All-trans-lutein

After illumination for 60 min with fluorescent lamps with total intensity of 3750 lux at 20°C, degradation rates of all-trans P-carotene and all-trans lutein, both dissolved in toluene, were very similar 21%, accompanied by only marginally increasing in the levels of cis isomers of P-carotene and lutein. On the other hand. 

Fig. 2.16. HPLC profile of carotenoids in an extract of vegetable soup. An expansion of the profile from 30 to 39 is shown in the inset (A). Monitored wavelengths were 436, 440, 464, and 409 nm for peaks 9,10,11,12, and 14, respectively, in the inset (A). Peak identification 1 + 1" = all-trans-lutein and cw-lutein 2 = 5,6-dihydroxy-5,6-dihydrolycopene (lycopene-5,6-diol) 3 = j3-apo-8 -carotenal (internal standard) 4 = lycopene 1,2-epoxide 5 = lycopene 5,6-epoxide 6 = 1,2-dimethoxyproly-copene (tentative identification) 7 = 5,6-dimethoxy-5,6-dihydrolycopene 8 = lycopene 9 = pheo-phytin b 10 = neurosporene 11 = (-carotene 12 = pheophytin a 13 = (-carotene 14 = pheophytin a isomer and (-carotene 15 = a-carotene 16 and 16" = all-trans-/fcarotene, cis-/J-carotene 17 and 17" = all-trans- or cA-phytofluene 18 and 18" = all-trans- or cw-phytoene. Reprinted with permisson from L. H. Tonucci et al. [40].

Fig. 11 HPLC of carotenoids solvent-extracted from (A) raw and (B) thermally processed carrots. Column, 5-/um polymeric C1(J (250 X 4.6-mm ID) mobile phase, methyl tert-butyl ether/methanol (11 89), 1 ml/min absorbance detection, 453 nm. Tentative peak identifications (1) all-trans-lutein (2) 13-cis-a-carotene (3) a cis-a-carotene isomer (4) 13 -cA-a-carotene (5) 15-cis-/3-carotene (6) 13-cis-/3-carotene (7 and 8) cis-fi-carotene isomers (9) all-frans-a-carotene (10) 9-cis-a-carotene (11) all-frans-/3-carotene (12) 9-ci. -/3-carotene. (Reprinted with permission from Ref. 192. Copyright 1996, American Chemical Society.)...

A C30 column can be used to distinguish between all-trans -lutein and all-tra 5-zeaxanthin and their cis isomers (Updike and Schwartz, 2003), P-carotene and P-carotene cis isomers (Emenhiser et al., 1995), and lycopene and cA-lycopene isomers (Frohlich et al., 2007). C30 columns can allow the separation of isomers induced by heat processing (Figure 4.4) and induced in vivo (Figure 4.5). Extensive reviews on... 

Bo-Xan p,c-Carotene-3,3 -diol p,s-Carotene-3,3-diol, (3R,3 R,6 R)- EINECS 204-840-0 Lutein all-trans-Lutein Lutein, ali-trans- Lutein ester Luteine NSC 59193 Vegetable lutein Vegetable luteol Xanthophyll all-trans-(-r)-Xanthophyll Xanthophyll, all-trans-(+)-. The yellow pigment occurring in green vegetafon and some animal products. Yellow or violet prisms mp = 196° [af D = 160° (c = 0.7, CHCI3) Xm = 340, 457, 488 nm (e = 6607, 123027, 112202, CsHs) insoluble in H2O, very soluble in CeHs, EtOH, EtaO,... 

First, among these results, the content of lutein (all trans-lutein, 6)in total xanthophylls was most abundant, followed by violaxanthin (8), 9"-cis-violaxanthin (64) and 9 -c/s-neoxanthin (67, lutein-5,6-epoxide (lutein epoxide, 61), and others. Interestingly, on their percentage on the enzymatic conversion of lutein (all trans-lutein, 6)to lutein-5,6-epoxide (lutein epoxide, 61), Abbot 9.3% was more efficient, followed by Monty, Heyward and Bruno, respectively. 

Second, a-carotene (1) could not be found in these four kiwifruit cultivars. The absence of a-carotene (1) could be suggested as follows this reason might come the reactivity for the formation of 3-hydroxycyclic carotenoids and epoxy carotenoids. Therefore, the absence of a-carotene (1) in four kiwifruit cultivars might be related to the complete conversion to lutein (all trans-lutein, 6) (Table 6) [32]. 

Third, additionally, the existence of abundant 9 -czs-neoxanthin (67) might be associated with violaxanthin (8) and lutein (all trans-lutein, 6). Therefore, the differences between their rates of neoxanthin (7), violaxanthin... 

Both MS and NMR coupling to HPLC have been employed for the analysis of p-carotene isomers and determination of lutein and zeaxanthin isomers in spinach, sweet com, and in retina. Capillary high performance hquid chromatography with stop flow connected to NMR (600 MHz) was used for stracture elucidation of all-trans deoxylutein 11 and its isomers.Efforts are in progress to eliminate the remaining major drawbacks such as obligatory use of deuterated solvents in the mobile phase, poor sensitivity, and low throughput of HPLC-NMR analyses. 

All-trans p-carotene 13-cis p-Carotene 9-cis p-Carotene a-Carotene Lutein Lycopene... 

Fig. 2.24. C30 chromatograms of carotenoids extracted from human serum (a) xanthophylls fraction, 7 93 (v/v) MTBE-methanol mobile phase (b) a- and / -carotenes fraction, 11 89 (v/v) MTBE-methanol mobile phase (c) lycopene fraction, 38 62 (v/v) MTBE-methanol mobile phase. Tentative peak identifications (a) 1, 13-c/s-lu- lutein 2, 13 r/.vlutein 3, a//-/ra s-lutein 4, zeaan-thin 5-7, unidentified P,e-carotenoids and 8, / -cyrptoanthin (b) 1-2, unidentified ae-carotene isomers 3, 15-eH -/f-carotenc 4, 13-cw-/ -carotene 5, all-trans-a-carotene 6, all-trans-P-carotene and 7, 9-ci.v-/3-carotene and (c) 1-11 and 13, c/s-lycopene isomers and 12, all-trans-lycopene. Reprinted with permission from C. Emenhiser el al. [51].

T, y-T, a-T, p-cryptoxanthin, lycopene, a-carotene, p-carotene, all trans retinol, 5-T3, y-T3, a-T3, lutein, zeaxanthin (27 min)... 

Table 3 shows that the ratio ofthe intensity ofthe Aj Ay band to the Ay -4 B band increases in the order from the all-trans isomer < peripheral-cts isomer < central-c/s isomer for all the carotenoids except for lutein and p-apo-S -carotenal. In these exceptions, however, the difference between the values is small. The wavelength ofthe A -4 (0-0) absorption is in... 

Two essential carotenoids, lutein and zeaxanthin, play an important role in the visual process. For the treatment of age-related macular degeneration (AMD), knowledge of the isomeric composition within the macula is of particular interest [7], Full assignment of isomeric configuration is possible by the registration of two-dimensional proton-proton correlated NMR spectra. Figure 7-7 shows, as an example, the COSY stopped-flow NMR spectrum of all-trans zeaxanthin isolated from ox retina. 

Nuclear Overhauser effects 142) of appropriate model compounds were studied for assignment of the all-trans configuration of the polyene chain of eschscholtzxanthin (27) 8) and for identification of the H-7 and H-8 signals of the furanoxides flavoxanthin and crysanthemaxanthin 46 a) derived from lutein epoxide (46). 

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