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

Resultado de la investigación: Article

3 Citas (Scopus)

Resumen

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.

Idioma originalEnglish
Número de artículo516
PublicaciónInternational Journal of Molecular Sciences
Volumen18
N.º3
DOI
EstadoPublished - 8 mar 2017
Publicado de forma externa

Huella dactilar

plant growth regulators
Brassinosteroids
Plant Growth Regulators
rice
analogs
acids
elongation
Acids
Elongation
synthesis
cells
hormones
Growth
Hormones
activity (biology)
Bioactivity
Ketones
Cholic Acid
ketones
organs

ASJC Scopus subject areas

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

Citar esto

Duran, María Isabel ; González, Cesar ; Acosta, Alison ; Olea, Andrés F. ; Díaz, Katy ; Espinoza, Luis. / Synthesis of five known brassinosteroid analogs from hyodeoxycholic acid and their activities as plant-growth regulators. En: International Journal of Molecular Sciences. 2017 ; Vol. 18, N.º 3.
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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.",
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Synthesis of five known brassinosteroid analogs from hyodeoxycholic acid and their activities as plant-growth regulators. / Duran, María Isabel; González, Cesar; Acosta, Alison; Olea, Andrés F.; Díaz, Katy; Espinoza, Luis.

En: International Journal of Molecular Sciences, Vol. 18, N.º 3, 516, 08.03.2017.

Resultado de la investigación: Article

TY - JOUR

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AU - Duran, María Isabel

AU - González, Cesar

AU - Acosta, Alison

AU - Olea, Andrés F.

AU - Díaz, Katy

AU - Espinoza, Luis

PY - 2017/3/8

Y1 - 2017/3/8

N2 - 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.

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