Biosynthesis of 20-hydroxyecdysone in Ajuga hairy roots: fate of 6alpha- and 6beta-hydrogens of lathosterol.
The fate of 6alpha- and 6beta-hydrogens of lathosterol during the transformation into 20-hydroxyecdysone was chased by feeding [3alpha,6beta-2H2]- and [3alpha,6alpha-2H2]-lathosterols to hairy roots of Ajuga reptans var. atropurpurea. The behavior of 6beta-hydrogen, which mostly migrated to the C-5 position of 20-hydroxyecdysone, was in agreement with that of C-6 hydrogen of cholesterol. The results strongly supported the view that cholesterol and lathosterol are first metabolized into 7-dehydrocholesterol, which is then converted into 20-hydroxyecdysone via 7-dehydrocholesterol 5alpha,6alpha-epoxide in the hairy roots.
Ohyama
K
K
Department of Chemistry and Materials Science, Tokyo Institute of Technology, Meguro, Japan.
Kushiro
T
T
Nakamura
K
K
Fujimoto
Y
Y
D002784:Cholesterol / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism*; D004441:Ecdysterone / Q000096:biosynthesis* / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D019686:Lamiaceae / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D018517:Plant Roots / Q000378:metabolism
D004441:Ecdysterone; D006859:Hydrogen; C001521:lathosterol; D002784:Cholesterol