In vitro anti-Trypanosoma cruzi evaluation of sesquiterpenes from the branches of Oxandra sessiliflora

[Display omitted] •EtOH extract from Oxandra sessiliflora branches was phytochemically investigated.•Five know sesquiterpenes (1–5) and one new compound (6 - 4β,6β,7β,10α-tetrahydroxy-guaiane) were isolated.•Compounds 1–6 displayed activity against Trypanosoma cruzi (EC50 16.3–47.5 μM).•Sesquiterpen...

Full description

Saved in:
Bibliographic Details
Published in:Phytochemistry letters 2020-06, Vol.37, p.59-62
Main Authors: de Carvalho A. da Silva, Armenio A., de Sousa, Elcilene A., Alves Veras, Márcia D., Araújo, Bruno Q., Thevenard, Fernanda, Lago, João Henrique G., Costa-Silva, Thais A., Tempone, Andre G., Chaves, Mariana H.
Format: Article
Language:English
Subjects:
10α-tetrahydroxy-guaiane
Oxandra sessiliflora
Sesquiterpenes
Trypanosoma cruzi
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:[Display omitted] •EtOH extract from Oxandra sessiliflora branches was phytochemically investigated.•Five know sesquiterpenes (1–5) and one new compound (6 - 4β,6β,7β,10α-tetrahydroxy-guaiane) were isolated.•Compounds 1–6 displayed activity against Trypanosoma cruzi (EC50 16.3–47.5 μM).•Sesquiterpenes 5 and 6 exhibited higher selectivity index (SI > 12.3 and 11.4, respectively). In this work, the CH2Cl2 phase from the EtOH extract of Oxandra sessiliflora (Annonaceae) branches was subjected to chromatographic fractionation to afford six sesquiterpenoids: 4α,10β-aromadendranediol (1), 4β,10α-aromadendranediol (2), 4α,10α-aromadendranediol (3), 1β,6α-dihydroxy-4(15)-eudesmene (4), 4β,10α-dihydroxy-guai-6-ene (5), and 4β,6β,7β,10α-tetrahydroxy-guaiane (6), the last one identified as a new natural product. The structures of isolated compounds were identified by analysis of NMR and HRESIMS spectral data. Compounds 1–6 exhibited activity against T. cruzi with EC50 values ranging from 16.3–47.5 μM. Additionally, no cytotoxicity to mammalian cells (NCTC- L929 clone) was observed for tested compounds at the highest concentration (200 μM). Sesquiterpenes 5 and 6 exhibited higher selectivity index (SI) with values higher than 12.3 and 11.4, respectively. This data suggests that guaiane sesquiterpenes 5 and 6, isolated from O. sessiliflora, may contribute as scaffolds for the design of novel and selective drug candidates for treatment of neglected diseases, mainly for Chagas disease.
ISSN:1874-3900
1876-7486
DOI:10.1016/j.phytol.2020.04.005