Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Phenolic Constituents of Licorice. VIII. Structures of Glicophenone and Glicoisoflavanone, and Effects of Licorice Phenolics on Methicillin-Resistant Staphylococcus aureus
Tsutomu HATANOYasushi SHINTANIYasuhiro AGASumiko SHIOTATomofusa TSUCHIYATakashi YOSHIDA
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2000 Volume 48 Issue 9 Pages 1286-1292

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Abstract

Two new phenolic compounds, glicophenone (1) and glicoisoflavanone (2), were isolated from commercial licorice, and their structures were elucidated on the basis of spectroscopic data. Antibacterial assays of licorice phenolics for Staphylococcus aureus, including four strains of methicillin-resistant S. aureus (MRSA), and also for Escherichia coli K12 and Pseudomonas aeruginosa PAO1, were then examined. Two compounds among them, 8-(γ, γ-dimethylallyl)-wighteone (21) and 3'-(γ, γ-dimethylallyl)-kievitone (28), showed remarkable antibacterial effects [minimum inhibitory concentrations (MICs), 8 μg/ml] on the MRSA strains and methicillin-sensitive S. aureus. Licochalcone A (14), gancaonin G (20), isoangustone A (24), glyasperins C (30) and D (31), glabridin, (32), licoricidin (33), glycycoumarin (34) and licocoumarone (40) showed antibacterial effects on the MRSA strains with MIC values of 16 μg/ml. Effects on the β-lactam resistance of the MRSA strains were also examined, and licoricidin (33) noticeably decreased the resistance of the MRSA strains against oxacillin, as shown by the reduction in the MICs of oxacillin (lower than 1/128-1/1000 in the presence of 8 μg/ml of 33, and 1/8-1/32 in the presence of 4 μg/ml of 33). Mechanistic study suggested that 33 does not inhibit the formation of penicillin-binding protein 2' (PBP2'), but affects the enzymatic function of PBP2'.

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