Metabolism of lutein and zeaxanthin in rhesus monkeys: Identification of (3R,6′R)- and (3R,6′S)-3′-dehydro-lutein as common metabolites and comparison to humans

Gesa I. Albert, Ulrich Hoeller, Joseph Schierle, Martha Neuringer, Elizabeth J. Johnson, Wolfgang Schalch

    Research output: Contribution to journalArticle

    14 Citations (Scopus)

    Abstract

    Lutein and zeaxanthin are xanthophylls that can be found highly concentrated in the macula of the retina. They are thought to protect the macula through their role as blue-light filters and because of their antioxidant and singlet oxygen quenching properties. Examination of metabolites unique to lutein and zeaxanthin such as 3′-dehydro-lutein, and of their stereochemistry may provide insight to the mechanism by which they are formed and by which they exert protection. To evaluate the formation of such metabolites, eleven monkeys were raised on a xanthophyll-free diet, and supplemented with pure lutein or pure zeaxanthin (2.2 mg/kg body weight/d). The period of supplementation ranged between 12 and 92 weeks. At study start and throughout the study, serum samples were taken and analyzed for xanthophylls using different HPLC systems. Xanthophyll metabolites were identified using UV/VIS and HR-MS detection. Lutein and zeaxanthin metabolites were found in detectable amounts with 3′-dehydro-lutein being a common metabolite of both. Using chiral-phase HPLC, two diastereomers, (3R,6′R)-3′-dehydro-lutein and (3R,6′S)-3′-dehydro-lutein, were identified and shown to be present in nearly equimolar amounts. A pathway for their formation from either lutein or zeaxanthin is proposed. These findings were comparable to results obtained with human plasma.

    Original languageEnglish (US)
    Pages (from-to)70-78
    Number of pages9
    JournalComparative Biochemistry and Physiology - B Biochemistry and Molecular Biology
    Volume151
    Issue number1
    DOIs
    StatePublished - Sep 2008

    Fingerprint

    Lutein
    Metabolites
    Macaca mulatta
    Metabolism
    Xanthophylls
    High Pressure Liquid Chromatography
    Plasma (human)
    Zeaxanthins
    Singlet Oxygen
    Stereochemistry
    Optical filters
    Nutrition
    Haplorhini
    Retina
    Quenching
    Antioxidants
    Body Weight
    Diet
    Light

    Keywords

    • 3′-Dehydro-lutein
    • Chiral analysis
    • Human plasma
    • Lutein
    • Rhesus monkey serum
    • Serum metabolites
    • Zeaxanthin

    ASJC Scopus subject areas

    • Biochemistry
    • Physiology

    Cite this

    Metabolism of lutein and zeaxanthin in rhesus monkeys : Identification of (3R,6′R)- and (3R,6′S)-3′-dehydro-lutein as common metabolites and comparison to humans. / Albert, Gesa I.; Hoeller, Ulrich; Schierle, Joseph; Neuringer, Martha; Johnson, Elizabeth J.; Schalch, Wolfgang.

    In: Comparative Biochemistry and Physiology - B Biochemistry and Molecular Biology, Vol. 151, No. 1, 09.2008, p. 70-78.

    Research output: Contribution to journalArticle

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    abstract = "Lutein and zeaxanthin are xanthophylls that can be found highly concentrated in the macula of the retina. They are thought to protect the macula through their role as blue-light filters and because of their antioxidant and singlet oxygen quenching properties. Examination of metabolites unique to lutein and zeaxanthin such as 3′-dehydro-lutein, and of their stereochemistry may provide insight to the mechanism by which they are formed and by which they exert protection. To evaluate the formation of such metabolites, eleven monkeys were raised on a xanthophyll-free diet, and supplemented with pure lutein or pure zeaxanthin (2.2 mg/kg body weight/d). The period of supplementation ranged between 12 and 92 weeks. At study start and throughout the study, serum samples were taken and analyzed for xanthophylls using different HPLC systems. Xanthophyll metabolites were identified using UV/VIS and HR-MS detection. Lutein and zeaxanthin metabolites were found in detectable amounts with 3′-dehydro-lutein being a common metabolite of both. Using chiral-phase HPLC, two diastereomers, (3R,6′R)-3′-dehydro-lutein and (3R,6′S)-3′-dehydro-lutein, were identified and shown to be present in nearly equimolar amounts. A pathway for their formation from either lutein or zeaxanthin is proposed. These findings were comparable to results obtained with human plasma.",
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