Spectroscopic Characterization of Crocetin Derivatives from <i>Crocus sativus</i> and <i>Gardenia </i><i>jasminoides</i>

Abstract

Crocetin derivatives were extracted and purified from saffron stigmas and gardenia fruits by reversed-phase HPLC. They were characterized by 1D and 2D 1 H and 13 C NMR and UV−vis spectroscopies and mass spectrometry. The following compounds were found in saffron: all - trans -crocetin di(β- d -gentiobiosyl) ester 1a, all - trans -crocetin β- d -gentiobiosyl-β- d -glucosyl ester 1b, all - trans -crocetin di(β- d -glucosyl) ester 1c, and all - trans -crocetin mono(β- d -gentiobiosyl) ester 1d, as well as 13- cis -crocetin di(β- d -gentiobiosyl) ester 2a and 13- cis -crocetin β- d -gentiobiosyl-β- d -glucosyl ester 2b . Compounds 1a, 1b, and 1d were also present in gardenia, in addition to all - trans -crocetin mono(β- d -glucosyl) ester 1e . Keywords: Saffron; gardenia; Crocus sativus; Gardenia jasminoides; crocetin derivatives; carotenoid pigments; mass spectrometry; UV − vis spectroscopy; NMR spectroscopy