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. 2011 May 10;286(27):24046–24056. doi: 10.1074/jbc.M111.251496

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© 2011 by The American Society for Biochemistry and Molecular Biology, Inc.

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FIGURE 3. — Identification of oxygenated EOS ceramides in pig epidermis. A, normal phase HPLC with UV detection reveals KODE-EOS (270 nm, black trace), containing a keto derivative of linoleate, HODE-EOS (235 nm, red trace) containing hydroxy-linoleate, and EpOH-EOS (205 nm, blue trace) containing an epoxyalcohol derivative of linoleate. Unmodified EOS and other known ceramides are also detected at 205 nm (5–7 min). B, following transesterification, the main hydroxy product is identified as 9-HODE, and chiral HPLC reveals that it is predominantly 9R-HODE. C, transesterified EpOH-EOS shows a single peak (top panels), corresponding to a standard of 9,10-trans-epoxy-13-hydroxy-octadeca-11E-enoate methyl ester (details in SI Methods). Chiral HPLC analysis of the natural diastereomer (top panels) shows that it corresponds exclusively to the 9R,10R,13R enantiomer of a racemic standard (bottom panels).