Isolation, Crystal Structure, and In Silico Aromatase Inhibition Activity of Ergosta-5, 22-dien-3β-ol from the Fungus Gyromitra esculenta
| Autor: | Buddha Bahadur Basnet, Hongwei Liu, Ahmed M. Metwaly, Raigul Nurbekkyzy Suleimen, Margarita Yulayevna Ishmuratova, Yerlan Suleimen, Ahmad E. Mostafa, Eslam B. Elkaeed, Koblandy Muboryakovich Turdybekov, Kristof Van Heсke |
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| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Article Subject
Stereochemistry medicine.medical_treatment In silico ERGOSTEROL PEROXIDE Steroid VIVO chemistry.chemical_compound medicine ANTICANCER ACTIVITY ALPHA-PYRONE DERIVATIVES QD1-999 STEROLS chemistry.chemical_classification Ergosterol biology Ergosterol peroxide QSAR Absolute configuration General Chemistry biology.organism_classification Ligand (biochemistry) Gyromitra esculenta Chemistry Enzyme chemistry X-RAY BRASSICASTEROL GROWTH |
| Zdroj: | JOURNAL OF CHEMISTRY Journal of Chemistry, Vol 2021 (2021) |
| ISSN: | 2090-9063 2090-9071 |
| DOI: | 10.1155/2021/5529786 |
| Popis: | 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 structural 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. |
| Databáze: | OpenAIRE |
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