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Isoflavonoids and Coumarins from Glycyrrhiza uralensis: Antibacterial Activity against Oral Pathogens and Conversion of Isoflavans into Isoflavan-Quinones during Purification

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† Tom’s of Maine, 302 Lafayette Center, Kennebunk, Maine 04043, United States
‡ Bruker-Biospin, Silberstreifen 4, 76287 Rheinstetten, Germany
§ ReevesGroup, 9374 Highlander Boulevard, Walkersville, Maryland 21793, United States
⊥ Department of Pharmacognosy and National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, University, Mississippi 38677, United States
∥ Groupe de Recherche en Écologie Buccale, Faculté de Médecine Dentaire, Université Laval, Quebec City, Quebec G1 V 0A6, Canada
*Tel: +1-207-467-2227. Fax: +1-207-985-2196. E-mail: [email protected]
Cite this: J. Nat. Prod. 2011, 74, 12, 2514–2519
Publication Date (Web):November 10, 2011
https://doi.org/10.1021/np2004775
Copyright © 2011 The American Chemical Society and American Society of Pharmacognosy
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    Abstract

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    Phytochemical investigation of a supercritical fluid extract of Glycyrrhiza uralensis has led to the isolation of 20 known isoflavonoids and coumarins, and glycycarpan (7), a new pterocarpan. The presence of two isoflavan-quinones, licoriquinone A (8) and licoriquinone B (9), in a fraction subjected to gel filtration on Sephadex LH-20 is due to suspected metal-catalyzed oxidative degradation of licoricidin (1) and licorisoflavan A (2). The major compounds in the extract, as well as 8, were evaluated for their ability to inhibit the growth of several major oral pathogens. Compounds 1 and 2 showed the most potent antibacterial activities, causing a marked growth inhibition of the cariogenic species Streptococcus mutans and Streptococcus sobrinus at 10 μg/mL and the periodontopathogenic species Porphyromonas gingivalis (at 5 μg/mL) and Prevotella intermedia (at 5 μg/mL for 1 and 2.5 μg/mL for 2). Only 1 moderately inhibited growth of Fusobacterium nucleatum at the highest concentration tested (10 μg/mL).

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