Synthesis of five known brassinosteroid analogs from hyodeoxycholic acid and their activities as plant-growth regulators

María Isabel Duran, Cesar González, Alison Acosta, Andrés F. Olea, Katy Díaz, Luis Espinoza

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Brassinosteroids (BRs) are plant hormones that promote growth in different plant organs and tissues. The structural requirements that these compounds should possess to exhibit this biological activity have been studied. In this work, a series of known BR analogs 5-15, were synthesized starting from hyodeoxycholic acid 4, and maintaining the alkyl side chain as cholic acid or its methyl ester. The growth-promoting effects of brassinolide (1) and synthesized analogs were evaluated by using the rice lamina inclination assay at concentrations ranging from 1 × 10- 8-1 × 10- 6 M. Our results indicate that in this concentration range the induced bending angle of rice seedlings increases with increasing concentration of BRs. Analysis of the activities, determined at the lowest tested concentration, in terms of BR structures shows that the 2α,3α-dihydroxy-7-oxa-6-ketone moiety existing in brassinolide is required for the plant growing activity of these compounds, as it has been proposed by some structure-activity relationship studies. The effect of compound 8 on cell elongation was assessed by microscopy analysis, and the results indicate that the growth-promoting effect of analog 8 is mainly due to cell elongation of the adaxial sides, instead of an increase on cell number.

Original languageEnglish
Article number516
JournalInternational Journal of Molecular Sciences
Volume18
Issue number3
DOIs
Publication statusPublished - 8 Mar 2017
Externally publishedYes

Keywords

  • Brassinosteroid analogs
  • Lamina inclination test
  • Plant-growth regulators
  • Synthesis

ASJC Scopus subject areas

  • Catalysis
  • Molecular Biology
  • Computer Science Applications
  • Spectroscopy
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Medicine(all)

Fingerprint Dive into the research topics of 'Synthesis of five known brassinosteroid analogs from hyodeoxycholic acid and their activities as plant-growth regulators'. Together they form a unique fingerprint.

  • Cite this