Screening inhibitory effects of selected flavonoids on human recombinant aldose reductase enzyme: <i>in vitro</i> and <i>in silico</i> study

Çomaklı, Veysel; Adem, Şevki; Öztekіn, Aykut; Demirdağ, Ramazan

doi:10.1080/13813455.2020.1771377

Cited by 10 publications

(4 citation statements)

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“…Additionally, aldose reductase was predicted as a target of medium probability, while other proteins such as NADPH oxidase 4 showed lower probability. Again, it should be considered that flavonoids have been previously reported as ligands and inhibitors of aldose reductase, and their contribution to the development of compounds against diabetic complications has been proposed [50,51]. Even if it is very preliminary, this target prediction study further supports the potential of transilitin and agrees with literature data, as this compound may synergically act on targets of relevance in pathogenic conditions.…”

Section: Computational Studiessupporting

confidence: 83%

Studies on the Inhibition of Ectonucleotide Pyrophosphatase/Phosphodiesterase 1 (ENPP1) by 2-(3,4-Dihydroxyphenyl)-7,8-dihydroxy-3-methoxychromen-4-one, a Flavonoid from Pistacia chinensis

Rauf,

Akram,

Naveed

et al. 2023

Chemistry

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Ectonucleotide pyrophosphatase/phosphodiesterase 1 (ENPP1) regulates skeletal and soft tissue mineralization by hydrolyzing nucleotide triphosphates and cyclic nucleotides, and is involved in the modulation of immune system. In fact, ENPP1 degrades 2′,3′-cyclic GMP-AMP dinucleotide (2′,3′-cGAMP), which is an agonist of surface receptor stimulator of interferon genes (STING), thus downregulating immune response. Consequently, ENPP1 inhibitors are being studied as adjuvant agents in infections and cancer. Pistacia chinensis is a medicinal plant endowed with several biological activities and traditional uses. In the current study, we report the isolation of transilitin (2-(3,4-dihydroxyphenyl)-7,8-dihydroxy-3-methoxychromen-4-one) from the methanolic extract of P. chinensis barks and the investigation of its activity as ENPP1 inhibitor. The compound was tested in vitro against snake venom phosphodiesterase, which is structurally related to ENPP1, and dose-dependently inhibited the enzyme. Moreover, molecular modeling studies were employed to assess the binding motif of the transilitin with the macromolecular target. Our findings support the traditional medical application of P. chinensis and its extracts by shedding new light on the mechanisms underlying their biological action.

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Section: Computational Studiessupporting

confidence: 83%

Studies on the Inhibition of Ectonucleotide Pyrophosphatase/Phosphodiesterase 1 (ENPP1) by 2-(3,4-Dihydroxyphenyl)-7,8-dihydroxy-3-methoxychromen-4-one, a Flavonoid from Pistacia chinensis

Rauf,

Akram,

Naveed

et al. 2023

Chemistry

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“…Rutin is a flavonol that has exhibited a variety of pharmacological efficacies including antioxidant, cytoprotective, anticarcinogenic, neuroprotective, and cardioprotective activities ( Ganeshpurkar and Saluja, 2017 ; Enogieru et al, 2018 ). Flavonoids have the hydroxyl groups and functional substitutions that provide their bioactivity and have an important role in non-covalent interactions such as electrostatic interactions, hydrogen bonds, van der Waals interactions, and hydrophobic interactions with their targets in drug-enzyme interactions and are critical in drug design ( Comakli et al, 2020 ). Phenolic structures often have the potential to strongly interact with proteins, due to their hydrophobic benzenoid rings and the hydrogen-bonding potential of the phenolic hydroxyl groups.…”

Section: Discussionmentioning

confidence: 99%

In Vitro and In Silico Antioxidant Efficiency of Bio-Potent Secondary Metabolites From Different Taxa of Black Seed-Producing Plants and Their Derived Mycoendophytes

Hassane

Hussien

Abouelela

et al. 2022

Front. Bioeng. Biotechnol.

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Oxidative stress is involved in the pathophysiology of multiple health complications, and it has become a major focus in targeted research fields. As known, black seeds are rich sources of bio-active compounds and widely used to promote human health due to their excellent medicinal and pharmaceutical properties. The present study investigated the antioxidant potency of various black seeds from plants and their derived mycoendophytes, and determined the total phenolic and flavonoid contents in different extracts, followed by characterization of major constituents by HPLC analysis. Finally, in silico docking determined their binding affinities to target myeloperoxidase enzymes. Ten dominant mycoendophytes were isolated from different black seed plants. Three isolates were then selected based on high antiradical potency and further identified by ITS ribosomal gene sequencing. Those isolated were Aspergillus niger TU 62, Chaetomium madrasense AUMC14830, and Rhizopus oryzae AUMC14823. Nigella sativa seeds and their corresponding endophyte A. niger had the highest content of phenolics in their n-butanol extracts (28.50 and 24.43 mg/g), flavonoids (15.02 and 11.45 mg/g), and antioxidant activities (90.48 and 81.48%), respectively, followed by Dodonaea viscosa and Portulaca oleracea along with their mycoendophytic R. oryzae and C. madrasense. Significant positive correlations were found between total phenolics, flavonoids, and the antioxidant activities of different tested extracts. The n-butanol extracts of both black seeds and their derived mycoendophytes showed reasonable IC50 values (0.81–1.44 mg/ml) compared to the control with significant correlations among their phytochemical contents. Overall, seventeen standard phenolics and flavonoids were used, and the compounds were detected in different degrees of existence and concentration in the examined extracts through HPLC analysis. Moreover, the investigation of the molecular simulation results of detected compounds against the myeloperoxidase enzyme revealed that, as a targeted antioxidant, rutin possessed a high affinity (−15.3184 kcal/mol) as an inhibitor. Taken together, the black seeds and their derived mycoendophytes are promising bio-prospects for the broad industrial sector of antioxidants with several valuable potential pharmaceutical and nutritional applications.

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“…Diosmetin might well contribute to the antidiabetic action of C. arabicus extracts because it has been shown to ameliorate glucose metabolism in diabetic mice via the regulation of the PI3K/AKT signaling pathway and a restoration of the unbalanced gut microbiota [79]. It is an inhibitor of aldose reductase (IC 50 = 15.7 µM), an enzyme of the polyol pathway implicated in hyperglycemia, and a useful compound to combat type 2 diabetes mellitus [80,81].…”

Section: Discussionmentioning

confidence: 99%

The Medicinal Moroccan Plant Cladanthus arabicus as a Prominent Source of Sesquiterpenes Cladantholide and Sintenin

Bouissane,

Bailly

2024

AppliedChem

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The yellow-flowering plant Cladanthus arabicus (L.) Cass., commonly called Arabian Cladanthus or palm springs daisy, is typical of the West Mediterranean region and is particularly abundant in Morocco. The plant is used in traditional Moroccan medicine for the treatment of diabetes and other ailments. Over the past 20 years, this abundant wild plant has been neglected from a phytochemical viewpoint. For the first time, the present review provides a survey of the pharmacological properties reported from extracts of C. arabicus and from essential oils derived from the aerial parts, mainly antimicrobial, antioxidant, and anti-inflammatory properties. The main bioactive natural products are discussed, with a focus on two rare sesquiterpenes of major interest, which are abundant in the stems and leaves: the 6,12-guaianolide cladantholide and the germacranolide sintenin. These sesquiterpene lactones and their analogues are presented to highlight their properties, extraction or total synthesis, and their therapeutic benefits. They both represent convenient biosourced precursors for the synthesis of derivatives. Sintenin may be used as a starting material for the design of hemi-synthetic germacradienolide-type costunolide or parthenolide derivatives. The 6,12-guaianolide scaffold of cladantholide offers opportunities to design novel arglabin derivatives. The therapeutic potential of the neglected and under-utilized plant Cladanthus arabicus and its original phytochemicals shall be explored further.

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Screening inhibitory effects of selected flavonoids on human recombinant aldose reductase enzyme: in vitro and in silico study

Cited by 10 publications

References 45 publications

Studies on the Inhibition of Ectonucleotide Pyrophosphatase/Phosphodiesterase 1 (ENPP1) by 2-(3,4-Dihydroxyphenyl)-7,8-dihydroxy-3-methoxychromen-4-one, a Flavonoid from Pistacia chinensis

Studies on the Inhibition of Ectonucleotide Pyrophosphatase/Phosphodiesterase 1 (ENPP1) by 2-(3,4-Dihydroxyphenyl)-7,8-dihydroxy-3-methoxychromen-4-one, a Flavonoid from Pistacia chinensis

In Vitro and In Silico Antioxidant Efficiency of Bio-Potent Secondary Metabolites From Different Taxa of Black Seed-Producing Plants and Their Derived Mycoendophytes

The Medicinal Moroccan Plant Cladanthus arabicus as a Prominent Source of Sesquiterpenes Cladantholide and Sintenin

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