4-Benzyloxylonchocarpin and muracatanes A-C from Ranunculus muricatus L. and their biological effects

Hussain, Hidayat ; Ali, Iftikhar ; Wang, Daijie ; Mamadalieva, Nilufar Z. ; Hussain, Wahid ; Csuk, Rene ; Loesche, Anne ; Fischer, Lucie ; Staerk, Dan ; Anam, Syariful ; AlZain, Mashail N. ; Mushtaq, Maria ; Ul-Haq, Zaheer ; Ullah, Riaz ; Noman, Omar M. ; Abbas, Ghulam ; Green, Ivan R. (2020-11-17)

CITATION: Hussain, H. et al. 2020. 4-Benzyloxylonchocarpin and muracatanes A-C from Ranunculus muricatus L. and their biological effects, Biomolecules, 10(11):1562, doi:10.3390/biom10111562.

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Article

ENGLISH ABSTRACT: 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).

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