Identification of lutein and zeaxanthin oxidation products in human and monkey retinas.
OBJECTIVE
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.
Khachik
F
F
Beltsville Human Nutrition Research Center, Carotenoids Research Unit, US Department of Agriculture, Beltsville, Maryland 20705, USA.
Bernstein
P S
PS
Garland
D L
DL
D000818:Animals; D002851:Chromatography, High Pressure Liquid; D006801:Humans; D014975:Lutein / Q000031:analogs & derivatives / Q000032:analysis*; D008253:Macaca mulatta; D013058:Mass Spectrometry; D010084:Oxidation-Reduction; D012160:Retina / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D024341:Xanthophylls; D065146:Zeaxanthins; D019207:beta Carotene / Q000031:analogs & derivatives* / Q000032:analysis
D024341:Xanthophylls; D065146:Zeaxanthins; D019207:beta Carotene; D014975:Lutein