4-Benzyloxylonchocarpin and muracatanes A-C from Ranunculus muricatus L. and their biological effects
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- biomolecules-10-01562-v2
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Ranunculus muricatus L. is a spiny fruit buttercup that is used in various traditional medicinal systems. In the current investigation of R. muricatus, the new chalcone 4-benzyloxylonchocarpin (1), the new anthraquinone muracatanes A (2), the new-to-nature anthraquinone muracatanes B (3), and the
new naphthalene analog muracatanes C (4) were isolated, in addition to the three previously reported
compounds, 4-methoxylonchocarpin (5), β-sitosterol (6), and β-sitosterol β-D-glucopyranoside (7). Their structures were elucidated using 1D (1H and 13C) and 2D (COSY, HSQC, and HMBC) NMR
spectroscopy and HR-ESI-MS. Chalcone 1 showed potent acetylcholinesterase inhibitory effects with
Ki of 5.39 μM and Ki' of 3.54 μM, but none of the isolated compounds showed inhibitory activity
towards butyrylcholinesterase. Anthraquinone 3 illustrated α-glucosidase inhibitory effects with
IC50-values of 164.46 ± 83.04 μM. Compound 5 displayed moderate cytotoxic activity towards ovarian carcinoma (A2780, IC50 = 25.4 μM), colorectal adenocarcinoma (HT29, IC50 = 20.2 μM), breast cancer (MCF7, IC50 = 23.7 μM), and thyroid carcinoma (SW1736, IC50 = 26.2 μM) while it was inactive towards pharynx carcinoma (FaDu: IC50 > 30 μM).
new naphthalene analog muracatanes C (4) were isolated, in addition to the three previously reported
compounds, 4-methoxylonchocarpin (5), β-sitosterol (6), and β-sitosterol β-D-glucopyranoside (7). Their structures were elucidated using 1D (1H and 13C) and 2D (COSY, HSQC, and HMBC) NMR
spectroscopy and HR-ESI-MS. Chalcone 1 showed potent acetylcholinesterase inhibitory effects with
Ki of 5.39 μM and Ki' of 3.54 μM, but none of the isolated compounds showed inhibitory activity
towards butyrylcholinesterase. Anthraquinone 3 illustrated α-glucosidase inhibitory effects with
IC50-values of 164.46 ± 83.04 μM. Compound 5 displayed moderate cytotoxic activity towards ovarian carcinoma (A2780, IC50 = 25.4 μM), colorectal adenocarcinoma (HT29, IC50 = 20.2 μM), breast cancer (MCF7, IC50 = 23.7 μM), and thyroid carcinoma (SW1736, IC50 = 26.2 μM) while it was inactive towards pharynx carcinoma (FaDu: IC50 > 30 μM).
Original language | English |
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Article number | 1562 |
Journal | Biomolecules |
Volume | 10 |
Issue number | 11 |
Number of pages | 15 |
ISSN | 2218-273X |
DOIs | |
Publication status | Published - 2020 |
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