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

作者：Vouffo Bertin; Dongo Etienne; Facey Petrea; Thom Andrea; Sheldrick George; Maier Armin; Fiebig Heinz Herbert; Laatsch Hartmut^*

来源：Planta Medica, 2010, 76(15): 1717-1723.

DOI：10.1055/s-0030-1249958

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

From the methanol extract of the stem bark of the African tree Antiaris africana Engler, two new bioactive metabolites were isolated, namely, the alpha-amyrin derivative 1,beta,11 alpha-dihydroxy-3 beta-cinnamoyl-alpha-amyrin (antiarol cinnamate, 1) and a cardiac glycoside, 3 beta-O-(alpha-L-rhamnopyranosyl)-14 beta-hydroperoxy-5 beta-hydroxy-19-oxo-17 beta- card-20(22)-enolide (africanoside, 2a), together with the known compounds P-amyrin and its acetate, beta-sitosterol and its 3-O-beta-D-glucopyranoside, friedelin, ursolic and oleanolic acid, 19-norperiplogenin, strophanthidol, strophanthidinic acid, periplogenin (3a), 3-epiperiplogenin, strophanthidin (3b) and 3,3'-dimethoxy-4'-O-beta-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 sauna and a selective antitumor activity against human tumor cell lines. Africanoside (2a) effected a concentration-dependent inhibition of tumor cell growth with a mean IC(50) value of 5.3 nM.

• 出版日期2010-10