Acetylcholinesterase and monoamine oxidase-B inhibitory activities by ellagic acid derivatives isolated from Castanopsis cuspidata var. sieboldii

Oh, Jong Min; Jang, Hyun‐Jae; Kang, Myung-Gyun; Song, Soobin; Kim, Doo-Young; Kim, Jung‐Hee; Noh, Ji-In; Park, Jong Eun; Park, Daeui; Yee, Sung‐Tae; Kim, Hoon

doi:10.1038/s41598-021-93458-4

Cited by 14 publications

(5 citation statements)

References 63 publications

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“…It was observed that the non-glycosylated derivative of ellagic acid, 3,3′-di-O-methyl ellagic acid, was the most active against the cholinesterases compared to the glycosylated derivatives 3,3′,4′-tri-O-methyl ellagic acid-4-O-β-D-xylopyranoside, 3,3′,4′-tri-O-methyl ellagic acid-4-O-β-D-glucopyranoside, and 3,3′-di-O-methyl ellagic acid-4-O-β-D-glucopyranoside. This observation corroborates with the findings reported elsewhere, in which a non-glycosylated derivative of ellagic acid was more active than glycosylated ones [ 38 ]. Therefore, the presence of a sugar moiety could impede cholinesterase inhibitory effects.…”

Section: Discussionsupporting

confidence: 93%

In Vitro and Molecular Docking Evaluation of the Anticholinesterase and Antidiabetic Effects of Compounds from Terminalia macroptera Guill. & Perr. (Combretaceae)

Feunaing,

Tamfu,

Gbaweng

et al. 2024

Molecules

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Alzheimer’s disease (AD) and diabetes are non-communicable diseases with global impacts. Inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) are suitable therapies for AD, while α-amylase and α-glucosidase inhibitors are employed as antidiabetic agents. Compounds were isolated from the medicinal plant Terminalia macroptera and evaluated for their AChE, BChE, α-amylase, and α-glucosidase inhibitions. From 1H and 13C NMR data, the compounds were identified as 3,3′-di-O-methyl ellagic acid (1), 3,3′,4′-tri-O-methyl ellagic acid-4-O-β-D-xylopyranoside (2), 3,3′,4′-tri-O-methyl ellagic acid-4-O-β-D-glucopyranoside (3), 3,3′-di-O-methyl ellagic acid-4-O-β-D-glucopyranoside (4), myricetin-3-O-rhamnoside (5), shikimic acid (6), arjungenin (7), terminolic acid (8), 24-deoxysericoside (9), arjunglucoside I (10), and chebuloside II (11). The derivatives of ellagic acid (1–4) showed moderate to good inhibition of cholinesterases, with the most potent being 3,3′-di-O-methyl ellagic acid, with IC50 values of 46.77 ± 0.90 µg/mL and 50.48 ± 1.10 µg/mL against AChE and BChE, respectively. The compounds exhibited potential inhibition of α-amylase and α-glucosidase, especially the phenolic compounds (1–5). Myricetin-3-O-rhamnoside had the highest α-amylase inhibition with an IC50 value of 65.17 ± 0.43 µg/mL compared to acarbose with an IC50 value of 32.25 ± 0.36 µg/mL. Two compounds, 3,3′-di-O-methyl ellagic acid (IC50 = 74.18 ± 0.29 µg/mL) and myricetin-3-O-rhamnoside (IC50 = 69.02 ± 0.65 µg/mL), were more active than the standard acarbose (IC50 = 87.70 ± 0.68 µg/mL) in the α-glucosidase assay. For α-glucosidase and α-amylase, the molecular docking results for 1–11 reveal that these compounds may fit well into the binding sites of the target enzymes, establishing stable complexes with negative binding energies in the range of −4.03 to −10.20 kcalmol−1. Though not all the compounds showed binding affinities with cholinesterases, some had negative binding energies, indicating that the inhibition was thermodynamically favorable.

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Section: Discussionsupporting

confidence: 93%

In Vitro and Molecular Docking Evaluation of the Anticholinesterase and Antidiabetic Effects of Compounds from Terminalia macroptera Guill. & Perr. (Combretaceae)

Feunaing,

Tamfu,

Gbaweng

et al. 2024

Molecules

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“…Among them, EG had the highest content at 330.00 mg/g, followed by gallic acid and chlorogenic acid. Notably, ellagic acid and its derivatives, as well as hexahydroxydiphenoyl esters and phenazine derivatives, were identified in CCS leaves [42,43]. Gallic acid, a well-known secondary metabolite of biosynthesis, was also found in high concentrations of ellagic acid and its derivatives in CCS leaves [44].…”

Section: Polyphenol Content Analysis Using Hplc Ms/msmentioning

confidence: 97%

Ethyl Gallate Isolated from Castanopsis cuspidata var. sieboldii Branches Inhibits Melanogenesis and Promotes Autophagy in B16F10 Cells

et al. 2023

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The Castanopsis cuspidata var. sieboldii (CCS) plant grows predominantly in temperate regions of Asian countries, such as South Korea. Research on CCS has so far concentrated on the nutritional analysis, antioxidant activity, and anti-inflammation properties of its branches. However, the isolation of compounds and structural elucidation of effective single molecules remain unexplored, necessitating further exploration of CCS branches. Therefore, this study demonstrates the antioxidant and antimelanogenic activity of a single substance of ethyl gallate (EG) isolated from CCS branch extracts. Notably, the antimelanogenic (whitening) activity of EG extracted from CCS branches remains unexplored. Tyrosinase inhibition, kinetic enzyme assays, and molecular docking studies were conducted using mushroom tyrosinase in order to examine the antioxidant mechanism and antimelanin activity of EG in B16F10 melanoma cells. Nontoxic EG concentrations were found to be below 5 µg/mL. While EG significantly reduced the levels of whitening-associated proteins, p-CREB, and p-PKA, it dose-dependently inhibited the expression of TYR, TRP-1, TRP-2, and transcription factor (MITF). In addition, EG downregulated melanogenetic gene expression and activated autophagy signals. Therefore, EG extracted from CCS branches could serve as a novel functional cosmetic material with antimelanogenic and autophagy-enhancing activity.

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“…For example, some authors reported that ellagic acid is a potent inhibitor of AChE. [80,81] In addition, flavonoids such as quercetin, vitexin, or kaempferol showed significant inhibitory effects on cholinesterases. [82][83][84]…”

Section: Ache At the Central Level Previous Studies Have Reported Thatmentioning

confidence: 99%

UHPLC‐ESI‐QTOF‐MS metabolite profiles of different extracts from Pelargonium endlicherianum parts and their biological properties based on network pharmacological approaches

Zengin,

Leyva‐Jiménez,

Fernández‐Ochoa

et al. 2024

Archiv der Pharmazie

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In the present study, we aimed to investigate the chemical profiles and biological activities of different extracts (ethyl acetate, dichloromethane, ethanol, and water) of Pelargonium endlicherianum parts (aerial parts and roots). Free radical scavenging, reducing power, phosphomolybdenum, and metal chelating were assayed for antioxidant properties. To detect enzyme inhibitory properties, cholinesterase, amylase, glucosidase, and tyrosinase were chosen as target enzymes. The ethanol extract of the aerial parts contained higher amounts of total bioactive compounds (120.53 mg GAE/g‐24.46 mg RE/g). The ethanol and water extracts of these parts were tentatively characterized by UHPLC‐ESI‐QTOF‐MS and 95 compounds were annotated. In addition, the highest acetylcholiesterase (3.74 mg GALAE/g) and butyrylcholinesterase (3.92 mg GALAE/g) abilities were observed by the ethanol extract of roots. The water extract from aerial parts exhibited the most pronounced inhibitory effects on multiple cancer cell lines, especially A549 (IC50: 23.2 µg/mL) and HT‐29 (IC50: 27.43 µg/mL) cells. Using network pharmacology, P. endlicherianum compounds were studied against cancer, revealing well‐connected targets such as epidermal growth factor receptor (EGFR), phosphoinositide‐3‐kinase (PI3K), AKT, receptor tyrosine‐protein kinase erbB‐2, and growth factor receptor bound protein 2 (GRB2) with significant impact on cancer‐related pathways. The results could open a new path from natural treasure to functional applications with P. endlicherianum and highlight a new study on other uninvestigated Pelargonium species.

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Acetylcholinesterase and monoamine oxidase-B inhibitory activities by ellagic acid derivatives isolated from Castanopsis cuspidata var. sieboldii

Cited by 14 publications

References 63 publications

In Vitro and Molecular Docking Evaluation of the Anticholinesterase and Antidiabetic Effects of Compounds from Terminalia macroptera Guill. & Perr. (Combretaceae)

In Vitro and Molecular Docking Evaluation of the Anticholinesterase and Antidiabetic Effects of Compounds from Terminalia macroptera Guill. & Perr. (Combretaceae)

Ethyl Gallate Isolated from Castanopsis cuspidata var. sieboldii Branches Inhibits Melanogenesis and Promotes Autophagy in B16F10 Cells

UHPLC‐ESI‐QTOF‐MS metabolite profiles of different extracts from Pelargonium endlicherianum parts and their biological properties based on network pharmacological approaches

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