Carotenylflavonoids, a novel group of potent, dual-functional antioxidants

Beutner, Stefan; Frixel, Susanne; Ernst, Hansgeorg; Hoffmann, Thomas; Hernandez-Blanco, Ines; Hundsdoerfer, Claas; Kiesendahl, Nicole; Kock, Sebastian; Martin, Hans-Dieter; Mayer, Bernhard; Noack, Peter; Perez-Galvez, Antonio; Kock, Grit; Scherrers, Roger; Schrader, Wolfgang; Sell, Stefan; Stahl, Wilhelm

doi:10.3998/ark.5550190.0008.822

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Carotenylflavonoids, a novel group of potent, dual-functional antioxidants

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Schrader, Wolfgang
Service Department Schrader (MS), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Beutner, S., Frixel, S., Ernst, H., Hoffmann, T., Hernandez-Blanco, I., Hundsdoerfer, C., et al. (2007). Carotenylflavonoids, a novel group of potent, dual-functional antioxidants. ARKIVOC, (8), 279-295. doi:10.3998/ark.5550190.0008.822.

Cite as: https://hdl.handle.net/11858/00-001M-0000-000F-91D5-1

Abstract

We report here on the synthesis and antioxidant properties of novel covalently linked flavonoidcarotenoid
hybrids, hereinafter referred to as carotenylflavonoids. By this strategy the essential
properties of the protecting systems are improved. Compared with the parent carotenoids or flavonoids,
e.g. ß-carotene and a hydroxyflavone, these molecular combinations exhibit improved
photoprotective properties, as seen from their UV spectra, and they outperform the individual
constituents in their antioxidant properties. The dual functionality is revealed from the time evolution
of the peroxidation inhibition assay which clearly displays both phenolic and carotenoidpolyenic
contributions to the antioxidant efficiency. Furthermore, these compounds have amphiphilic
character, in contrast to symmetrical carotenes and hydroxylated flavones. The antioxidative
potential of the carotenylflavonoids is high. They protect cumene against peroxidation
more than β-carotene by a factor of about 2.3-2.5, and more than the individual components.