Novel hypervalent iodine catalyzed synthesis of α-sulfonoxy ketones: Biological activity and molecular docking studies

Atmaca, Ufuk; Alp, Cemalettin; Akıncıoğlu, Hülya; Karaman, Halide Sedef; Gülçın, İlhami

doi:10.1016/j.molstruc.2021.130492

Cited by 16 publications

(5 citation statements)

References 118 publications

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“…Studies have proven that the cholinergic hypothesis is a clinically appropriate strategy. [20,21] This disease is clinically affected by damage to brain tissue caused by a deficiency in ACh molecules. [22] AChE is a hydrolytic enzyme and turns ACh into acetate (CH 3 COO À ) and choline (Ch) as the main element of the nervous systems.…”

Section: Introductionmentioning

confidence: 99%

Polyphenol Contents, Potential Antioxidant, Anticholinergic and Antidiabetic Properties of Mountain Mint (Cyclotrichium leucotrichum)

Gülçın

Bingöl

Taslimi

et al. 2022

Chemistry & Biodiversity

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In the present work, antioxidant and antidiabetic potentials of mountain mint [Cyclotrichium leu-cotrichum (Stapf ex Rech. Fil.) Leblebici] was the first time appraised. In this sense, methanol (MECL) and water (WECL) extracts were obtained from aerial parts of mountain mint (Cyclotrichium leucotrichum) and studied for their antioxidant ability by several bioanalytical assays. Also, their inhibition profiles were realized toward several metabolic enzymes connected to some diseases, including butyrylcholinesterase (BChE), α-glycosidase, acetylcholinesterase (AChE), and α-amylase enzymes. Additionally, their phenolic contents were determined by putative chromatographic method of LC/MS/MS. Consequently, nineteen phenolic molecules were identified in MECL and fifteen phenolic molecules were found in WECL. Also, antioxidant effects of both extracts were studied using by the methods of 1,1-diphenyl-2-picryl-hydrazyl (DPPH * ), 2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS * + ) and N,N-dimethyl-p-phenylenediamine (DMPD * + ) scavenging activities, ferric (Fe 3 + ) and cupric (Cu 2 + ) ions and Fe 3 + -2,4,6-tri(2-pyridyl)-s-triazine (TPTZ) reducing capacities. MECL and WECL were found as powerful DPPH * (IC 50 : 23.74 and 28.85 μg/mL), ABTS * + (IC 50 : 12.53 and 14.05 μg/mL) and DMPD * + scavenging effects (IC 50 : 43.52 and 54.80 μg/mL). Also, both extracts demonstrated the effective inhibition on AChE (IC 50 : 69.31 and 115.51 μg/mL), BChE (IC 50 : 57.75 and 86.62 μg/mL), α-glycosidase (IC 50 : 36.47 and 62.94 μg/mL) and αamylase (IC 50 : 1.01 and 3.43 μg/mL). This study will be useful for future studies to determine the antioxidant properties and enzyme inhibition profile of food, medical and industrially important plants.

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Section: Introductionmentioning

confidence: 99%

Polyphenol Contents, Potential Antioxidant, Anticholinergic and Antidiabetic Properties of Mountain Mint (Cyclotrichium leucotrichum)

Gülçın

Bingöl

Taslimi

et al. 2022

Chemistry & Biodiversity

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“…The α-Gly inhibitors have a large drug potential. [29,35,36] α-Gly hydrolase enzymes are responsible for the digestion of carbohydrates. This enzyme hydrolyzes carbohydrates by acting on 1,4-α bonds and releases D-glucose from the nonreducing end of the sugar.…”

Section: Introductionmentioning

confidence: 99%

Benzimidazolium salts bearing the trifluoromethyl group as organofluorine compounds: Synthesis, characterization, crystal structure, in silico study, and inhibitory profiles against acetylcholinesterase and α‐glycosidase

Tezcan

Gök

Sevinçek

et al. 2022

J Biochem & Molecular Tox

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Here, we report the synthesis, characterization, and biological activities of a series of benzimidazolium salts bearing the trifluoromethylbenzyl group. All benzimidazolium salts were characterized by using nuclear magnetic resonance (NMR) ( 1 H NMR and 13 C NMR), Fourier transform-infrared spectroscopy, and elemental analysis techniques. The crystal structures of some of these compounds were obtained by the single-crystal X-ray diffraction method. Furthermore, the acetylcholinesterase (AChE) and α-glycosidase (α-Gly) enzyme inhibition activities of these compounds were investigated. The obtained results revealed that 2e, with K i value of 1.36 ± 0.34 µM against AChE and 3d with K i value of 91.37 ± 10.38 µM against α-Gly, were the most potent compounds against both assigned enzymes. It should be noted that most of the synthesized compounds were more potent than standard inhibitor tacrine (TAC) against AChE. In silico studies, we focused on compound 2e, 3d, 3e, and 3f as potent inhibitors of AChE and α-Gly, the compound 2e showed good binding energy (−10.23 kcal/mol), among the three selected compounds and positive control (−10.18, −10.08, and −7.37 kcal/mol for 3d, 3f, and TAC, respectively). Likewise, as a result of the same compounds against the α-Gly enzyme, the compound 3d had the highest binding affinity (−8.39 kcal/mol) between the four selected compounds and the positive control (−8.27, −8.10, −8.06, and −7.53 kcal/mol for 3f, 3e, 2e, and acarbose, respectively). From the absorption, distribution, metabolism, excretion, and toxicity analyses, it can be concluded that the compounds under consideration exhibited more drug-likeness properties in the prediction studies compared to positive controls.

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“…Thus, DEIs compete with oligosaccharides for binding to the active site of the enzyme. Acarbose is one of the best examples of this form of inhibition [ 40 ].…”

Section: Introductionmentioning

confidence: 99%

Comprehensive Metabolite Profiling of Cinnamon (Cinnamomum zeylanicum) Leaf Oil Using LC-HR/MS, GC/MS, and GC-FID: Determination of Antiglaucoma, Antioxidant, Anticholinergic, and Antidiabetic Profiles

Mutlu

Bingöl

Üç

et al. 2023

Life

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In this study, for the first time, the antioxidant and antidiabetic properties of the essential oil from cinnamon (Cinnamomum zeylanicum) leaves were evaluated and investigated using various bioanalytical methods. In addition, the inhibitory effects of cinnamon oil on carbonic anhydrase II (hCA II), acetylcholinesterase (AChE), and α-amylase, which are associated with various metabolic diseases, were determined. Further, the phenolic contents of the essential oil were determined using LC-HRMS chromatography. Twenty-seven phenolic molecules were detected in cinnamon oil. Moreover, the amount and chemical profile of the essential oils present in cinnamon oil was determined using GC/MS and GC-FID analyses. (E)-cinnamaldehyde (72.98%), benzyl benzoate (4.01%), and trans-Cinnamyl acetate (3.36%) were the most common essential oils in cinnamon leaf oil. The radical scavenging activities of cinnamon oil were investigated using 1,1-diphenyl-2-picryl-hydrazil (DPPH·), 2,2’-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid), and (ABTS•+) bioanalytical scavenging methods, which revealed its strong radical scavenging abilities (DPPH·, IC50: 4.78 μg/mL; and ABTS•+, IC50: 5.21 μg/mL). Similarly, the reducing capacities for iron (Fe3+), copper (Cu2+), and Fe3+-2,4,6-tri(2-pyridyl)-S-triazine (TPTZ) were investigated. Cinnamon oil also exhibited highly effective inhibition against hCA II (IC50: 243.24 μg/mL), AChE (IC50: 16.03 μg/mL), and α-amylase (IC50: 7.54μg/mL). This multidisciplinary study will be useful and pave the way for further studies for the determination of antioxidant properties and enzyme inhibition profiles of medically and industrially important plants and their oils.

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Novel hypervalent iodine catalyzed synthesis of α-sulfonoxy ketones: Biological activity and molecular docking studies

Cited by 16 publications

References 118 publications

Polyphenol Contents, Potential Antioxidant, Anticholinergic and Antidiabetic Properties of Mountain Mint (Cyclotrichium leucotrichum)

Polyphenol Contents, Potential Antioxidant, Anticholinergic and Antidiabetic Properties of Mountain Mint (Cyclotrichium leucotrichum)

Benzimidazolium salts bearing the trifluoromethyl group as organofluorine compounds: Synthesis, characterization, crystal structure, in silico study, and inhibitory profiles against acetylcholinesterase and α‐glycosidase

Comprehensive Metabolite Profiling of Cinnamon (Cinnamomum zeylanicum) Leaf Oil Using LC-HR/MS, GC/MS, and GC-FID: Determination of Antiglaucoma, Antioxidant, Anticholinergic, and Antidiabetic Profiles

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