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 H-1 and C-13 NMR and UV-vis spectroscopies and mass spectrometry. The following compounds were found in saffron: all-trans-crocetin di(beta-D-gentiobiosyl) ester la, all-trans-crocetin beta-D-gentiobiosyl-beta-D-glucosyl ester Ib, all-trans-crocetin di(beta-D-glucosyl) ester Ic, and all-trans-crocetin mono(beta-D-gentiobiosyl) ester Id, as well as 13-cis-crocetin di(beta-D-gentiobiosyl) ester 2a and 13-cis-crocetin beta-D-gentiobiosyl-beta-D-glucosyl ester 2b. Compounds la, Ib, and Id were also present in gardenia, in addition to all-trans-crocetin mono(beta-D-glucosyl) ester le.