UVA Photoprotective Properties of an Artificial Carotenylflavonoid Hybrid Molecule

• Published in: Chemical research in toxicology 2012-08, Vol.25 (8), p.1692-1698
• Main Authors: Hundsdörfer, Claas, Stahl, Wilhelm, Müller, Thomas J. J, De Spirt, Silke
• Format: Article
• Language: English
• Subjects: Antioxidants - chemical synthesis; Antioxidants - chemistry; Antioxidants - pharmacology; Carotenoids - chemical synthesis; Carotenoids - chemistry; Carotenoids - pharmacology; Cell Line; Cell Survival - drug effects; Fibroblasts - drug effects; Fibroblasts - metabolism; Fibroblasts - radiation effects; Flavones - chemical synthesis; Flavones - chemistry; Flavones - pharmacology; Heme Oxygenase-1 - metabolism; Humans; Lipid Peroxidation - drug effects; Malondialdehyde - metabolism; Reactive Oxygen Species - metabolism; Ultraviolet Rays
• ISSN: 0893-228X; 1520-5010
• DOI: 10.1021/tx300158r

Carotenoids and flavonoids represent two classes of natural antioxidants, a biological activity, which is determined by their chemical structure. To combine their antioxidant properties, a dual functional carotenylflavonoid hybrid molecule was synthesized. The antioxidant activity of this compound was tested in human dermal fibroblasts exposed to UVA irradiation. Test parameters were hemeoxygenase-1 (HO-1) expression, malondialdehyde (MDA), and reactive oxygen species (ROS) formation and cell viability. For comparison, the substructure components of the carotenylflavonoid, 4-hydroxyflavone and 11′-apo-β-carotenylbenzene, were also tested. Incubation of cells with the carotenylflavonoid and 11′-apo-β-carotenylbenzene attenuated UVA-induced HO-1 expression. In the MDA assay, the carotenylflavonoid and 11′-apo-β-carotenylbenzene were moderately effective at low concentrations. At higher concentrations, the compound provoked an increase of MDA, which was confirmed by the H2DCF-DA assay measuring ROS formation. 4-Hydroxyflavone moderately inhibited the formation of MDA at all levels that were tested. The study showed that the carotenylflavonoid counteracts UVA-induced HO-1 expression. However, a photoprotection against lipid oxidation, ROS formation, and cell toxicity could not be proven in the experimental setting.