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The Difference of Lutein and Zeaxanthin

Lutein and zeaxanthin are relatively polar carotenoid pigments found at high levels in parsley, spinach, kale, egg yolk and lutein-fortified foods. They have demonstrated several beneficial health effects due to their ability to act as scavengers for reactive oxygen species and to bind with physiological proteins in humans. In general, carotenoids are tetra-terpenoid having 40 carbon skeleton made up of 8 isoprene units and comprise of two classes, namely carotenes (purely unsaturated hydrocarbons) and carotenoids with oxygen atoms which are referred to as oxygenated carotenoids or xanthophyll carotenoids. The macular carotenoids are dietary lutein and zeaxanthin, and their conversion isomer meso-zeaxanthin, which are non-provitamin A carotenoids, (i.e., it cannot be converted into vitamin A).

Important members of oxygenated carotenoids are lutein, zeaxanthin, β-cryptoxanthin, capsanthin, astaxanthin, and fucoxanthin. Figure 1 lists the chemical structure of the macular pigments found in the retina. It is estimated that about 90% of the total carotenoids in North American diets consist of lycopene, β-carotene, α-carotene, lutein, β-cryptoxanthin and zeaxanthin. In nature more than 600 carotenoids have been isolated and characterized, yet only about 40 carotenoids have been detected in human milk, serum and tissues.

Percentage of main carotenoids inhuman serum is lutein (20%), lycopene (20%), β-carotene (10%); β-cryptoxanthin (8%), α-carotene (6%) and zeaxanthin (3%). Lutein and zeaxanthin are the main dietary carotenoids found in human retina and they protect the macula from damage by blue light, improve visual acuity and scavenge harmful reactive oxygen. Lutein and zeaxanthin along with their common metabolite meso-zeaxanthin, commonly referred to as macular pigments (MP). The ratio between lutein, zeaxanthin and meso-zeaxanthin changes as the eccentricity moves away from fovea. Although lutein and zeaxanthin were also detected in prenatal eyes, they did not form visible yellow spot.

No age-related (between the ages of 3 and 95 years) differences were observed in the quantity of lutein and zeaxanthin. But, the ratio of lutein to zeaxanthin differed between infants and adults. In infants, lutein predominates over zeaxanthin in fovea, and the opposite is true after 3 years of age. Structurally the difference between lutein and zeaxanthin is in the type of ionone ring, lutein contains a β-ionone ring and a ε-ionone ring, whereas zeaxanthin has two β-ionone rings. Lutein and zeaxanthin are isomers, but not stereoisomers, which differ in the location of a double bond unsaturation in the end ring. Lutein can exist in possible eight stereoisomeric forms because of three chiral centers, but in nature it exists mainly in Z (cis)-form (R,R,R). Zeaxanthin, on the other hand, has two chiral centers but, because of symmetry exists only in 3-stereoisomeric forms (R,R), (S,S) and (R,S-meso)

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