Kinetics and molecular docking studies of cholinesterase inhibitors derived from water layer of Lycopodiella cernua (L.) Pic. Serm. (II)

Hung, Tran Manh; Lee, Joo Sang; Chuong, Nguyen Ngoc; Kim, Jeong Ah; Woo, Mi Hee; Choi, Jae Sue; Min, Byung Sun

doi:10.1016/j.cbi.2015.07.008

Cited by 16 publications

(6 citation statements)

References 36 publications

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“…The best pose found for vitexin ( 33 ) in the interaction to the enzymatic pocket of BchE was stabilized by the formation of three hydrogen bonds, respectively, with Gln197, Asp70, Thr120, and a much lower docking score: −11.24 Kcal/mol. These data are in agreement with the literature data in which isoschaftoside ( 22 ) has shown a high inhibitory activity to AchE and BChE with IC 50 of 0.23 μM and 3.11 μM respectively (Hung et al, 2015 ).…”

Section: Resultssupporting

confidence: 93%

Traditionally Used Lathyrus Species: Phytochemical Composition, Antioxidant Activity, Enzyme Inhibitory Properties, Cytotoxic Effects, and in silico Studies of L. czeczottianus and L. nissolia

et al. 2017

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Members of the genus Lathyrus are used as food and as traditional medicines. In order to find new sources of biologically-active compounds, chemical and biological profiles of two Lathyrus species (L. czeczottianus and L. nissolia) were investigated. Chemical profiles were evaluated by HPLC-ESI-MSn, as well as by their total phenolic and flavonoid contents. In addition, antioxidant, enzyme inhibitory, and cytotoxic effects were also investigated. Antioxidant properties were tested by using different assays (DPPH, ABTS, CUPRAC, FRAP, phosphomolybdenum, and metal chelation). Cholinesterases (AChE and BChE), tyrosinase, α-amylase, and α-glucosidase were used to evaluate enzyme inhibitory effects. Moreover, vitexin (apigenin-8-C-glucoside) and 5-O-caffeoylquinic acid were further subjected to molecular docking experiments to provide insights about their interactions at molecular level with the tested enzymes. In vitro cytotoxic effects were examined against human embryonic kidney cells (HEK293) by using iCELLigence real time cell analysis system. Generally, L. czeczottianus exhibited stronger antioxidant properties than L. nissolia. However, L. nissolia had remarkable enzyme inhibitory effects against cholinesterase, amylase and glucosidase. HPLC-ESI-MSn analysis revealed that flavonoids were major components in these extracts. On the basis of these results, Lathyrus extracts were rich in biologically active components; thus, these species could be utilized to design new phytopharmaceutical and nutraceutical formulations.

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Section: Resultssupporting

confidence: 93%

Traditionally Used Lathyrus Species: Phytochemical Composition, Antioxidant Activity, Enzyme Inhibitory Properties, Cytotoxic Effects, and in silico Studies of L. czeczottianus and L. nissolia

et al. 2017

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“…However, efforts to discover naturally occurring ChEs and BACE1 inhibitors have been relatively limited. Several plant-derived ChEs and BACE1 inhibitors, including coumarins, anthraquinones, triterpenoids, lignin, flavonoids, and alkaloids [ 19 , 38 , 39 , 40 , 41 ] have been reported. Most of the previously discovered natural BACE1 and ChEs inhibitors have a low molecular weight, exhibit structural similarities, such as aromatic rings, and may have some adverse side effects.…”

Section: Discussionmentioning

confidence: 99%

Kinetics and Molecular Docking Studies of 6-Formyl Umbelliferone Isolated from Angelica decursiva as an Inhibitor of Cholinesterase and BACE1

et al. 2017

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Coumarins, which have low toxicity, are present in some natural foods, and are used in various herbal remedies, have attracted interest in recent years because of their potential medicinal properties. In this study, we report the isolation of two natural coumarins, namely umbelliferone (1) and 6-formyl umbelliferone (2), from Angelica decursiva, and the synthesis of 8-formyl umbelliferone (3) from 1. We investigated the anti-Alzheimer disease (anti-AD) potential of these coumarins by assessing their ability to inhibit acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and β-site amyloid precursor protein (APP) cleaving enzyme 1 (BACE1). Among these coumarins, 2 exhibited poor inhibitory activity against AChE and BChE, and modest activity against BACE1. Structure–activity relationship analysis showed that 2 has an aldehyde group at the C-6 position, and exhibited strong anti-AD activity, whereas the presence or absence of an aldehyde group at the C-8 position reduced the anti-AD activity of 3 and 1, respectively. In addition, 2 exhibited concentration-dependent inhibition of peroxynitrite-mediated protein tyrosine nitration. A kinetic study revealed that 2 and 3 non-competitively inhibited BACE1. To confirm enzyme inhibition, we predicted the 3D structures of AChE and BACE1, and used AutoDock 4.2 to simulate binding of coumarins to these enzymes. The blind docking studies demonstrated that these molecules could interact with both the catalytic active sites and peripheral anionic sites of AChE and BACE1. Together, our results indicate that 2 has an interesting inhibitory activity in vitro, and can be used in further studies to develop therapeutic modalities for the treatment of AD.

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“…In addition, Schaftoside isolated from the water layer of Lycopodiella cernua (L.) Pic.Serm. showed strong inhibitory activity against BChE (Hung et al, 2015).…”

Section: Cholinesterase Inhibitory Activitymentioning

confidence: 99%

Chemical Profiling, Antioxidant, Anticholinesterase, and Antiprotozoal Potentials of Artemisia copa Phil. (Asteraceae)

Larrazábal

Fernández-Galleguillos

Palma-Ramírez

et al. 2020

Front. Pharmacol.

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Artemisia copa Phil. (Asteraceae) (known as copa-copa) is a native species of Chile used as an infusion in traditional medicine by Atacameños people in the Altiplano, highlands of northern Chile. In this research, we have investigated for the first time the cholinesterase inhibition potential against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), and the chemical profiling of the infusions prepared from the aerial parts of A. copa by high resolution spectrometry. In addition, total phenolic, total flavonoid content, antioxidant (DPPH, FRAP, and ORAC) and antiprozoal activity were tested. Artemisia copa showed good inhibitory activity against AChE and BChE (3.92 ± 0.08 µg/ml and 44.13 ± 0.10 µg/ml). The infusion displayed a total phenolics content of 155.6 ± 2.9 mg of gallic acid equivalents/g and total flavonoid content of 5.5 ± 0.2 mg quercetin equivalents/g. Additionally, trypanocidal activity against Trypanosoma cruzi was found (LD50 of 131.8 µg/ml). Forty-seven metabolites were detected in the infusion of A. copa including several phenolic acids and flavonoids which were rapidly identified using ultrahigh performance liquid chromatography orbitrap mass spectrometry analysis (UHPLC-Orbitrap-MS) for chemical profiling. The major compounds identified in the infusions were studied by molecular docking against AChE and BChE. The UHPLC-MS fingerprints generated can be also used for the authentication of these endemic species. These findings reveal that A. copa infusions can be used as beverages with protective effects.

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Kinetics and molecular docking studies of cholinesterase inhibitors derived from water layer of Lycopodiella cernua (L.) Pic. Serm. (II)

Cited by 16 publications

References 36 publications

Traditionally Used Lathyrus Species: Phytochemical Composition, Antioxidant Activity, Enzyme Inhibitory Properties, Cytotoxic Effects, and in silico Studies of L. czeczottianus and L. nissolia

Traditionally Used Lathyrus Species: Phytochemical Composition, Antioxidant Activity, Enzyme Inhibitory Properties, Cytotoxic Effects, and in silico Studies of L. czeczottianus and L. nissolia

Kinetics and Molecular Docking Studies of 6-Formyl Umbelliferone Isolated from Angelica decursiva as an Inhibitor of Cholinesterase and BACE1

Chemical Profiling, Antioxidant, Anticholinesterase, and Antiprotozoal Potentials of Artemisia copa Phil. (Asteraceae)

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