Potential α-glucosidase inhibitors from thermal transformation of (+)-catechin.
Thermal transformation of the (+)-catechin (1) with heating processing afforded a new oxidation product, gambiriin D (2), along with catechin [6'-8]-catechin (3), and (+)-epicatechin (4). The structure of a new catechin dimer with C-C linkage was determined on the basis of spectroscopic data interpretation. The catechin dimers 2 and 3 exhibited significantly improved inhibitory activities against α-glucosidase, with IC50 values of 0.16±0.2 and 0.14±0.2μM, respectively, when compared to parent (+)-catechin. Kinetic analysis showed that the two effective compounds 2 and 3 have noncompetitive modes of action.
Department of Food Science and Biotechnology, Andong National University, Andong 760-749, Republic of Korea.
Taewan
T
Kim
College of Pharmacy, Kyungpook National University, Daegu 702-701, Republic of Korea.
Hyo Jin
HJ
Choi
Department of Food Science and Technology, Pukyong National University, Busan 608-737, Republic of Korea.
Sung-Hwan
SH
Eom
Department of Herbal Medicinal Pharmacology, Daegu Haany University, Gyeongsan 712-715, Republic of Korea.
Jaemin
J
Lee
Department of Herbal Medicinal Pharmacology, Daegu Haany University, Gyeongsan 712-715, Republic of Korea; Blue-Bio Industry RIC, Dongeui University, Busan 614-714, Republic of Korea. Electronic address: skyey7@dhu.ac.kr.
Tae Hoon
TH
Kim
D002392:Catechin / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000378:metabolism; D019281:Dimerization; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000378:metabolism; D065089:Glycoside Hydrolase Inhibitors; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D011485:Protein Binding; D013237:Stereoisomerism; D013696:Temperature; D000520:alpha-Glucosidases / Q000378:metabolism
D004791:Enzyme Inhibitors; D065089:Glycoside Hydrolase Inhibitors; C000592791:catechin (6'-8)-catechin; C000592790:gambiriin D; D002392:Catechin; D000520:alpha-Glucosidases
(+)-Catechin; (+)-Catechin dimers; Kinetic analysis; Thermal transformation; α-Glucosidase