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

Chem Pharm Bull (Tokyo). 1996 Oct;44(10):1915-22. doi: 10.1248/cpb.44.1915.


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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Carbohydrate Sequence
  • Central Nervous System Depressants / pharmacokinetics*
  • Chemical Phenomena
  • Chemistry, Physical
  • Depression, Chemical
  • Ethanol / pharmacokinetics*
  • Intestinal Absorption / drug effects*
  • Magnetic Resonance Spectroscopy
  • Male
  • Molecular Sequence Data
  • Oleanolic Acid / chemistry
  • Oleanolic Acid / pharmacology
  • Plant Epidermis / chemistry*
  • Plants, Medicinal / chemistry*
  • Rats
  • Rats, Wistar
  • Saponins / chemistry
  • Saponins / isolation & purification
  • Saponins / pharmacology*
  • Structure-Activity Relationship


  • Central Nervous System Depressants
  • Saponins
  • elatoside A
  • elatoside B
  • Ethanol
  • Oleanolic Acid