Hydroxybenzoic Acids as Acetylcholinesterase Inhibitors: Calorimetric and Docking Simulation Studies

Budryn, Grażyna; Majak, Iwona; Grzelczyk, Joanna; Szwajgier, Dominik; Rodriguez-Martínez, Alejandro; Pérez‐Sánchez, Horacio

doi:10.3390/nu14122476

Cited by 20 publications

(23 citation statements)

References 38 publications

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“…[35] Budryn et al deter- mined that 4-hydroxybenzoic acid inhibited AChE with an IC 50 value of 6.36 μmol/μmol. [36] Therefore, it can be argued that the extracts obtained within the scope of the study show an inhibitory effect on cholinesterases, thanks to the phytochemicals in their content. Cholinesterase inhibitors are a therapeutic approach used to eliminate cholinergic deficiency in AD, and AChE inhibitors are among the leading therapeutics used in AD treatment.…”

Section: Cholinesterase Inhibition Resultsmentioning

confidence: 89%

Enzyme Inhibition and Antioxidant Activities of Asparagus officinalis L. and Analysis of Its Phytochemical Content by LC/MS/MS

Çomaklı¹,

Kaya²,

Kuzu³

et al. 2023

Chemistry & Biodiversity

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In the study, water, ethanol, methanol, dichloromethane, and acetone extracts of Asparagus officinalis L. were obtained by maceration. DPPH⋅, ABTS⋅+, FRAP, and CUPRAC methods determined the antioxidant capacities of all extracts. Moreover, the in vitro effects of extracts on acetylcholinesterase (AChE), butyrylcholinesterase (BChE), carbonic anhydrase (CA)‐I, CA‐II and α‐Glycosidase were investigated. At a 10 μg/ml concentration, the extract with the highest Fe3+ reduction capacity was ethanol (AE), and the extract with the highest Cu2+ reduction capacity was acetone (AA). AE for AChE (IC50=21.19 μg/ml) and α‐Glycosidase (IC50: 70.00 μg/ml), methanol (AM) for BChE (IC50=17.33 μg/ml), CA−I and II (IC50=79.65 and 36.09 μg/ml, respectively) showed the most potent inhibition effect. The content analysis of acetone extract was performed with LC/MS‐MS, the first three phytochemicals found most were p‐Coumaric acid, rutin, and 4‐hydroxybenzoic acid (284.29±3.97, 135.39±8.19, and 102.06±5.51 μg analyte/g extract, respectively).

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Section: Cholinesterase Inhibition Resultsmentioning

confidence: 89%

Enzyme Inhibition and Antioxidant Activities of Asparagus officinalis L. and Analysis of Its Phytochemical Content by LC/MS/MS

Çomaklı¹,

Kaya²,

Kuzu³

et al. 2023

Chemistry & Biodiversity

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“…[34] Hydroxybenzoic acid, an important member of phenolic compounds, has both antioxidant activity and AChE inhibition. [35,36] In an another LC/MS-MS research of the Salvia officinalis plant, 163.20 mg/ kg hydroxybenzoic acid was discovered. C. niveum, on the other hand, contained a significant concentration of hydroxybenzoic acid (2757.425.06 mg/kg).…”

Section: Resultsmentioning

confidence: 99%

“…Phenolic compounds have bioactivities such as antioxidant, anti‐microbial, anti‐diabetic, anti‐mutagenic, anti‐inflammatory, and anti‐carcinogenic [34] . Hydroxybenzoic acid, an important member of phenolic compounds, has both antioxidant activity and AChE inhibition [35,36] . In an another LC/MS‐MS research of the Salvia officinalis plant, 163.20 mg/kg hydroxybenzoic acid was discovered.…”

Section: Resultsmentioning

confidence: 99%

Relationship Between Phenolic Content Determined by LC/MS/MS and Antioxidant Capacity and Enzyme Inhibition of Cyclotrichium niveum L.

Güzel

2023

Chemistry & Biodiversity

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Cyclotrichium niveum (Boiss.) Manden & Scheng belonging to the Lamiaceae family, which is an endemic species in the eastern Anatolian region of Turkey, has an important place in terms of ethno-botany. The phytochemical composition of the plant, inhibition of acetylcholinesterase (AChE) (which hydrolyzes the neurotransmitter acetylcholine), inhibition of paraoxonase for antiatherosclerotic activity (hPON 1) (which detoxifies organophosphates), and antioxidant capacity were all investigated in this study. Phytochemical content was determined by LC/MS/MS, and enzyme inhibition and antioxidant capacity studies were determined by spectrophotometer. Antioxidant capacity of C. niveum extracts (methanol, hexane, and water) was determined by applying ABTS * + , DPPH * , FRAP, and CUPRAC methods. Both the water and the methanol extracts of the C. niveum exhibited significant inhibition on the AChE (IC 50 value for methanol and water extract 0.114 � 0.14 mg/ mL (R2:0.997) and 0.178 � 0.12 mg/mL (R 2 : 0.994), respectively). In contrast, the methanol and water extracts of the C. niveum did not exhibit the inhibition effect on hPON 1. The highest activity for ABTS * + was 66.53 % in the water extract, and DPPH * was 55.03 % in the methanol extract. In the metal-reducing power assay, the absorbance was 0.168 � 0.04 for FRAP water extract and 0.621 � 0.01 for CUPRAC methanol extract. According to LC/MS/MS analyses, hydroxybenzoic acid, salicylic acid, syringic acid, acetohydroxamic acid and luteolin determined in the plant extract. As a consequence, C. niveum which has antioxidant, anti-atherogenic and antineurodegenerative properties has the potential to be used as a natural medication instead of synthetic drugs used in Alzheimer's patients.

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“…Recently, a study analyzed 16 hydroxybenzoic acids using calorimetry and docking simulation as AchE inhibitors. All tested compounds were shown to inhibit the hydrolysis of ACh, and the best properties were shown by methyl syringinate; syringic acid also showed a high inhibition percentage [ 104 ]. Considering that AChE inhibitory potential has been mainly investigated for essential oils in the Lamiaceae family, these findings suggest the great influence of other chemical constituents such as syringic, which may have great relevance in pharmacological fields and open a new research line.…”

Section: Resultsmentioning

confidence: 99%

Anticholinesterase Activity of Selected Medicinal Plants from Navarra Region of Spain and a Detailed Phytochemical Investigation of Origanum vulgare L. ssp. vulgare

2022

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Alzheimer’s disease is a neurodegenerative disease characterized by progressive memory loss and cognitive impairment due to a severe loss of cholinergic neurons in specific brain areas. It is the most common type of dementia in the aging population. Although many anti-acetylcholinesterase (AChE) drugs are already available on the market, their performance sometimes yields unexpected results. For this reason, research works are ongoing to find potential anti-AChE agents both from natural and synthetic sources. In this study, 90 extracts from 30 native and naturalized medicinal plants are tested by TLC and Ellman’s colorimetric assay at 250, 125 and 62.5 mg/mL in order to determine the inhibitory effect on AChE. In total, 21 out of 90 extracts show high anti-AChE activity (75–100% inhibition) in a dose-dependent manner. Among them, ethanolic extract from aerial parts of O. vulgare ssp. vulgare shows an IC50 value 7.7 times lower than galantamine. This research also establishes the chemical profile of oregano extract by TLC, HPLC-DAD and LC-MS, and twenty-three compounds are identified and quantified. Dihydroxycinnamic acids and flavonoids are the most abundant ones (56.90 and 25.94%, respectively). Finally, total phenolic compounds and antioxidant properties are quantified by colorimetric methods. The total phenolic content is 207.64 ± 0.69 µg/mg of extract. The antioxidant activity is measured against two radicals, DPPH and ABTS. In both assays, the oregano extract shows high activity. The Pearson correlation matrix shows the relationship between syringic acids, a type of dihydroxybenzoic acid, and anti-AChE (r2 = −0.9864) and antioxidant activity (r2 = 0.9409 and 0.9976). In conclusion, the results of this study demonstrate promising potential new uses of these medicinal herbs for the treatment of Alzheimer’s. Origanum vulgare ssp. vulgare and syringic acids, which have anti-AChE activity and beneficial antioxidant capacity, can be highlighted as potential candidates for the development of drugs for the treatment of Alzheimer’s disease and other diseases characterized by a cholinergic deficit.

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Hydroxybenzoic Acids as Acetylcholinesterase Inhibitors: Calorimetric and Docking Simulation Studies

Cited by 20 publications

References 38 publications

Enzyme Inhibition and Antioxidant Activities of Asparagus officinalis L. and Analysis of Its Phytochemical Content by LC/MS/MS

Enzyme Inhibition and Antioxidant Activities of Asparagus officinalis L. and Analysis of Its Phytochemical Content by LC/MS/MS

Relationship Between Phenolic Content Determined by LC/MS/MS and Antioxidant Capacity and Enzyme Inhibition of Cyclotrichium niveum L.

Anticholinesterase Activity of Selected Medicinal Plants from Navarra Region of Spain and a Detailed Phytochemical Investigation of Origanum vulgare L. ssp. vulgare

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