Cytotoxic triterpenoid saponins from the root of Olax subscorpioidea Oliv. (Olacaceae).

Autor: Adekunle YA; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Ibadan, Nigeria; Centre for Natural Products Discovery, School of Pharmacy and Biomolecular Sciences, Faculty of Science, Liverpool John Moores University, Byrom Street, L3 3AF, Liverpool, United Kingdom; Department of Pharmaceutical and Medicinal Chemistry, College of Pharmacy, Afe Babalola University, Ado-Ekiti, Nigeria. Electronic address: yemiadekunle03@yahoo.com., Samuel BB; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Ibadan, Nigeria. Electronic address: tundebsamuel@gmail.com., Nahar L; Laboratory of Growth Regulators, Palacký University and Institute of Experimental Botany, The Czech Academy of Sciences, Šlechtitelů 27, 78371, Olomouc, Czech Republic. Electronic address: nahar@ueb.cas.cz., Fatokun AA; Centre for Natural Products Discovery, School of Pharmacy and Biomolecular Sciences, Faculty of Science, Liverpool John Moores University, Byrom Street, L3 3AF, Liverpool, United Kingdom., Sarker SD; Centre for Natural Products Discovery, School of Pharmacy and Biomolecular Sciences, Faculty of Science, Liverpool John Moores University, Byrom Street, L3 3AF, Liverpool, United Kingdom.
Jazyk: angličtina
Zdroj: Phytochemistry [Phytochemistry] 2023 Nov; Vol. 215, pp. 113853. Date of Electronic Publication: 2023 Sep 07.
DOI: 10.1016/j.phytochem.2023.113853
Abstrakt: Bioactivity-guided phytochemical fractionation of the methanol extract of Olax subscorpioidea root has led to the isolation of six triterpenes. Three of these compounds are previously undescribed triterpenoid saponins: oleanolic acid 3-O-[α-L-rhamnopyranosyl-(1→3)-β-D-glucopyranosyl-(1 → 2)-6-O-methyl-β-D-glucuronopyranoside]-28-O-β-D-glucopyranosyl ester (2), oleanolic acid 3-O-[β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranoside] (3), and oleanolic acid 3-O-[β-D-glucopyranosyl-(1 → 4)-6-O-methyl-β-D-glucuronopyranoside] ester (5). Other reported known compounds include two triterpene glycosides: oleanolic acid 3-O-[β-D-glucopyranosyl-(1 → 4)-6-O-methyl-β-D-glucuronopyranoside]-28-O-β-D-glucopyranosyl ester (1) and oleanolic acid 3-O-[β-D-glucopyranosyl-(1 → 4)-β-D-glucuronopyranoside] (4); and a triterpene acid, oleanolic acid (6). The structures of these compounds were elucidated by spectroscopic means. The isolated compounds were tested against human cervical cancer (HeLa), colorectal cancer (Caco-2) and breast cancer (MCF-7) cell lines using the in vitro 3-[4,5-dimethylthiazole-2-yl] 3,5-diphenyltetrazolium bromide (MTT) assay, with vincristine as positive control. The cytotoxicity assay showed that compounds 3 and 5 exhibited significant inhibitory effects on the HeLa cell line, with IC 50 values of 7.42 ± 0.34 μM and 10.27 ± 1.26 μM; and moderate effects on MCF-7 (IC 50 values, 36.67 ± 1.23 μM and 43.83 ± 0.65 μM) and Caco-2 (IC 50 values, 35.83 ± 0.55 μM and 39.03 ± 4.38 μM, respectively) cell lines. They were also more selectively cytotoxic than vincristine against the cancer cell lines, when compared with cytotoxicity against the normal lung cell line MRC5.
Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
(Copyright © 2023 The Authors. Published by Elsevier Ltd.. All rights reserved.)
Databáze: MEDLINE
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