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Antiprotozoal activity of Buxus sempervirens and activity-guided isolation of O-tigloylcyclovirobuxeine-B as the main constituent active against Plasmodium falciparum

Althaus, Julia B. and Jerz, Gerold and Winterhalter, Peter and Kaiser, Marcel and Brun, Reto and Schmidt, Thomas J.. (2014) Antiprotozoal activity of Buxus sempervirens and activity-guided isolation of O-tigloylcyclovirobuxeine-B as the main constituent active against Plasmodium falciparum. Molecules : a journal of synthetic chemistry and natural product chemistry, Vol. 19, H. 5. pp. 6184-6201.

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Official URL: http://edoc.unibas.ch/dok/A6271929

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Abstract

Buxus sempervirens L. (European Box, Buxaceae) has been used in ethnomedicine to treat malaria. In the course of our screening of plant extracts for antiprotozoal activity, a CH2Cl2 extract from leaves of B. sempervirens showed selective in vitro activity against Plasmodium falciparum (IC50 = 2.79 vs. 20.2 µg/mL for cytotoxicity against L6 rat cells). Separation of the extract by acid/base extraction into a basic and a neutral non-polar fraction led to a much more active and even more selective fraction with alkaloids while the fraction of non-polar neutral constituents was markedly less active than the crude extract. Thus, the activity of the crude extract could clearly be attributed to alkaloid constituents. Identification of the main triterpene-alkaloids and characterization of the complex pattern of this alkaloid fraction was performed by UHPLC/+ESI-QTOF-MS analyses. ESI-MS/MS target-guided larger scale preparative separation of the alkaloid fraction was performed by 'spiral coil-countercurrent chromatography'. From the most active subfraction, the cycloartane alkaloid O-tigloylcyclovirobuxeine-B was isolated and evaluated for antiplasmodial activity which yielded an IC50 of 0.455 µg/mL (cytotoxicity against L6 rat cells: IC50 = 9.38 µg/mL). O-tigloylcyclovirobuxeine-B is thus most significantly responsible for the high potency of the crude extract.
Faculties and Departments:09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH)
09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH) > Department of Medical Parasitology and Infection Biology > Parasite Chemotherapy (Mäser)
UniBasel Contributors:Kaiser, Marcel and Brun, Reto
Item Type:Article, refereed
Article Subtype:Research Article
Bibsysno:Link to catalogue
Publisher:MDPI
ISSN:1420-3049
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:18 Jul 2014 09:10
Deposited On:18 Jul 2014 09:10

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