Salaterpene E, a eudesmane-type sesquiterpene from Salacia longipes var. camerunensis

Author:

Mba’ning Brice Mittérant1,Ndjakou Bruno Lenta2,Talontsi Ferdinand Mouafo3,Lannang Alain Meli4,Dittrich Birger5,Ngouela Silvère Augustin1,Tsamo Etienne1,Sewald Norbert4,Laatsch Hartmut6

Affiliation:

1. Department of Organic Chemistry, University of Yaoundé 1, Yaoundé, Cameroon

2. Department of Chemistry, Higher Teacher Training College, University of Yaoundé 1, P.O. Box 47, Yaoundé, Cameroon

3. Institute of Environmental Research (INFU), Department of Chemistry and Chemical Biology, Technical University of Dortmund, Otto-Hahn-Strasse 6, D-44221 Dortmund, Germany

4. Department of Chemistry, Organic, and Bioorganic Chemistry, Bielefeld University, D-33501 Bielefeld, Germany

5. Institute of Inorganic Chemistry, University of Göttingen, Tammannstrasse 4, D-37077 Göttingen, Germany

6. Institute of Organic and Biomolecular Chemistry, University of Göttingen, Tammannstrasse 2, D-37077 Göttingen, Germany

Abstract

Abstract A mixture of two compounds with potent antiplasmodial activity in vitro against the W2 strain of Plasmodium falciparum (half maximal inhibitory concentration, 1.12 μg/mL) was obtained in a previous investigation of the CH2Cl2-MeOH extract of the seeds of Salacia longipes var. camerunensis. Separation by column chromatography led now to the isolation of salaterpene E (1) and (1R,2R,4S,5S,6R,7R,9S,10R)-2-acetoxy-1,6,9-tribenzoyloxy-4-hydroxy-dihydro-β-agarofuran (2). The structure of 1 was elucidated by spectroscopic analysis, and its absolute configuration was established unambiguously by means of single-crystal X-ray diffraction. Also the absolute configurations of the recently described salaterpenes A (2a) and D (2b) were determined by this method using the anomalous scattering of the oxygen atoms only.

Publisher

Walter de Gruyter GmbH

Subject

General Chemistry

Reference39 articles.

1. N. Halle, Flore du Cameroun: Celastracées (Hippocrateoidées), Vol. 32, Ministère de l’Enseignement Supérieur de l’Informatique et de la Recherche Scientifique (MESIRES), Paris, 1990, pp. 3, 18, 50, and 80.

2. Y. Li, T. H. Huang, J. Yamahara, Life Sci.2008, 82, 1045.

3. P. M. Paarakh, L. J. Patil, S. A. Thanga, J. Nat. Rem. 2008, 8, 116.

4. F. R. P. Carvalho, S. H. D. Silva, S. V. Bolzani, M. Furlan, Chem. Bio. 2005, 2, 367.

5. T. Morikawa, A. Kishi, Y. Pongpiriyadacha, H. Matsuda, M. Yoshikawa, J. Nat. Prod. 2003, 66, 1191.

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