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,... 

In the egg yolk, zeaxanthin and lutein appear to be the primary carotenoids responsible for yellow color (Smith and Perdue, 1966 Schiedt et al, 1985 Schaeffer et al, 1988). Schaeffer et al. (1988) utilized HPLC analysis to reveal over 20 carotenoid species in the yolks of hens fed typical layer diets. Hamilton et al (1990) recently reported that the oleoresin of red pepper could be supplemented to laying hens to yield egg yolks with increased redness and yellowness. The three major pigments isolated were trans-lutein, trans-zeaxanthin and trans-capsanthin. The authors noted that the incorporation of small amounts of reddish capsanthin is advantageous for intensifying the yellow color of yolks. 

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... 

Aman, R., Schieber, A., and Carle, R., Effects of heating and illumination on trans-cis isomerization and degradation of (3-carotene and lutein in isolated spinach chlo-roplasts, J. Agric. Food Chem., 53, 9512, 2005. 

The National Institute of Standards and Technology (NIST) released certified standard materials of a baby food composite (SRM 2383) and an infant formula (SRM 1846) containing carotenoids however, the relative uncertainties of certified values are considerably high, ranging Irom 20% for P-carotene (cis + trans) to 28% for lutein (including esters) and to a 47% for free lutein reference value in SRM 2383. ... 

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... 

High, E. G. and H. G. Day (1951). Effects of different amounts of lutein, squalene, phytol and related substances on the utilization of carotene and vitamin A for storage and growth in the rat. J. Nutr. 43 245-260. Johnson, E. J. et al. (1997). Beta-carotene isomers in human serum, breast milk and buccal mucosa cells after continuous oral doses of -trans and 9-cis beta-carotene. J. Nutr. 127(10) 1993-1999. 

Carotenoids are a class of lipophilic compounds with a polyisoprenoid structure. Most carotenoids contain a series of conjugated double bonds, which are sensitive to oxidative modification and cis-trans isomerization. There are six major carotenoids (ji-carotenc, a-carotene, lycopene, P-cryptoxanthin, lutein, and zeaxanthin) that can be routinely found in human plasma and tissues. Among them, p-carotene has been the most extensively studied. More recently, lycopene has attracted considerable attention due to its association with a decreased risk of certain chronic diseases, including cancers. Considerable efforts have been expended in order to identify its biological and physiochemical properties. Relative to P-carotene, lycopene has the same molecular mass and chemical formula, yet lycopene is an open-polyene chain lacking the P-ionone ring structure. While the metabolism of P-carotene has been extensively studied, the metabolism of lycopene remains poorly understood. 

Fig. 6. Comparison of different action-and absorption spectra of (1) lactat oxidase1 1U, (2) 0-cis carotene183), (3) ft-trans carotene183), (4) lutein in ethanol/ water76). (5) same action spectrum as in Fig. 3 5...

Another study employed both TLC and HPLC for the analysis of carotenoids of Calendula officinalis L. TLC separation of all E(trans)-a,3-carotene, cryptoxanthin, zeaxanthin and lutein was performed on a silica layer using petroleum ether-j-propanol-CIICI, (90 10 70 v/v). The same carotenoid pigments were separated by RP-HPLC using an ODS column (250X4 mm, i.d.). The organic modifiers were methanol, THF and ethyl octane. The flow rate was 1 ml/min, pigments were detected at 440 nm [20],... 

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].

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