Antimicrobial activity of 9-O-acyl- and 9-O-alkylberberrubine derivatives.
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.
Kim
Sung Han
SH
Lee
Sang Jun
SJ
Lee
Joo Hyoung
JH
Sun
Won Suck
WS
Kim
Jung Han
JH
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
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D010936:Plant Extracts; D001599:Berberine; C115958:berberrubine