title: Structure-activity relationships of trans-cinnamic acid derivatives on alpha-glucosidase inhibition.
abstract: 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.
authors.affiliation: Department of Pharmacology, 39, Faculty of Veterinary Science, Chulalongkorn University, Bangkok 10330, Thailand.
authors.forename: Sirichai
authors.initials: S
authors.lastname: Adisakwattana
authors.forename: Kasem
authors.initials: K
authors.lastname: Sookkongwaree
authors.forename: Sophon
authors.initials: S
authors.lastname: Roengsumran
authors.forename: Amorn
authors.initials: A
authors.lastname: Petsom
authors.forename: Nattaya
authors.initials: N
authors.lastname: Ngamrojnavanich
authors.forename: Warinthorn
authors.initials: W
authors.lastname: Chavasiri
authors.forename: Sujitra
authors.initials: S
authors.lastname: Deesamer
authors.forename: Sirintorn
authors.initials: S
authors.lastname: Yibchok-anun
mesh_terms: 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
chemical_list: D002934:Cinnamates; D004791:Enzyme Inhibitors; D005656:Fungal Proteins; D065089:Glycoside Hydrolase Inhibitors; C029010:cinnamic acid