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Planta Med 2013; 79(02): 150-156
DOI: 10.1055/s-0032-1328063
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Abietane Diterpenoids from Salvia sahendica – Antiprotozoal Activity and Determination of Their Absolute Configurations

Samad N. Ebrahimi
1   Division of Pharmaceutical Biology, University of Basel, Basel, Switzerland
2   Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, G. C., Tehran, Iran
,
Stefanie Zimmermann
1   Division of Pharmaceutical Biology, University of Basel, Basel, Switzerland
3   Department of Medical Parasitology and Infection Biology, Swiss Tropical and Public Health Institute and University of Basel, Basel, Switzerland
,
Janine Zaugg
1   Division of Pharmaceutical Biology, University of Basel, Basel, Switzerland
,
Martin Smiesko
4   Division of Molecular Modeling, University of Basel, Basel, Switzerland
,
Reto Brun
3   Department of Medical Parasitology and Infection Biology, Swiss Tropical and Public Health Institute and University of Basel, Basel, Switzerland
,
Matthias Hamburger
1   Division of Pharmaceutical Biology, University of Basel, Basel, Switzerland
› Author Affiliations
Further Information

Publication History

received 27 June 2012
revised 31 October 2012

accepted 17 November 2012

Publication Date:
08 January 2013 (online)

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Abstract

In a screening of Iranian plants for antiprotozoal activity, an n-hexane extract of the roots of Salvia sahendica potently inhibited the growth of Plasmodium falciparum K1 strain. Subsequent HPLC-based activity profiling led to the identification of seven known and one new abietane-type diterpenoid. Structure elucidation was achieved by analysis of spectroscopic data including 1D and 2D NMR. The absolute configuration of sahandol (7) and sahandone (8) were assigned by comparison of experimental ECD spectra with calculated ECD data, using time-dependent density functional theory and methanol as the solvent. In vitro biological activity against P. falciparum and Trypanosoma brucei rhodesiense STIB 900 strain and cytotoxicity in rat myoblast (L6) cells were determined. The IC50 values of the compounds ranged from 0.8 µM to over 8.8 µM against P. falciparum, and from 1.8 µM to over 32.3 µM against T. brucei rhodesiense. The cytotoxic IC50 values ranged from 0.5–15.5 µM. Selectivity indices for P. falciparum were 0.1 to 18.2, and 0.1 to 1.2 for T. brucei rhodesiense.

Key words

Salvia sahendica - Lamiaceae - diterpenes - Plasmodium falciparum - Trypanosoma brucei rhodesiense

Supporting Information

 

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