Identification of Novel Glycosidic Aroma Precursors in Saffron ( Crocus s ativus L.)

The methanolic extract of saffron was separated with the aid of multilayer coil countercurrent chromatography. After purification by HPLC, the following seven novel carotenoid metabolites were identified on the basis of their spectral (UV, FTIR, MS, NMR, CD) data: (4 R )-4-hydroxy-2,6,6-trimethylcyclohex-1-enecarbaldehyde O -β- d -gentiobioside ( 1 ), (4 R )-4-hydroxy-2,6,6-trimethylcyclohex-1-enecarboxylic acid O -β- d -glucopyranoside ( 2 ), 6-hydroxy-3-(hydroxymethyl)-2,4,4-trimethylcyclohexa-2,5-dienone 6- O -β- d -glucopyranoside ( 3 ), (2 Z )-3-methylpent-2-enedioic acid 1-[1-(2,4,4-trimethyl-3,6-dioxocyclohexenyloxy)- O -β- d -glucopyranosid-6-yl] ester ( 4 ), (5 S )-5-hydroxy-7,7-dimethyl-4,5,6,7-tetrahydro-3 H -isobenzofuran-1-one O -β- d -glucopyranoside ( 5 ), (1 R,5 S,6 R )-5-(hydroxymethyl)-4,4,6-trimethyl-7-oxabicyclo[4.1.0]heptan-2-one O -β- d -glucopyranoside ( 6 ), and (1 R )- 3,5,5-trimethylcyclohex-3-enol O -β- d -glucopyranoside ( 7 ).