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Exceptional molecular organization of canthaxanthin in lipid membranes

100%

Sujak A.

2012

vol. 59

issue 1

31-33

Canthaxanthin (β,β-carotene 4,4' dione) used widely as a drug or as a food and cosmetic colorant may have some undesirable effects on human health, caused mainly by the formation of crystals in the macula lutea membranes of the retina of an eye. Experiments show the exceptional molecular organization of canthaxanthin and a strong effect of this pigment on the physical properties of lipid membranes. The most striking difference between canthaxanthin and other macular pigments is that the effects of canthaxanthin at a molecular level are observed at much lower concentration of this pigment with respect to lipid (as low as 0.05 mol%). An analysis of the molecular interactions of canthaxanthin showed molecular mechanisms such as: strong van der Waals interactions between the canthaxanthin molecule and the acyl chains of lipids, restrictions to the segmental molecular motion of lipid molecules, modifications of the surface of the lipid membranes, effect on the membrane thermotropic properties and finally interactions based on the formation of the hydrogen bonds. Such interactions can lead to a destabilization of the membrane and loss of membrane compactness. In the case of the retinal vasculature, it can lead to an increase in the permeability of the retinal capillary walls and the development of retinopathy.

Synthesis of highly 13C enriched carotenoids: access to carotenoids enriched with 13C at any position and combination of positions

88%

Lugtenburg J., Dawadi P. B. S.

2012

vol. 59

issue 1

11-16

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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2 Acta Biochimica Polonica

2 2012

1 Dawadi P. B. S.

1 Lugtenburg J.

1 Sujak A.

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Exceptional molecular organization of canthaxanthin in lipid membranes

Synthesis of highly 13C enriched carotenoids: access to carotenoids enriched with 13C at any position and combination of positions