3,3′-Dihydroxyisorenieratene, a Natural Carotenoid with Superior Antioxidant and Photoprotective Properties

Authors

  • Hans-Dieter Martin Prof.,

    1. Institute of Organic Chemistry and Macromolecular Chemistry, Natural Compounds, and Photoprotection, Heinrich-Heine-University Düsseldorf, Universitätsstrasse 1, 40225 Düsseldorf (Germany), Fax: (+49) 211-811-4324
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  • Sebastian Kock Dr.,

    1. Institute of Organic Chemistry and Macromolecular Chemistry, Natural Compounds, and Photoprotection, Heinrich-Heine-University Düsseldorf, Universitätsstrasse 1, 40225 Düsseldorf (Germany), Fax: (+49) 211-811-4324
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  • Roger Scherrers Dr.,

    1. Institute of Organic Chemistry and Macromolecular Chemistry, Natural Compounds, and Photoprotection, Heinrich-Heine-University Düsseldorf, Universitätsstrasse 1, 40225 Düsseldorf (Germany), Fax: (+49) 211-811-4324
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  • Kaya Lutter,

    1. Institute of Biochemistry and Molecular Biology I, Heinrich-Heine-University Düsseldorf, Universitätsstrasse 1, 40225 Düsseldorf (Germany)
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  • Tanja Wagener,

    1. Institute of Biochemistry and Molecular Biology I, Heinrich-Heine-University Düsseldorf, Universitätsstrasse 1, 40225 Düsseldorf (Germany)
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  • Claas Hundsdörfer,

    1. Institute of Organic Chemistry and Macromolecular Chemistry, Natural Compounds, and Photoprotection, Heinrich-Heine-University Düsseldorf, Universitätsstrasse 1, 40225 Düsseldorf (Germany), Fax: (+49) 211-811-4324
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  • Susanne Frixel Dr.,

    1. Institute of Organic Chemistry and Macromolecular Chemistry, Natural Compounds, and Photoprotection, Heinrich-Heine-University Düsseldorf, Universitätsstrasse 1, 40225 Düsseldorf (Germany), Fax: (+49) 211-811-4324
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  • Klaus Schaper Dr.,

    1. Institute of Organic Chemistry and Macromolecular Chemistry, Organic Photochemistry, Heinrich-Heine-University Düsseldorf
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  • Hansgeorg Ernst Dr.,

    1. GVF/A, BASF SE, 67056 Ludwigshafen (Germany)
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  • Wolfgang Schrader Dr.,

    1. Max-Planck-Institut für Kohlenforschung, 45470 Mülheim an der Ruhr (Germany)
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  • Helmut Görner Dr.,

    1. Biophysicalische Chemie, Max-Planck-Institut für Bioanorganische Chemie, 45413 Mülheim an der Ruhr (Germany)
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  • Wilhelm Stahl Prof.

    1. Institute of Biochemistry and Molecular Biology I, Heinrich-Heine-University Düsseldorf, Universitätsstrasse 1, 40225 Düsseldorf (Germany)
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  • The present work has been performed as a project of the SFB 663 (B1) at the Heinrich-Heine-University Düsseldorf and is printed at its instigation with financial support provided by the Deutsche Forschungsgemeinschaft.

Abstract

original image

The color of red smear cheeses arises from naturally occurring carotenoids like 3,3′-dihydroxyisorenieratene (1). This compound and its oxidation product 2, which have unusual phenolic and quinoid end groups, respectively, were synthesized. The antioxidant and photoprotective properties of a series of carotenoids were tested with eight different model systems, and 1 proved to be superior to other carotenoids.

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