Preventive effects of soyasapogenol B derivatives on liver injury in a concanavalin A-induced hepatitis model.
To shed light on the structure-activity relationship, various soyasapogenol B derivatives were synthesized and evaluated for preventive effects on liver injury in the concanavalin A (Con A)-induced hepatitis model in mice. Con A injection into mice induces some pathophysiology of human liver disease such as autoimmune or viral hepatitis. Two hydroxyl groups on the A ring of soyasapogenol B are required for amelioration of liver damage. Modification of the C-22 hydroxyl moiety with an acyloxy or alkyloxy group, or removal of the hydroxyl group, resulted in a greatly enhanced percentage of alleviation. Among the series of soyasapogenol B derivatives examined, six compounds exhibited preventive effects on liver damage.
Sasaki
Kazue
K
Medicinal Chemistry Research Laboratory, Pharmaceutical Research Department, Meiji Seika Kaisha, Ltd., 760 Morooka-cho, Yokohama 222-8567, Japan.
Minowa
Nobuto
N
Kuzuhara
Hiroyuki
H
Nishiyama
Shoji
S
D000818:Animals; D003208:Concanavalin A; D018360:Crystallography, X-Ray; D004195:Disease Models, Animal; D006520:Hepatitis, Animal / Q000473:pathology / Q000517:prevention & control*; D008099:Liver / Q000473:pathology; D008111:Liver Function Tests; D008297:Male; D051379:Mice; D008807:Mice, Inbred BALB C; D019906:Nuclear Magnetic Resonance, Biomolecular; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D012503:Saponins / Q000138:chemical synthesis / Q000494:pharmacology*
D012503:Saponins; D003208:Concanavalin A; C407096:soyasapogenol B; D009828:Oleanolic Acid