UVA photoprotective properties of an artificial carotenylflavonoid hybrid molecule.
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 H(2)DCF-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.
Institute of Organic Chemistry and Macromolecular Chemistry, Faculty of Medicine, Heinrich-Heine University, D-40001 Düsseldorf, Germany.
Claas
C
Hundsdörfer
Wilhelm
W
Stahl
Thomas J J
TJ
Müller
Silke
S
De Spirt
D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002338:Carotenoids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D005347:Fibroblasts / Q000187:drug effects / Q000378:metabolism / Q000528:radiation effects; D047309:Flavones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D051547:Heme Oxygenase-1 / Q000378:metabolism; D006801:Humans; D015227:Lipid Peroxidation / Q000187:drug effects; D008315:Malondialdehyde / Q000378:metabolism; D017382:Reactive Oxygen Species / Q000378:metabolism; D014466:Ultraviolet Rays
D000975:Antioxidants; D047309:Flavones; D017382:Reactive Oxygen Species; D002338:Carotenoids; D008315:Malondialdehyde; D051547:Heme Oxygenase-1