Triterpenoids from Brazilian Ilex Species and Their in Vitro Antitrypanosomal Activity

Abstract

From the leaves of Ilex affinis and Ilex buxifolia, two adulterant species of "erva mate" (Ilex paraguariensis), three new triterpenoid glycosides were isolated. Affinoside 1 (3beta-O-[beta-D-glucopyranosyl-(1-->3)-[2-O-acetyl-(1-->2]]-alpha-L-arabinopyranosyl pomolic acid 28-O-beta-D-glucopyranosyl ester, 1) was isolated from I. affinis, while buxifolioside I (28-O-beta-D-glucopyranosyl ester of (20S)-3alpha,19alpha-dihydroxyurs-12-ene-23,28-dioic acid, 7) and buxifolioside II (28-O-beta-D-glucopyranosyl ester of (20S)-3beta,19alpha-dihydroxyurs-12-en-24,28-dioic acid, 8) were isolated from I. buxifolia. Along with these new compounds, ilexoside II (2), ursolic acid (3), 28-nor-ursolic acid (4), 3beta-O-acetylursolic acid (5), and uvaol (6) were also isolated. The observed results confirm the structural specificity of the I. paraguariensis triterpenoids and reinforce a previous proposal to detect mate adulteration by triterpenoid analysis. In addition, the in vitro antitrypanosomal activity of some Ilex triterpenoids is also reported.

In vitro antitrypanosomal and antileishmanial activity of plants used in Benin in traditional medicine and bio-guided fractionation of the most active extract

“…These compounds have previously shown an activity on Tbb with IC 50 = 2.9 g/ml with SI of 20.6 for oleanolic acid and IC 50 = 1.1 g/ml with SI of 6.0 for ursolic acid (Hoet et al, 2007). Others studies showed antitrypanosomal activity with IC 50 = 8.8 g/ml on Tbb and Trypanosoma brucei congolense for ursolic acid (Taketa et al, 2004) and an in vivo significant reduction of parasites of 75.7% at 2 mg/kg/d intraperitoneally during 13 days (Cunha et al, 2006). At a concentration of 20 mg/kg/d intraperitoneally during 20 days, reductions of parasitaemia of 60% for ursolic acid and 40% for oleanolic acid were observed (Ferreira et al, 2010).…”

Recent advances on Ilex paraguariensis research: Minireview

“…Topical use of Ilex paraguariensis extract could be then an alternative antifungal agent used for this infection. Triterpenoids from Ilex paraguariensis display inhibitory activities against Trypanosoma Cruzi (Taketa et al, 2004) Angiogenesis plays a key role in inflammation and repair as well as in cancer biology. Treatments performed with aqueous extract of maté and caffeine in the vascular membranes of chick embryos yolk sac revealed pro-vasculo-and angiogenic properties as well as embryonic growth enhancement (Strassmann et al, 2008).…”

Composition and Bioactive Properties of Yerba Mate (llex paraguariensis A. St.-Hil.): A Review

“…Saponins have been reported to provide a hypocholesteremic effect by inhibiting the passive diffusion of colic acid through the formation of micelles preventing absorption, anticancer, antiparasitic (Taketa et al, 2004a;2004b), and anti-inflammatory properties.…”