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. 2015 Mar:111:59-64.
doi: 10.1016/j.phytochem.2014.12.019. Epub 2015 Jan 12.

Biosynthesis of 20-hydroxyecdysone in plants: 3β-hydroxy-5β-cholestan-6-one as an intermediate immediately after cholesterol in Ajuga hairy roots

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Biosynthesis of 20-hydroxyecdysone in plants: 3β-hydroxy-5β-cholestan-6-one as an intermediate immediately after cholesterol in Ajuga hairy roots

Yoshinori Fujimoto et al. Phytochemistry. 2015 Mar.

Abstract

3β-Hydroxy-5β-cholestan-6-one was identified in the EtOAc extract of Ajuga hairy roots by micro-analysis using LC-MS/MS in the multiple reaction mode (MRM). Furthermore, administration of (2,2,4,4,7,7-(2)H6)- and (2,2,4,4,6,7,7-(2)H7)-cholesterols to the hairy roots followed by LC-MS/MS analysis of the EtOAc extract of the hairy roots indicated that cholesterol was converted to the 5β-ketone with hydrogen migration from the C-6 to the C-5 position. These findings, in conjunction with the previous observation that the ketone was efficiently converted to 20-hydroxyecdysone, strongly suggest that the 5β-ketone is an intermediate immediately formed after cholesterol during 20-hydroxyecdysone biosynthesis in Ajuga sp. In addition, the mechanism of the 5β-ketone formation from cholesterol is discussed.

Keywords: 20-Hydroxyecdysone; Ajuga reptans var. atropurpurea; Hairy root; LC–MS/MS; Labiatae; NIH shift; Phytoecdysteroid.

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