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Analysis, isolation and insecticidal activity of linear furanocoumarins and other coumarin derivatives from Peucedanum (Apiaceae: Apioideae)

Hadacek, F., Muller, C., Werner, A., Greger, H., Proksch, P.
Journal of chemical ecology 1994 v.20 no.8 pp. 2035-2054
Peucedanum, roots, furans, coumarins, bioassays, insecticidal properties, Spodoptera littoralis, insect control, chemical constituents of plants
Peucedanum arenarium Waldst, & Kit., P. austriacum (Jacq.) Koch, P. coriaceum Reichenb., P. longifolium Waldst. & Kit, P. officinale L., P. oreoselinum (L.) Moench, P. ostruthium L., and P. palustre (L.) Moench accumulate different structural types of coumarins including simple coumarins, linear furanocoumarins, linear dihydropyranocoumarins, angular dihydrofuranocoumarins and angular dihydropyranocoumarins. Linear furanocoumarins, known for venous biological activities, include some well-known antifeedants, such as bergapten, isopimpinellin, and xanthotoxin. The aim of this investigation was to screen the diverse coumarins from Peucedanum for insecticidal activity. LC was used to analyze and isolate coumarins for the bioassays. A growth inhibition bioassay with 17 derivatives, comprising all structural types from Peucedanum, carried out with Spodoptera littoralis (Boisduval) (Lepidoptera: Noctuidae) as test organism, indicated the majority of the linear furanocoumarins and the angular dihydrofuranocoumarin athamantin as active compounds. Oxygenation of the prenyl residue of linear furanocoumarins decreased activity. Further formation of an ester with angelic acid even resulted in complete inactivity. Five active linear furanocoumarins, bergapten, isopimpinellin, xanthotoxin, isoimperatorin, and imperatorin, and two linear furanocoumarins with a substituted furan ring, peucedanin and 8-methoxypeucedanin, were compared in a dietary utilization bioassay. Relative growth rate (RGR) and relative consumption rate (RCR) divided the tested coumarins in three groups of similar activity. Isopimpinellin and peucedanin slightly decreased RGR and RCR of the treated larvae, and xanthotoxin, isoimperatorin, and 8-methoxypeucedanin heavily decreased RGR and RCR. Bergapten and imperatorin differed by the lowest RGR values and rather high RCR values. The effects caused by these two coumarins indicate specific postingestive toxicity. The results obtained in this study add to the reputation of coumarins to be an effective chemical defense, postulating that chemical diversity is a necessary trait for well-defended plants.