Synthesis and Biological Activity of Brassinosteroid Analogues with a Nitrogen-Containing Side Chain

Abstract

Brassinosteroids are a class of plant hormones that regulate a broad range of physiological processes such as plant growth, development and immunity, including the suppression of biotic and abiotic stresses. In this paper, we report the synthesis of new brassinosteroid analogues with a nitrogen-containing side chain and their biological activity on Arabidopis thaliana. Based on molecular docking experiments, two groups of brassinosteroid analogues were prepared with short and long side chains in order to study the impact of side chain length on plants. The derivatives with a short side chain were prepared with amide, amine and ammonium functional groups. The derivatives with a long side chain were synthesized using amide and ammonium functional groups. A total of 25 new brassinosteroid analogues were prepared. All 25 compounds were tested in an Arabidopsis root sensitivity bioassay and cytotoxicity screening. The synthesized substances showed no significant inhibitory activity compared to natural 24-epibrassinolide. In contrast, in low concentration, several compounds (8a, 8b, 8e, 16e, 22a and 22e) showed interesting growth-promoting activity. The cytotoxicity assay showed no toxicity of the prepared compounds on cancer and normal cell lines.

Cold Acclimation and Deacclimation of Winter Oilseed Rape, with Special Attention Being Paid to the Role of Brassinosteroids

“…For example, brassinosteroids include brassinolide, castasterone, 24-epibrassinolide, and 28-homocastasterone. Synthetic analogues of BRs, the physiological activity of which is still being tested [ 22 ], are also available. Generally, the role of brassinosteroids in plants is important for regulating their growth and development, while BRs also have a protective effect in plants that are growing under stressful conditions such as drought [ 23 ], salinity [ 24 ], heavy metal stress [ 25 , 26 ], or low temperatures [ 27 , 28 ].…”

New Brassinosteroid Analogs with 23,24-Dinorcholan Side Chain, and Benzoate Function at C-22: Synthesis, Assessment of Bioactivity on Plant Growth, and Molecular Docking Study

“…One of the main difficulties found in the synthesis of BRs is the replication of the side alkyl chain due to the presence of at least three chiral centers. Thus, in the quest for new active analogs, various BRs analogs have been obtained by incorporating important structural modifications in their side chain [ 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 ].…”

Luteoloside Induces G0/G1 Phase Arrest of Neuroblastoma Cells by Targeting p38 MAPK

“…It is commonly used in research on multitarget and multiaction traditional Chinese medicine. Molecular docking allows a receptor–ligand complex to be docked according to an analysis of the specific receptor docking sites and the drug molecule [ 20 ]. Although studies have shown that luteoloside has anti-tumor effects, the specific targets are still unclear, and neuroblastoma has not yet been studied to determine the effects and mechanisms of luteoloside.…”