August 1997
Volume 38, Issue 9
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Articles  |   August 1997
Identification of lutein and zeaxanthin oxidation products in human and monkey retinas.
Author Affiliations
  • F Khachik
    Beltsville Human Nutrition Research Center, Carotenoids Research Unit, US Department of Agriculture, Beltsville, Maryland 20705, USA.
  • P S Bernstein
    Beltsville Human Nutrition Research Center, Carotenoids Research Unit, US Department of Agriculture, Beltsville, Maryland 20705, USA.
  • D L Garland
    Beltsville Human Nutrition Research Center, Carotenoids Research Unit, US Department of Agriculture, Beltsville, Maryland 20705, USA.
Investigative Ophthalmology & Visual Science August 1997, Vol.38, 1802-1811. doi:
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    • Get Citation

      F Khachik, P S Bernstein, D L Garland; Identification of lutein and zeaxanthin oxidation products in human and monkey retinas.. Invest. Ophthalmol. Vis. Sci. 1997;38(9):1802-1811.

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Abstract

PURPOSE: To characterize fully all the major and minor carotenoids and their metabolites in human retina and probe for the presence of the oxidative metabolites of lutein and zeaxanthin. METHODS: Carotenoids of a composite of 58 pairs of human retinas and a monkey retina were elucidated by comparing their high-performance liquid chromatography (HPLC)-ultraviolet/visible absorption spectrophotometry (UV/Vis)-mass spectrometry (MS) profile with those of authentic standards prepared by organic synthesis. RESULTS: In addition to lutein and zeaxanthin, several oxidation products of these compounds were present in the extracts from human retina. A major carotenoid resulting from direct oxidation of lutein was identified as 3-hydroxy-beta, epsilon-caroten-3'-one. Minor carotenoids were identified as: 3'-epilutein, epsilon,epsilon-carotene-3,3'-diol, epsilon,epsilon-carotene-3,3'-dione, 3'-hydroxy-epsilon,epsilon-caroten-3-one, and 2,6-cyclolycopene-1,5-diol. Several of the geometric isomers of lutein and zeaxanthin were also detected at low concentrations. These were as follows: 9-cis-lutein, 9'-cislutein, 13-cis-lutein, 13'-cis-lutein, 9-cis-zeaxanthin, and 13-cis-zeaxanthin. Similar results were also obtained from HPLC analysis of a freshly dissected monkey retina. CONCLUSIONS: Lutein, zeaxanthin, 3'-epilutein, and 3-hydroxy-beta,epsilon-caroten-3'-one in human retina may be interconverted through a series of oxidation-reduction reactions similar to our earlier proposed metabolic transformation of these compounds in humans. The presence of the direct oxidation product of lutein and 3'-epilutein (metabolite of lutein and zeaxanthin) in human retina suggests that lutein and zeaxanthin may act as antioxidants to protect the macula against short-wavelength visible light. The proposed oxidative-reductive pathways for lutein and zeaxanthin in human retina, may therefore play an important role in prevention of age-related macular degeneration and cataracts.

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