Bioactive saponins and glycosides. VI. Elatosides A and B, potent inhibitors of ethanol absorption, from the bark of Aralia elata SEEM. (Araliaceae): the structure-requirement in oleanolic acid glucuronide-saponins for the inhibitory activity.
Potent inhibitors of ethanol absorption, elatosides A and B, were isolated from the bark of Aralia elata SEEM, through bioassay-guided separation together with elatosides C and D and four known oleanolic acid glucuronide-saponins, spinasaponin A, spinasaponin A 28-O-glucoside, and stipuleanosides R1 and R2. The structures of elatosides A, B, C, and D were determined on the basis of chemical and physicochemical evidence as oleanolic acid 3-O-¿[beta-D-xylopyranosyl (1-->2)] [beta-D-galactopyranosyl (1-->3)]¿-beta-D-glucopyranosiduronic acid, oleanolic acid 3-O-¿[beta-D-galactopyranosyl (1-->2)] [beta-D-galactopyranosyl (1-->3)]¿-beta-D-glucopyranosiduronic acid, and their 28-O-glucopyranosyl esters, respectively. The inhibitory effect of various oleanolic acid 3, 28-O-bisdesmosides, oleanolic acid 3-O-monodesmosides, and oleanolic acid on ethanol absorption was examined and it was found that the 3-O-glucuronide moiety and the 28-carboxyl group in oleanolic acid glucuronide-saponin were required to exert the inhibitory activity.
Kyoto Pharmaceutical University, Japan.
M
M
Yoshikawa
T
T
Murakami
E
E
Harada
N
N
Murakami
J
J
Yamahara
H
H
Matsuda
D000818:Animals; D002240:Carbohydrate Sequence; D002492:Central Nervous System Depressants / Q000493:pharmacokinetics*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D003864:Depression, Chemical; D000431:Ethanol / Q000493:pharmacokinetics*; D007408:Intestinal Absorption / Q000187:drug effects*; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D008969:Molecular Sequence Data; D009828:Oleanolic Acid / Q000737:chemistry / Q000494:pharmacology / Q000031:analogs & derivatives; D019441:Plant Epidermis / Q000737:chemistry*; D010946:Plants, Medicinal / Q000737:chemistry*; D051381:Rats; D017208:Rats, Wistar; D012503:Saponins / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D002492:Central Nervous System Depressants; D012503:Saponins; C102411:elatoside A; C102412:elatoside B; D000431:Ethanol; D009828:Oleanolic Acid