Secondary metabolites from the leaves of the medicinal plant goldenseal (Hydrastis canadensis) |
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| Institution: | 2. Chair and Department of Pharmacognosy, Faculty of Pharmacy, Medical University of Gdansk, al. gen. J. Hallera 107, 80-416 Gdańsk, Poland;1. National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS 38677, USA;2. Division of Pharmacognosy, Department of BioMolecular Sciences, School of Pharmacy, University of Mississippi, University, MS 38677, USA;1. Division of Ethnopharmacology, Entomology Research Institute, Loyola College, Chennai 600 034, India;2. Division of Bioinformatics, Entomology Research Institute, Loyola College, Chennai 600 034, India;3. Department of Botany and Microbiology, Addiriyah Chair for Environmental Studies, College of Science, King Saudi University, P. O. Box 2455, Riyadh 11451, Saudi Arabia;4. Visiting Professor Programme, Deanship of Scientific Research, College of Science, King Saudi University, Saudi Arabia;1. Laboratorio de Química Orgánica, Unidad de Biotecnología, Centro de Investigación Científica de Yucatán, Calle 43 No. 130, Chuburná de Hidalgo, CP 97205, Mérida, Yucatán, México;2. Unidad de Recursos Naturales, Centro de Investigación Científica de Yucatán, Calle 43 No. 130, Chuburná de Hidalgo, CP 97205, Mérida, Yucatán, México;3. SONAS EA921, SFR4207 QUASAV, University of Angers, 42, rue Georges Morel 49070, Beaucouzé, France;1. Department of Medicinal Chemistry and Pharmacognosy, Faculty of Pharmacy, Jordan University of Science and Technology, Irbid, 22110, Jordan;2. Department of Pharmaceutical Sciences, College of Pharmacy, University of Illinois at Chicago, Chicago, IL, 60612, USA;3. Faculty of Medicine, Jordan University of Science and Technology, Irbid, 22110, Jordan;4. Department of Plant Production, Faculty of Agriculture, Jordan University of Science and Technology, Irbid, 22110, Jordan;5. Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, NC, 27402, USA;1. Department of Chemistry & Biochemistry and the Center for Nanoscience, University of Missouri St. Louis, St. Louis, MO 63121, United States;2. Department of Chemistry, Lewis and Clark College, Portland, OR 97219, United States |
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| Abstract: | The study presented herein constitutes an extensive investigation of constituents in Hydrastis canadensis L. (Ranunculaceae) leaves. It describes the isolation and identification of two previously unknown compounds, 3,4-dimethoxy-2-(methoxycarbonyl)benzoic acid (1) and 3,5,3′-trihydroxy-7,4′-dimethoxy-6,8-C-dimethyl-flavone (2), along with the known compounds (±)-chilenine (3), (2R)-5,4′-dihydroxy-6-C-methyl-7-methoxy-flavanone (4), 5,4′-dihydroxy-6,8-di-C-methyl-7-methoxy-flavanone (5), noroxyhydrastinine (6), oxyhydrastinine (7) and 4′,5′-dimethoxy-4-methyl-3′-oxo-(1,2,5,6-tetrahydro-4H-1,3-dioxolo-4′,5′:4,5]-benzo1,2-e]-1,2-oxazocin)-2-spiro-1′-phtalan (8). Compounds 3–8 have been reported from other sources, but this is the first report of their presence in H. canadensis extracts. A mass spectrometry based assay was employed to demonstrate bacterial efflux pump inhibitory activity against Staphylococcus aureus for 2, with an IC50 value of 180 ± 6 μM. This activity in addition to that of other bioactive compounds such as flavonoids and alkaloids, may explain the purported efficacy of H. canadensis for treatment of bacterial infections. Finally, this report includes high mass accuracy fragmentation spectra for all compounds investigated herein which were uploaded into the Global Natural Products Social molecular networking library and can be used to facilitate their future identification in H. canadensis or other botanicals. |
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| Keywords: | Goldenseal Alkaloids Flavonoids Efflux pump inhibitors |
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