Chemical Composition of Aspidosperma ulei Markgr. and Antiplasmodial Activity of Selected Indole Alkaloids

Molecules

Zelina Estevam dos Santos Torres²  Edilberto Rocha Silveira³  Luiz Francisco Rocha e Silva²  Emerson Silva Lima⁴  Marne Carvalho de Vasconcellos⁴  Daniel Esdras de Andrade Uchoa³  Raimundo Braz Filho¹ 

[1] Universidade Estadual do Norte Fluminense Darcy Ribeiro, CEP 28013-602 Campos dos Goytacazes, Rio de Janeiro, Brasil; E-Mail:;Instituto Nacional de Pesquisas da Amazônia, Caixa Postal 2223 - CEP 69080-971, Manaus, Amazonas, Brasil; E-Mails:;Universidade Federal do Ceará, Caixa Postal 12.200 - CEP 60021-940, Fortaleza, Ceará, Brasil; E-Mails:;Universidade Federal do Amazonas, Avenida General Rodrigo Otávio Jordão Ramos, 3000, CEP 69077-000 Campus Universitário, Manaus, Amazonas, Brasil; E-Mails:

关键词: Apocynaceae;    indole alkaloids;    antiplasmodial;    Plasmodium falciparum K1;    murine fibroblasts;    cytotoxic evaluation;    NMR;    Aspidosperma ulei;    dasycarpane;   

DOI  :  10.3390/molecules18066281

来源: mdpi

【 摘 要 】

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), β-yohimbine (5), yohimbine (6), 19,20-dehydro-17-α-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 δ-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) μg/mL (μM) 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 μg/mL). Of the five compounds screened for in vitro antiplasmodial activity, only 11 was active.

【 授权许可】

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