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Chemical Composition of Aspidosperma ulei Markgr. and Antiplasmodial Activity of Selected Indole Alkaloids
Instituto Nacional de Pesquisas da Amazônia, Caixa Postal 2223 - CEP 69080-971, Manaus, Amazonas, Brasil
Universidade Federal do Ceará, Caixa Postal 12.200 - CEP 60021-940, Fortaleza, Ceará, Brasil
Universidade Federal do Amazonas, Avenida General Rodrigo Otávio Jordão Ramos, 3000, CEP 69077-000 Campus Universitário, Manaus, Amazonas, Brasil
Universidade Estadual do Norte Fluminense Darcy Ribeiro, CEP 28013-602 Campos dos Goytacazes, Rio de Janeiro, Brasil
* Author to whom correspondence should be addressed.
Received: 1 April 2013; in revised form: 15 May 2013 / Accepted: 16 May 2013 / Published: 29 May 2013
Abstract: A new indole alkaloid, 12-hydroxy-N-acetyl-21(N)-dehydroplumeran-18-oic acid (13), and 11 known indole alkaloids: 3,4,5,6-tetradehydro-β-yohimbine (3), 19(E)-hunteracine (4), b-yohimbine (5), yohimbine (6), 19,20-dehydro-17-a-yohimbine (7), uleine (10), 20-epi-dasycarpidone (11), olivacine (8), 20-epi-N-nor-dasycarpidone (14), N-demethyluleine (15) and 20(E)-nor-subincanadine E (12) and a boonein d-lactone 9, ursolic acid (1) and 1D,1O-methyl-chiro-inositol (2) were isolated from the EtOH extracts of different parts of Aspidosperma ulei Markgr. (Apocynaceae). Identification and structural elucidation were based on IR, MS, 1H- and 13C-NMR spectral data and comparison to literature data. The antiplasmodial and antimalarial activity of 1, 5, 6, 8, 10 and 15 has been previously evaluated and 1 and 10 have important in vitro and in vivo antimalarial properties according to patent and/or scientific literature. With the aim of discovering new antiplasmodial indole alkaloids, 3, 4, 11, 12 and 13 were evaluated for in vitro inhibition against the multi-drug resistant K1 strain of the human malaria parasite Plasmodium falciparum. IC50 values of 14.0 (39.9), 4.5 (16.7) and 14.5 (54.3) mg/mL (mM) were determined for 3, 11 and 12, respectively. Inhibitory activity of 3, 4, 11, 12 and 13 was evaluated against NIH3T3 murine fibroblasts. None of these compounds exhibited toxicity to fibroblasts (IC50 > 50 mg/mL). Of the five compounds screened for in vitro antiplasmodial activity, only 11 was active.
Keywords: Apocynaceae; indole alkaloids; antiplasmodial; Plasmodium falciparum K1; murine fibroblasts; cytotoxic evaluation; NMR; Aspidosperma ulei; dasycarpane
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dos Santos Torres, Z.E.; Silveira, E.R.; Rocha e Silva, L.F.; Lima, E.S.; de Vasconcellos, M.C.; de Andrade Uchoa, D.E.; Filho, R.B.; Pohlit, A.M. Chemical Composition of Aspidosperma ulei Markgr. and Antiplasmodial Activity of Selected Indole Alkaloids. Molecules 2013, 18, 6281-6297.
dos Santos Torres ZE, Silveira ER, Rocha e Silva LF, Lima ES, de Vasconcellos MC, de Andrade Uchoa DE, Filho RB, Pohlit AM. Chemical Composition of Aspidosperma ulei Markgr. and Antiplasmodial Activity of Selected Indole Alkaloids. Molecules. 2013; 18(6):6281-6297.
dos Santos Torres, Zelina E.; Silveira, Edilberto R.; Rocha e Silva, Luiz F.; Lima, Emerson S.; de Vasconcellos, Marne C.; de Andrade Uchoa, Daniel E.; Filho, Raimundo B.; Pohlit, Adrian M. 2013. "Chemical Composition of Aspidosperma ulei Markgr. and Antiplasmodial Activity of Selected Indole Alkaloids." Molecules 18, no. 6: 6281-6297.