Novel Brassinosteroid Analogues with 3,6 Dioxo Function, 24-Nor-22( S )-Hydroxy Side Chain and p -Substituted Benzoate Function at C-23-Synthesis and Evaluation of Plant Growth Effects.

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  • Additional Information
    • Source:
      Publisher: MDPI Country of Publication: Switzerland NLM ID: 101092791 Publication Model: Electronic Cited Medium: Internet ISSN: 1422-0067 (Electronic) Linking ISSN: 14220067 NLM ISO Abbreviation: Int J Mol Sci Subsets: MEDLINE
    • Publication Information:
      Original Publication: Basel, Switzerland : MDPI, [2000-
    • Subject Terms:
      Brassinosteroids*/chemistry ; Brassinosteroids*/chemical synthesis ; Oryza*/growth & development ; Oryza*/drug effects ; Oryza*/metabolism ; Benzoates*/chemistry ; Benzoates*/pharmacology ; Benzoates*/chemical synthesis; Plant Growth Regulators/chemical synthesis ; Plant Growth Regulators/chemistry ; Plant Growth Regulators/pharmacology ; Plant Development/drug effects ; Deoxycholic Acid
    • Abstract:
      Brassinosteroids (BRs) are an important group of polyhydroxylated naturally occurring steroidal phytohormones found in the plant kingdom in extremely low amounts. Due to the low concentrations in which these compounds are found, much effort has been dedicated to synthesizing these compounds or their structural analogs using natural and abundant sterols. In this work, we report the synthesis of new brassinosteroid analogs obtained from hyodeoxycholic acid, with a 3,6 dioxo function, 24-Nor-22( S )-hydroxy side chain and p -substituted benzoate function at C-23. The plant growth activities of these compounds were evaluated by two different bioassays: rice lamina inclination test (RLIT) and BSI. The results show that BRs' analog with p -Br (compound 41f ) in the aromatic ring was the most active at 1 × 10 -8 M in the RLIT and BSI assays. These results are discussed in terms of the chemical structure and nature of benzoate substituents at the para position. Electron-withdrawing and size effects seems to be the most important factor in determining activities in the RLIT assay. These results could be useful to propose a new structural requirement for bioactivity in brassinosteroid analogs.
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    • Contributed Indexing:
      Keywords: brassinosteroid analogs; molecular docking; plant growth; synthesis
    • Accession Number:
      0 (Brassinosteroids)
      0 (Benzoates)
      0 (Plant Growth Regulators)
      7A33Y6EHYK (hyodeoxycholic acid)
      005990WHZZ (Deoxycholic Acid)
    • Publication Date:
      Date Created: 20240727 Date Completed: 20240728 Latest Revision: 20240729
    • Publication Date:
      20240729
    • Accession Number:
      PMC11276741
    • Accession Number:
      10.3390/ijms25147515
    • Accession Number:
      39062767