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Article

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

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Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, D-06120 Halle (Salle), Germany
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School of Pharmaceutical Sciences and Key Laboratory for Applied Technology of Sophisticated Analytical Instruments of Shandong Province, Shandong Analysis and Test Center, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250014, China
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Department of Chemistry, Karakoram International University, Gilgit 15100, Pakistan
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Department of Botany, Government Post Graduate College Parachinar, Parachinar 26300, District Kurram, Pakistan
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Organic Chemistry, Martin-Luther University Halle-Wittenberg, Kurt-Mothes-Str. 2, D-06120 Halle (Saale), Germany
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Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, 1165 Copenhagen, Denmark
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Department of Pharmacy, Faculty of Sciences, Tadulako University, Palu 94118, Indonesia
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Department of Biology, College of Sciences, Princess Nourah Bint Abdulrahman University, Riyadh 11451, Saudi Arabia
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Dr. Panjwani Center for Molecular Medicine and Drug Research, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
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Department of Pharmacognosy (MAPPRC), College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
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Department of Biological Sciences and Chemistry, College of Arts and Sciences, University of Nizwa, Nizwa 616, Oman
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Department of Chemistry and Polymer Science, University of Stellenbosch, Private Bag X1, Matieland, Stellenbosch 7600, South Africa
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Authors to whom correspondence should be addressed.
Biomolecules 2020, 10(11), 1562; https://doi.org/10.3390/biom10111562
Received: 16 October 2020 / Revised: 13 November 2020 / Accepted: 13 November 2020 / Published: 17 November 2020
(This article belongs to the Collection Pharmacology of Medicinal Plants)
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). View Full-Text
Keywords: Ranunculus muricatus L; structure elucidation; acetylcholinesterase; α-glucosidase Ranunculus muricatus L; structure elucidation; acetylcholinesterase; α-glucosidase
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MDPI and ACS Style

Hussain, H.; Ali, I.; Wang, D.; Mamadalieva, N.Z.; Hussain, W.; Csuk, R.; Loesche, A.; Fischer, L.; Staerk, D.; Anam, S.; AlZain, M.N.; Mushtaq, M.; Ul-Haq, Z.; Ullah, R.; Noman, O.M.; Abbas, G.; Green, I.R. 4-Benzyloxylonchocarpin and Muracatanes A-C from Ranunculus muricatus L. and Their Biological Effects. Biomolecules 2020, 10, 1562. https://doi.org/10.3390/biom10111562

AMA Style

Hussain H, Ali I, Wang D, Mamadalieva NZ, Hussain W, Csuk R, Loesche A, Fischer L, Staerk D, Anam S, AlZain MN, Mushtaq M, Ul-Haq Z, Ullah R, Noman OM, Abbas G, Green IR. 4-Benzyloxylonchocarpin and Muracatanes A-C from Ranunculus muricatus L. and Their Biological Effects. Biomolecules. 2020; 10(11):1562. https://doi.org/10.3390/biom10111562

Chicago/Turabian Style

Hussain, Hidayat, Iftikhar Ali, Daijie Wang, Nilufar Z. Mamadalieva, Wahid Hussain, René Csuk, Anne Loesche, Lucie Fischer, Dan Staerk, Syariful Anam, Mashail N. AlZain, Maria Mushtaq, Zaheer Ul-Haq, Riaz Ullah, Omar M. Noman, Ghulam Abbas, and Ivan R. Green. 2020. "4-Benzyloxylonchocarpin and Muracatanes A-C from Ranunculus muricatus L. and Their Biological Effects" Biomolecules 10, no. 11: 1562. https://doi.org/10.3390/biom10111562

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