Chemical Constituents from Aerial Parts of Baccharis sphenophylla and Effects against Intracellular Forms of Trypanosoma cruzi

Abstract

The hexane extract from aerial parts Baccharis sphenophylla Dusén ex Malme (Asteraceae) displayed activity against amastigote forms of Trypanossoma cruzi and was subjected to chromatographic steps to afford one unreported – 7α‐hydroxy‐ent‐abieta‐8(14),13(15)‐dien‐16,12β‐olide (1) and three known diterpenes – ent‐kaur‐16‐en‐19‐oic acid, (2), grandifloric acid (3), and 15β‐tiglinoyloxy‐ent‐kaur‐16‐en‐19‐oic acid (4), two sesquiterpenes – spathulenol (5) and oplopanone (6) – as well as hexacosyl p‐coumarate (7). Isolated compounds were characterized by NMR and ESI‐HR‐MS spectra and were evaluated in vitro for activity against amastigote forms of the parasite T. cruzi – the relevant clinical form in the chronic phase of Chagas disease. In addition, the activity of compounds 1–7 against NCTC cells was evaluated. Compounds 1 and 7 showed effectiveness with EC50 values of 21.3 and 16.9 μM, respectively. Both compounds also exhibited reduced toxicity against NCTC cells (CC50>200 μM) with SI values higher than 9.4 and 11.9. Obtained results suggest that the new ent‐abietane diterpene 1 and alkyl coumarate 7 could be used as prototypes for the development of novel and selective semisynthetic derivatives against intracellular forms of T. cruzi.

Chemical Constituents from Leaves of Baccharis sphenophylla (Asteraceae) and Their Antioxidant Effects

“…The chromatographic fractionation of the DCM fraction allowed the isolation of compounds 1–3 ( Figure 2 ). Compound 1 exhibited both 1 H and 13 C NMR data compatible with the ent -kaurenoic acid, a diterpenoid previously isolated from B. sphenophylla [ 26 ]. Compounds 2 and 3 showed singlets at δ 6.80 and δ 6.66 in their 1 H NMR spectra, respectively, which were assigned to H-3 from a flavone skeleton.…”

“…In our continuing efforts to search for bioactive compounds in Baccharis species [ 24 , 25 ], we have focused on B. sphenophylla Dusén ex Malme ( Figure 1 ), a rare and endemic plant found in the highlands of south and southeast Brazil; specifically, in the states of Paraná, São Paulo, and Minas Gerais. Previously, the n -hexane extract of this species was studied, demonstrating a long-chain ester of p -coumaric acid, two sesquiterpenoids, and four diterpenoids with antitrypanosomal effects [ 26 ]. Herein, we describe the isolation, structure, and antiradical activities of compounds obtained from polar extracts of the leaves of B. sphenophylla .…”

Enyne acetogenins from Porcelia macrocarpa fruit peels displayed anti-Trypanosoma cruzi activity in vitro and cause a reduction in the intracellular calcium level in the parasites

“…BALB/c mice were utilized for T. cruzi maintenance infection and peritoneal macrophage collection. 33 The mice were obtained from the animal breeding facility at the Instituto Adolfo Lutz -São Paulo, Brazil and maintained in sterilized boxes with absorbent material under a controlled environment. Food and water were given ad libitum.…”

Selective cytotoxicity of ent‐kaurene diterpenoids isolated from Baccharis lateralis and Baccharis retusa (Asteraceae)

“…Four diterpenoids (Figure 1 previously reported in the literature. [10,11] 2.2 | Absorption, distribution, metabolism, and excretion (ADME) properties evaluation of compounds 1-4…”

“…Ent-kaurenoic acid (1) has been reported in the literature as the main metabolite isolated from different plants belonging to Baccharis species and its biological potential includes antiviral, [20] anthelminthic, [21] and antiparasitic [10,11] activities. Additionally, it has been reported that ent-kaurenoic acid (1) displayed activity against human leukemia [22] and gastric cancer [23] cell lines, as well as induced apoptosis in HeLa cells.…”