title: Anthraquinones from the seeds of Cassia tora with inhibitory activity on protein glycation and aldose reductase.
abstract: Nine anthraquinones, aurantio-obtusin (1), chryso-obtusin (2), obtusin (3), chryso-obtusin-2-O-beta-D-glucoside (4), physcion (5), emodin (6), chrysophanol (7), obtusifolin (8), and obtusifolin-2-O-beta-D-glucoside (9), isolated from an EtOAc-soluble extract of the seeds of Cassia tora, were subjected to in vitro bioassays to evaluate their inhibitory activity against advanced glycation end products (AGEs) formation and rat lens aldose reductase (RLAR). Among the isolates, compounds 6 and 8 exhibited a significant inhibitory activity on AGEs formation with observed IC(50) values of 118 and 28.9 microM, respectively, in an AGEs-bovine serum albumin (BSA) assay by specific fluorescence. Furthermore, compounds 6 and 8 inhibited AGEs-BSA formation more effectively than aminoguanidine, an AGEs inhibitor, by indirect AGEs-ELISA. N(epsilon)-Carboxymethyllysine (CML)-BSA formation was also inhibited by compounds 6 and 8. Whereas compounds 1, 4, and 6 showed a significant inhibitory activity on RLAR with IC(50) values of 13.6, 8.8, and 15.9 microM, respectively.
authors.affiliation: Department of Herbal Pharmaceutical Development, Korea Institute of Oriental Medicine, 461-24 Jeonmin-dong, Yuseong-gu, Daejeon, Korea.
authors.forename: Dae Sik
authors.initials: DS
authors.lastname: Jang
authors.forename: Ga Young
authors.initials: GY
authors.lastname: Lee
authors.forename: Young Sook
authors.initials: YS
authors.lastname: Kim
authors.forename: Yun Mi
authors.initials: YM
authors.lastname: Lee
authors.forename: Chan-Sik
authors.initials: CS
authors.lastname: Kim
authors.forename: Jeong Lim
authors.initials: JL
authors.lastname: Yoo
authors.forename: Jin Sook
authors.initials: JS
authors.lastname: Kim
mesh_terms: D000449:Aldehyde Reductase / Q000032:analysis / Q000037:antagonists & inhibitors*; D000818:Animals; D000880:Anthraquinones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D001681:Biological Assay; D002366:Cassia / Q000737:chemistry*; D002417:Cattle; D004305:Dose-Response Relationship, Drug; D004797:Enzyme-Linked Immunosorbent Assay; D000431:Ethanol / Q000737:chemistry; D017127:Glycation End Products, Advanced / Q000032:analysis / Q000037:antagonists & inhibitors* / Q000096:biosynthesis; D020128:Inhibitory Concentration 50; D007908:Lens, Crystalline / Q000201:enzymology; D008239:Lysine / Q000031:analogs & derivatives / Q000032:analysis / Q000037:antagonists & inhibitors / Q000096:biosynthesis; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry; D051381:Rats; D017207:Rats, Sprague-Dawley; D012639:Seeds / Q000737:chemistry*; D012710:Serum Albumin, Bovine / Q000037:antagonists & inhibitors; D012995:Solubility; D012997:Solvents / Q000737:chemistry; D013050:Spectrometry, Fluorescence
chemical_list: D000880:Anthraquinones; D017127:Glycation End Products, Advanced; D010936:Plant Extracts; D012997:Solvents; D012710:Serum Albumin, Bovine; D000431:Ethanol; D000449:Aldehyde Reductase; D008239:Lysine