Structures of steroidal alkaloid oligoglycosides, robeneosides A and B, and antidiabetogenic constituents from the Brazilian medicinal plant Solanum lycocarpum

J Nat Prod. 2007 Feb;70(2):210-4. doi: 10.1021/np0680580. Epub 2007 Jan 24.

Abstract

In the course of our studies on antidiabetogenic compounds from natural medicines and medicinal foodstuffs, a methanolic extract of the fruits of Solanum lycocarpum showed an inhibitory effect on the increase of serum glucose levels in oral sucrose-loaded rats. Through bioassay-guided separation, three known steroidal alkaloid oligoglycosides, solamargine (1), solasonine (3), and 12-hydroxysolasonine (5), were isolated from the active fraction together with two new steroidal alkaloid oligoglycosides, robeneosides A (2) and B (4). The major constituents, solamargine (1) and solasonine (3), exhibited an inhibitory effect on the increase of serum glucose levels in oral sucrose-loaded rats. In addition, these compounds suppressed gastric emptying in mice. However, this methanolic extract from S. lycocarpum fruits did not have any effect on intestinal alpha-glucosidase (sucrase and maltase) in vitro. It was concluded that these steroidal alkaloid oligoglycosides, 1 and 3, inhibited the increase of rat serum glucose levels by suppressing the transfer of sucrose from the stomach to the small intestine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids* / chemistry
  • Alkaloids* / isolation & purification
  • Alkaloids* / pharmacology
  • Animals
  • Blood Glucose / drug effects
  • Brazil
  • Glycosides* / chemistry
  • Glycosides* / isolation & purification
  • Glycosides* / pharmacology
  • Hypoglycemic Agents* / chemistry
  • Hypoglycemic Agents* / isolation & purification
  • Hypoglycemic Agents* / pharmacology
  • Male
  • Mice
  • Mice, Inbred Strains
  • Molecular Structure
  • Plants, Medicinal / chemistry*
  • Rats
  • Rats, Wistar
  • Solanum / chemistry*
  • Steroids* / chemistry
  • Steroids* / isolation & purification
  • Steroids* / pharmacology
  • alpha-Glucosidases / drug effects

Substances

  • Alkaloids
  • Blood Glucose
  • Glycosides
  • Hypoglycemic Agents
  • Steroids
  • robeneoside A
  • robeneoside B
  • alpha-Glucosidases