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

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...

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Published in:Angewandte Chemie (International ed.) 2009-01, Vol.48 (2), p.400-403
Main Authors: Martin, Hans-Dieter, Kock, Sebastian, Scherrers, Roger, Lutter, Kaya, Wagener, Tanja, Hundsdörfer, Claas, Frixel, Susanne, Schaper, Klaus, Ernst, Hansgeorg, Schrader, Wolfgang, Görner, Helmut, Stahl, Wilhelm
Format: Article
Language:English
Subjects:
Antioxidants - chemical synthesis
Antioxidants - chemistry
Antioxidants - pharmacology
carotenoids
Carotenoids - chemical synthesis
Carotenoids - chemistry
Carotenoids - pharmacology
Cells, Cultured
Fibroblasts - drug effects
Fibroblasts - metabolism
Fibroblasts - radiation effects
Free Radicals - antagonists & inhibitors
Heme Oxygenase-1 - antagonists & inhibitors
Heme Oxygenase-1 - biosynthesis
Heme Oxygenase-1 - radiation effects
Humans
Liposomes - chemistry
Liposomes - radiation effects
Lutein - pharmacology
Molecular Structure
Oxidation-Reduction - drug effects
Oxidation-Reduction - radiation effects
Oxygen - antagonists & inhibitors
Oxygen Consumption - drug effects
Phospholipids - chemistry
Phospholipids - radiation effects
photooxidation
photoprotection
Pyrimidine Dimers - antagonists & inhibitors
Pyrimidine Dimers - biosynthesis
Pyrimidine Dimers - radiation effects
quinones
Radiation-Protective Agents - chemical synthesis
Radiation-Protective Agents - chemistry
Radiation-Protective Agents - pharmacology
singlet oxygen
Skin - drug effects
Skin - metabolism
Skin - radiation effects
Stereoisomerism
Ultraviolet Rays
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Summary: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200803668