Phytochemical studies of seeds of medicinal plants. III. Ursolic acid and oleanolic acid glycosides from seeds of Patrinia scabiosaefolia Fischer.
Three isomeric pairs of ursolic acid (1, 3, and 5) and oleanolic acid (2, 4, and 6) glycosides were isolated as predominant constituents from seeds of Patrinia scabiosaefolia Fischer (Valerianaceae). Based on chemical and spectral evidence, their structures were established to be 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl] ursolic acid (1) and oleanolic acid (2), 3-O-[beta-D-glucopyranosyl-(1-->3)-alpha-L-arabinopyranosyl] ursolic acid (3) and oleanolic acid (4), and 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-[beta-D-glucopyranosyl- (1-->3)]-alpha-L-arabinopyranosyl] ursolic acid (5) and oleanolic acid (6), respectively. Glycosides 1, 5, and 6 are new compounds and named as patrinia-glycosides A-I, B-I, and B-II, respectively. Glycoside 3 is a known but is the first naturally occurring product. Ursolic acid glycosides were first found from this plant specimen.
Nakanishi
T
T
Faculty of Pharmaceutical Sciences, Setsunan University, Osaka, Japan.
Tanaka
K
K
Murata
H
H
Somekawa
M
M
Inada
A
A
D002240:Carbohydrate Sequence; D006027:Glycosides / Q000032:analysis; D008516:Medicine, Chinese Traditional; D008969:Molecular Sequence Data; D009828:Oleanolic Acid / Q000032:analysis*; D010946:Plants, Medicinal / Q000737:chemistry*; D014315:Triterpenes / Q000032:analysis*; D000097245:Ursolic Acid
D006027:Glycosides; D009828:Oleanolic Acid; D014315:Triterpenes; D000097245:Ursolic Acid