Anthocyanins protect against A2E photooxidation and membrane permeabilization in retinal pigment epithelial cells.
The pyridinium bisretinoid A2E, an autofluorescent pigment that accumulates in retinal pigment epithelial cells with age and in some retinal disorders, can mediate a detergent-like perturbation of cell membranes and light-induced damage to the cell. The photodynamic events initiated by the sensitization of A2E include the generation of singlet oxygen and the oxidation of A2E at carbon-carbon double bonds. To assess the ability of plant-derived anthocyanins to modulate adverse effects of A2E accumulation on retinal pigment epithelium (RPE) cells, these flavylium salts were isolated from extracts of bilberry. Nine anthocyanin fractions reflecting monoglycosides of delphinidin, cyanidin, petunidin and malvidin were obtained and all were shown to suppress the photooxidation of A2E at least in part by quenching singlet oxygen. The anthocyanins tested exhibited antioxidant activity of variable efficiency. The structural characteristics relevant to this variability likely included the ability to form a stable quinonoidal anhydro base at neutral pH, a conjugated diene structure in the C (pyrane) ring, the presence of hydroxyl groups on the B (benzene) ring and the relative hydrophobicity conferred by the arrangement of substituents on the B ring. Cells that had taken up anthocyanins also exhibited a resistance to the membrane permeabilization that occurs as a result of the detergent-like action of A2E.
Jang
Young P
YP
Department of Ophthalmology, Columbia University, New York, NY 10032, USA.
Zhou
Jilin
J
Nakanishi
Koji
K
Sparrow
Janet R
JR
D000872:Anthocyanins / Q000737:chemistry / Q000145:classification / Q000627:therapeutic use*; D001190:Arylsulfonates / Q000737:chemistry; D001554:Benzene / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D004847:Epithelial Cells / Q000166:cytology / Q000187:drug effects / Q000528:radiation effects; D006863:Hydrogen-Ion Concentration; D057927:Hydrophobic and Hydrophilic Interactions; D008566:Membranes / Q000187:drug effects* / Q000378:metabolism; D010084:Oxidation-Reduction; D010539:Permeability; D010777:Photochemistry; D010857:Pigment Epithelium of Eye / Q000187:drug effects* / Q000378:metabolism / Q000528:radiation effects; D011726:Pyridinium Compounds / Q000378:metabolism*; D011832:Radiation Injuries / Q000209:etiology / Q000517:prevention & control*; D012176:Retinoids / Q000378:metabolism*; D026082:Singlet Oxygen / Q000378:metabolism
C112040:A2-E (N-retinylidene-N-retinylethanolamine); D000872:Anthocyanins; D001190:Arylsulfonates; D011726:Pyridinium Compounds; D012176:Retinoids; D026082:Singlet Oxygen; D002244:Carbon; C005047:pyranine; D001554:Benzene
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