Photochemical transformation of 20-hydroxyecdysone: Production of monomeric and dimeric ecdysteroid analogues
Abstract
Structural modification of 20-hydroxyecdysone (20E) based on photochemical transformation yielded dimeric ecdysteroid 7alphaH,7'alphaH-bis-[(20R,22R)-2beta,3beta,20,22,25-pentahydroxy-5beta-cholest-8(14)-en-6-one-7-yl] as a main product. Its structure was determined by detailed NMR analysis. Furthermore, two new monomeric analogues: 14-epi-20-hydroxyecdysone and 14-deoxy-14,18-cyclo-20-hydroxyecdysone were identified in addition to the earlier described 14-deoxy and 14-hydroperoxy derivatives of 20E. Formation of the specific and so far unique ecdysteroid dimer has not been observed in earlier photo-transformation studies. The transformed dimeric analogue of 20-hydroxyecdysone retained the high agonistic activity on the ecdysone receptor in the B(II)-bioassay compared with the original 20E.
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The chemical space provided by natural ecdysteroids is being extended by the preparation and biological assessment of numerous semi-synthetic analogues.
“The chemical space provided by the natural ecdysteroids is being extended by the preparation and biological assessment of numerous semi-synthetic analogues (e.g., [37][38][39][40][41]).”
From Ecdysteroids (2021) · cites this paper as [39]
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- Authors
- Harmatha, J., Buděšínský, M., & Vokáč, K.
- Affiliations
- Czech Academy of Sciences (CZ)
- Corresponding author
- Harmatha, Juraj
- ORCID
- Harmatha, Juraj
- Venue
- Steroids
- Publisher
- Elsevier BV
- Published
- 2002-02
- Volume
- 67
- Issue
- 2
- Pages
- 127-135
- ISSN
- 0039-128X (ISSN-L)
- OpenAlex
- W2015410853
- Cited by
- 38
- References
- 17
- Citations by year
- 2026: 2 · 2024: 1 · 2021: 5 · 2017: 2 · 2016: 1 · 2015: 2 · 2014: 1 · 2013: 1 · 2012: 3
- FWCI
- 0.46
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Steroids (publishedVersion)
- PubMed (publishedVersion)
- Funders
- Ministerstvo Školství, Mládeže a Tělovýchovy (LB98233)
- Grantová Agentura České Republiky (203/98/0451, Z4 055 905)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Steroid Chemistry and Biochemistry
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Genetics › Estrogen and related hormone effects
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Phytochemical Studies and Bioactivities
- Keywords
- 20-hydroxyecdysone, photochemical transformation, steroid structure elucidation
- MeSH terms
- Animals, Chromatography, High Pressure Liquid, Drosophila melanogaster, Ecdysterone, Models, Molecular, Molecular Conformation, Magnetic Resonance Spectroscopy, Photochemistry, Receptors, Steroid, Spectrophotometry, Infrared, Structure-Activity Relationship, Dimerization, Ecdysteroids
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