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Complete Structural Assignment of Serratol, a Cembrane-Type Diterpene from Boswellia serrata, and Evaluation of Its Antiprotozoal Activity

Schmidt, Thomas, Kaiser, Marcel, Brun, Reto·2011·Planta Medica

Abstract

From the dichloromethane extract obtained from the gum resin of Boswellia serrata Roxb. (Burseraceae), a well-known medicinal plant resin ("Indian Olibanum"), the cembrane-type diterpene serratol was isolated in high yield. Its structure, previously reported without clear specification of double-bond geometry and without specification of stereochemistry, was reanalysed by means of spectroscopic measurements and unambiguously assigned as S(-)-cembra-3E,7E,11E‑triene-1-ol. Full assignment of all NMR data is reported for the first time. The compound was found to be identical with a cembrenol previously isolated from B. carteri. Serratolwas tested for in vitro activity against four protozoan human pathogens, namely, Trypanosoma brucei rhodesiense (East African Human Trypanosomiasis, sleeping sickness), T. cruzi (Chagas' disease), Leishmania donovani (Kala-Azar), and Plasmodium falciparum (Tropical Malaria). It was found active against T. brucei and P. falciparum. These activities were 10- to 15-fold higher than its cytotoxicity against rat skeletalmyoblasts. While some reports exist on potential anti-inflammatory activity of Boswellia diterpenes, this is the first report on antiprotozoal activity of such a compound.

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Crossref · 10.1055/s-0030-1250612

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Metadata

Authors
Schmidt, T., Kaiser, M., & Brun, R.
Venue
Planta Medica
Published
2010-12-14
Volume
77
Issue
08
Pages
849-850
ISSN
  • 0032-0943
  • 1439-0221
Cited by
36
References
0
Language
en

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