38 網膜色素上皮細胞のレチナール異常代謝産物に関する研究(口頭発表の部)

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With age, fluorescent granules called lipofuscin or age pigments accumulate in the retinal pigment epithelium. These granules may be involved in age related macular degeneration (AMD), a leading cause of blindness in elderly people for which no remedy exists. The major hydrophobic human fluorescent pigment of lipofuscin (less than 100μg) was isolated from 250 human eyes and was assigned as structure 1 in 1993 by Eldred et al. In these studies, we revised the structure of this compound as A2E (2), containing two molecules of vitamin A and one molecule of ethanolamine. This amphiphilic structure contains a pyridinium head group and two retinoid side chains. The identity of this fluorophore was confirmed by total chemical synthesis that involved coupling of a pyridine framework with the aliphatic side chains. Further, an investigation aimed at optimizing the yield of a biomimetic synthesis from two mols of all-trans-retinal and ethanolamine provided A2E in 49% yield in only one step. These results have allowed for the development of HPLC conditions that allow nanogram quantities of A2E to be detected from the extracts of tissue samples. By using 5% of individual aged human eyes, this protocol has led to the quantification of A2E and the characterization of iso-A2E, a new double bond isomer, and the identification of retinols in these HPLC chromatograms. Exposure of either A2E or isa-A2E to light gave rise to 4:1 A2E:iso-A2E equilibrium mixtures, similar to the composition of these two pigments in eye extracts. The biological properties of A2E in retinal pigment epithelium cells will also be discussed.
天然有機化合物討論会の論文
1999-09-01

38 網膜色素上皮細胞のレチナール異常代謝産物に関する研究(口頭発表の部)

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