4-OXO-β-IONOL AND LINALOOL GLYCOSIDES FROM RASPBERRY FRUITS

Article abstract of DOI:10.1016/0031-9422(92)80440-P

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.Identification were based on results of (1)H and (13)C 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. Key words: Rubus idaeus; Rosaceae; raspberry fruit; 4-oxo-β-ionol β-D-glucopyranoside; 3-<3'-(β-D-glucopyranosyloxy)-1'-butenyl>-2,4,4-trimethyl-2-cyclohexen-1-one; linalool disaccharide glycoside; 1-ethenyl-1,5-dimethyl-4-hexenyl 6-O-α-L-arabinofuranosyl-β-D-glucopyranoside.