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Planta Med 2010; 76(15): 1717-1723
DOI: 10.1055/s-0030-1249958
Natural Product Chemistry
Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Antiarol Cinnamate and Africanoside, a Cinnamoyl Triterpene and a Hydroperoxy-cardenolide from the Stem Bark of Antiaris africana

Bertin Vouffo1 , 2 , Etienne Dongo2 , Petrea Facey1 , Andrea Thorn3 , George Sheldrick3 , Armin Maier4 , Heinz Herbert Fiebig4 , Hartmut Laatsch1
  • 1Department of Organic and Biomolecular Chemistry, University of Göttingen, Göttingen, Germany
  • 2Department of Organic Chemistry, Faculty of Science, University of Yaounde I, Yaounde, Cameroon
  • 3Department of Inorganic Chemistry, University of Göttingen, Göttingen, Germany
  • 4Oncotest GmbH, Freiburg, Germany
Further Information

Publication History

received October 28, 2009 revised April 9, 2010

accepted April 20, 2010

Publication Date:
08 June 2010 (online)

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Abstract

From the methanol extract of the stem bark of the African tree Antiaris africana Engler, two new bioactive metabolites were isolated, namely, the α-amyrin derivative 1β,11α-dihydroxy-3β-cinnamoyl-α-amyrin (antiarol cinnamate, 1) and a cardiac glycoside, 3β-O-(α-L-rhamnopyranosyl)-14β-hydroperoxy-5β-hydroxy-19-oxo-17β-card-20(22)-enolide (africanoside, 2a), together with the known compounds β-amyrin and its acetate, β-sitosterol and its 3-O-β-D-glucopyranoside, friedelin, ursolic and oleanolic acid, 19-norperiplogenin, strophanthidol, strophanthidinic acid, periplogenin (3a), 3-epiperiplogenin, strophanthidin (3b) and 3,3′-dimethoxy-4′-O-β-D-xylopyronosyl-ellagic acid. Their structures were established on the basis of their spectroscopic data and by chemical methods, while 3a was additionally confirmed by X‐ray crystal structure analysis. The aglycone moiety possessing a hydroperoxy group was found for the first time in cardenolides. Compounds 1 and 2a showed no activity against bacteria, fungi, and microalgae; however, the crude extract exhibited a high toxicity against Artemia salina and a selective antitumor activity against human tumor cell lines. Africanoside (2a) effected a concentration-dependent inhibition of tumor cell growth with a mean IC50 value of 5.3 nM.

Key words

Antiaris africana - Moraceae - antiarol cinnamate - africanoside - sterol hydroperoxide - periplogenin

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Prof. Dr. Hartmut Laatsch

Institute for Organic and Biomolecular Chemistry
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