Phytosterol Glycosides from Olax subscorpioidea Oliv. Exhibit Cytotoxic Effects in In Vitro and In Silico Studies

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389030%3A_____%2F25%3A00638620" target="_blank" >RIV/61389030:_____/25:00638620 - isvavai.cz</a>

Výsledek na webu

<a href="https://doi.org/10.34172/PS.025.40914" target="_blank" >https://doi.org/10.34172/PS.025.40914</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.34172/PS.025.40914" target="_blank" >10.34172/PS.025.40914</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Phytosterol Glycosides from Olax subscorpioidea Oliv. Exhibit Cytotoxic Effects in In Vitro and In Silico Studies

Popis výsledku v původním jazyce

Background: Olax subscorpioidea is traditionally used to treat arthritis, cancer, diabetes, neurodegenerative disorders, and oxidative stress. This study carried out chromatographic isolation, cytotoxicity, and molecular docking studies of bioactive compounds from O. subscorpioidea. Methods: The root of O. subscorpioidea was extracted with methanol using the Soxhlet extraction method. The extract was partitioned into n-hexane, dichloromethane (DCM), and methanol/ water. The DCM fraction was subjected to column chromatography. Bioactive compounds were isolated and their chemical structures were established by one-dimensional (1D) and twodimensional (2D) nuclear magnetic resonance (NMR) spectroscopy, and by comparing their NMR data with those previously reported in the literature. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay was used to evaluate the cytotoxic activity of these compounds against three human cancer cell lines: breast (MCF-7), cervical (HeLa), and colorectal (Caco-2) cell lines. Molecular docking was used to gain insights into the favourable binding conformations and energies of the compounds when interacting with ten selected cancer-related protein targets. Results: The phytochemical investigation of the extract of O. subscorpioidea afforded two sterol glycosides, stigmast-5,22-dien-3-O-fl-D-glucoside (1a) and sitosterol-3-O-fl-D-glucoside (1b), as a mixture. The compounds were found to be active against HeLa (IC50: 37.0 +/- 4.51 mu g/mL) and MCF-7 (137.07 +/- 19.43 mu g/mL) cell lines. The compounds showed strong interactions with the colchicine-binding site on the fl-subunit of tubulin protein, epidermal growth factor receptor kinase domain, poly(ADP-ribose) polymerase-1, and 17fl-hydroxysteroid dehydrogenase type 1 (binding energies:10.3 and-10.0 kcal/mol-9.3 and-9.3 kcal/mol-9.2 and-9.2 kcal/ mol and-9.3 and-9.1 kcal/mol, respectively). Stigmast-5,22-dien-3-O-fl-D-glucoside was consistently ranked higher in some of the proteins tested. The compounds stabilised in the binding sites of the proteins via hydrogen bonds and hydrophobic interactions. Conclusion: To the best of our knowledge, this is the first report on the isolation of these compounds from this plant. The cytotoxic effects of O. subscorpioidea root extract could be partly attributed to stigmast-5,22-dien-3-O-fl-D-glucoside and sitosterol-3-O-fl-D-glucoside.

Název v anglickém jazyce

Phytosterol Glycosides from Olax subscorpioidea Oliv. Exhibit Cytotoxic Effects in In Vitro and In Silico Studies

Popis výsledku anglicky

Background: Olax subscorpioidea is traditionally used to treat arthritis, cancer, diabetes, neurodegenerative disorders, and oxidative stress. This study carried out chromatographic isolation, cytotoxicity, and molecular docking studies of bioactive compounds from O. subscorpioidea. Methods: The root of O. subscorpioidea was extracted with methanol using the Soxhlet extraction method. The extract was partitioned into n-hexane, dichloromethane (DCM), and methanol/ water. The DCM fraction was subjected to column chromatography. Bioactive compounds were isolated and their chemical structures were established by one-dimensional (1D) and twodimensional (2D) nuclear magnetic resonance (NMR) spectroscopy, and by comparing their NMR data with those previously reported in the literature. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay was used to evaluate the cytotoxic activity of these compounds against three human cancer cell lines: breast (MCF-7), cervical (HeLa), and colorectal (Caco-2) cell lines. Molecular docking was used to gain insights into the favourable binding conformations and energies of the compounds when interacting with ten selected cancer-related protein targets. Results: The phytochemical investigation of the extract of O. subscorpioidea afforded two sterol glycosides, stigmast-5,22-dien-3-O-fl-D-glucoside (1a) and sitosterol-3-O-fl-D-glucoside (1b), as a mixture. The compounds were found to be active against HeLa (IC50: 37.0 +/- 4.51 mu g/mL) and MCF-7 (137.07 +/- 19.43 mu g/mL) cell lines. The compounds showed strong interactions with the colchicine-binding site on the fl-subunit of tubulin protein, epidermal growth factor receptor kinase domain, poly(ADP-ribose) polymerase-1, and 17fl-hydroxysteroid dehydrogenase type 1 (binding energies:10.3 and-10.0 kcal/mol-9.3 and-9.3 kcal/mol-9.2 and-9.2 kcal/ mol and-9.3 and-9.1 kcal/mol, respectively). Stigmast-5,22-dien-3-O-fl-D-glucoside was consistently ranked higher in some of the proteins tested. The compounds stabilised in the binding sites of the proteins via hydrogen bonds and hydrophobic interactions. Conclusion: To the best of our knowledge, this is the first report on the isolation of these compounds from this plant. The cytotoxic effects of O. subscorpioidea root extract could be partly attributed to stigmast-5,22-dien-3-O-fl-D-glucoside and sitosterol-3-O-fl-D-glucoside.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

30104 - Pharmacology and pharmacy

Projekt

<a href="/cs/project/GA23-05389S" target="_blank" >GA23-05389S: Nové CB2 a BChE modulátory proti Parkinsonově chorobě a souvisejícím patologiím</a><br>

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2025

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Pharmaceutical Sciences

ISSN

1735-403X

e-ISSN

2383-2886

Svazek periodika

31

Číslo periodika v rámci svazku

3

Stát vydavatele periodika

IR - Íránská islámská republika

Počet stran výsledku

10

Strana od-do

294-303

Kód UT WoS článku

001531298600008

EID výsledku v databázi Scopus

2-s2.0-105014616860