Enzyme-assisted modification of flavonoids from Matricaria chamomilla: antioxidant activity and inhibitory effect on digestive enzymes.

Abstract:

:Matricaria chamomilla L. contains antioxidant flavonoids that can have their bioactivity enhanced by enzymatic hydrolysis of specific glycosyl groups. This study implements an untargeted metabolomics approach based on ultra-performance liquid chromatography coupled with electrospray ionisation quadrupole time-of-flight mass spectrometry technique operating in MSE mode (UPLC-QTOF-MSE) and spectrophotometric analysis of chamomile aqueous infusions, before and after hydrolysis by hesperidinase and β-galactosidase. Several phenolic compounds were altered in the enzymatically treated infusion, with the majority being flavonoid derivatives of apigenin, esculetin, and quercetin. Although enzymatically modifying the infusion only led to a small increase in antioxidant activity (DPPH• method), its inhibitory effect on pancreatic lipase was of particular interest. The enzymatically treated infusion exhibited a greater inhibitory effect (EC50 of 35.6 µM) than unmodified infusion and kinetic analysis suggested mixed inhibition of pancreatic lipase. These results are of great relevance due to the potential of enzymatically treated functional foods in human health.

authors

Franco EPD,Contesini FJ,Lima da Silva B,Alves de Piloto Fernandes AM,Wielewski Leme C,Gonçalves Cirino JP,Bueno Campos PR,de Oliveira Carvalho P

doi

10.1080/14756366.2019.1681989

subject

Has Abstract

pub_date

2020-12-01 00:00:00

pages

42-49

issue

1

eissn

1475-6366

issn

1475-6374

journal_volume

35

pub_type

杂志文章
  • Synthesis and inhibition potency of novel ureido benzenesulfonamides incorporating GABA as tumor-associated carbonic anhydrase IX and XII inhibitors.

    abstract::New ureido benzenesulfonamides incorporating a GABA moiety as a linker between the ureido and the sulfonamide functionalities were synthesized and their inhibition potency determined against both the predominant cytosolic (hCA I and II) and the transmembrane tumor-associated (hCA IX and XII) isoforms of the metalloenz...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.3109/14756366.2015.1014477

    authors: Ceruso M,Antel S,Scozzafava A,Supuran CT

    更新日期:2016-01-01 00:00:00

  • alpha-Glucosidase inhibitory activity of cyanidin-3-galactoside and synergistic effect with acarbose.

    abstract::Cyanidin-3-galactoside, a natural anthocyanin, was investigated for its alpha-glucosidase inhibitory activity. The IC(50) value of cyanidin-3-galactoside was 0.50 +/- 0.05 mM against intestinal sucrase. A low dose of cyanidin-3-galactoside showed a synergistic inhibition on intestinal alpha-glucosidase (maltase and su...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.1080/14756360801906947

    authors: Adisakwattana S,Charoenlertkul P,Yibchok-Anun S

    更新日期:2009-02-01 00:00:00

  • Synthesis of some novel heterocylic compounds derived from 2-[3-(4-chlorophenyl)-5-(4-methoxybenzyl)-4H-1,2,4-triazol-4-yl]acetohydrazide and investigation of their lipase and α-glucosidase inhibition.

    abstract::In the present study, 2-[3-(4-chlorophenyl)-5-(4-methoxybenzyl)-4H-1,2,4-triazol-4-yl]acetohydrazide (1) was used as starting compound for the synthesis of 2-{[3-(4-chlorophenyl)-5-(4-methoxybenzyl)-4H-1,2,4-triazol-4-yl]acetyl}-4-thiosemicarbazides (2a-c) and 5-{[3-(4-chlorophenyl)-5-(4-methoxybenzyl)-4H-1,2,4-triazo...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.3109/14756366.2014.1003213

    authors: Bekircan O,Ülker S,Menteşe E

    更新日期:2015-12-01 00:00:00

  • In vitro inhibition of cytosolic carbonic anhydrases I and II by some new dihydroxycoumarin compounds.

    abstract::A new series of 6, 7-dihydroxy-3-(methylphenyl) chromenones, including three new derivatives, i.e. 6,7-dihydroxy-3-(2-methylphenyl)-2H-chromen-2-one (OPC); 6,7-dihydroxy-3-(3-methylphenyl)-2H-chromen-2-one (MPC); 6,7-dihydroxy-3-(4-methylphenyl)-2H-chromen-2-one (PPC) and one previously described, namely 6,7-dihydroxy...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.1080/14756360701404100

    authors: Basaran I,Sinan S,Cakir U,Bulut M,Arslan O,Ozensoy O

    更新日期:2008-02-01 00:00:00

  • Design, synthesis, and evaluation of guanylhydrazones as potential inhibitors or reactivators of acetylcholinesterase.

    abstract::Analogs of pralidoxime, which is a commercial antidote for intoxication from neurotoxic organophosphorus compounds, were designed, synthesized, characterized, and tested as potential inhibitors or reactivators of acetylcholinesterase (AChE) using the Ellman's test, nuclear magnetic resonance, and molecular modeling. T...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.3109/14756366.2015.1094468

    authors: Petronilho Eda C,Rennó Mdo N,Castro NG,da Silva FM,Pinto Ada C,Figueroa-Villar JD

    更新日期:2016-12-01 00:00:00

  • Synthesis, structure elucidation, DNA-PK, PI3K, anti-platelet and anti-bacteria activity of linear 5, 6, and 10-substituted-2-morpholino-chromen-oxazine-dione and angular 3, 4, 6-substituted-8-morpholino-chromen-oxazine-2,10-dione.

    abstract::Coumarin, a naturally occurring or synthesised phytochemical, displays a wide range of biological activities. However, chromen-2-ones fused with 1,3-benzoxazine rings is not well documented and there is a gap in the literature which required engaging. The substituted-2-thioxo-chromen-oxazine linear compounds 14a-i and...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.1080/14756366.2016.1190710

    authors: Morrison R,Al-Rawi JM

    更新日期:2016-01-01 00:00:00

  • Design, synthesis, molecular modelling, and biological evaluation of novel substituted pyrimidine derivatives as potential anticancer agents for hepatocellular carcinoma.

    abstract::New anticancer agents are highly needed to overcome cancer cell resistance. A novel series of pyrimidine pyrazoline-anthracene derivatives (PPADs) (4a-t) were designed and synthesised. The anti-liver cancer activity of all compounds was screened in vitro against two hepatocellular carcinoma (HCC) cell lines (HepG2 and...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.1080/14756366.2019.1612889

    authors: Ahmed NM,Youns M,Soltan MK,Said AM

    更新日期:2019-12-01 00:00:00

  • Synthesis, molecular modeling and NAD(P)H:quinone oxidoreductase 1 inducer activity of novel cyanoenone and enone benzenesulfonamides.

    abstract:UNLABELLED:Abstract In biological systems, the Keap1/Nrf2/antioxidant response element pathway determines the ability of mammalian cells to adapt and survive conditions of oxidative, electrophilic and inflammatory stress by regulating the production of cytoprotective enzymes NAD(P)H:quinone oxidoreductase 1 (NQO1, EC ...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.3109/14756366.2013.858146

    authors: Ghorab MM,Higgins M,Alsaid MS,Arafa RK,Shahat AA,Dinkova-Kostova AT

    更新日期:2014-12-01 00:00:00

  • Biological evaluation of dimethylpyridine-platinum complexes with potent antiproliferative activity.

    abstract::This study investigates the effect of three new platinum complexes: Pt2(2,4-dimethylpyridine)4(berenil)2 (Pt14), Pt2(3,4-dimethylpyridine)4(berenil)2 (Pt15) and Pt2(3,5-dimethylpyridine)4(berenil)2 (Pt16) on growth and viability of breast cancer cells and their putative mechanism(s) of cytotoxicity. Cytotoxicity was m...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.1080/14756366.2016.1212191

    authors: Czarnomysy R,Bielawski K,Muszynska A,Bielawska A,Gornowicz A

    更新日期:2016-01-01 00:00:00

  • Synthesis of novel 6,7-dimethoxy-4-anilinoquinolines as potent c-Met inhibitors.

    abstract::HGF/c-Met signalling pathway plays an important role in the development of cancers. A series of 6,7-dimethoxy-4-anilinoquinolines possessing benzimidazole moiety were synthesised and identified as potent inhibitors of the tyrosine kinase c-Met. Their in vitro biological activities against three cancer cell lines (A549...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.1080/14756366.2018.1533822

    authors: Zhang QW,Ye ZD,Shen C,Tie HX,Wang L,Shi L

    更新日期:2019-12-01 00:00:00

  • Microwave-assisted synthesis of novel thiazolocarbazoles and evaluation as potential anticancer agents. Part III.

    abstract::Novel 6-substituted thiazolocarbazole derivatives have been synthesized under microwave irradiation via the corresponding imino-1,2,3-dithiazoles. In vitro antitumor potential of these polyheterocyclic compounds was evaluated. Among all the tested thiazolocarbazoles, compound 10 is the most effective in inhibiting cel...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.1080/14756360412331280491

    authors: Testard A,Picot L,Fruitier-Arnaudin I,Piot JM,Chabane H,Domon L,Thiery V,Besson T

    更新日期:2004-12-01 00:00:00

  • Synthesis, anticandidal activity and cytotoxicity of some tetrazole derivatives.

    abstract::In this study, 14 different 2-[(1-methyl-1H-tetrazole-5-yl)thio]-1-(phenyl)ethanone derivatives (1-14) were synthesized. The structures of the obtained compounds were elucidated using IR, (1)H-NMR, (13)C-NMR and FAB(+)-MS spectral data and elemental analyses results. The compounds were screened for their anticandidal ...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.3109/14756366.2012.752363

    authors: Kaplancikli ZA,Yurttaş L,Özdemir A,Turan-Zitouni G,Işcan G,Akalın G,Abu Mohsen U

    更新日期:2014-02-01 00:00:00

  • Evaluation of effect of some corticosteroids on glucose-6-phosphate dehydrogenase and comparative study of antioxidant enzyme activities.

    abstract::Corticosteroids are anti-inflammatory drugs that are similar to the natural corticosteroid hormones produced by the cortex of the adrenal glands. The objective of this study was to scrutinize effects of some corticosteroids on glucose-6-phosphate dehydrogenase (G6PD) and some antioxidant enzymes. Initially, G6PD was p...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.1080/14756360412331295026

    authors: Ozmen I

    更新日期:2005-02-01 00:00:00

  • Carbonic anhydrase inhibitors: synthesis of water soluble sulfonamides incorporating a 4-sulfamoylphenylmethylthiourea scaffold, with potent intraocular pressure lowering properties.

    abstract::Reaction of thiophosgene with 4-aminomethyl-benzenesulfonamide afforded 4-isothiocyanatomethyl-benzenesulfonamide, which by reaction with amines, amino acids and oligopeptides, lead to a series of new sulfonamides incorporating a 4-sulfamoylphenylmethylthiourea scaffold. These new thioureas showed strong affinities to...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.1080/1475636021000010950

    authors: Casini A,Scozzafava A,Mincione F,Menabuoni L,Supuran CT

    更新日期:2002-10-01 00:00:00

  • Resorcinol-, catechol- and saligenin-based bronchodilating β2-agonists as inhibitors of human cholinesterase activity.

    abstract::We investigated the influence of bronchodilating β2-agonists on the activity of human acetylcholinesterase (AChE) and usual, atypical and fluoride-resistant butyrylcholinesterase (BChE). We determined the inhibition potency of racemate and enantiomers of fenoterol as a resorcinol derivative, isoetharine and epinephrin...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.1080/14756366.2017.1326109

    authors: Bosak A,Knežević A,Gazić Smilović I,Šinko G,Kovarik Z

    更新日期:2017-12-01 00:00:00

  • Cruzain inhibition by hydroxymethylnitrofurazone and nitrofurazone: investigation of a new target in Trypanosoma cruzi.

    abstract::Nitrofurazone (NF) and its derivative, hydroxymethylnitrofurazone (NFOH), have presented antichagasic activity. NFOH has higher activity and lower mutagenicity. The aim of this work was to assess whether NF and its derivative NFOH would also be inhibitors of cruzain, besides their trypanothione reductase inhibitory ac...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.3109/14756360902941058

    authors: Trossini GH,Malvezzi A,T-do Amaral A,Rangel-Yagui CO,Izidoro MA,Cezari MH,Juliano L,Chin CM,Menezes CM,Ferreira EI

    更新日期:2010-02-01 00:00:00

  • A nonmainstream approach against cancer.

    abstract::The discovery of antibiotics as specific and effective drugs against infectious agents has generated the belief that the famous Paul Erlich theory on magic bullet should be applied to cancer as well. However, after around 60 years of failures in finding a magic bullet against cancer, a question appears mandatory: does...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.3109/14756366.2016.1156105

    authors: Fais S

    更新日期:2016-12-01 00:00:00

  • Kinetic and docking studies of cytosolic/tumor-associated carbonic anhydrase isozymes I, II and IX with some hydroxylic compounds.

    abstract::A series of hydroxylic compounds (1-10, NK-154 and NK-168) have been assayed for the inhibition of three physiologically relevant carbonic anhydrase isozymes, the cytosolic isozymes I, II and tumor-associated isozyme IX. The investigated compounds showed inhibition constants in the range of 0.068-4003, 0.012-9.9 and 0...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.3109/14756366.2015.1114930

    authors: Durdagi S,Korkmaz N,Işık S,Vullo D,Astley D,Ekinci D,Salmas RE,Senturk M,Supuran CT

    更新日期:2016-12-01 00:00:00

  • Soluble epoxide hydrolase inhibitory components from Rheum undulatum and in silico approach.

    abstract::Continuous efforts to identify sEH inhibitors using activity-guided fractionation have revealed 12 known compounds, 2-13, from Rheum undulatum. Compounds 2-13 and 1, which was obtained from the in-house library, were tested for inhibitory activity against sEH. Compounds 1-9, 11, and 12 were shown to have inhibitory ac...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.1080/14756366.2016.1189421

    authors: Jo AR,Kim JH,Yan XT,Yang SY,Kim YH

    更新日期:2016-01-01 00:00:00

  • Quantitative structure-activity relationships (QSARs) in inhibitors of various cytochromes P450: the importance of compound lipophilicity.

    abstract::The results of extensive quantitative structure-activity relationship (QSAR) analyses on 15 series of cytochrome P450 inhibitors, covering a total of 7 enzymes and 199 compounds, are reported. In general, it is found that lipophilicity represents the most important single factor in describing differences in inhibitory...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.1080/14756360600952183

    authors: Lewis DF,Lake BG,Dickins M

    更新日期:2007-02-01 00:00:00

  • Quantitative insights towards the design of potent deazaxanthine antagonists of adenosine 2B receptors.

    abstract::Adenosine receptors have been considered as potential targets for drug development, but one of the main obstacles to this goal is to selectively inhibit one receptor subtype over the others. This subject is particularly crucial for adenosine A2b receptor antagonists (AdoRA2B). The structure–activity relationships of x...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.3109/14756366.2013.830113

    authors: Paz OS,Brito CC,Castilho MS

    更新日期:2014-08-01 00:00:00

  • Inhibitory effect of cisplatin and [Pt(dach)Cl2] on the activity of phospholipase A2.

    abstract::This work has been focused on testing the influence of two selected Pt(II) complexes cisplatin, Pt(NH₃)₂Cl₂, and [Pt(dach)Cl₂] on the activity of porcine pancreatic phospholipase A₂ (PLA₂). It has been assumed that this enzyme plays a role in carcinogenesis and that it could be a target in the tumour therapy. The resu...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.3109/14756366.2012.666539

    authors: Radisavljević M,Kamčeva T,Bugarčić ŽD,Petković M

    更新日期:2013-08-01 00:00:00

  • Synthesis of novel benzoxanthone analogues as non-Camptothecin topoisomerase I inhibitors.

    abstract::Structure modification of the side chain of the lead compound benzoxanthone provided a series of benzoxanthone analogues and 12 of them were first reported. The results showed that most of these compounds had moderate cytotoxicity against tumour cells with the 50% inhibition concentration in the micromolar range. Furt...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.3109/14756366.2011.595712

    authors: Cheng P,Zhu L,Guo W,Liu W,Yao J,Dong G,Zhang Y,Zhuang C,Sheng C,Miao Z,Zhang W

    更新日期:2012-06-01 00:00:00

  • Kinetic analysis of a general model of activation of aspartic proteinase zymogens involving a reversible inhibitor. I. Kinetic analysis.

    abstract::Starting from a simple general reaction mechanism of activation of aspartic proteinases zymogens involving a uni- and a bimolecular simultaneous activation route and a reversible inhibition step, the time course equation of the zymogen, inhibitor and activated enzyme concentrations have been derived. Likewise, express...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.1080/14756360601114601

    authors: Muñoz-López A,Sotos-Lomas A,Arribas E,Masia-Perez J,Garcia-Molina F,García-Moreno M,Varon R

    更新日期:2007-04-01 00:00:00

  • Prediction of caspase-3 inhibitory activity of 1,3-dioxo-4-methyl-2,3-dihydro-1h-pyrrolo[3,4-c] quinolines: QSAR study.

    abstract::Neurodegenerative disorders are consequences of progressive and irreversible loss of neurons due to unwanted apoptosis which involves caspases, a group of cysteine proteases that cleave other proteins and inactivate them. Among several different groups of caspase enzymes, caspases-3 plays a key role in apoptosis and a...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.1080/14756360701652476

    authors: Sharma S,Ravichandran V,Jain PK,Mourya VK,Agrawal RK

    更新日期:2008-06-01 00:00:00

  • Design, synthesis of 4-aminoquinoline-derived thiazolidines and their antimalarial activity and heme polymerization inhibition studies.

    abstract::The present study describes the synthesis of a series of new 4-aminoquinoline-derived thiazolidines and evaluation of their antimalarial activity against a NF-54 strain of Plasmodium falciparum in vitro and N-67 strain of Plasmodium yoelii in vivo. Among the series, two compounds, 2-(4-chloro-phenyl)-thiazolidine-4-ca...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.3109/14756366.2012.666537

    authors: Solomon VR,Haq W,Srivastava K,Puri SK,Katti SB

    更新日期:2013-06-01 00:00:00

  • Molecular modelling studies of new potential human DNA polymerase α inhibitors.

    abstract::The human polymerase α (pol α) is a promising target for the therapy of cancer e.g. of the skin. The authors recently built a homology model of the active site of human DNA pol α. This 3D model was now used for molecular modelling studies with eight novel analogues of 2-butylanilino-dATP, which is a highly selective n...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.3109/14756366.2010.503609

    authors: Zdrazil B,Schwanke A,Schmitz B,Schäfer-Korting M,Höltje HD

    更新日期:2011-04-01 00:00:00

  • Brucella suis carbonic anhydrases and their inhibitors: Towards alternative antibiotics?

    abstract::Carbonic anhydrases have started to emerge as new potential antibacterial targets for several pathogens. Two β-carbonic anhydrases, denominated bsCA I and bsCA II, have been isolated and characterized from the bacterial pathogen Brucella suis, the causative agent of brucellosis or Malta fever. These enzymes have been ...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1080/14756366.2017.1295451

    authors: Köhler S,Ouahrani-Bettache S,Winum JY

    更新日期:2017-12-01 00:00:00

  • Measurement of antioxidant ability of melatonin and serotonin by the DMPD and CUPRAC methods as trolox equivalent.

    abstract::Melatonin (N-acetyl-5-methoxytryptamine) is the chief secretory product of the pineal gland and synthesized enzymatically from serotonin (5-hydroxytryptamine). These indoleamine derivatives play an important role in the prevention of oxidative damage. In the present study, DMPD radical scavenging and cupric ion (Cu(2+...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章

    doi:10.1080/14756360701626223

    authors: Gulçin I

    更新日期:2008-12-01 00:00:00

  • Antioxidant properties of benzylchroman derivatives from Caesalpinia sappan L. against oxidative stress evaluated in vitro.

    abstract::The antioxidant activity of extracts from Caesalpinia sappan L. (CSL) was studied in vitro by evaluating the total phenolics, measuring the antioxidant activity by TEAC, measuring the scavenging effects on reactive oxygen species (ROS) and on reactive nitrogen species (RNS), and measuring the inhibitory effect on Cu(2...

    journal_title:Journal of enzyme inhibition and medicinal chemistry

    pub_type: 杂志文章,收录出版

    doi:10.3109/14756360903373376

    authors: Lee MJ,Lee HS,Kim H,Yi HS,Park SD,Moon HI,Park WH

    更新日期:2010-10-01 00:00:00