Anthraquinones from the seeds of Cassia tora with inhibitory activity on protein glycation and aldose reductase.
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.
Jang
Dae Sik
DS
Department of Herbal Pharmaceutical Development, Korea Institute of Oriental Medicine, 461-24 Jeonmin-dong, Yuseong-gu, Daejeon, Korea.
Lee
Ga Young
GY
Kim
Young Sook
YS
Lee
Yun Mi
YM
Kim
Chan-Sik
CS
Yoo
Jeong Lim
JL
Kim
Jin Sook
JS
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
D000880:Anthraquinones; D017127:Glycation End Products, Advanced; D010936:Plant Extracts; D012997:Solvents; D012710:Serum Albumin, Bovine; D000431:Ethanol; D000449:Aldehyde Reductase; D008239:Lysine