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EN
Lateral organization of membranes made from binary mixtures of dimyristoylphosphatidylcholine (DMPC) or dipalmitoylphosphatidylcholine (DPPC) and macular xanthophylls (lutein or zeaxanthin) was investigated using the saturation-recovery (SR) EPR spin-labeling discrimination by oxygen transport (DOT) method in which the bimolecular collision rate of molecular oxygen with the nitroxide spin label is measured. This work was undertaken to examine whether or not lutein and zeaxanthin, macular xanthophylls that parallel cholesterol in its function as a regulator of both membrane fluidity and hydrophobicity, can parallel other structural functions of cholesterol, including formation of the liquid-ordered phase in membranes. The DOT method permits discrimination of different membrane phases when the collision rates (oxygen transport parameter) differ in these phases. Additionally, membrane phases can be characterized by the oxygen transport parameter in situ without the need for separation, which provides information about the dynamics of each phase. In gel-phase membranes, two coexisting phases were discriminated in the presence of macular xanthophylls - namely, the liquid-ordered-like and solid-ordered-like phases. However, in fluid-phase membranes, xanthophylls only induce the solitary liquid-ordered-like phase, while at similar concentrations, cholesterol induces coexisting liquid-ordered and liquid-disordered phases. No significant differences between the effects of lutein and zeaxanthin were found.
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2012
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vol. 59
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issue 1
11-16
EN
Carotenoids and their metabolites are essential factors for the maintenance of important life processes such as photosynthesis. Animals cannot synthesize carotenoids de novo, they must obtain them via their food. In order to make intensive animal husbandry possible and maintain human and animal health synthetic nature identical carotenoids are presently commercially available at the multi-tonnes scale per year. Synthetically accessible 13C enriched carotenoids are essential to apply isotope sensitive techniques to obtain information at the atomic level without perturbation about the role of carotenoids in photosynthesis, nutrition, vision, animal development, etc. Simple highly 13C enriched C1, C2 and C3 building blocks are commercially available via 99% 13CO. The synthetic routes for the preparation of the 13C enriched building blocks starting from the commercially available systems are discussed first. Then, how these building blocks are used for the synthesis of the various 13C enriched carotenoids and apocarotenoids are reviewed next. The synthetic Schemes that resulted in 13C enriched β-carotene, spheroidene, β-cryptoxanthin, canthaxanthin, astaxanthin, (3R,3'R)-zeaxanthin and (3R,3'R,6'R)-lutein are described. The Schemes that are reviewed can also be used to synthetically access any carotenoid and apocarotenoid in any 13C isotopically enriched form up to the unitarily enriched form.
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