Design, Synthesis, and Bioactivity of the First Nonsteroidal Mimetics of Brassinolide
Abstract
Ten novel compounds, each consisting of two subunits and a linker, were designed with the aid of molecular modeling to resemble the natural steroidal phytohormone brassinolide. The mimetics were synthesized and subjected to the rice leaf lamina inclination bioassay to test for brassinosteroid activity. Most of the mimetics displayed very weak or no bioactivity, but two were strongly active when coapplied with the auxin indole-3-acetic acid (IAA), which synergizes the activity of brassinosteroids. Thus, 1-(4,6 alpha,7 alpha-trihydroxy-5,6,7,8-tetrahydronaphthyl)-2-(6 alpha',7 alpha'-dihydroxy-5',6',7',8'-tetrahydronaphthyl)ethyne (4) and (E)-1,2-bis[trans-(4a alpha,8a beta)-4-oxo-6 alpha,7 alpha-dihydroxy-4a,5,6,7,8,8a-hexahydro-(3H)-naphthyl]ethylene (11) showed exceptional activity at doses as low as 0.01 ng and 0.001 ng/plant, respectively. These compounds are the first biologically active nonsteroidal brassinolide mimetics.
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In the rice leaf lamina inclination bioassay, 5α-configuration is required for optimum brassinosteroid activity, but the B-ring tolerates considerable variation provided a polar functional group is maintained.
“Recent structure-activity studies of brassinosteroids in the rice leaf lamina inclination bioassay have revealed that 5α-configuration is required for optimum activity, but the B-ring tolerates considerable variation, providing that the presence of a polar functional group is maintained 17.”
From Akt-dependent anabolic activity of natural and synthetic brassinosteroids in rat skeletal muscle cells (2011) · cites this paper as [17]
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- Authors
- Andersen, D. L., Back, T. G., Janzen, L., Michalak, K., Pharis, R. P., & Sung, G. C. Y.
- Affiliations
- University of Calgary (CA)
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2001-09-20
- Volume
- 66
- Issue
- 21
- Pages
- 7129-7141
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W2949657936
- Cited by
- 20
- References
- 25
- Citations by year
- 2026: 1 · 2022: 1 · 2019: 1 · 2017: 1 · 2016: 1 · 2015: 2 · 2013: 1
- FWCI
- 0.69
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- The Journal of Organic Chemistry (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Steroid Chemistry and Biochemistry
- Physical Sciences › Chemistry › Organic Chemistry › Synthesis and biological activity
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Biological Activity of Diterpenoids and Biflavonoids
- Keywords
- brassinosteroids, molecular modeling, compound synthesis, plant growth regulators
- MeSH terms
- Cholestanols, Dose-Response Relationship, Drug, Drug Synergism, Indoleacetic Acids, Models, Molecular, Plant Growth Regulators, Oryza, Steroids, Heterocyclic, Structure-Activity Relationship, Drug Design, Molecular Structure, Plant Leaves, Molecular Mimicry, Brassinosteroids
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