Abstract
3β,14α-Dihydroxy-5α-cholest-7-en-6-one (5α-ketodiol) ( 1) is metabolized by the prothoracic glands to 2,22-dideoxy-5α-ecdysone ( 4) and 2-deoxy-5α-ecdysone ( 3) but not to ecdysone ( 5) or any other 5β-metabolites. Similarly, 3β,5α,14α-trihydroxy-cholest-7-en-6-one (5α-ketotriol) ( 8) is hydroxylated at C-22 and C-25 ( 9, 10) of the side chain. However, 3β,14α-dihydroxy-cholesta-4,7-diene-6-one (ketodienediol) ( 11) is not metabolized. The absence of 2β-hydroxymetabolites for substrates ( 1) and ( 8) implies that hydroxylation at C-2 can occur only when the A–B rings are cis fused (5β-configuration). By contrast, the enzyme complexes that introduce hydroxyls at C-22 and C-25 do not exhibit a preference for cis over trans fusion and apparently cannot recognize the planar A–B ring configuration.
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