Antimicrobial Activity of 8-Alkyl- and 8-Phenyl-Substituted Berberines and Their 12-Bromo Derivatives
| Autor: | Wolfgang Wiegrebe, So-Im Kang, Kinuko Iwasa, Dong-Ung Lee |
|---|---|
| Rok vydání: | 1998 |
| Předmět: |
Pharmacology
chemistry.chemical_classification biology Stereochemistry Organic Chemistry Pharmaceutical Science Antimicrobial biology.organism_classification Analytical Chemistry chemistry.chemical_compound Berberine Complementary and alternative medicine chemistry Drug Discovery Molecular Medicine Phenyl group Aliphatic compound Candida albicans Antibacterial activity Alkyl Antibacterial agent |
| Zdroj: | Journal of Natural Products. 61:1150-1153 |
| ISSN: | 1520-6025 0163-3864 |
| Popis: | The 8-alkyl- (3−6), 8-phenyl- (7), 12-bromo- (8), 8-alkyl-12-bromo- (9−12), and 12-bromo-8-phenyl- (13) berberine derivatives were prepared and tested for their antimicrobial activity in vitro to evaluate structure−activity relationships. Introduction of the alkyl or phenyl group and the bromine atom into the C-8 and C-12 positions of berberine (1), respectively, led to significant increases of the antimicrobial activity. In both the 8-alkyl- and 8-alkyl-12-bromo-berberines (3−6 and 9−12, respectively), the antibacterial activity increased as the length of the aliphatic chain increased. The exception was the activity against Candida albicans and Escherichia coli, which did not always increase as the alkyl side chain lengthened. Among the compounds tested, 12-bromo-8-n-hexylberberine (12) was 64, 256, 128, 16, and 32 times more active against Staphylococcus aureus, Bacillus subtilis, Salmonella enteritidis, E. coli, and C. albicans, respectively, in comparison to the clinically used berberine. Compound 12 ... |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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