Spectroscopic Characterization of Crocetin Derivatives from Crocus sativus and Gardenia jasminoides

Crocetin derivatives were extracted and purified from saffron stigmas and gardenia fruits by reversed-phase HPLC. They were characterized by 1D and 2D 1H and 13C 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