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Article

Synthesis of New Brassinosteroid 24-Norcholane Type Analogs Conjugated in C-3 with Benzoate Groups

1
Departamento de Química, Universidad Técnica Federico Santa María, Avenida España 1680, Valparaíso 2340000, Chile
2
Laboratory of Growth Regulators, Institute of Experimental Botany, The Czech Academy of Sciences, Palacký University, Šlechtitelů 27, 78371 Olomouc, Czech Republic
3
Department of Experimental Biology, Faculty of Science, Palacký University, Šlechtitelů 27, 78371 Olomouc, Czech Republic
4
Instituto de Ciencias Químicas Aplicadas, Facultad de Ingeniería, Universidad Autónoma de Chile, El Llano Subercaseaux 2801, Santiago 8900000, Chile
5
Facultad de Farmacia, Escuela de Química y Farmacia, Universidad de Valparaíso, Av. Gran Bretaña 1093, Valparaíso 2340000, Chile
*
Authors to whom correspondence should be addressed.
Academic Editor: Silvia Socoro
Received: 25 January 2021 / Revised: 13 February 2021 / Accepted: 18 February 2021 / Published: 22 February 2021
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. View Full-Text
Keywords: synthesis; brassinosteroids; analogs; 24-norcholane; benzoate esters; Rice Lamina Inclination Test; conjugated in C-3 synthesis; brassinosteroids; analogs; 24-norcholane; benzoate esters; Rice Lamina Inclination Test; conjugated in C-3
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MDPI and ACS Style

Ferrer, K.; Díaz, K.; Kvasnica, M.; Olea, A.F.; Cuellar, M.; Espinoza, L. Synthesis of New Brassinosteroid 24-Norcholane Type Analogs Conjugated in C-3 with Benzoate Groups. Molecules 2021, 26, 1173. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26041173

AMA Style

Ferrer K, Díaz K, Kvasnica M, Olea AF, Cuellar M, Espinoza L. Synthesis of New Brassinosteroid 24-Norcholane Type Analogs Conjugated in C-3 with Benzoate Groups. Molecules. 2021; 26(4):1173. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26041173

Chicago/Turabian Style

Ferrer, Karoll; Díaz, Katy; Kvasnica, Miroslav; Olea, Andrés F.; Cuellar, Mauricio; Espinoza, Luis. 2021. "Synthesis of New Brassinosteroid 24-Norcholane Type Analogs Conjugated in C-3 with Benzoate Groups" Molecules 26, no. 4: 1173. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26041173

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