Biosynthesis of 20-hydroxyecdysone in Ajuga hairy roots: fate of 6alpha- and 6beta-hydrogens of lathosterol |
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Authors: | Ohyama K Kushiro T Nakamura K Fujimoto Y |
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Institution: | Department of Chemistry and Materials Science, Tokyo Institute of Technology, Meguro, Japan. |
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Abstract: | 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. |
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