Selligueain A, a novel highly sweet proanthocyanidin from the rhizomes of Selliguea feei.
Selligueain A, a novel sweet trimeric proanthocyanidin with a doubly linked A unit, has been isolated from the rhizomes of Selliguea feei collected in Indonesia. The structure of this substance was established as epiafzelechin-(4 beta-->8, 2 beta-->O-->7)-epiafzelechin-(4 beta-->8)-afzelechin [1], on the basis of a combination of spectral and chemical methods. The compound was not acutely toxic for mice and not mutagenic in a forward mutation assay utilizing Salmonella typhimurium strain TM677. Selligueain A [1] was rated by a taste panel as exhibiting about 35 times the sweetness intensity of a 2% w/v aqueous sucrose solution, and at a concentration of 0.5% w/v in H2O was perceived as pleasant-tasting rather than astringent.
Baek
N I
NI
Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago 60612.
Chung
M S
MS
Shamon
L
L
Kardono
L B
LB
Tsauri
S
S
Padmawinata
K
K
Pezzuto
J M
JM
Soejarto
D D
DD
Kinghorn
A D
AD
D000818:Animals; D000872:Anthocyanins / Q000009:adverse effects / Q000302:isolation & purification* / Q000494:pharmacology / Q000633:toxicity; D006801:Humans; D007214:Indonesia; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051379:Mice; D009152:Mutagenicity Tests; D010946:Plants, Medicinal / Q000737:chemistry*; D044945:Proanthocyanidins; D012486:Salmonella typhimurium / Q000187:drug effects / Q000235:genetics; D013549:Sweetening Agents / Q000302:isolation & purification* / Q000494:pharmacology / Q000633:toxicity; D013649:Taste / Q000187:drug effects
D000872:Anthocyanins; D044945:Proanthocyanidins; D013549:Sweetening Agents; C084699:selligueain A; C013221:proanthocyanidin