Biosynthesis of 20-hydroxyecdysone in Ajuga hairy roots: The possibility of 7-ene introduction at a late stage
Abstract
Administration of [3alpha-2H]-3beta-hydroxy-5beta-cholestan-6-one to hairy roots of Ajuga reptans var. atropurpurea followed by 2H-NMR spectroscopic analysis of the resulting 20-hydroxyecdysone so formed revealed that the substrate was efficiently incorporated into the latter. Additionally, [5beta,7alpha,7beta-2H3]-2beta,3beta-dihydroxy-+ ++5beta-cholestan-6-one was converted into 20-hydroxyecdysone. These findings clearly indicate that Ajuga hairy roots are capable of introducing a double bond at the 7-position at a late stage of 20-hydroxyecdysone biosynthesis, suggesting the possibility of an alternative biosynthetic pathway which does not involve 7-dehydrocholesterol as an obligatory intermediate.
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In Ajaga reptans hairy roots, 3β-hydroxy-5β-cholestan-6-one is converted into 2β,3β-dihydroxy-5β-cholestan-6-one and subsequently converted into 20-HE; therefore, 7-ene is added afterward during biosynthesis.
“In Ajaga reptans hairy roots, 3β-hydroxy-5β-cholestan-6-one is converted into 2β,3β-dihydroxy-5β-cholestan-6-one and subsequently converted into 20-HE; therefore, this concludes that 7-ene is added afterward during biosynthesis [146].”
From Phytoecdysteroids: Distribution, Structural Diversity, Biosynthesis, Activity, and Crosstalk with Phytohormones (2022) · cites this paper as [146]
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- Authors
- Hyodo, R., & Fujimoto, Y.
- Affiliations
- Tokyo Institute of Technology (JP)
- ORCID
- Fujimoto, Yoshinori
- Venue
- Phytochemistry
- Publisher
- Elsevier BV
- Published
- 2000-04
- Volume
- 53
- Issue
- 7
- Pages
- 733-737
- ISSN
- 0031-9422 (ISSN-L)
- OpenAlex
- W1969925710
- Cited by
- 19
- References
- 20
- Citations by year
- 2026: 2 · 2025: 1 · 2023: 1 · 2022: 1 · 2020: 1 · 2018: 2 · 2016: 2 · 2015: 2 · 2014: 1
- FWCI
- 0.24
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Phytochemistry (publishedVersion)
- PubMed (publishedVersion)
- Funders
- Ministry of Education, Culture, Sports, Science and Technology
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Plant biochemistry and biosynthesis
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Plant tissue culture and regeneration
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Steroid Chemistry and Biochemistry
- Keywords
- Ajuga reptans, hairy roots, steroidogenesis, 7-dehydrocholesterol, alternative biosynthetic pathway
- MeSH terms
- Ecdysterone, Magnetic Resonance Spectroscopy, Mass Spectrometry, Plant Roots
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