The metabolism of brassinosteroid leads to structural modifications in the ring skeleton or the side alkyl chain. The esterification and glycosylation at C-3 are the most common metabolic pathways, and it has been suggested that conjugate brassinosteroids are less active or inactive. In this way, plants regulate the content of active brassinosteroids. In this work, the synthesis of brassinosteroid 24-norcholane type analogs conjugated at C-3 with benzoate groups, carrying electron donor and electron attractant substituents on the aromatic ring, is described. Additionally, their growth-promoting activities were evaluated using the Rice Lamina Inclination Test (RLIT) and compared with that exhibited by brassinolide (used as positive control) and non-conjugated analogs. The results indicate that at the lowest tested concentrations (10-8-10-7 M), all analogs conjugated at C-3 exhibit similar or higher activities than brassinolide, and the diasteroisomers with S configuration at C-22 are the more active ones. Increasing concentration (10-6 M) reduces the biological activities of analogs as compared to brassinolide.

Departamento de Química Universidad Técnica Federico Santa María Avenida España 1680 Valparaíso 2340000 Chile

Department of Experimental Biology Faculty of Science Palacký University Šlechtitelů 27 78371 Olomouc Czech Republic

Facultad de Farmacia Escuela de Química y Farmacia Universidad de Valparaíso Av Gran Bretaña 1093 Valparaíso 2340000 Chile

Instituto de Ciencias Químicas Aplicadas Facultad de Ingeniería Universidad Autónoma de Chile El Llano Subercaseaux 2801 Santiago 8900000 Chile

Laboratory of Growth Regulators Institute of Experimental Botany The Czech Academy of Sciences Palacký University Šlechtitelů 27 78371 Olomouc Czech Republic

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