Abrusosides A-D, four novel sweet-tasting triterpene glycosides from the leaves of Abrus precatorius.
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.
Choi
Y H
YH
Program for Collaborative Research in the Pharmaceutical Sciences, University of Illinois, Chicago 60612.
Hussain
R A
RA
Pezzuto
J M
JM
Kinghorn
A D
AD
Morton
J F
JF
D000818:Animals; D002240:Carbohydrate Sequence; D006027:Glycosides / Q000302:isolation & purification / Q000494:pharmacology* / Q000633:toxicity; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051379:Mice; D008969:Molecular Sequence Data; D009152:Mutagenicity Tests; D010944:Plants / Q000032:analysis*; D012486:Salmonella typhimurium / Q000187:drug effects; D013549:Sweetening Agents / Q000302:isolation & purification* / Q000633:toxicity; D014315:Triterpenes / Q000302:isolation & purification / Q000494:pharmacology* / Q000633:toxicity
D006027:Glycosides; D013549:Sweetening Agents; D014315:Triterpenes