Novel 3-O-acyl mesquitol analogues as free-radical scavengers and enzyme inhibitors: synthesis, biological evaluation and structure-activity relationship.
A new isomer of mesquitol (2,3-trans-3',4',7,8-tetrahydroxyflavan-3-ol) was isolated from Dichrostachys cinerea in excellent yields. It has shown free-radical scavenging property and alpha-glucosidase inhibitory activities but, it could not display xanthine oxidase inhibitory property. However, it was observed that acylation of 3-OH group significantly enhanced the alpha-glucosidase inhibition and displayed xanthine oxidase inhibitory potential. The structure activity relationship revealed that the degree of lipophilicity played a major role in improving enzyme inhibitory activities. A positive correlation was observed between enzyme inhibitory potential and acyl chain length (upto C-16) of aliphatic esters.
Jagadeeshwar Rao
R
R
Division of Organic Chemistry I, Indian Institute of Chemical Technology, Hyderabad-500 007, India.
Tiwari
Ashok K
AK
Kumar
U Sampath
US
Reddy
S Venkat
SV
Ali
Amtul Z
AZ
Rao
J Madhusudana
JM
D000215:Acylation; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D005419:Flavonoids / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology; D016166:Free Radical Scavengers / Q000138:chemical synthesis* / Q000494:pharmacology; D065089:Glycoside Hydrolase Inhibitors; D010944:Plants / Q000737:chemistry; D013329:Structure-Activity Relationship
D004791:Enzyme Inhibitors; D005419:Flavonoids; D016166:Free Radical Scavengers; D065089:Glycoside Hydrolase Inhibitors; C479778:tetrahydroxyflavanol