Novel 3‐Oxo‐ and 3,24‐Dinor‐2,4‐secooleanane‐Type Triterpenes from Terminalia ivorensis A. Chev. |
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| Authors: | Beaudelaire Kemvoufo Ponou Rémy Bertrand Teponno Massimo Ricciutelli Télesphore Bénoit Nguelefack Luana Quassinti Massimo Bramucci Giulio Lupidi Luciano Barboni Léon Azefack Tapondjou |
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| Affiliation: | 1. Laboratory of Environmental and Applied Chemistry, Department of Chemistry, Faculty of Science, University of Dschang, Box 183, Dschang, Cameroon, (phone: +237‐75004826, fax: +237‐33451735);2. School of Science and Technology, Chemistry Division, University of Camerino, Via S. Agostino 1, I‐62032 Camerino (phone: +39‐0737402240;3. fax: +39‐0737637345);4. Laboratory of HPLC‐MS, University of Camerino, Via S. Agostino 1, I‐62032 Camerino;5. Department of Animal Biology, Faculty of Science, University of Dschang, Box 67, Dschang, Cameroon;6. School of Pharmacy: Drugs and Health Products, University of Camerino, Via Gentile III da Varano, I‐62032 Camerino |
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| Abstract: | Two new oleanane‐type triterpenes named ivorengenin A (=3‐oxo‐2α,19α,24‐trihydroxyolean‐12‐en‐28‐oic acid; 1 ) and ivorengenin B (=4‐oxo‐19α‐hydroxy‐3,24‐dinor‐2,4‐secoolean‐12‐ene‐2,28‐dioic acid; 2 ), together with five known compounds, arjungenin, arjunic acid, betulinic acid, sericic acid, and oleanolic acid, were isolated from the barks of Terminalia ivorensis A. Chev . (Combretaceae). Their structures were established on the basis of 1D‐ and 2D‐NMR data, and mass spectrometry. A biogenetic pathway to the formation of these compounds from sericic acid, isolated as the major compound from this plant, was proposed. The antioxidant activities of different compounds were investigated by means of the 2,2‐azinobis(3‐ethylbenzothiazoline‐6‐sulfonic acid) (ABTS) and 1,1‐diphenyl‐2‐picrylhydrazyl (DPPH) assays, and IC50 values were calculated and compared with Trolox activity. Antiproliferative activities of the isolated compounds were also evaluated against MDA‐MB‐231, PC3, HCT116, and T98G human cancer cell lines, against which the compounds showed significant cytotoxic activities. |
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| Keywords: | Oleananes Terminalia ivorensis Secooleananes Ivorengenins A and B Triterpenes Cytotoxic activity Radical‐scavenging activity |
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