Structure-activity relationships of trans-cinnamic acid derivatives on alpha-glucosidase inhibition.
trans-Cinnamic acid and its derivatives were investigated for the alpha-glucosidase inhibitory activity. 4-Methoxy-trans-cinnamic acid and 4-methoxy-trans-cinnamic acid ethyl ester showed the highest potent inhibitory activity among those of trans-cinnamic acid derivatives. The presence of substituents at 4-position in trans-cinnamic acid altered the alpha-glucosidase inhibitory activity. Increasing of bulkiness and the chain length of 4-alkoxy substituents as well as the increasing of the electron withdrawing group have been shown to decrease the inhibitory activity. 4-Methoxy-trans-cinnamic acid was a noncompetitive inhibitor for alpha-glucosidase, whereas, 4-methoxy-trans-cinnamic acid ethyl ester was a competitive inhibitor. These results indicated that trans-cinnamic acid derivatives could be classified as a new group of alpha-glucosidase inhibitors.
Adisakwattana
Sirichai
S
Department of Pharmacology, 39, Faculty of Veterinary Science, Chulalongkorn University, Bangkok 10330, Thailand.
Sookkongwaree
Kasem
K
Roengsumran
Sophon
S
Petsom
Amorn
A
Ngamrojnavanich
Nattaya
N
Chavasiri
Warinthorn
W
Deesamer
Sujitra
S
Yibchok-anun
Sirintorn
S
D002934:Cinnamates / Q000737:chemistry / Q000494:pharmacology*; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000494:pharmacology; D005656:Fungal Proteins; D065089:Glycoside Hydrolase Inhibitors; D020128:Inhibitory Concentration 50; D007700:Kinetics; D013329:Structure-Activity Relationship
D002934:Cinnamates; D004791:Enzyme Inhibitors; D005656:Fungal Proteins; D065089:Glycoside Hydrolase Inhibitors; C029010:cinnamic acid