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Insecticidal compounds from Evodia rutaecarpa against Drosophila melanogaster

Miyazawa, Mitsuo, Fujioka, Jun, Ishikawa, Yukio
Journal of the science of food and agriculture 2002 v.82 no.13 pp. 1574-1578
Drosophila melanogaster, Euodia, acute toxicity, adults, alkaloids, diet, drugs, fractionation, fruits, insecticidal properties, insecticides, larvae, lethal concentration 50, lethal dose 50, screening
In the course of screening for novel naturally occurring insecticides from Chinese crude drugs, the MeOH extract of the fruits of Evodia rutaecarpa Benth was found to give insecticidal activity against larvae of Drosophila melanogaster Meigen. Three alkaloids, evodiamine (1), rutaecarpine (2) and rhetsinine (3), were isolated by bioassay-guided fractionation of the extract. Insecticidal activity against larvae of D melanogaster was demonstrated; compounds 1 and 2 gave LC50 values of 0.30 and 0.28 µmol ml−1 diet respectively. Acute toxicity against adults of D melanogaster was also found; compound 2 had the most potent activity, with an LD50 value of 3.58 µg per adult. However, compound 3 had only weak activity in this study. Therefore compounds 1 and 2 were identified as insecticidal compounds from the fruits of E rutaecarpa. Compound 3 was obtained by the photoxidation of evodiamine. Investigation of the structure–activity relationship indicated the importance of the indoloquinazoline unit at the C-14 position.