The ecdysteroid agonist/antagonist and brassinosteroid-like activities of synthetic brassinosteroid/ecdysteroid hybrid molecules
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A series of synthetic hybrid brassinosteroid/ecdysteroid structures has been assessed for their ecdysteroid agonist/antagonist activities in the Drosophila melanogaster B(II) cell bioassay and for brassinosteroid-like activity in the rice lamina inclination test. Most of the compounds proved inactive for ecdysteroid agonist activity, demonstrating the specificity of the ecdysteroid receptor for compounds closely structurally related to 20-hydroxyecdysone. However, compound 18, with 14alpha-hydroxy-7-en-6-one and 22S-hydroxy functionalities (as in most active ecdysteroids), possessed distinct agonist activity (median effective concentration = 1.4 x 10(-5) M), although this is still almost 2000-fold less active than 20-hydroxyecdysone (25). Compounds 13 and 15 possessed weak agonist activity. Compounds 5, 11 and 14 weakly antagonised the action of 20-hydroxyecdysone (at 5 x 10(-8) M) on B(II) cells. In the brassinosteroid bioassay, most of the tested compounds showed activity. This may reflect the metabolic capability of plant tissue to convert test compounds to more active analogues. However, it is clear that biological activity declines as the structure of the test compound deviates further from that of castasterone (16). Three ecdysteroids (25, 26 and 27) are completely inactive in the rice lamina inclination test. These studies demonstrate the high specificities of the insect ecdysteroid receptor and the plant brassinosteroid receptor and indicate that phytoecdysteroids, even in high concentrations, would not interfere with brassinosteroid signalling pathways in plants where the two classes of compounds co-occur. Equally, brassinosteroids would not interfere with ecdysteroid signalling in insects, especially if one takes into account the low concentrations of brassinosteroids in the diet of phytophagous insects.
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Brassinosteroids assessed as ecdysteroid agonists or antagonists show at best only very weak activity.
“This has led to the assessment of brassinosteroids as ecdysteroid agonists or antagonists [100,101], where, at best, only very weak activity is found”
From Ecdysteroids (2021) · cites this paper as [101]
Among synthetic analogs, only a single compound shows a PE-synergistic relationship, albeit at higher doses and with weaker activity (2000-fold) than 20-HE.
“Among them, only a single compound shows a PE-synergistic relationship, albeit at higher doses and with weaker activity (2000-fold) than 20-HE [214].”
From Phytoecdysteroids: Distribution, Structural Diversity, Biosynthesis, Activity, and Crosstalk with Phytohormones (2022) · cites this paper as [214]
In Oryza sativa lamina inclination bioassay and Drosophila melanogaster BII cell bioassay, synthetic analogs of BRs and ECs are made in labs to detect their synergistic or antagonist relationships.
“In Oryza sativa lamina inclination bioassay and Drosophila melanogaster BII cell bioassay, synthetic analogs of BRs and ECs are made in labs to detect their synergistic or antagonist relationships.”
From Phytoecdysteroids: Distribution, Structural Diversity, Biosynthesis, Activity, and Crosstalk with Phytohormones (2022) · cites this paper as [214]
Most of the substances show activity in the BR bioassay; biological activity decreases as the structure deviates from that of castasterone, which is used as a standard for BRs.
“Most of the substances show activity in the BR bioassay; it has been found that biological activity decreases as the structure deviates from that of castasterone, which is used as a standard for BRs.”
From Phytoecdysteroids: Distribution, Structural Diversity, Biosynthesis, Activity, and Crosstalk with Phytohormones (2022) · cites this paper as [214]
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- Authors
- Voigt, B., Whiting, P., & Dinan, L.
- Affiliations
- Leibniz Institute of Plant Biochemistry (DE)
- University of Exeter (GB)
- ORCID
- Dinan, L.
- Venue
- Cellular and Molecular Life Sciences
- Published
- 2001-07
- Volume
- 58
- Issue
- 8
- Pages
- 1133-1140
- ISSN
- 1420-682X (ISSN-L)
- PMC
- PMC11337392
- OpenAlex
- W2329908197
- Cited by
- 34
- References
- 0
- Citations by year
- 2022: 1 · 2021: 2 · 2020: 2 · 2018: 1 · 2017: 1 · 2016: 1 · 2015: 6 · 2014: 2 · 2012: 1
- FWCI
- 0.70
- Type
- journal article
- Language
- en
- Open access
- green
- www.ncbi.nlm.nih.gov
- Licence
- www.springer.com/tdm (tdm)
- Locations
- Cellular and Molecular Life Sciences (publishedVersion)
- PubMed Central (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Steroid Chemistry and Biochemistry
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Plant biochemistry and biosynthesis
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Phytochemical Studies and Bioactivities
- Keywords
- ecdysteroid agonists, brassinosteroids, 20-hydroxyecdysone, castasterone, phytoecdysteroids, plant-insect interactions
- MeSH terms
- Animals, Biological Assay, Drosophila melanogaster, Steroids, Molecular Structure, Ecdysteroids
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