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J. Lipid Res.
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Originally published In Press as doi:10.1194/jlr.R000687 on August 7, 2009

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Journal of Lipid Research, Vol. 51, 247-261, February 2010
Copyright © 2010 by American Society for Biochemistry and Molecular Biology

Thematic Review

Phospholipid meets all-trans-retinal: the making of RPE bisretinoids

Janet R. Sparrow1, Yalin Wu, Chul Y. Kim and Jilin Zhou

Departments of Ophthalmology and Pathology and Cell Biology, Columbia University, 630 W. 168th Street, New York, NY 10032

1 To whom correspondence should be addressed. e-mail: jrs88{at}columbia.edu

The lipid phase of the photoreceptor outer segment membrane is essential to the photon capturing and signaling functions of rhodopsin. Rearrangement of phospholipids in the bilayer accompanies the formation of the active intermediates of rhodopsin following photon absorption. Furthermore, evidence for the formation of a condensation product between the photolyzed chromophore all-trans-retinal and phosphatidylethanolamine indicates that phospholipid may also participate in the movement of the retinoid in the membrane. The downside of these interactions is the formation of bisretinoid-phosphatidylethanolamine compounds that accumulate in retinal pigment epithelial cells with age and that are particularly abundant in some retinal disorders. The propensity of these compounds to negatively impact on the cells has been linked to the pathogenesis of some retinal disorders including juvenile onset recessive Stargardt disease and age-related macular degeneration.

Supplementary key words bisretinoids • photooxidation • fluorescence • lipofuscin • retina • light • visible spectrum • absorbance • all-trans-retinal dimer • retinal pigment epithelium

Abbreviations: ABCA4/ABCR, ATP-binding cassette transporter; all-trans-retinal dimer-E, all-trans-retinal dimer-ethanolamine; all-trans-retinal dimer-PE, all-trans-retinal dimer-phosphatidylethanolamine; AMD, age-related macular degeneration; CEP, carboxyethyl pyrrole; DHA, docosahexaenoic acid; PC, phosphatidylcholine; PE, phosphatidylethanolamine; PLD, phospholipase D; PS, phosphatidylserine; RCS, Royal College of Surgeon rat; RDH, NADPH-dependent retinol dehydrogenase; RPE, retinal pigment epithelium; VEGF, vascular endothelial growth factor


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