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

Abstract

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), 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, 6282Plasmodium falciparum. IC 50 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 (IC 50 > 50 μg/mL). Of the five compounds screened for in vitro antiplasmodial activity, only 11 was active.

Ethnopharmacological evaluation of medicinal plants used against malaria by quilombola communities from Oriximiná, Brazil

“…However, the most cited species in the Amazon used as a remedy against malaria is A. nitidum, which has proven to be the most active species based on its specific activity (Penna- Coutinho et al, 2013), superior than the other species less cited as antimalarial, such as A. ollivaceum, also studied by the same group (Chierrito et al, 2014). Other species tested showed variable in vitro activity against the P. falciparum with IC 50 values ranging from 0.019 to 42 µM (Brandão et al, 1985;Carvalho et al, 1992;Mitaine-Offer et al, 2002;Paula et al, 2014;Torres et al, 2013). The biological activity of the genus has been attributed to indole alkaloids (Frederich et al, 2008;Vieira et al, 2013).…”

Aspidosperma (Apocynaceae) plant cytotoxicity and activity towards malaria parasites. Part II: experimental studies withAspidosperma ramiflorum in vivo and in vitro

“…Plants of the Aspidosperma genus tested in vitro and in vivo were active, like the compounds from the barks of Artemisia vargasii , Artemisia ulei and Artemisia desmanthum ( de Andrade-Neto et al 2007 , Rocha e Silva et al. 2012 , Torres et al 2013 ), as well as Artemisia nitidum , which is used in the Amazon against fever and malaria ( Coutinho et al 2013 ), and Artemisia olivaceum , a plant from South Brazil ( Aguiar et al. 2012 ).…”

Dehydrobufotenin extracted from the Amazonian toad Rhinella marina (Anura: Bufonidae) as a prototype molecule for the development of antiplasmodial drugs

“…Gleeson [ 52 ] suggests in his study that compounds with CLogP less than 4 and molecular weight less than 400 have a more favorable ADMET profile than those suggested by Lipinski. Following the Gleeson theory, all compounds have CLogP < 3 and compounds dehydrobufotenin, marinobufagin and bufalin have molecular mass below 400.…”