenols - pharmacology; Plant Extracts - pharmacology; Plants and fungi; Protozoa. Invertebrata; Seeds - chemistry; Spectrum analysis
• ISSN: 0098-0331; 1573-1561
• DOI: 10.1023/A:1022971430463

A methanol extract of the pod surfaces of Cajanus cajan, a feeding stimulant for fifth-instar Helicoverpa armigera, was shown to contain four main phenolic compounds. Three of these were identified as isoquercitrin, quercetin, and quercetin-3-methyl ether, by comparing UV spectra and HPLC retention times with authentic standards. The fourth compound was isolated by semipreparative HPLC and determined to be 3-hydroxy-4-prenyl-5-methoxystilbene-2-carboxylic acid (stilbene) by NMR spectroscopy and mass spectrometry. Quercetin, isoquercitrin, and quercetin-3-methyl did not affect the selection-behavior of fifth-instar H. armigera. However, larvae were deterred from feeding on glass-fiber disks impregnated with the stilbene. Furthermore, larvae exposed to quercetin-3-methyl ether consumed significant amounts of both disks. In a binary-choice bioassay, a combination of quercetin-3-methyl ether and the stilbene on one disk and pure quercetin-3-methyl ether on the other disk resulted in increased consumption of both glass-fiber disks by larvae. In contrast, consumption was reduced if the combination was presented to larvae on one disk with purified stilbene on the other disk. Cajanus cajan cultivars that varied in their susceptibility to H. armigera were surveyed forthe presence of the four phenolic compounds. An absence of quercetin and higher concentrations of isoquercitrin than the cultivated variety characterized pod surface extracts of pod-borer-resistant cultivars. In addition, the ratio of the stilbene to quercetin-3-methyl ether was greater in the pod-borer-resistant cultivars. These findings are discussed in relation to the identification of chemical characters that can be used for crop improvement.