Synthesis, Characterization, Molecular Docking, and Biological Activities of Some Natural and Synthetic Urolithin Analogs

Noshadi, Bahareh; Erçetin, Tuğba; Luise, Chiara; Yüksel, Mine Yarim; Sippl, Wolfgang; Şahi̇n, Mustafa; Gazi, Mustafa; Gülcan, Hayrettin Ozan

doi:10.1002/cbdv.202000197

Cited by 22 publications

(21 citation statements)

References 32 publications

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“…Following the evaporation of collected organic phases, the compounds were purified through column chromatography employing ethyl acetate -n-hexane (1:1) as the mobile phase. Spectral characterizations of the molecules have also been previously stated (14).…”

Section: Chemistrymentioning

confidence: 93%

The Compound Specific Antibacterial Activities of Major Urolithins and Their Methyl Ethers

Gülcan¹,

İlktaç²,

Noshadi³

et al. 2021

Journal of the Turkish Chemical Society Section A: Chemistry

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The investigation of biological activities of natural products, particularly considering the secondary metabolites, continuously receives attention. Urolithins, the bioavailable metabolites of ellagitannins, were shown to possess enzyme inhibitor, antioxidant, and anti-inflammatory compounds in scientific studies conducted in the last two decades. Regarding the limited number of studies related to their antimicrobial activity, this study aimed to synthesize major urolithins (Urolithin A and B) concomitant to their methyl ether derivatives and screen their antibacterial activity against some Gram positive and Gram negative bacteria. In parallel to the antibacterial activity, the synergistic and antagonist properties of the compounds were also analyzed in the presence of reference beta-lactam antibiotics. The results displayed the improvable characteristics of urolithin scaffold to be employed in antibiotic drug design studies. In addition, the antagonist effect of some compounds on the antibacterial action of standard molecules also pointed out the compound specific activities of the title molecules.

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Section: Chemistrymentioning

confidence: 93%

The Compound Specific Antibacterial Activities of Major Urolithins and Their Methyl Ethers

Gülcan¹,

İlktaç²,

Noshadi³

et al. 2021

Journal of the Turkish Chemical Society Section A: Chemistry

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“…Resorcinol was employed to obtain both URO-1 and THU-1 through, respectively, treating it with 2-iodobenzoic acid in basic aqueous under reflux, and ethyl 2-oxocyclohexanecarboxylate in the presence of a Lewis acid under neat conditions, according to the previously published procedures. [18,24] These two compounds were used as starting materials for the synthesis of the title URO and THU series (i.e., 6Hbenzo[c]chromen-6-one and 7,8,9,10-tetrahydro-benzo[c]chromen-6one derivatives, respectively). Williamson ether synthesis conditions were employed to convert URO-1 and THU-1, respectively, to their ester analogs (i.e., URO-2 and THU-2).…”

Section: Chemistrymentioning

confidence: 99%

“…To screen the potential of the title molecules and synthesis intermediates (i.e., URO-1-10 and THU-1-10) to inhibit AChE and BuChE, modified Ellmann's method was employed. [15,18] Each enzyme assay…”

Section: Cholinesterase Inhibition Assaysmentioning

confidence: 99%

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Design, synthesis, and biological evaluation of new urolithin amides as multitarget agents against Alzheimer's disease

Shukur

Erçetin

Luise

et al. 2021

Archiv der Pharmazie

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A series of urolithin amide (i.e., URO-4-URO-10 and THU-4-THU-10) derivatives was designed and synthesized, and their chemical structures were confirmed with spectroscopic techniques and elemental analysis. The title compounds and synthesis intermediates (THU-1-THU-10 and URO-1-URO-10) were evaluated for their potential to inhibit acetylcholinesterase (AChE), butyrylcholinesterase (BuChE), and monoamine oxidase B (MAO-B). Compounds THU-4 and THU-8 were found to be the most potent inhibitors for the cholinesterases and MAO-B, respectively. The docking studies were also employed to evaluate the binding modes of the most active compounds with AChE, BuChE, and MAO-B. Furthermore, the moderate-tostrong activities of the compounds were also displayed in amyloid-beta inhibition and antioxidant assay systems. The results pointed out that the urolithin scaffold can be employed in drug design studies for the development of multitarget ligands acting on various cascades shown to be important within the pathophysiology of Alzheimer's disease.

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“…Urolithins are the bioavailable metabolites of an ellagitannin-rich diet including pomegranate, nuts, and berries. Gastrointestinal microflora directed metabolism of ellagitannins generate urolithin derivatives and they act as biomarkers of ellagitannin exposure in systemic circulation [13][14].…”

Section: Introductionmentioning

confidence: 99%

3-Hydroxy-7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-one and 3-hydroxy-6H-benzo[c] chromen-6-one act as on-off selective fluorescent sensors for Iron (III) under in vitro and ex vivo conditions

Shukur¹,

Fallah²,

Teralı³

et al. 2021

Turk J Chem

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Regarding the abundant use of metals for different purposes, it becomes more critical from various scientific and technological perspectives to discover novel agents as selective probes for the detection of specific metals. In our previous studies, we have shown that aqueous solutions of natural urolithins (i.e., hydroxyl-substituted benzo[c]chromen-6-one derivatives) are selective Iron (III) sensors in fluorescence assays. In this study, we have extrapolated these findings to another coumarine compound (i.e., 3-Hydroxy-7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-one) and compared the selective metal binding properties with Urolithin B (i.e., 3-Hydroxy-6Hbenzo[c]chromen-6-one). Following the synthesis and structure identification studies, the fluorometric studies pointed out that the lactam group in the structure still persists to be the important scaffold for maintaining selective ON-OFF sensor capacity that renders the compound a selective Iron (III) binding probe. Moreover, for the first time, fluorescence cellular imaging studies concomitant to cytotoxicity assays with the title compounds were also performed and the results displayed the cell-penetrative, safe, and fluorescent detectable characteristics of the compounds in neuroblastoma and glioblastoma cells through servings as intracellular Iron (III) on-off sensors.

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Synthesis, Characterization, Molecular Docking, and Biological Activities of Some Natural and Synthetic Urolithin Analogs

Cited by 22 publications

References 32 publications

The Compound Specific Antibacterial Activities of Major Urolithins and Their Methyl Ethers

The Compound Specific Antibacterial Activities of Major Urolithins and Their Methyl Ethers

Design, synthesis, and biological evaluation of new urolithin amides as multitarget agents against Alzheimer's disease

3-Hydroxy-7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-one and 3-hydroxy-6H-benzo[c] chromen-6-one act as on-off selective fluorescent sensors for Iron (III) under in vitro and ex vivo conditions

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