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Biosynthesis of 20-hydroxyecdysone in Ajuga hairy roots: Stereochemistry of C-25 hydroxylation
β Scribed by Takayoshi Nakagawa; Noriyuki Hara; Yoshinori Fujimoto
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 208 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Feeding of [13C2]acetate to hairy roots of Ajuga reptans var. atropurpurea followed by 13C.NM R analysis of the biosynthesized cholesterol and 20-hydroxyecdysone indicated that C-25 hydroxylation in 20-hydroxyecdysone biosynthesis proceeds both in retention and inversion mechanisms. Feeding studies of [26 -13C]-and [27-13C]cholesterols established that the ratio of retention and inversion mechanisms is ca. 3:1.
π SIMILAR VOLUMES
Feeding of deuterium labeled cholesterols including [6-2H]cholesterol and [3ct,6-2H2 Icholesterol to hairy roots of Ajuga reptans var. atropurpurea followed by 2H-NMR analysis of the biosynthesized 20-hydroxyecdysone revealed that most of the deuterium atom located at C-6 of cholesterol migrated to
Biosynthesis of clerosterol, (24S)-ethylcholesta-5,25-dien-3b-ol (1), involves transfer of the methyl group from S-adenosylmethionine to the C-28 position of a 24-methylene-sterol precursor. The resulting C-24 cationic species undergoes migration of hydrogen from C-25 to C-24, followed by deprotonat
Feeding studies of six 13 C-labeled sterols, including clerosterol, to hairy roots of Ajuga reptans var. atropurpurea have established that clerosterol is a precursor of three phytoecdysteroids, cyasterone, isocyasterone and 29-norcyasterone.