Light-mediated allelochemical effects of naturally occurring polyacetylenes and thiophenes from asteraceae on herbivorous insects |
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Authors: | D E Champagne J T Arnason B J R Philogène P Morand J Lam |
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Affiliation: | (1) Ottawa Carleton Centre for Graduate Studies and Research in Biology and Chemistry, University of Ottawa, K1N 6N5 Ottawa, Ontario, Canada;(2) Department of Organic Chemistry, University of Aarhus, 8000 Aarhus, Denmark;(3) Present address: Botany Department, University of British Columbia, V6T 1W5 Vancouver, British Columbia, Canada |
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Abstract: | Polyacetylenes and their thiophene derivatives, characteristic secondary metabolites of the Asteraceae, were examined for their effects on herbivorous insects. Three thiophenes (a monothiophene, a bithiophene, and -terthienyl) and four polyacetylenes (phenylheptatriyne, phenylheptadiynene, phenylheptadiyene acetate, and matricaria lactone) were studied for their phototoxicity and light-independent toxicity to (1) a polyphagous lepidopteran,Ostrinia nubilalis, whose host range includes a number of phototoxic Asteraceae, (2) a polyphagous lepidoteran,Euxoa messoria, whose host range includes very few species of Asteraceae, and (3) an oligophagous lepidopteran,Manduca sexta, which is a specialist on Solanaceae. Several compounds were phototoxic toM. sexta andE. messoria even at very low irradiance levels, but behavioral adaptations, including spinning silk and boring into diet, allowedO. nubilalis to avoid photosensitization. Light-independent activity of the compounds to all three species involved feeding deterrence increasing in the orderO. nubilalis, E. messoria, andM. sexta, and longterm metabolic toxicity in the form of impaired nutrient utilization. The biosynthetically derived thiophenes were more toxic than their acetylenic precursors, and toxicity increased with increasing number of thiophene rings. The results are discussed in terms of plant-insect coevolution. |
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Keywords: | Polyacetylenes thiophenes Asteraceae phototoxicity Ostrinia nubilalis Euxoa messoria Manduca sexta Lepidoptera Pyralidae Sphingidae Noctuidae coevolution photosensitization feeding deterrence |
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