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Int. J. Mol. Sci. 2017, 18(3), 516; doi:10.3390/ijms18030516

Synthesis of Five Known Brassinosteroid Analogs from Hyodeoxycholic Acid and Their Activities as Plant-Growth Regulators

1
Departamento de Química, Universidad Técnica Federico Santa María, Avenida España 1680, Valparaíso 2340000, Chile
2
Escuela de Ingeniería en Biotecnología, Facultad de Ciencias Biológicas, Universidad Andrés Bello, Quillota 980, Viña del Mar 2520000, Chile
3
Instituto de Ciencias Químicas Aplicadas, Facultad de Ingeniería, Universidad Autónoma de Chile, Santiago 8910339, Chile
*
Authors to whom correspondence should be addressed.
Academic Editor: María Serrano
Received: 23 January 2017 / Revised: 17 February 2017 / Accepted: 23 February 2017 / Published: 8 March 2017
(This article belongs to the Section Molecular Botany)
View Full-Text   |   Download PDF [5998 KB, uploaded 8 March 2017]   |  

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 515, 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. View Full-Text
Keywords: brassinosteroid analogs; synthesis; plant-growth regulators; lamina inclination test brassinosteroid analogs; synthesis; plant-growth regulators; lamina inclination test
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Duran, M.I.; González, C.; Acosta, A.; Olea, A.F.; Díaz, K.; Espinoza, L. Synthesis of Five Known Brassinosteroid Analogs from Hyodeoxycholic Acid and Their Activities as Plant-Growth Regulators. Int. J. Mol. Sci. 2017, 18, 516.

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