Design, Synthesis, and Bioactivity of the First Nonsteroidal Mimetics of Brassinolide

Andersen, Denise L.; Back, Thomas G.; Janzen, Loeke; Michalak, Karol; Pharis, Richard P.; Sung, Gabriel C. Y.

doi:10.1021/jo015832+

Cited by 20Steroid Chemistry and BiochemistryHeterocyclic Compound Synthesis and BioactivityBiological Activity of Diterpenoids and Biflavonoids

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Design, Synthesis, and Bioactivity of the First Nonsteroidal Mimetics of Brassinolide

Andersen, Denise L., Back, Thomas G., Janzen, Loeke, Michalak, Karol, Pharis, Richard P., Sung, Gabriel C. Y.·2001·The Journal of Organic Chemistry

DOI 10.1021/jo015832+

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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.
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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)
ORCID: Back, Thomas G.
Michalak, Karol
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
DOI: 10.1021/jo015832+
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: Physical Sciences › Chemistry › Organic Chemistry › Steroid Chemistry and Biochemistry
Physical Sciences › Chemistry › Organic Chemistry › Heterocyclic Compound Synthesis and Bioactivity
Physical Sciences › Chemistry › Organic Chemistry › 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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Design, Synthesis, and Bioactivity of the First Nonsteroidal Mimetics of Brassinolide

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