Isolation and structure elucidation of a new thermal breakdown product of glucobrassicin, the parent indole glucosinolate.
The thermal breakdown of glucobrassicin, the major natural indole glucosinolate present in cruciferous vegetables, has been studied. This study has been conducted using pure synthetic glucobrassicin instead of raw vegetable material to eliminate possible other sources (i.e., enzymatic or chemical) of degradation. After 1 h in aqueous solution at 100 degrees C, 10% of the original glucobrassicin is degraded and yields a unique degradation compound. This compound is described for the first time and has been identified as 2-(3'-indolylmethyl)glucobrassicin on the basis of data obtained by (1)H nuclear magnetic resonance spectroscopy as well as tandem mass spectrometric experiments carried out from positive and negative electrospray produced ions.
INRA, UMR 1089 Xénobiotiques, INRA-ENVT-INP/ENSAT, 180 chemin de Tournefeuille, B.P. 3, 31931 Toulouse Cedex 9, France. schevoll@toulouse.inra.fr
Sylvie
S
Chevolleau
Laurent
L
Debrauwer
Gérard
G
Boyer
Jacques
J
Tulliez
D002851:Chromatography, High Pressure Liquid; D005961:Glucosinolates / Q000737:chemistry*; D006358:Hot Temperature; D007211:Indoles; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D021241:Spectrometry, Mass, Electrospray Ionization
D005961:Glucosinolates; D007211:Indoles; C048308:glucobrassicin