Antimicrobial activity of 3-O-acyl-(-)-epicatechin and 3-O-acyl-(+)-catechin derivatives.
As an exploratory investigation of antimicrobial promoting compounds, 3- O-acyl-(-)-epicatechins and 3- O-acyl-(+)-catechins possessing various aromatic groups and aliphatic chains of varying length from C4 to C16 for increasing lipophilicity were synthesized and tested for antimicrobial activities against Gram-positive, Gram-negative bacteria and fungi. The (-)-epicatechin and (+)-catechin derivatives comprised of aromatic groups increased activity and derivatives with acyl chain groups of carbon atoms in the close vicinity of C8 to C10 showed strong antimicrobial activity (MIC = 2 - 8 microg/ml) against Gram-positive bacteria and weak activity against fungi. However, the activity decreased when the carbon chain length of the substituents was too short (C4 to C6) or too long (C16). These results suggest that the presence of lipophilic substituents with moderate sizes might be crucial for the optimal antimicrobial activity.
Park
Ki Duk
KD
Department of Biotechnology, College of Engineering, Yonsein University, Seoul, Korea.
Park
Yoon Sun
YS
Cho
Sung Jin
SJ
Sun
Won Suck
WS
Kim
Sung Han
SH
Jung
Do Hyun
DH
Kim
Jung Han
JH
D000890:Anti-Infective Agents / Q000008:administration & dosage / Q000494:pharmacology* / Q000627:therapeutic use; D028241:Camellia sinensis; D002392:Catechin / Q000008:administration & dosage / Q000494:pharmacology / Q000627:therapeutic use; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D006801:Humans; D008826:Microbial Sensitivity Tests; D003904:Mitosporic Fungi / Q000187:drug effects; D008517:Phytotherapy; D010936:Plant Extracts / Q000008:administration & dosage / Q000494:pharmacology* / Q000627:therapeutic use
D000890:Anti-Infective Agents; D010936:Plant Extracts; D002392:Catechin