Isolation and cytotoxic activities of undescribed iridoid and xanthone glycosides from Centaurium erythraea Rafn. (Gentianaceae)

Akşit, Hüseyin; Gözcü, Sefa; Altay, Ahmet

doi:10.1016/j.phytochem.2022.113484

Cited by 12 publications

(4 citation statements)

References 26 publications

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“…Thus, natural therapies can be less harmful than synthetic agents, even at high doses. Alternative and complementary therapies, such as traditional herbal medicine, are becoming increasingly important in developing new cancer treatments (Akşit et al., 2023). Therefore, isolated compounds and extracts in this study can be used to treat colon and prostate cancers without affecting the normal cells too much.…”

Section: Resultsmentioning

confidence: 99%

Two new compounds from endemic Centaurea paphlagonica (Bornm.) Wagenitz and their cytotoxic activities

Tüfekçi,

Demirtaş,

Akşit

et al. 2023

Chem Biol Drug Des

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Centaurea paphlagonica (Bornm.) Wagenitz is an endemic plant in Turkey. Pyrocatechol, vanillic acid, 3,4‐dihydroxy benzoic acid, 5‐O‐caffeoylshikimic acid, tamarixetin, chlorogenic acid methyl ester, quercetin, 1,3‐dicaffeoylquinic acid, tamarixetin‐7‐O‐β‐D‐glucopyranoside, quercimetrin, daucosterin, paphlagonicanin B, tamarixetin‐7‐O‐β‐rutinoside, rutin, chlorogenic acid, isoorientin, orientin, 3‐O‐feruloylquinic acid, quercetagetin‐3‐methyl ether 6‐O‐β‐glucopyranoside, diosmetin 6‐C‐β‐glucopyranoside, quercetagetin 4′‐methyl ether 7‐O‐β‐glucopyranoside, paphlagonicanin A, nepetin, cirsiliol, desacylcynaropicrin, and 8α‐O‐(2′,3′‐dihydroxyisobutyryl) desacylcynaropicrin were isolated from both flower and aerial parts of C. paphlagonica. These compounds were identified using 1D and 2D NMR methods and ESI‐MS. The MTT assay assessed the antiproliferative activities of all isolated (known and new compounds) compounds on Caco‐2, LNCaP, A549, HeLa, and HEK‐293 cell lines. The 8α‐O‐(2′,3′‐dihydroxyisobutyryl) desacylcynaropicrin demonstrated the highest activity against CaCo‐2 and HeLa cancer cell lines.

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Section: Resultsmentioning

confidence: 99%

Two new compounds from endemic Centaurea paphlagonica (Bornm.) Wagenitz and their cytotoxic activities

Tüfekçi,

Demirtaş,

Akşit

et al. 2023

Chem Biol Drug Des

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“…Cell culture, cell growth inhibition, apoptosis, mitochondrial membrane potential (MMP), and caspase activity assays were performed according to the procedures described in our previously published works [25–31] …”

Section: Methodsmentioning

confidence: 99%

“…After determining the active site of the target, ligand-target interaction constitutes the last step. In detail, the molecular docking protocol was applied as in previous studies.. [22,[29][30][31][32][33][34]…”

Section: General Procedures For the Preparation Of N'-(benzofuran-2-y...mentioning

confidence: 99%

Novel Pyrazole‐Based Benzofuran Derivatives as Anticancer Agents: Synthesis, Biological Evaluation, and Molecular Docking Investigations

Ameziane El Hassani,

Altay,

Karrouchi

et al. 2023

Chemistry & Biodiversity

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In this work, the design, synthesis and mechanistic studies of a novel pyrazole‐based benzofuran derivatives 1‐8 as anticancer agents were discussed. Cytotoxic potency of the title compounds was evaluated against the lung carcinoma A‐549, human‐derived colorectal adenocarcinoma HT‐29, breast adenocarcinoma MCF‐7 cells as well as mouse fibroblast 3T3‐L1 cells using XTT assay. Anticancer mechanistic studies were carried out with flow cytometry. XTT results revealed that all compounds exhibited dose‐dependent anti‐proliferative activity against the tested cancer cells, and especially compound 2 showed the strongest anti‐proliferative activity with an IC50 value of 7.31 µM and the highest selectivity (15.74) on MCF‐7 cells. Flow cytometry results confirmed that the cytotoxic power of the compound 2 on MCF‐7 cells is closely related to the mitochondrial membrane damage, caspase activation, and apoptosis orientation. Finally, molecular docking studies were applied to determine the interactions between compound 2 and caspase‐3 via in‐silico approaches. By molecular docking studies, free binding energy (ΔGBind), docking score, Glide score values as well as amino acid residues in the active binding site were determined. Consequently, these results constitute a preliminary data for in vivo anticancer studies and have the potential as a chemotherapeutic agent.

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“…Many studies have reported that flavonoids inhibit the α-glucosidase supporting our results. [35][36][37][38][39] Therefore, these compounds may have potential therapeutic effects in managing diabetes and other conditions associated with high blood sugar levels, as α-glucosidase inhibitors can slow down the digestion of carbohydrates and prevent a rapid increase in blood glucose levels after meals.…”

Section: α-Glucosidase Inhibition Activitymentioning

confidence: 99%

Ferruginoside D: A Novel Phenylethanoid from Verbascum leiocarpum

Şimşek,

Akşit,

Aydın

et al. 2023

Chemistry & Biodiversity

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A novel phenylethanoid, ferruginoside D, together with fourteen known compounds were isolated from the Verbascum leiocarpum for the first time. Chemical structures of isolated compounds were determined by spectroscopic analysis including HR‐ESI‐MS and NMR spectra. The antioxidant, α‐glucosidase inhibitory properties, and antiproliferative activities against multiple cell lines (A172, C6, HeLa, A2780, SW620, HT29, Beas2B, RPE, and HSF) of the isolated compounds were evaluated in vitro. According to the results, iridoids, flavonoids (luteolin and apigenin), and phenylethanoids (poliumoside and isoverbascoside) with strong antiproliferative potential were also found to have cytostatic effects. Furthermore, the investigation revealed that compounds luteolin, poliumoside, verbascoside, isoverbascoside, ferruginoside C, ferruginoside D, and ursolic acid show potent alpha‐glucosidase inhibitory activity, while compounds luteolin, verbascoside, and isoverbascoside exhibit substantial antioxidant activity. The new compound (ferruginoside D) was found moderately active against cancer cell lines, with strong alpha‐glucosidase inhibitory activity, and moderate antioxidant properties.

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Isolation and cytotoxic activities of undescribed iridoid and xanthone glycosides from Centaurium erythraea Rafn. (Gentianaceae)

Cited by 12 publications

References 26 publications

Two new compounds from endemic Centaurea paphlagonica (Bornm.) Wagenitz and their cytotoxic activities

Two new compounds from endemic Centaurea paphlagonica (Bornm.) Wagenitz and their cytotoxic activities

Novel Pyrazole‐Based Benzofuran Derivatives as Anticancer Agents: Synthesis, Biological Evaluation, and Molecular Docking Investigations

Ferruginoside D: A Novel Phenylethanoid from Verbascum leiocarpum

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