Novel Glycosidic Constituents from Saffron

Abstract

The methanolic extract of saffron was prefractionated with the aid of multilayer coil countercurrent chromatography (MLCCC). After subsequent purification of certain fractions by high-performance liquid chromatography, the following glycoconjugates were isolated and identified on the basis of their spectral (UV, MS, NMR) data: the β- d -glucosides of (4 R )-4-hydroxy-3,5,5-trimethylcyclohex-2-enone ( 5), (4 S )-4-hydroxy-3,5,5-trimethylcyclohex-2-enone (6), and (4 S )-4-(hydroxymethyl)-3,5,5-trimethylcyclohex-2-enone ( 7), as well as the β- d -gentiobiosyl ester of 2-methyl-6-oxohepta-2,4-dienoic acid ( 4) . In addition to these new natural products, known saffron constituents, i.e., the di-β- d -gentiobiosyl and β- d -gentiobiosyl-β- d -glucopyranosyl esters of crocetin, have also been isolated and separated using MLCCC. Keywords: (4 R )-4-Hydroxy-3,5,5-trimethylcyclohex-2-enone 4- O -β- d -glucopyranoside; (4 S )-4-hydroxy-3,5,5-trimethylcyclohex-2-enone 4- O -β- d -glucopyranoside; (4 S )-4-(hydroxymethyl)-3,5,5-trimethylcyclohex-2-enone 4- O -β- d -glucopyranoside; β- d -gentiobiosyl ester of 2-methyl-6-oxohepta-2,4-dienoic acid; crocetin derivatives; carotenoid degradation products; multilayer coil countercurrent chromatography; saffron; Crocus sativus; Iridaceae