Figure 7. Schematic representation of
phospholipids with different ClogP values, membrane-sequestered IsoPG
endoperoxides, and the hydrate of iso[4]LGE2. Previous
studies of phospholipid conformations in membranes showed that sn-2
acyl groups whose methyl esters have ClogP of less than 2 protrude into
the aqueous phase whereas with ClogP greater than 5, they are buried in
the lipid bilayer. IsoPG endoperoxides that are generated have been
schematically shown (iso[4]PGH2 and iso[4]LGE2).
They remain sequestered in membranes where they slowly rearrange to
isoLGs that become hydrated and protrude into the aqueous phase
(iso[4]LGE2·H2O) allowing them to react with
pyridoxamine or proteins.