Synthesis and bioactivity of natural and C-3 fluorinated biosynthetic precursors of 28-homobrassinolide
Abstract
In this paper we describe the synthesis of two new fluorinated brassinosteroids: (22R,23R)-22,23-dihydroxy-3alpha-fluorostigmastan-6-one and (22R,23R)-22,23-dihydroxy-3beta-fluorostigmastan-6-one. Their bioactivities were evaluated in the rice lamina inclination test and compared with that of 28-homocastasterone, 28-homotyphasterol and 28-homoteasterone, possible biosynthetic precursors of 28-homobrassinolide. Results confirmed expected similarities between the biosynthesis of 24-ethylbrassinosteroids (named as the 28-homo series) and that described for 24-methylbrassinosteroids, and also indicated that these precursors might exhibit per se activities.
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Replacement of the 3-hydroxy function by a 3-fluoro group yielded compounds active at the rice lamina inclination assay, but not as active as their parent compounds.
“Similarly, replacement of 3-hydroxy function by a 3-fluoro group yielded compounds active at the rice lamina inclination assay, but not as active as their parent compounds 27.”
From Akt-dependent anabolic activity of natural and synthetic brassinosteroids in rat skeletal muscle cells (2011) · cites this paper as [27]
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Brassinosteroid phytohormones: structure, bioactivity and applications
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- Authors
- Galagovsky, L. R., Gros, E. G., & Ramı́rez, J. A.
- Affiliations
- Universidad de Buenos Aires (AR)
- ORCID
- Galagovsky, Lydia R
- Venue
- Phytochemistry
- Publisher
- Elsevier BV
- Published
- 2001-11
- Volume
- 58
- Issue
- 6
- Pages
- 973-980
- ISSN
- 0031-9422 (ISSN-L)
- OpenAlex
- W1974524881
- Cited by
- 16
- References
- 26
- Citations by year
- 2019: 2 · 2017: 1 · 2015: 2 · 2013: 1
- FWCI
- 0.35
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Phytochemistry (publishedVersion)
- PubMed (publishedVersion)
- Funders
- Universidad de Buenos Aires
- National Institutes of Health (5p41rr000954-34)
- National Center for Research Resources (P41 RR-00954)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Plant biochemistry and biosynthesis
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Steroid Chemistry and Biochemistry
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Phytochemical Studies and Bioactivities
- Keywords
- 28-homobrassinolide, brassinosteroid biosynthesis, biosynthetic precursors, plant growth regulators
- MeSH terms
- Cholestanones, Fluorine, Magnetic Resonance Spectroscopy, Mass Spectrometry, Molecular Structure
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