Isolation, Crystal Structure, and In Silico Aromatase Inhibition Activity of Ergosta-5, 22-dien-3β-ol from the Fungus Gyromitra esculenta

Yerlan Melsuly Suleimen, Ahmed M. Metwaly, Ahmad E. Mostafa, Eslam B. Elkaeed, Hong-Wei Liu, Buddha Bahadur Basnet, Raigul Nurbekkyzy Suleimen, Margarita Yulayevna Ishmuratova, Koblandy Muboryakovich Turdybekov, Kristof Van Heсke
2021 Journal of Chemistry  
Ergosterol derivatives exhibited copious promising biological activities. The fungus Gyromitra esculenta is widely distributed in Europe and North America. In order to examine the chemical properties of Gyromitra esculenta, a phytochemical study has been preceded and resulted in the isolation of the steroid, ergosta-5, 22-dien-3β-ol (brassicasterol), from its methanol extract. The complete identification and absolute configuration of the isolated compound have been established by X-ray
more » ... l analysis to be (22E, 24R)-24-methylcholesta-5, 22-dien-3beta-ol. The reported cytotoxicity and the great structural similarity of the isolated compound with the cocrystallized ligand of the aromatase enzyme inspired us to run molecular docking studies against that protein. Ergosta-5, 22-dien-3β-ol occupied the target protein with a binding mode almost the same as the cocrystallized ligand and a binding affinity of −33.55 kcal/mol, which was better than that of the cocrystallized ligand (−22.61 kcal/mol). This promising result encouraged us to conduct in silico ADMET and toxicity studies of ergosta-5, 22-dien-3β-ol against 6 models, and the results expected the likeness of the isolated compound to be a drug. In conclusion, ergosta-5, 22-dien-3β-ol has been isolated from Gyromitra esculenta, identified by X-ray structural analysis, and exhibited promising in silico activities against aromatase enzyme.
doi:10.1155/2021/5529786 doaj:96fb68779bd246c8941bc70e3ca4cea3 fatcat:valgivbhi5canfyaiqvvdcujmm