Antitrypanosomal isothiocyanate and thiocarbamate glycosides from Moringa peregrina

Ayyari, Mahdi and Salehi, Peyman and Ebrahimi, Samad Nejad and Zimmermann, Stefanie and Portmann, Lena and Krauth-Siegel, R. Luise and Kaiser, Marcel and Brun, Reto and Rezadoost, Hassan and Rezazadeh, Shamsali and Hamburger, Matthias. (2014) Antitrypanosomal isothiocyanate and thiocarbamate glycosides from Moringa peregrina. Planta Medica, 80 (1). pp. 86-89.

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Official URL: http://edoc.unibas.ch/dok/A6338918

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O-Methyl (1), O-ethyl (2), and O-butyl (3) 4-[(α-L-rhamnosyloxy) benzyl] thiocarbamate (E), along with 4-(α-L-rhamnosyloxy) benzyl isothiocyanate (4) have been isolated from the aerial parts of Moringa peregrina. The compounds were tested for in vitro activity against Trypanosoma brucei rhodesiense and cytotoxicity in rat skeletal myoblasts (L6 cells). The most potent compound was 4 with an IC50 of 0.10 µM against T.b. rhodesiense and a selectivity index of 73, while the thiocarbamate glycosides 1, 2, and 3 showed only moderate activity. Intraperitoneal administration of 50 mg/kg body weight/day of 4 in the T.b. rhodesiense STIB 900 acute mouse model revealed significant in vivo toxicity. Administration of 10 mg/kg body weight/day resulted in a 95% reduction of parasitemia on day 7 postinfection, but did not cure the animals. Because of its high in vitro activity and its ability to irreversibly inhibit trypanothione reductase, an attractive parasite-specific target enzyme, 4-[(α-L-rhamnosyloxy) benzyl] isothiocyanate (4), can be considered as a lead structure for the development and characterization of novel antitrypanosomal drugs.
Faculties and Departments:05 Faculty of Science > Departement Pharmazeutische Wissenschaften > Pharmazie > Pharmazeutische Biologie (Hamburger)
09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH) > Department of Medical Parasitology and Infection Biology (MPI)
UniBasel Contributors:Hamburger, Matthias and Ebrahimi, Samad Nejad and Brun, Reto and Kaiser, Marcel
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Georg Thieme Verlag
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:28 Nov 2017 08:41
Deposited On:06 Mar 2015 07:44

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