The Synthesis of Schiff bases and new secondary amine derivatives of p-vanillin and evaluation of their neuroprotective, antidiabetic, antidepressant and antioxidant potentials

Yuldasheva, Nilufar; Acikyildiz, Nihan; Akyüz, Mehmet; Yabo-Dambagi, Lawali; Aydin, Tuba; Çakır, Ahmet; Kazaz, Cavit

doi:10.1016/j.molstruc.2022.133883

Cited by 24 publications

(12 citation statements)

References 44 publications

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“…According to the results obtained in this study, ursolic acid was determined to be a very strong α ‐glycosidase inhibitor. The IC 50 value of acarbose for α ‐glycosidase is given as 22.41 (mM) (Table 2) in the literature [52] . In the study, the IC 50 value calculated for ursolic acid was found to be 10.40 mM (4.75±0.06 mg/ml).…”

Section: Resultsmentioning

confidence: 79%

“…The IC 50 value of acarbose for α-glycosidase is given as 22.41 (mM) (Table 2) in the literature. [52] In the study, the IC 50 value calculated for ursolic acid was found to be 10.40 mM (4.75 � 0.06 mg/ml). This finding shows that ursolic acid was evaluated as a stronger inhibitor for α-glycosidase than acarbose, a commercial antidiabetic agent.…”

Section: Antidiabetic Effects Of the Extracts And Ursolic Acidmentioning

confidence: 85%

“…When the IC 50 values of the extracts for AChE were compared among themselves, no direct relationship [a] It was used as a standard inhibitor for α-glycosidase. [52] Table 3 [a] 3.80 (μM) 0.9913 3.13 (μM) 0.9906 [a] It was used as a standard inhibitor for AChE and BChE enzymes.…”

Section: Neuroprotective Effects Of the Extracts And Ursolic Acidmentioning

confidence: 99%

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Lavandula stoechas L. subsp. stoechas, a New Herbal Source for Ursolic Acid: Quantitative Analysis, Purification and Bioactivity Studies

Aydin¹,

Kaya

Gümüştaş

et al. 2023

Chemistry & Biodiversity

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In this study, methanol, ethanol, methanol‐dichloromethane (1 : 1, v/v), acetone, ethyl acetate, diethyl ether, and chloroform extracts of lavender (Lavandula stoechas L. subsp. stoechas) were prepared by maceration, and the ursolic acid contents in the extracts were determined quantitatively by HPLC analyses. The present results show that the methanol‐dichloromethane (1 : 1, v/v) solvent system is the most efficient solvent system for the extraction of ursolic acid from the plant sample with the highest yield (2.22 g/100 g plant sample). In the present study, a new practical method for the isolation of ursolic acid from polar extracts was also demonstrated for the first time. The inhibition effects of the extracts and ursolic acid were also revealed on α‐glycosidase, acetylcholinesterase, butyrylcholinesterase, and human carbonic anhydrase I and II enzymes by determining IC50 values for the first time. The extracts and ursolic acid acted as potent antidiabetic agents by strongly inhibiting the α‐glycosidase activity, whereas they were found to be very weak neuroprotective agents. In view of the present results, L. stoechas and its major metabolite, ursolic acid, can be recommended as a herbal source to control postprandial blood sugar levels and prevent diabetes by delaying the digestion of starch in food.

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Section: Resultsmentioning

confidence: 79%

Section: Antidiabetic Effects Of the Extracts And Ursolic Acidmentioning

confidence: 85%

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Lavandula stoechas L. subsp. stoechas, a New Herbal Source for Ursolic Acid: Quantitative Analysis, Purification and Bioactivity Studies

Aydin¹,

Kaya

Gümüştaş

et al. 2023

Chemistry & Biodiversity

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“…When the literature is reviewed, it is seen that Schiff bases exhibit antioxidant ability by removing ROS [ 31 ]. Additionally, the connection between the chemical structures of Schiff bases and their antioxidant ability is well established [ 32 ]. Additionally, Schiff bases and derivatives containing the azomethine group (–N=CH–) have different applications.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Schiff Bases Containing Phenol Rings and Investigation of Their Antioxidant Capacity, Anticholinesterase, Butyrylcholinesterase, and Carbonic Anhydrase Inhibition Properties

et al. 2023

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The widespread usage of Schiff bases in chemistry, industry, medicine, and pharmacy has increased interest in these compounds. Schiff bases and derivative compounds have important bioactive properties. Heterocyclic compounds containing phenol derivative groups in their structure have the potential to capture free radicals that can cause diseases. In this study, we designed and synthesized eight Schiff bases (10–15) and hydrazineylidene derivatives (16–17), which contain phenol moieties and have the potential to be used as synthetic antioxidants, for the first time using microwave energy. Additionally, the antioxidant effects of Schiff bases (10–15) and hydrazineylidene derivatives (16–17) were studied using by the bioanalytical methods of 2,2’-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) cation radical (ABTS•+) and 1,1-diphenyl-2-picrylhydrazyl (DPPH•) scavenging activities, and Fe3+, Cu2+, and Fe3+-TPTZ complex reducing capacities. In the context of studies on antioxidants, Schiff bases (10–15) and hydrazineylidene derivatives (16–17) were found to be as powerful DPPH (IC50: 12.15–99.01 μg/mL) and ABTS•+ (IC50: 4.30–34.65 μg/mL). Additionally, the inhibition abilities of Schiff bases (10–15) and hydrazineylidene derivatives (16–17) were determined towards some metabolic enzymes including acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and human carbonic anhydrase I and II (hCAs I and II), enzymes that are linked to some global disorders including Alzheimer’s disease (AD), epilepsy, and glaucoma. In the context of studies on enzyme inhibition, it was observed that the synthesized Schiff bases (10–15) and hydrazineylidene derivatives (16–17) inhibited AChE, BChE, hCAs I, and hCA II enzymes with IC50 values in ranges of 16.11–57.75 nM, 19.80–53.31 nM, 26.08 ± 8.53 nM, and 85.79 ± 24.80 nM, respectively. In addition, in light of the results obtained, we hope that this study will be useful and guiding for the evaluation of biological activities in the fields of the food, medical, and pharmaceutical industries in the future.

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“…[9] Schiff bases are a signi cant class of organic and bioinorganic compounds because they have substantial pharmacological activities such as cytotoxicity, DNA cleavages, antifungal, antibacterial, antimalarial, antiproliferative, anti-in ammatory, antiviral, antioxidant, anticancer, analgesic, antipyretic, antidiabetic and anti-HIV activities. [10][11][12][13][14][15][16][17][18][19][20][21][22][23][24] Schiff bases containing heterocycles have drawn much attention due to their diverse biological activity. [25] Extra hydroxyl group at ortho and para position with respect to imines linkage increases antifungal activity against C.albicans fungi.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Crystal structure, in vitro, and in silico biological studies of 2, 5-dihydroxybenzaldehyde based novel Schiff bases

Todarwal

Sancheti

Shah

et al. 2023

Preprint

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The present study reports the synthesis of novel Schiff base ligands (S1-S8) derived from 2, 5-dihydroxybenzaldehyde by coupling with substituted amines. Further, the electron-donating and electron-withdrawing substituents on the amines are intended to tune the properties of the new Schiff base ligands. The chemical structures of these compounds were extensively elucidated by FT-IR, 1H-NMR, 13C-NMR, and ESI-MS. The X-ray analyses show that the compounds crystallized in a triclinic crystal system with a space group of P-1 and Z = 2 for S1. Besides, antimicrobial potency against gram-positive bacteria and gram-negative bacteria, as well as against fungi, was studied. S3 has superior inhibitory activity against all bacterial strains. The consortium of different substituent atoms on the phenyl ring and the heterocyclic ring counterpart is one of the reasons behind the recorded optimal activity. Compound S8 has potent antifungal inhibitory action against C.albicans compared to the standard antifungal, whereas Schiff base S5 also has well to moderate activity against all fungal strains. A molecular docking result indicates that these compounds could also be effective against the resistance β-ketoacyl-ACP (acyl carrier protein) synthase-I enzyme of E.coli.

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The Synthesis of Schiff bases and new secondary amine derivatives of p-vanillin and evaluation of their neuroprotective, antidiabetic, antidepressant and antioxidant potentials

Cited by 24 publications

References 44 publications

Lavandula stoechas L. subsp. stoechas, a New Herbal Source for Ursolic Acid: Quantitative Analysis, Purification and Bioactivity Studies

Lavandula stoechas L. subsp. stoechas, a New Herbal Source for Ursolic Acid: Quantitative Analysis, Purification and Bioactivity Studies

Synthesis of Schiff Bases Containing Phenol Rings and Investigation of Their Antioxidant Capacity, Anticholinesterase, Butyrylcholinesterase, and Carbonic Anhydrase Inhibition Properties

Synthesis, Crystal structure, in vitro, and in silico biological studies of 2, 5-dihydroxybenzaldehyde based novel Schiff bases

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