Identification and Quantification of All-Trans-Zeaxanthin and Its Cis-Isomers During Illumination in a Model System

Figures & data

FIGURE 1 HPLC chromatogram of all-trans-zeaxanthin and its cis-isomers; (a) HPLC chromatogram of all-trans-zeaxanthin and its cis-isomers obtained from iodine-catalyzed illumination at 450 nm; (b) Absorption spectrum of all-trans-zeaxanthin and its cis-isomers.

TABLE 1 Identification data for all-trans and cis-form of zeaxanthin

Peak	Compound	λ (nm)^a	λ (nm) (reported)	Q-ratio^a	Q-ratio (reported)	MS/MS (m/z)^a
1	13,15-di-cis	338,418,439,460		0.08		569.4[M+H]^+
2	9,15-di-cis	338,414,439,464		0.07		569.4[M+H]^+ 551.4[M+H-18]^+
3	9,13-di-cis	336,416,440,466		0.18		569.4[M+H]^+, 551.4[M+H-18]^+
4	15/15’-cis	337,421,445,472	338,422,446,47^b	0.29		569.4[M+H]^+, 551.4[M+H-18]^+
5	13/13’-cis	336,421,444,468	338,424,446,47^b	0.47	0.49^b	569.4[M+H]^+, 551.4[M+H-18]^+
6	All-trans	428,450,478	450,476^b			569.4[M+H]^+, 551.4[M+H-18]^+
7	9,9’-di-cis	336,418,440,464		0.06		569.4[M+H]^+, 551.4[M+H-18]^+
8	9/9’-cis	340,422,446,468	338,422,446,47^b	0.11	0.14^b	569.4[M+H]^+, 551.4[M+H-18]^+

^aA gradient mobile phase of MeOH-MTBE-water (80:15:5, v/v/v) and MeOH-MTBE (1:10, v/v); ^bA gradient mobile phase of MTBE-MeOH-water. Values in bold face represent the main maximum.^[18]

FIGURE 2 The chemical structures of all-trans-zeaxanthin and its cis-isomers.

FIGURE 3 Iodine-catalyzed illumination of all-trans-zeaxanthin; (a) Concentration changes of all-trans-zeaxanthin and its cis-isomers during iodine-catalyzed illumination for the indicated time periods; (b) First-order plot for the degradation of total all-trans-zeaxanthin during iodine-catalyzed illumination; (c) Concentration changes of cis-isomers derived from all-trans-zeaxanthin during iodine-catalyzed illumination for the indicated time periods.

FIGURE 4 Illumination of all-trans-zeaxanthin; (a) Concentration changes of all-trans-zeaxanthin and its cis-isomers during illumination without iodine as catalyst for the indicated time periods; (b) First-order plot for the degradation of total all-trans-zeaxanthin during non-iodine-catalyzed illumination; (c) Concentration changes of cis-isomers derived from all-trans-zeaxanthin during non-iodine-catalyzed illumination for the indicated time periods.

Aman, R.; Biehl, J.; Carle, R.; Conrad, J.; Beifuss, U.; Schieber, A. Application of HPLC Coupled with DAD, APcI-MS and NMR to the Analysis of Lutein and Zeaxanthin Stereoisomers in Thermally Processed Vegetables. Food Chemistry 2005, 92, 753–763.

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