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. 2020 Nov 17;10(11):1562.
doi: 10.3390/biom10111562.

4-Benzyloxylonchocarpin and Muracatanes A-C from Ranunculus muricatus L. and Their Biological Effects

Hidayat Hussain  1 , Iftikhar Ali  2   3 , Daijie Wang  2 , Nilufar Z Mamadalieva  1 , Wahid Hussain  4 , René Csuk  5 , Anne Loesche  5 , Lucie Fischer  5 , Dan Staerk  6 , Syariful Anam  6   7 , Mashail N AlZain  8 , Maria Mushtaq  9 , Zaheer Ul-Haq  9 , Riaz Ullah  10 , Omar M Noman  10 , Ghulam Abbas  11 , Ivan R Green  12
Affiliations

4-Benzyloxylonchocarpin and Muracatanes A-C from Ranunculus muricatus L. and Their Biological Effects

Hidayat Hussain et al. Biomolecules. .

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).

Keywords: Ranunculus muricatus L; acetylcholinesterase; structure elucidation; α-glucosidase.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
(A): Comparison between the docked pose of galantamine derivative (pink) and the co-crystallized ligand (yellow) within AChE (cyan, PDB code: 4EY6); (B) comparison between the docked pose of α-D-glucose (orange) and the co-crystallized ligand (yellow) within α-glucosidase (cyan, PDB code: 3A4A).
Figure 2
Figure 2
Structures of compounds 1–7 isolated from R. muricatus.
Figure 3
Figure 3
Selected COSY and HMBC correlations for 4-benzyloxylonchocarpin (1).
Figure 4
Figure 4
Selected COSY and HMBC correlations for muracatanes A-C (2–4).
Figure 5
Figure 5
Cornish–Bowden (A) and Dixon (B) plots for the inhibition of AChE by compound 1.
Figure 6
Figure 6
Docking and binding pattern of chalcone 1 (pink) with acetylcholinesterase (cyan).
Figure 7
Figure 7
Docking and binding pattern of anthraquinone 3 (orange) with α-glucosidase (cyan).
See this image and copyright information in PMC

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