Synthesis and Biological Evaluation of Spirostanes Including Butyrolactone Moieties

Pérez, Carolina; Leliebre-Lara, Vivian; Concepción, Omar; Coll, Francisco; Rivera, Daniel G.; Pando, Orlando

doi:10.2174/157017806778341870

Cited by 4 publications

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“…Diosgenin ( 6 ) has been used to prepare a significant number of spirostanic BRs analogs, which have shown a promising plant growth-promoting activity [ 17 , 33 , 34 , 35 , 36 , 37 ]. Considering these antecedents, we were interested in the possibility of preparing new diosgenin derivatives with the incorporation of carbamate functions in C3, modifications to ring B and evaluating the effect that these chemical modifications could have on plant growth-promoting activity.…”

Section: Resultsmentioning

confidence: 99%

“…Synthetic advances have allowed obtaining a series of BRs analogs with novel structures and substituent functions, which exhibit similar or even higher biological effects as compared to natural molecules [ 15 , 16 ]. Thus, in the last years different research groups have reported the synthesis of new BRs analogs to study their structure/activity relationship [ 16 , 17 , 18 , 19 , 20 ], resulting in very active and stable compounds [ 21 , 22 ]. Several studies have proved that some synthetic BRs analogs can produce a wide range of physiological responses in plants, like potentiate plant growth and development and protection from several conditions of stress [ 15 , 23 , 24 ].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of New Steroidal Carbamates with Plant-Growth-Promoting Activity: Theoretical and Experimental Evidence

Pacheco

Ceballos

Castro

et al. 2021

IJMS

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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 1H and 13C 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 Arabidopsis thaliana and three of the docked compounds displayed a binding energy lower than brassinolide.

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