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Synthesis of new brassinosteroid 24-norcholane type analogs conjugated in C-3 with benzoate groups
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SYSNO ASEP 0545889 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Synthesis of new brassinosteroid 24-norcholane type analogs conjugated in C-3 with benzoate groups Author(s) Ferrer, Karoll (UEB-Q) ORCID
Díaz, K. (ES)
Kvasnica, Miroslav (UEB-Q) RID, ORCID
Olea, A. F. (CL)
Cuellar, M. (CL)
Espinoza, L. (ES)Number of authors 6 Article number 1173 Source Title Molecules. - : MDPI
Roč. 26, č. 4 (2021)Number of pages 18 s. Language eng - English Country CH - Switzerland Keywords 24-norcholane ; Analogs ; Benzoate esters ; Brassinosteroids ; Conjugated in C-3 ; Rice Lamina Inclination Test ; Synthesis OECD category Biochemistry and molecular biology R&D Projects EF16_019/0000827 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) Method of publishing Open access Institutional support UEB-Q - RVO:61389030 UT WOS 000624160100001 EID SCOPUS 85102604613 DOI 10.3390/molecules26041173 Annotation 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. Workplace Institute of Experimental Botany Contact David Klier, knihovna@ueb.cas.cz, Tel.: 220 390 469 Year of Publishing 2022 Electronic address http://doi.org/10.3390/molecules26041173
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