Insecticidal compounds from Evodia rutaecarpa against Drosophila melanogaster

Abstract

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 LC 50 values of 0.30 and 0.28 mmol ml À1 diet respectively. Acute toxicity against adults of D melanogaster was also found; compound 2 had the most potent activity, with an LD 50 value of 3.58 mg 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.

Evodiamine: A Novel Anti-Cancer Alkaloid from Evodia rutaecarpa

“…However, the safety, tolerance and pharmacokinetics of evodiamine have not been fully tested on either animals or humans. Some studies have been done to test the acute toxicity of evodiamine in mice (LD 50 , 77.79 mg/kg) [ 37 ] and Drosophila melanogaster (LD 50 , 3.58 μg per adult) [ 38 ], providing a rationale for clinical development of evodiamine as a novel remedy in cancer therapy. Unfortunately, to date, no attempts have yet been made to test the chemotherapeutic potential and safety of evodiamine at the clinical level.…”

Nematocidal Constituents from the Ethanol Extract of Evodia rutaecarpa Hort Unripe Fruits

“…Rutaecarpine has shown a variety of intriguing biological properties such as antithrombotic, anticancer, anti-in�ammatory and analgesic, antiobesity and thermoregulatory, vasorelaxing activity, as well as effects on the cardiovascular and endocrine systems [22]. Moreover, the two isolated alkaloids, evodiamine and rutaecarpine, exhibited insecticidal activity against the fruit �ies (D. melanogaster) [13]. However, the two isolated constituent compounds were �rst time to be evaluated for nematocidal activity against the root-knot nematodes.…”

“…Two quinolone alkaloids isolated from the herb exhibited toxicity to brine shrimp (Artemia salina) [12]. Moreover, three alkaloids, evodiamine, rutaecarpine, and rhetsinine, isolated from E. rutaecarpa by bioassayguided fractionation showed insecticidal activity against fruit �ies (Drosophila melanogaster) [13]. e ethanol extract of E. rutaecarpa also possessed strong antifeedant activity against the two stored product insect pests (T. castaneum and S. zeamais) [14].…”

Japon Balıklarında (Carassius auratus) Gyrodactylus kobayashii’ye (Monogenea) Karşı Çin Şifalı Otlarının Anthelmintik Etkinliklerinin İncelenmesi

“…Also, the n-hexane extract of E. rutaecarpa has been demonstrated to have strong antifeedant activity against the grain storage insects Sitophilus zeamais and Tribolium castaneum [26] . Moreover, two alkaloids isolated from the methanol extract of E. rutaecarpa, evodiamine and rutaecarpine, have shown insecticidal activity against fruit flies (Drosophila melanogaster), with LC 50 values of 3.9 and 3.6 mg per adult, respectively [27] . In the present study, the ethyl acetate extract of E. rutaecarpa showed good anthelmintic efficacy, with EC 50 and EC 90 values of 24.0 and 50.3 mg/L, after 48 h of exposure.…”