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Planta Med 2014; 80(01): 86-89
DOI: 10.1055/s-0033-1351102
Biological and Pharmacological Activity
Letters
Georg Thieme Verlag KG Stuttgart · New York

Antitrypanosomal Isothiocyanate and Thiocarbamate Glycosides from Moringa peregrina

Mahdi Ayyari
1   Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, G. C., Evin, Tehran, Iran
,
Peyman Salehi
1   Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, G. C., Evin, Tehran, Iran
,
Samad Nejad Ebrahimi
1   Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, G. C., Evin, Tehran, Iran
2   Department of Pharmaceutical Sciences, Division of Pharmaceutical Biology, University of Basel, Basel, Switzerland
,
Stefanie Zimmermann
2   Department of Pharmaceutical Sciences, Division of Pharmaceutical Biology, University of Basel, Basel, Switzerland
3   Department of Medical Parasitology and Infection Biology, Swiss Tropical and Public Health Institute, Basel, Switzerland
,
Lena Portmann
2   Department of Pharmaceutical Sciences, Division of Pharmaceutical Biology, University of Basel, Basel, Switzerland
,
R. Luise Krauth-Siegel
4   Center of Biochemistry, Heidelberg University, Heidelberg, Germany
,
Marcel Kaiser
3   Department of Medical Parasitology and Infection Biology, Swiss Tropical and Public Health Institute, Basel, Switzerland
5   University of Basel, Basel, Switzerland
,
Reto Brun
3   Department of Medical Parasitology and Infection Biology, Swiss Tropical and Public Health Institute, Basel, Switzerland
5   University of Basel, Basel, Switzerland
,
Hassan Rezadoost
1   Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, G. C., Evin, Tehran, Iran
,
Shamsali Rezazadeh
6   Department of Pharmacognosy and Phytochemistry, Institute of Medicinal Plants, ACECR, Karaj, Iran
,
Matthias Hamburger
2   Department of Pharmaceutical Sciences, Division of Pharmaceutical Biology, University of Basel, Basel, Switzerland
› Author Affiliations
Further Information

Publication History

received 29 August 2013
revised 24 October 2013

accepted 28 October 2013

Publication Date:
05 December 2013 (online)

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Abstract

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.

Key words

isothiocyanate - Moringa peregrina - Moringaceae - Trypanosoma brucei rhodesiense - thiocarbamate glycoside

Supporting Information

 

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