title: Isolation and identification of phenolic compounds from the seeds of Perilla frutescens (L.) and their inhibitory activities against α-glucosidase and aldose reductase.
abstract: Five phenolic compounds were isolated from the seeds of Perilla (Perilla frutescens L.) using gradient solvent fractionation, silica gel column chromatography, and preparative high-performance liquid chromatography (HPLC). Their chemical structures were identified as caffeic acid-3-O-glucoside (1), rosmarinic acid-3-O-glucoside (2), rosmarinic acid (3), luteolin (4), and apigenin (5) using NMR spectroscopy and HPLC-ESI/MS analysis. Among them, luteolin (4) inhibited α-glucosidase (EC 3.2.1.20) with IC(50) value of 45.4μM. The inhibition kinetic analysed by Dixon plot indicate that luteolin is a noncompetitive inhibitor, and the inhibition constant K(I) was calculated at 45.0μM. Moreover, rosmarinic acid (3) and luteolin (4) inhibited recombinant human aldose reductase (EC 1.1.1.21) with IC(50) values of 11.2 and 0.6μM, respectively. Notably, the inhibition kinetic of luteolin (4) follows a hyperbolic dependence on aldose reductase inhibition by Dixon plot. Thus, inhibition kinetic indicates that luteolin (4) is a mixed-type inhibitor.
authors.affiliation: Department of Functional Crop, National Institute of Crop Science, Rural Development Administration, 1085 Neidong, Miryang 627-803, Republic of Korea. taejoung@korea.kr
authors.forename: Tae Joung
authors.initials: TJ
authors.lastname: Ha
authors.forename: Jin Hwan
authors.initials: JH
authors.lastname: Lee
authors.forename: Myoung-Hee
authors.initials: MH
authors.lastname: Lee
authors.forename: Byeong Won
authors.initials: BW
authors.lastname: Lee
authors.forename: Hyun Sook
authors.initials: HS
authors.lastname: Kwon
authors.forename: Chang-Hwan
authors.initials: CH
authors.lastname: Park
authors.forename: Kang-Bo
authors.initials: KB
authors.lastname: Shim
authors.forename: Hyun-Tae
authors.initials: HT
authors.lastname: Kim
authors.forename: In-Youl
authors.initials: IY
authors.lastname: Baek
authors.forename: Dae Sik
authors.initials: DS
authors.lastname: Jang
mesh_terms: D000449:Aldehyde Reductase / Q000032:analysis / Q000037:antagonists & inhibitors*; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D065089:Glycoside Hydrolase Inhibitors; D006801:Humans; D031344:Perilla frutescens / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D010936:Plant Extracts / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D012639:Seeds / Q000737:chemistry; D000520:alpha-Glucosidases / Q000032:analysis
chemical_list: D004791:Enzyme Inhibitors; D065089:Glycoside Hydrolase Inhibitors; D010636:Phenols; D010936:Plant Extracts; D000449:Aldehyde Reductase; D000520:alpha-Glucosidases