title: Isoflavonoids and coumarins from Glycyrrhiza uralensis: antibacterial activity against oral pathogens and conversion of isoflavans into isoflavan-quinones during purification.
abstract: 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).
authors.affiliation: Tom's of Maine, 302 Lafayette Center, Kennebunk, Maine 04043, USA. stefang@tomsofmaine.com
authors.forename: Stefan
authors.initials: S
authors.lastname: Gafner
authors.forename: Chantal
authors.initials: C
authors.lastname: Bergeron
authors.forename: Jacquelyn R
authors.initials: JR
authors.lastname: Villinski
authors.forename: Markus
authors.initials: M
authors.lastname: Godejohann
authors.forename: Pavel
authors.initials: P
authors.lastname: Kessler
authors.forename: John H
authors.initials: JH
authors.lastname: Cardellina
authors.forename: Daneel
authors.initials: D
authors.lastname: Ferreira
authors.forename: Karine
authors.initials: K
authors.lastname: Feghali
authors.forename: Daniel
authors.initials: D
authors.lastname: Grenier
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D001578:Benzopyrans / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D003374:Coumarins / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D004305:Dose-Response Relationship, Drug; D016967:Fusobacterium nucleatum / Q000187:drug effects; D005858:Germany; D029882:Glycyrrhiza uralensis; D006801:Humans; D007529:Isoflavones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D016966:Porphyromonas gingivalis / Q000187:drug effects; D036343:Pterocarpans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D011809:Quinones / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology; D013295:Streptococcus mutans / Q000187:drug effects; D016986:Streptococcus sobrinus / Q000187:drug effects
chemical_list: D000900:Anti-Bacterial Agents; D001578:Benzopyrans; D003374:Coumarins; D007529:Isoflavones; D036343:Pterocarpans; D011809:Quinones; C558581:licorisoflavan A; C401293:licoricidin