4-Benzyloxylonchocarpin and Muracatanes A-C from <i>Ranunculus muricatus</i> L. and Their Biological Effects
Hidayat Hussain,
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,
Ivan R. Green
Affiliations
Hidayat Hussain
Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, D-06120 Halle (Salle), Germany
Iftikhar Ali
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
Daijie Wang
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
Nilufar Z. Mamadalieva
Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, D-06120 Halle (Salle), Germany
Wahid Hussain
Department of Botany, Government Post Graduate College Parachinar, Parachinar 26300, District Kurram, Pakistan
Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, 1165 Copenhagen, Denmark
Syariful Anam
Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, 1165 Copenhagen, Denmark
Mashail N. AlZain
Department of Biology, College of Sciences, Princess Nourah Bint Abdulrahman University, Riyadh 11451, Saudi Arabia
Maria Mushtaq
Dr. Panjwani Center for Molecular Medicine and Drug Research, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
Zaheer Ul-Haq
Dr. Panjwani Center for Molecular Medicine and Drug Research, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
Riaz Ullah
Department of Pharmacognosy (MAPPRC), College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
Omar M. Noman
Department of Pharmacognosy (MAPPRC), College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
Ghulam Abbas
Department of Biological Sciences and Chemistry, College of Arts and Sciences, University of Nizwa, Nizwa 616, Oman
Ivan R. Green
Department of Chemistry and Polymer Science, University of Stellenbosch, Private Bag X1, Matieland, Stellenbosch 7600, South Africa
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).
