Synthesis and molecular modeling: Related approaches to progress in brassinosteroid research

Abstract

In the field of brassinosteroids, which are potent plant growth regulators, we have developed a quantitative structure-activity relationship study to develop knowledge from a structural point of view and to find out new requirement definitions. This will help identify other suitable active brassinosteroid derivatives with a good activity/synthetic cost ratio for further application in agriculture. The methodology used to achieve this goal represents a multidisciplinary study involving synthesis, molecular modeling calculations, and bioactivity evaluation. The influence of different molecular properties in the bioactivity of a set of synthetic compounds (i.e., molecular electrostatic potential and the ability to form H bonds) is discussed. The molecular electrostatic potential is expressed in terms of the electrostatic Carbó similarity index (CI) between brassinolide (1) and other brassinosteroids. We have found that the electrostatic charges of the functional groups play an important role in the description of the activity, as evidenced by its good correlation with the CI in most cases. Deviation from this rule could be explained by the H bonding abilities of some of these compounds, which we believe may play an essential role in binding to the natural receptors.

NMR and X-ray studies of isomeric 22,23-dihydroxy stigmastanes

“…The preferred conformations of BS side chain were subject of numerous studies, especially those involving molecular modeling approaches [5][6][7][8][9][10][11]. The obtained conclusions can be based on some speculations and should be verified experimentally.…”

Antiviral Effect of Brassinosteroids against Herpes Virus and Arenaviruses

“…Brassinosteroids are a novel group of steroids that appear to be ubiquitous in plants and essential for normal plant growth and development. They have exciting potential use in agriculture because of their ability to improve crop yield and quality, minimize enviromental stress and herbicidal injury and control pathogenic diseases (Brosa, 1997;Brosa et al, 1997).…”

A theoretical approach to the solvation of brassinosteroids

“…The activity of BRs could be related with the formation of hydrogen bonds in the receptor binding sites [10,36]. Moreover the exploration of the sites of the BRs molecules that more likely will interact with water by hydrogen-bond interactions is important to understand how may occur the hydrophilic interactions of these phytohormones with the receptor.…”