Structure-Activity Relationships of Protoberberines Having Antimicrobial Activity

Kinuko Iwasa; Hiroaki Nanba; Dong-Ung Lee; So-lm Kang

doi:10.1055/s-2006-957572

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Planta Med 1998; 64(8): 748-751
DOI: 10.1055/s-2006-957572

Letters

Structure-Activity Relationships of Protoberberines Having Antimicrobial Activity

Kinuko Iwasa¹ , Hiroaki Nanba¹ , Dong-Ung Lee² , So-lm Kang²

¹Kobe Pharmaceutical University, 4-19-1 Motoyamakita, Higashinada-ku, Japan
²Department of Biochemistry, Dongguk University, Kyongju, Kyongbuk, Korea

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Publication History

1998

1998

Publication Date:
04 January 2007 (online)

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Abstract

13-Alkyl derivatives (2-6 and 8-12) of berberine (1) and palmatine (7) were subjected to in vitro antibacterial activity tests against Bacillus subtilis and Salmonella enteritidis. Antibacterial activity increased as the length of the C-13 aliphatic side chain increased. The effects of the oxygen substituents on aromatic rings A, C, and D of protoberberinium salts 13-20 on the antimicrobial activity against Staphylococcus aureus, B. subtilis, S. enteritidis, Escherichia coli, and Candida albicans are also discussed. The change in lipophilicity of the protoberberinium salts caused by modification of the substituents appears to influence the antibacterial activity. 13-Hexylberberine (6) and 13-hexylpalmatine (12) exhibited the greatest antibacterial activity.

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