title: Synthesis and antimicrobial activity of 8-alkylberberine derivatives with a long aliphatic chain.
abstract: The compounds 8-ethyl- (2), 8-butyl- (3), 8-hexyl- (4), 8-octyl- (5), 8-decyl- (6) and 8-dodecylberberine chloride (7) were synthesized and tested for their antimicrobial activity in vitro to evaluate structure-activity relationships. Substitution of the alkyl groups at C-8 led to significant changes in the antimicrobial activity. All compounds were more potent against the tested microorganisms than berberine (1), especially against Gram-positive bacteria. The antimicrobial activity increased as the length of aliphatic chain was elongated and then decreased gradually when the alkyl chain exceeded eight carbon atoms. 8-octylberberine (5) displayed the highest antimicrobial activity of all compounds. The toxicity of compounds 2 - 7 was stronger than that of 1. However, upon elongating the aliphatic chain, the toxicity decreased gradually.
authors.affiliation: Chemistry Institute of Pharmaceutical Resources, School of Pharmaceutical Science, Southwest University, Chongqing, P. R. China.
authors.forename: Yong
authors.initials: Y
authors.lastname: Yang
authors.forename: Xiao-li
authors.initials: XL
authors.lastname: Ye
authors.forename: Xue-gang
authors.initials: XG
authors.lastname: Li
authors.forename: Jing
authors.initials: J
authors.lastname: Zhen
authors.forename: Baoshun
authors.initials: B
authors.lastname: Zhang
authors.forename: Lujiang
authors.initials: L
authors.lastname: Yuan
mesh_terms: D000818:Animals; D000900:Anti-Bacterial Agents / Q000008:administration & dosage / Q000138:chemical synthesis / Q000494:pharmacology* / Q000627:therapeutic use; D001599:Berberine / Q000008:administration & dosage / Q000138:chemical synthesis / Q000494:pharmacology* / Q000627:therapeutic use; D028142:Berberis; D002176:Candida albicans / Q000187:drug effects; D005227:Fatty Acids / Q000737:chemistry; D005260:Female; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D008297:Male; D051379:Mice; D008826:Microbial Sensitivity Tests; D008517:Phytotherapy
chemical_list: D000900:Anti-Bacterial Agents; D005227:Fatty Acids; D001599:Berberine