Mechanism of C-2 hydroxylation during the biosynthesis of 20- hydroxyecdysone in Ajuga hairy roots

Article abstract of DOI:10.1248/cpb.48.344

Feeding synthetic [2β-²H]- and [2α-²H]-cholesterols to the hairy roots of Ajuga reptans var. atropurpurea and ²H-NMR analysis of the biosynthesized 20-hydroxyecdysone revealed that hydroxylation at C-2 proceeds with retention of configuration. Feeding [2α,3α-²H₂]cholesterol followed by ²H-NMR analysis of the 2,3,22-triacetate of the resulting 20- hydroxyecdysone ruled out a mechanism which involves a partial loss of the 2α-hydrogen. The steric course of C-2 hydroxylation in Ajuga hairy roots is identical with that reported in the insect, Schistocerca gregaria.

Full text of DOI:10.1248/cpb.48.344

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