From a methanolic extract of raspberry fruits, the β-D-glucopyranoside of 3-(3′-hydroxy-1′-butenyl)-2,4,4-trimethyl-2-cyclohexen-1-one (4-oxo-β-ionol) as well as the α-L-arabinofuranosyl-(1→6)-β-D-glucopyranoside of (S)-(+)-1-ethenyl-1,5-dimethyl-4-hexene [(S)-(+)-linalool] were isolated by adsorption chromatography on XAD-2 resin followed by liquid chromatography on Sephadex LH-20, RP-18 and silica gel as well as by HPLC on diol, RP-18 and RP-select 8 phases, respectively. Identifications were based on results of 1H and 13C NMR spectroscopy and DCI-mass spectral analysis. Absolute configuration of bound linalool was determined by direct chiral analysis using MDGC-mass spectrometry after enzymatic hydrolysis of the glycoside.
4, rosaceae, Rubus idaeus, raspberry fruit, 4-oxo-β-ionol β-D-glucopyranoside, 3-[3′-(β-D-glucopyranosyloxy)-1′-butenyl]-2, 4-trimethyl-2-cyclohexen-1-one, linalool disaccharide glycoside, 1-ethenyl-1, 5-dimethyl-4-hexenyl 6-O-α-L-arabinofuranosyl-β-D-glucopyranoside
Publication DOI: 10.1016/0031-9422(92)80440-PJournal NLM ID: 0151434Publisher: Elsevier
Institutions: Lehrstuhl für Lebensmittelchemie, Universität Würzburg, Am Hubland, 8700 Würzburg, Germany, Laboratoire de Pharmacognosie, Université Joseph Fourier-Grenoble I, UFR de Pharmacie, 38706 La Tronche, France, Laboratoire de Recherche sur les Arômes, INRA, BP 1540, 21034 Dijon Cédex, France
Methods: 13C NMR, 1H NMR, GC-MS, TLC, enzymatic hydrolysis, HPLC, UV, acetylation, DCI-MS, COSY, MPLC
Found