Pyrano-isoflavans from Glycyrrhiza uralensis with antibacterial activity against Streptococcus mutans and Porphyromonas gingivalis

Jacquelyn R Villinski; Chantal Bergeron; Joseph C Cannistra; James B Gloer; Christina M Coleman; Daneel Ferreira; Jabrane Azelmat; Daniel Grenier; Stefan Gafner

doi:10.1021/np400788r

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Pyrano-isoflavans from Glycyrrhiza uralensis with antibacterial activity against Streptococcus mutans and Porphyromonas gingivalis

Journal article

Peer reviewed

Pyrano-isoflavans from Glycyrrhiza uralensis with antibacterial activity against Streptococcus mutans and Porphyromonas gingivalis

Jacquelyn R Villinski, Chantal Bergeron, Joseph C Cannistra, James B Gloer, Christina M Coleman, Daneel Ferreira, Jabrane Azelmat, Daniel Grenier and Stefan Gafner

Journal of natural products (Washington, D.C.), Vol.77(3), pp.521-526

03/28/2014

DOI: 10.1021/np400788r

PMID: 24479468

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Abstract

Continuing investigation of fractions from a supercritical fluid extract of Chinese licorice (Glycyrrhiza uralensis) roots has led to the isolation of 12 phenolic compounds, of which seven were described previously from this extract. In addition to these seven metabolites, four known components, 1-methoxyerythrabyssin II (4), 6,8-diprenylgenistein, gancaonin G (5), and isoglycyrol (6), and one new isoflavan, licorisoflavan C (7), were characterized from this material for the first time. Treatment of licoricidin (1) with palladium chloride afforded larger amounts of 7 and also yielded two new isoflavans, licorisoflavan D (8), which was subsequently detected in the licorice extract, and licorisoflavan E (9). Compounds 1-9 were evaluated for their antibacterial activities against the cariogenic Streptococcus mutans and the periodontopathogenic Porphyromonas gingivalis. Licoricidin (1), licorisoflavan A (2), and 7-9 showed antibacterial activity against P. gingivalis (MICs of 1.56-12.5 μg/mL). The most potent activity against S. mutans was obtained with 7 (MIC of 6.25 μg/mL), followed by 1 and 9 (MIC of 12.5 μg/mL). This study provides further evidence for the therapeutic potential of licorice extracts for the treatment and prevention of oral infections.

Genistein - analogs & derivatives

Phenols - isolation & purification

Isoflavones - pharmacology

Isoflavones - chemistry

Benzopyrans - chemistry

Microbial Sensitivity Tests

Pterocarpans - isolation & purification

Pterocarpans - chemistry

Pyrans - chemistry

Anti-Bacterial Agents - chemistry

Nuclear Magnetic Resonance, Biomolecular

Molecular Structure

Pyrans - isolation & purification

Pyrans - pharmacology

Phenols - pharmacology

Glycyrrhiza uralensis - chemistry

Isoflavones - isolation & purification

Palladium - pharmacology

Genistein - chemistry

Glycyrrhiza - metabolism

Streptococcus mutans - drug effects

Anti-Bacterial Agents - isolation & purification

Plant Roots - chemistry

Phenols - chemistry

Anti-Bacterial Agents - pharmacology

Germany

Porphyromonas gingivalis - drug effects

Details

Title: Subtitle: Pyrano-isoflavans from Glycyrrhiza uralensis with antibacterial activity against Streptococcus mutans and Porphyromonas gingivalis
Creators: Jacquelyn R Villinski - Tom's of Maine , 302 Lafayette Center, Kennebunk, Maine 04043, United States
Chantal Bergeron
Joseph C Cannistra
James B Gloer
Christina M Coleman
Daneel Ferreira
Jabrane Azelmat
Daniel Grenier
Stefan Gafner
Resource Type: Journal article
Publication Details: Journal of natural products (Washington, D.C.), Vol.77(3), pp.521-526
Publisher: United States
DOI: 10.1021/np400788r
PMID: 24479468
ISSN: 0163-3864
eISSN: 1520-6025
Language: English
Date published: 03/28/2014
Academic Unit: Chemistry
Record Identifier: 9983985954802771

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