Mechanism of C-2 hydroxylation during the biosynthesis of 20-hydroxyecdysone in Ajuga hairy roots.
Feeding synthetic [2beta-2H]- and [2alpha-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 [2alpha,3alpha-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 2alpha-hydrogen. The steric course of C-2 hydroxylation in Ajuga hairy roots is identical with that reported in the insect, Schistocerca gregaria.
Nomura
K
K
Department of Chemistry and Materials Science, Tokyo Institute of Technology, Meguro, Japan.
Fujimoto
Y
Y
D004441:Ecdysterone / Q000096:biosynthesis* / Q000737:chemistry; D007887:Fabaceae / Q000378:metabolism*; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D018517:Plant Roots / Q000737:chemistry / Q000378:metabolism; D010946:Plants, Medicinal
D004441:Ecdysterone