title: Antimicrobial activity of 9-O-acyl- and 9-O-alkylberberrubine derivatives.
abstract: For the structure-activity relationship study on berberrubine derivatives, a series of compounds bearing 9-O-acyl- and 9-O-alkyl-substituents were synthesized and tested for antimicrobial activity against Gram-positive, Gram-negative bacteria and fungi. Octanoyl, decanoyl, lauroyl derivatives among the acyl analogs and hexyl, heptyl, octyl, nonyl, decyl, undecyl derivatives among the alkyl analogs showed strong antimicrobial activity against Gram-positive bacteria and fungi. As a whole, alkyl analogs were more active than acyl analogs for antimicrobial activity. Synthesized derivatives had no activity on Gram-negative bacteria. Too short or too long substituents decreased activity. These results suggest that the presence of lipophilic substituents with moderate sizes might be crucial for the optimal antimicrobial activity.
authors.forename: Sung Han
authors.initials: SH
authors.lastname: Kim
authors.forename: Sang Jun
authors.initials: SJ
authors.lastname: Lee
authors.forename: Joo Hyoung
authors.initials: JH
authors.lastname: Lee
authors.forename: Won Suck
authors.initials: WS
authors.lastname: Sun
authors.forename: Jung Han
authors.initials: JH
authors.lastname: Kim
mesh_terms: D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects*; D001599:Berberine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000302:isolation & purification / Q000494:pharmacology*; D028142:Berberis; D005658:Fungi / Q000187:drug effects*; D009682:Magnetic Resonance Spectroscopy; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology*; D021281:Quantitative Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D010936:Plant Extracts; D001599:Berberine; C115958:berberrubine