Medicinal foodstuffs. VII. On the saponin constituents with glucose and alcohol absorption-inhibitory activity from a food garnish "Tonburi", the fruit of Japanese Kochia scoparia (L.) Schrad.: structures of scoparianosides A, B, and C

Chem Pharm Bull (Tokyo). 1997 Aug;45(8):1300-5. doi: 10.1248/cpb.45.1300.

Abstract

The methanolic extract of a food garnish "Tonburi", the fruit of Japanese kochia scoparia (L.) Schrad. (Chenopodiaceae), was found to inhibit the increase in serum glucose-loaded rats. Through bioassay-guided separation, momordin Ic and its 2'-O-beta-D-glucopyranoside were isolated as the active principles from this medicinal foodstuff together with three new saponins named scoparianosides A, B, and C. The structures of scoparianosides A, B, and C were elucidated on the basis of chemical and physicochemical evidence as 3 beta, 22 alpha-dihydroxyolean-12en-28-oic acid (22 alpha-hydroxyoleanolic acid), 3-O-beta-D-xylopyranosyl (1 --> 3)-beta-D-glucopyranosiduronic acid, 3 beta-hydroxyolean -18-en-28-oic acid (morolic acid), 3-O-beta-D-xylopyranosyl(1 --> 3)-beta-D -glucopyranosiduronic acid, and 3 beta-hydroxyolean-13(18)-en-28-oic acid, 3-O-beta-D-xylopyranoxyl(1 --> 3) -beta-D-glucopyranosiduronic acid. Momordin Ic and its 2'-O-beta-D-glucopyranoside, both of which are the principal saponin constituents of this medicinal foodstuffs, were found to potently inhibit glucose and ethanol absorption in rats.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Central Nervous System Depressants / blood
  • Central Nervous System Depressants / pharmacokinetics*
  • Chemical Phenomena
  • Chemistry, Physical
  • Chenopodiaceae / chemistry
  • Ethanol / blood
  • Ethanol / pharmacokinetics*
  • Fruit / chemistry*
  • Glucose / pharmacokinetics*
  • Hydrolysis
  • Hypoglycemic Agents / isolation & purification*
  • Hypoglycemic Agents / pharmacology
  • Japan
  • Magnetic Resonance Spectroscopy
  • Male
  • Oleanolic Acid* / analogs & derivatives*
  • Plants, Medicinal / chemistry*
  • Rats
  • Rats, Wistar
  • Saponins / isolation & purification*
  • Saponins / pharmacology*
  • Structure-Activity Relationship

Substances

  • Central Nervous System Depressants
  • Hypoglycemic Agents
  • Saponins
  • scoparianoside A
  • scoparianoside B
  • scoparianoside C
  • Ethanol
  • Oleanolic Acid
  • Glucose