Center for Natural Product Research, Faculty of Chemistry, University of Havana, Zapata and G, Havana 10400, Cuba.
Sierra Maestra Science, Technology and Innovation Entity, Barlovento Complex, 5ta Ave. and 246, Havana 11300, Cuba.
Int J Mol Sci. 2021 Feb 26;22(5):2330. doi: 10.3390/ijms22052330.
A priority of modern agriculture is to use novel and environmentally friendly plant-growth promoter compounds to increase crop yields and avoid the indiscriminate use of synthetic fertilizers. Brassinosteroids are directly involved in the growth and development of plants and are considered attractive candidates to solve this problem. Obtaining these metabolites from their natural sources is expensive and cumbersome since they occur in extremely low concentrations in plants. For this reason, much effort has been dedicated in the last decades to synthesize brassinosteroids analogs. In this manuscript, we present the synthesis and characterization of seven steroidal carbamates starting from stigmasterol, β-sitosterol, diosgenin and several oxygenated derivatives of it. The synthesis route for functionalization of diosgenin included epoxidation and epoxy opening reactions, reduction of carbonyl groups, selective oxidation of hydroxyl groups, among others. All the obtained compounds were characterized by H and C NMR, HRMS, and their melting points are also reported. Rice lamina inclination test performed at different concentrations established that all reported steroidal carbamates show plant-growth-promoting activity. A molecular docking study evaluated the affinity of the synthesized compounds towards the BRI1-BAK1 receptor from and three of the docked compounds displayed a binding energy lower than brassinolide.
现代农业的一个重点是使用新型环保的植物生长促进化合物来提高作物产量，并避免滥用合成肥料。油菜素内酯直接参与植物的生长和发育，被认为是解决这个问题的有吸引力的候选物。由于它们在植物中含量极低，从天然来源获得这些代谢物既昂贵又繁琐。出于这个原因，过去几十年，人们投入了大量精力来合成油菜素内酯类似物。在本文中，我们从豆甾醇、β-谷甾醇、薯蓣皂苷元和几种其含氧衍生物出发，介绍了七种甾体氨基甲酸酯的合成和表征。薯蓣皂苷元的功能化合成路线包括环氧化和环氧化开环反应、羰基还原、羟基选择性氧化等。所有获得的化合物均通过 H 和 C NMR、高分辨质谱 (HRMS) 进行了表征，并报告了它们的熔点。在不同浓度下进行的水稻叶片倾斜试验表明，所有报道的甾体氨基甲酸酯均具有植物生长促进活性。分子对接研究评估了合成化合物与 和三个对接化合物之一对 BRI1-BAK1 受体的亲和力，其中三个对接化合物的结合能低于油菜素内酯。
