Abrusosides A-D, four novel sweet-tasting triterpene glycosides from the leaves of Abrus precatorius

J Nat Prod. 1989 Sep-Oct;52(5):1118-27. doi: 10.1021/np50065a032.

Abstract

In addition to abrusoside A [1], abrusosides B [2], C [3], and D [4], three further sweet glycosides based on the novel cycloartane-type aglycone, abrusogenin [5], were isolated from an n-BuOH-soluble extract of the leaves of Abrus precatorius. Using a combination of spectral methods, the structures of compounds 1-4 were assigned, respectively, as the 3-O-beta-D-glucopyranosyl, the 3-O-beta-D-glucopyranosyl-(1----2)-beta-D-6-methylglucuronopyranosyl+ ++, the 3-O-beta-D-glucopyranosyl-(1----2)-beta-D-glucopyranosyl, and the 3-O-beta-D-glucopyranosyl-(1----2)-beta-D-glucuronopyranosyl derivatives of compound 5. After it established that compounds 1-4 were neither acutely toxic with mice nor mutagenic with Salmonella typhimurium strain TM677, they were found by a human taste panel to exhibit sweetness potencies in the range 30-100 times greater than sucrose.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Carbohydrate Sequence
  • Glycosides / isolation & purification
  • Glycosides / pharmacology*
  • Glycosides / toxicity
  • Magnetic Resonance Spectroscopy
  • Male
  • Mice
  • Molecular Sequence Data
  • Mutagenicity Tests
  • Plants / analysis*
  • Salmonella typhimurium / drug effects
  • Sweetening Agents / isolation & purification*
  • Sweetening Agents / toxicity
  • Triterpenes / isolation & purification
  • Triterpenes / pharmacology*
  • Triterpenes / toxicity

Substances

  • Glycosides
  • Sweetening Agents
  • Triterpenes