Secondary metabolites from the leaves of the medicinal plant goldenseal (Hydrastis canadensis). (June 2017)

• Record Type: Journal Article
• Authors: Leyte-Lugo, Martha; Britton, Emily R.; Foil, Daniel H.; Brown, Adam R.; Todd, Daniel A.; Rivera-Chávez, José; Oberlies, Nicholas H.; Cech, Nadja B.
• Is Part Of: Phytochemistry letters. Volume 20(2017:Jun.)
• Page Start: 54
• Page End: 60
• Publication Date: 2017-06
• Subjects: Hydrastis canadensis -- Goldenseal -- Alkaloids -- Flavonoids -- Efflux pump inhibitors; Botanical chemistry -- Periodicals; Chimie végétale -- Périodiques; 572.205
• DOI: 10.1016/j.phytol.2017.03.012
• Languages: English
• ISSNs: 1874-3900

Abstract

Graphical abstract: Compounds1 and2 were isolated from the leaves of Hydrastis canadensis, and2 exhibited activity against efflux pumps in Staphylococcus aureus, which supports the use of this botanical as a treatment for infections. Highlights: Isolation and structure elucidation is reported for two new compounds from Hydrastis canadensis . High accuracy mass spectrometry data are included for 17 H. canadensis constituents. Compound1 demonstrates activity as an efflux pump inhibitor of Staphylococcus aureus . 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 ), (2 R )-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-4 H -1, 3-dioxolo-[4′, 5′:4, 5]-benzo[1, 2- e ]-1, 2-oxazocin)-2-spiro-1′-phtalan (8 ). Compounds3 –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 for2, 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.