Open AccessFriedelane Triterpenes with Cytotoxic Activity from the Leaves of Maytenus quadrangulata (Celastraceae)
Author(s) -
Mariana de Aguilar,
Grasiely Faria de Sousa,
Fernanda Cristina Gontijo Evangelista,
Adriano de Paula Sabino,
Karen Camargo,
Sidney Vieira Filho,
Yule Nunes,
Lucienir Pains Duarte
Publication year - 2022
Publication title -
journal of the brazilian chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.337
H-Index - 70
eISSN - 1678-4790
pISSN - 0103-5053
DOI - 10.21577/0103-5053.20220058
Subject(s) - cytotoxicity , chemistry , celastraceae , terpene , stereochemistry , biochemistry , in vitro
Three new triterpenes, 3,4-seco-3,11β-epoxyfriedel-4(23)-en-3β-ol (1), friedelan- 3α,11β‑diol (2), 7β,26-epoxyfriedelan-3a,7a-diol (3), a mixture of two new triterpenes 3a-hydroxyfriedelan-29-yl palmitate (4) and 3α-hydroxyfriedelan-29-yl stearate (5) and eleven known compounds were obtained from the hexane extract of Maytenus quadrangulata leaves. The structures and the relative stereochemistry of the new triterpenes were established through 1D/2D nuclear magnetic resonance (NMR), high resolution mass spectrometry (HRMS), and Fourier transform infrared (FTIR) spectral data. The hexane extract and isolated compounds were submitted to the cytotoxicity assays against leukemia (THP-1 and K562), ovarian (TOV-21G) and breast cancer (MDA-MB-231) cell lines. Compounds 1, 2 and 11β-hydroxyfriedelan-3-one (15) displayed high cytotoxicity and selectivity against leukemic cells when compared to positive control cytarabine (for THP-1) and imatinib (for K562). Furthermore, compound 2 showed similar cytotoxicity and an enhanced selectivity towards ovarian and breast cells in comparison to positive control etoposide.