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. Author manuscript; available in PMC: 2016 Sep 14.
Published in final edited form as: Angew Chem Int Ed Engl. 2015 Jul 29;54(38):11138–11142. doi: 10.1002/anie.201505002

Scheme 1.

Scheme 1

Structures of cholesterol 25-hydroperoxide (1), cholesterol 20α-hydroperoxide (2) and 20-iso-cholesterol 20β-hydroperoxide (3) and their metabolites. Incubation of (1) with either CYP27A1 or CYP11A1 gave 25-hydroxycholesterol (4) as major product. Secondary products include the 25,26-dihydroxycholesterol (5) from CYP27A1 and 25,22-dihydroxycholesterol (6) from CYP11A1. Incubation of 2 with CYP11A1 gave 20α,22R-dihydroxycholesterol (7), whereas the epimeric 20β-hydroperoxide 3 gave 20β,21-dihydroxy-20-iso-cholesterol (8) as single product.