{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,19]],"date-time":"2026-10-19T22:28:25Z","timestamp":1792448905065,"version":"4.5.0"},"reference-count":94,"publisher":"MDPI AG","issue":"23","license":[{"start":{"date-parts":[[2021,11,24]],"date-time":"2021-11-24T00:00:00Z","timestamp":1637712000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>In this study, the antioxidant and antiradical properties of some phyto lignans (nordihydroguaiaretic acid, secoisolariciresinol, secoisolariciresinol diglycoside, and \u03b1-(-)-conidendrin) and mammalian lignans (enterodiol and enterolactone) were examined by different antioxidant assays. For this purpose, radical scavenging activities of phyto and mammalian lignans were realized by 2,2\u2032-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) radical (ABTS\u2022+) scavenging assay and 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) scavenging assay. Additionally, the reducing ability of phyto and mammalian lignans were evaluated by cupric ions (Cu2+) reducing (CUPRAC) ability, and ferric ions (Fe3+) and [Fe3+-(TPTZ)2]3+ complex reducing (FRAP) abilities. Also, half maximal inhibitory concentration (IC50) values were determined and reported for DPPH\u2022 and ABTS\u2022+ scavenging influences of all of the lignan molecules. The absorbances of the lignans were found in the range of 0.150\u20132.320 for Fe3+ reducing, in the range of 0.040\u20132.090 for Cu2+ reducing, and in the range of 0.360\u20131.810 for the FRAP assay. On the other hand, the IC50 values of phyto and mammalian lignans were determined in the ranges of 6.601\u2013932.167 \u00b5g\/mL for DPPH\u2022 scavenging and 13.007\u201327.829 \u00b5g\/mL for ABTS\u2022+ scavenging. In all of the used bioanalytical methods, phyto lignans, as secondary metabolites in plants, demonstrated considerably higher antioxidant activity compared to that of mammalian lignans. In addition, it was observed that enterodiol and enterolactone exhibited relatively weaker antioxidant activities when compared to phyto lignans or standard antioxidants, including butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), Trolox, and \u03b1-tocopherol.<\/jats:p>","DOI":"10.3390\/molecules26237099","type":"journal-article","created":{"date-parts":[[2021,11,30]],"date-time":"2021-11-30T22:01:11Z","timestamp":1638309671000},"page":"7099","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":74,"title":["Evaluation of the Antioxidant and Antiradical Properties of Some Phyto and Mammalian Lignans"],"prefix":"10.3390","volume":"26","author":[{"given":"Leyla","family":"Polat Kose","sequence":"first","affiliation":[{"name":"Department of Pharmacy Services, Vocational School, Beykent University, Istanbul 34500, Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5993-1668","authenticated-orcid":false,"given":"\u0130lhami","family":"Gulcin","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Science, Ataturk University, Erzurum 25240, Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2021,11,24]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"215","DOI":"10.1016\/S1570-0232(04)00548-3","article-title":"Separation procedures applicable to lignan analysis","volume":"812","author":"Slanina","year":"2004","journal-title":"J. Chromatogr. B"},{"key":"ref_2","first-page":"558","article-title":"Inhibition effects of some lignans on carbonic anhydrase, acetylcholinesterase and butyrylcholinesterase enzymes","volume":"11","author":"Gulcin","year":"2017","journal-title":"Rec. Nat. Prod."},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"K\u0131z\u0131ltas, H., Bingol, Z., Goren, A.C., Polat Kose, L., Durmaz, L., Topal, F., Alwasel, S.H., and Gulcin, I. (2021). LC-HRMS profiling, antidiabetic, anticholinergic and anti-oxidant activities of aerial parts of k\u0131nkor (Ferulago stelleta). Molecules, 26.","DOI":"10.3390\/molecules26092469"},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"Ayres, D., and Loike, J.D. (1990). Chemistry and pharmacology of natural products. Lignans: Chemical, Biological and Clinical Properties, Cambridge University Press.","DOI":"10.1017\/CBO9780511983665"},{"key":"ref_5","first-page":"S48","article-title":"Antioxidant and antitumor effects of hydroxymatairesinol (HM-3000, HMR), a lignan isolated from the knots of spruce","volume":"11","author":"Kangas","year":"2002","journal-title":"Eur. J. Cancer Prev."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1687","DOI":"10.1016\/S0006-2952(96)00517-5","article-title":"The crucial antioxidant action of Schisandrin B in protecting against carbon tetrachloride hepatotoxicity in mice: A comparative study with butylated hydroxytoluene","volume":"52","author":"Ip","year":"1996","journal-title":"Biochem. Pharmacol."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"37","DOI":"10.1111\/j.1365-2672.1985.tb01427.x","article-title":"Production and metabolism of lignans by the human faecal flora","volume":"58","author":"Borriello","year":"1985","journal-title":"J. Appl. Bacteriol."},{"key":"ref_8","unstructured":"Adlercreutz, H. (1998). Reproductive and Developmental Toxicology, Marcel Dekker."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"345","DOI":"10.1007\/s00204-011-0774-2","article-title":"Antioxidant activity of food constituents: An overview","volume":"86","author":"Gulcin","year":"2012","journal-title":"Arch. Toxicol."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"651","DOI":"10.1007\/s00204-020-02689-3","article-title":"Antioxidants and antioxidant methods-An updated overview","volume":"94","author":"Gulcin","year":"2020","journal-title":"Arch. Toxicol."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1482","DOI":"10.1016\/j.foodres.2011.03.031","article-title":"Polyphenol contents and in vitro antioxidant activities of lyophilized aqueous extract of kiwifruit (Actinidia deliciosa)","volume":"44","author":"Bursal","year":"2011","journal-title":"Food Res. Int."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"C585","DOI":"10.1111\/j.1750-3841.2011.02142.x","article-title":"Pomological features, nutritional quality, polyphenol content analysis and antioxidant properties of domesticated and three wild ecotype forms of raspberries (Rubus idaeus L.)","volume":"76","author":"Gulcin","year":"2011","journal-title":"J. Food Sci."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"281","DOI":"10.1248\/cpb.53.281","article-title":"Determination of in vitro antioxidant and radical scavenging activities of propofol","volume":"53","author":"Gulcin","year":"2005","journal-title":"Chem. Pharm. Bull."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"266","DOI":"10.3109\/14756366.2015.1018244","article-title":"Antioxidant, antiradical and anticholinergic properties of cynarin purified from the illyrian thistle (Onopordum illyricum L.)","volume":"31","author":"Topal","year":"2016","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"513","DOI":"10.25135\/rnp.236.21.02.1983","article-title":"Anticholinergic, antidiabetic and antioxidant activities of Ferula orientalis L.\u2014Analysis of its polyphenol contents by LC-HRMS","volume":"15","author":"Kiziltas","year":"2021","journal-title":"Rec. Nat. Prod."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"2227","DOI":"10.1016\/j.fct.2010.05.053","article-title":"Polyphenol contents and antioxidant activity of lyophilized aqueous extract of propolis from Erzurum, Turkey","volume":"48","author":"Gulcin","year":"2010","journal-title":"Food Chem. Toxicol."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"101711","DOI":"10.1016\/j.bcab.2020.101711","article-title":"Assessments of anticholinergic, antidiabetic, antioxidant activities and phenolic content of Stachys annua","volume":"28","author":"Bursal","year":"2020","journal-title":"Biocat. Agric. Biotechnol."},{"key":"ref_18","first-page":"65","article-title":"Antioxidant activity of cauliflower (Brassica oleracea L.)","volume":"32","author":"Koksal","year":"2008","journal-title":"Turk. J. Agric. For."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"4528","DOI":"10.1016\/j.arabjc.2019.10.002","article-title":"Anti-Alzheimer, antidiabetic and antioxidant potential of Satureja cuneifolia and analysis of its phenolic contents by LC-MS\/MS","volume":"13","author":"Taslimi","year":"2020","journal-title":"Arab. J. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1607","DOI":"10.1007\/s11694-019-00077-9","article-title":"Measurement of anticancer, antidiabetic and anticholinergic properties of sumac (Rhus coriaria)\u2014Analysis of its phenolic compounds by LC-MS\/MS","volume":"13","author":"Tohma","year":"2019","journal-title":"J. Food Meas. Charact."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"103884","DOI":"10.1016\/j.bioorg.2020.103884","article-title":"Synthesis and antioxidant activities of phenol derivatives from 1,6-bis(dimethoxyphenyl)hexane-1,6-dione","volume":"100","author":"Menzek","year":"2020","journal-title":"Bioorg. Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"101441","DOI":"10.1016\/j.bcab.2019.101441","article-title":"Anticholinergic, antidiabetic and antioxidant activities of Anatolian pennyroyal (Mentha pulegium)\u2014Analysis of its polyphenol contents by LC-MS\/MS","volume":"23","author":"Taslimi","year":"2020","journal-title":"Biocat. Agric. Biotechnol."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"103333","DOI":"10.1016\/j.bioorg.2019.103333","article-title":"ICP-MS and HPLC analyses, enzyme inhibition and antioxidant potential of Achillea schischkinii Sosn","volume":"94","author":"Turkan","year":"2020","journal-title":"Bioorg. Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"e12908","DOI":"10.1111\/jfbc.12908","article-title":"Preliminary phytochemical analysis and evaluation of in vitro antioxidant, antiproliferative, antidiabetic and anticholinergics effects of endemic Gypsophila taxa from Turkey","volume":"43","author":"Altay","year":"2019","journal-title":"J. Food Biochem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"43","DOI":"10.1016\/j.arabjc.2009.12.008","article-title":"Radical scavenging and antioxidant activity of tannic acid","volume":"3","author":"Gulcin","year":"2010","journal-title":"Arab. J. Chem."},{"key":"ref_26","first-page":"175","article-title":"Antioxidant and antimicrobial activities of an aquatic plant: Duckweed (Lemna minor L.)","volume":"34","author":"Gulcin","year":"2010","journal-title":"Turk. J. Biol."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"712","DOI":"10.1016\/j.indcrop.2015.05.034","article-title":"LC-MS\/MS analysis, antioxidant and anticholinergic properties of galanga (Alpinia officinarum Hance) rhizomes","volume":"74","author":"Gulcin","year":"2015","journal-title":"Ind. Crops Prod."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"803","DOI":"10.1016\/j.lfs.2005.05.103","article-title":"Antioxidant and antiradical activities of L-carnitine","volume":"78","author":"Gulcin","year":"2006","journal-title":"Life Sci."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"1511","DOI":"10.1080\/10942912.2019.1656232","article-title":"Anticholinergic, antidiabetic and antioxidant activities of cinnamon (Cinnamomum verum) bark extracts: Polyphenol contents analysis by LC-MS\/MS","volume":"22","author":"Gulcin","year":"2019","journal-title":"Int. J. Food Prop."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"1273","DOI":"10.1016\/j.toxrep.2019.11.003","article-title":"Anticholinergic and antioxidant activities of usnic acid-An activity-structure insight","volume":"6","author":"Gulcin","year":"2019","journal-title":"Toxicol. Rep."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"657","DOI":"10.1080\/10942911003773916","article-title":"Antioxidant and radical scavenging activity of aerial parts and roots of Turkish liquorice (Glycyrrhiza glabra L.)","volume":"13","author":"Gulcin","year":"2010","journal-title":"Int. J. Food Prop."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"685","DOI":"10.3109\/14756360903514164","article-title":"Synthesis and antioxidant properties of diphenylmethane derivative bromophenols including a natural product","volume":"25","author":"Gulcin","year":"2010","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"431","DOI":"10.1007\/s00726-006-0379-x","article-title":"Comparison of in vitro antioxidant and antiradical activities of L-tyrosine and L-Dopa","volume":"32","author":"Gulcin","year":"2007","journal-title":"Amino Acids"},{"key":"ref_34","first-page":"496","article-title":"Antioxidant activity and polyphenol content of cranberries (Vaccinium macrocarpon)","volume":"9","author":"Kalin","year":"2015","journal-title":"Rec. Nat. Prod."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"944","DOI":"10.1002\/ardp.201600183","article-title":"Antioxidant activity, acetylcholinesterase and carbonic anhydrase inhibitory properties of novel ureas derived from phenethylamines","volume":"349","author":"Aksu","year":"2016","journal-title":"Arch. Pharm."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"193","DOI":"10.1556\/AAlim.34.2005.2.13","article-title":"Evaluation of antioxidant activity of cornelian cherry (Cornus mas L.)","volume":"34","author":"Gulcin","year":"2005","journal-title":"Acta Aliment."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"556","DOI":"10.1007\/s11694-016-9423-z","article-title":"Antioxidant activity and phenolic compounds of ginger (Zingiber officinale Rosc.) determined by HPLC-MS\/MS","volume":"11","author":"Tohma","year":"2017","journal-title":"J. Food Meas. Charact."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"323","DOI":"10.1002\/ardp.201100272","article-title":"Synthesis and antioxidant properties of (3,4-dihydroxyphenyl) (2,3,4-trihydroxyphenyl)methanone and its derivatives","volume":"345","author":"Cetinkaya","year":"2012","journal-title":"Arch. Pharm."},{"key":"ref_39","first-page":"17","article-title":"Evaluation of the in vitro antioxidant properties of extracts of broccoli (Brassica oleracea L.)","volume":"16","author":"Gulcin","year":"2004","journal-title":"Ital. J. Food Sci."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"66","DOI":"10.1016\/j.foodres.2012.11.022","article-title":"Antioxidant activity and polyphenol content of cherry stem (Cerasus avium L.) determined by LC-MS\/MS","volume":"51","author":"Bursal","year":"2013","journal-title":"Food Res. Int."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"878","DOI":"10.1080\/10942912.2020.1761829","article-title":"Anticholinergic and antioxidant activities of avocado (Folium perseae) leaves\u2014Phytochemical content by LC-MS\/MS analysis","volume":"23","author":"Kaya","year":"2020","journal-title":"Int. J. Food Prop."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"279","DOI":"10.1080\/15216540051081010","article-title":"Oxidative stress, antioxidant defenses, and damage removal, repair, and replacement systems","volume":"50","author":"Davies","year":"2000","journal-title":"IUBMB"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1016\/S0924-2244(02)00020-1","article-title":"Development of functional ingredients for gut health","volume":"13","author":"Aura","year":"2002","journal-title":"Trends Food Sci. Technol."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"e2100113","DOI":"10.1002\/ardp.202100113","article-title":"Synthesis and biological evaluation of some 1-naphthol derivatives as antioxidants, acetylcholinesterase, carbonic anhydrase inhibitors","volume":"354","author":"Essiz","year":"2021","journal-title":"Arch. Pharm."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"91","DOI":"10.1016\/j.bioorg.2019.03.010","article-title":"Synthesis and characterization of novel bromophenols: Determination of their anticholinergic, antidiabetic and antioxidant activities","volume":"87","author":"Oztaskin","year":"2019","journal-title":"Bioorg. Chem."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"871","DOI":"10.1080\/14756360701626223","article-title":"Measurement of antioxidant ability of melatonin and serotonin by the DMPD and CUPRAC methods as trolox equivalent","volume":"23","author":"Gulcin","year":"2008","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"14152","DOI":"10.1021\/acs.jafc.9b06264","article-title":"Structural modifications of a flaxseed lignan in pursuit of higher liposolubility: Evaluation of the antioxidant and permeability properties of the resulting derivatives","volume":"67","author":"Lan","year":"2019","journal-title":"J. Agric. Food Chem."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"373","DOI":"10.31413\/nativa.v9i4.11809","article-title":"Flaxseed meal feeding to dairy cows as a strategy to improve milk enterolactone concentration: A literature review","volume":"9","author":"Ghedini","year":"2021","journal-title":"Nativa"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"410","DOI":"10.1016\/j.foodres.2011.12.023","article-title":"Plant and mammalian lignans: A review of source, intake metabolism, intestinal bacteria and health","volume":"46","author":"Landete","year":"2012","journal-title":"Food Res. Int."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"1585","DOI":"10.1111\/j.1365-2672.2008.03922.x","article-title":"In vitro metabolism of flax lignans by ruminal and faecal microbiota of dairy cows","volume":"105","author":"Cortes","year":"2008","journal-title":"J. Appl. Microbiol."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"e1900341","DOI":"10.1002\/cbdv.201900341","article-title":"Phytochemical content, antidiabetic, anticholinergic, and antioxidant activities of endemic Lecokia cretica extracts","volume":"16","author":"Aras","year":"2019","journal-title":"Chem. Biodivers."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"91","DOI":"10.1023\/A:1007022329660","article-title":"Antioxidant activity of the flaxseed lignan secoisolariciresinol diglycoside and its mammalian lignan metabolites enterodiol and enterolactone","volume":"202","author":"Kitts","year":"1999","journal-title":"Mol. Cell. Biochem."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"455","DOI":"10.1007\/s11746-998-0248-8","article-title":"Antioxidant activity of burdock (Arctium lappa L.): It\u2019s scavenging effect on free radical and active oxygen","volume":"75","author":"Duh","year":"1998","journal-title":"J. Am. Oil Chem. Soc."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"130","DOI":"10.1002\/ptr.1821","article-title":"Antioxidant activity of a triterpenoid glycoside isolated from the berries of Hedera colchica: 3-O-(\u03b2-d-glucopyranosyl)-hederagenin","volume":"20","author":"Gulcin","year":"2006","journal-title":"Phytother. Res."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"195","DOI":"10.1007\/s00226-008-0234-1","article-title":"Antioxidant secoiridoids from fringe tree (Chionanthus virginicus L.)","volume":"43","author":"Gulcin","year":"2009","journal-title":"Wood Sci. Technol."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"443","DOI":"10.2174\/138620706777698544","article-title":"The antioxidant activity of two wild edible mushrooms (Morchella vulgaris and Morchella esculanta)","volume":"9","author":"Elmastas","year":"2006","journal-title":"Comb. Chem. High Throughput Screen."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"975","DOI":"10.1089\/jmf.2010.0197","article-title":"Antioxidant activity of eugenol\u2014A structure and activity relationship study","volume":"14","author":"Gulcin","year":"2011","journal-title":"J. Med. Food"},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"210","DOI":"10.1016\/j.ifset.2009.07.002","article-title":"Antioxidant properties of resveratrol: A structure-activity insight","volume":"11","author":"Gulcin","year":"2010","journal-title":"Innov. Food Sci. Emerg."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"674","DOI":"10.3109\/14756366.2015.1057723","article-title":"Antioxidant activity of taxifolin: An activity-structure relationship","volume":"31","author":"Topal","year":"2016","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"e12516","DOI":"10.1111\/jfbc.12516","article-title":"Antioxidant and anticholinergic properties of olivetol","volume":"42","author":"Taslimi","year":"2018","journal-title":"J. Food Biochem."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"2062","DOI":"10.1007\/s11694-019-00127-2","article-title":"Sage (Salvia pilifera): Determination its polyphenol contents, anticholinergic, antidiabetic and antioxidant activities","volume":"13","author":"Gulcin","year":"2019","journal-title":"J. Food Meas. Charact."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"27","DOI":"10.1016\/j.cbi.2008.05.003","article-title":"Antioxidant and radical scavenging properties of curcumin","volume":"174","author":"Ak","year":"2008","journal-title":"Chem. Biol. Interact."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"845","DOI":"10.1016\/j.ijbiomac.2016.10.096","article-title":"Novel eugenol derivatives: Potent acetylcholinesterase and carbonic anhydrase inhibitors","volume":"94","author":"Topal","year":"2017","journal-title":"Int. J. Biol. Macromol."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"e22221","DOI":"10.1002\/jbt.22221","article-title":"Synthesis, characterization, antioxidant, antidiabetic, anticholinergic, and antiepileptic properties of novel N-substituted tetrahydropyrimidines based on phenylthiourea","volume":"32","author":"Maharramova","year":"2018","journal-title":"J. Biochem. Mol. Toxicol."},{"key":"ref_65","first-page":"808","article-title":"The first synthesis, antioxidant and anticholinergic activities of 1-(4,5-dihydroxybenzyl)pyrrolidin-2-one derivative bromophenols including natural products","volume":"42","author":"Rezai","year":"2018","journal-title":"Turk. J. Chem."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"374","DOI":"10.1080\/10942912.2017.1416399","article-title":"Antioxidant activity of an Anatolian herbal tea-Origanum minutiflorum: Isolation and characterization of its secondary metabolites","volume":"21","author":"Elmastas","year":"2018","journal-title":"Int. J. Food Prop."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"e22019","DOI":"10.1002\/jbt.22019","article-title":"Synthesis and investigation of the conversion reactions of pyrimidine-thiones with nucleophilic reagent and evaluation of their acetylcholinesterase, carbonic anhydrase inhibition and antioxidant activities","volume":"32","author":"Taslimi","year":"2018","journal-title":"J. Biochem. Mol. Toxicol."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"347","DOI":"10.1021\/jm7009364","article-title":"Multi-target-directed ligands to combat neurodegenerative diseases","volume":"51","author":"Cavalli","year":"2008","journal-title":"J. Med. Chem."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"49","DOI":"10.1016\/j.bioorg.2015.04.006","article-title":"Antioxidant and acetylcholinesterase inhibition properties of novel bromophenol derivatives","volume":"60","author":"Oztaskin","year":"2015","journal-title":"Bioorg. Chem."},{"key":"ref_70","doi-asserted-by":"crossref","unstructured":"Tohma, H., Koksal, E., K\u0131l\u0131c, O., Alan, Y., Y\u0131lmaz, M.A., Gulcin, I., Bursal, E., and Alwasel, S.H. (2016). RP-HPLC\/MS\/MS analysis of the phenolic compounds, antioxidant and antimicrobial activities of Salvia, L. species. Antioxidants, 5.","DOI":"10.3390\/antiox5040038"},{"key":"ref_71","first-page":"205","article-title":"Evaluation of phenolic contents and bioactivity of root and nutgall extracts from Iraqian Quercus infectoria Olivier","volume":"11","author":"Hamad","year":"2017","journal-title":"Rec. Nat. Prod."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"1199","DOI":"10.1038\/1811199a0","article-title":"Antioxidant determinations by the use of a stable free radical","volume":"26","author":"Blois","year":"1958","journal-title":"Nature"},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"514","DOI":"10.1080\/10942912.2016.1168438","article-title":"Antioxidant activity and polyphenol content of Turkish thyme (Thymus vulgaris) monitored by LC-MS\/MS","volume":"20","author":"Koksal","year":"2017","journal-title":"Int. J. Food Prop."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"213","DOI":"10.1016\/j.tox.2005.09.011","article-title":"Antioxidant activity of caffeic acid (3,4-dihydroxycinnamic acid)","volume":"217","author":"Gulcin","year":"2006","journal-title":"Toxicology"},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"71","DOI":"10.1016\/j.cbi.2008.09.023","article-title":"Antioxidant activity of L-Adrenaline: An activity-structure insight","volume":"179","author":"Gulcin","year":"2009","journal-title":"Chem. Biol. Interact."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"395","DOI":"10.1080\/14756360802188081","article-title":"On the in vitro antioxidant activity of silymarin","volume":"24","author":"Koksal","year":"2009","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"89","DOI":"10.1016\/j.fct.2019.03.054","article-title":"Effects of thermal preparation and in vitro digestion on lignan profiles and antioxidant activity in defatted-sesame meal","volume":"128","author":"Chen","year":"2019","journal-title":"Food Chem. Toxicol."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"170","DOI":"10.1016\/j.foodchem.2016.03.001","article-title":"Effect of germination on lignan biosynthesis, and antioxidant and antiproliferative activities in flaxseed (Linum usitatissimum L.)","volume":"205","author":"Wang","year":"2016","journal-title":"Food Chem."},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"1364","DOI":"10.1080\/14786419.2014.905557","article-title":"Acutissimanide, a new lignan with antioxidant activity isolated from the bark of Quercus acutissima Carruth","volume":"28","author":"Zeng","year":"2014","journal-title":"Nat. Prod. Res."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"1876","DOI":"10.1080\/14786419.2011.619190","article-title":"A novel lignan glycoside with antioxidant activity from Tinospora sagittata var. yunnanensis","volume":"26","author":"Huang","year":"2012","journal-title":"Nat. Prod. Res."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"2219","DOI":"10.1016\/j.fct.2007.05.017","article-title":"Antioxidant activities of the flaxseed lignan secoisolariciresinol diglucoside, its aglycone secoisolariciresinol and the mammalian lignans enterodiol and enterolactone in vitro","volume":"45","author":"Hu","year":"2007","journal-title":"Food Chem. Toxicol."},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"480","DOI":"10.1007\/s11418-007-0182-3","article-title":"Lignan glycosides and flavonoids from Saraca asoca with antioxidant activity","volume":"61","author":"Sadhu","year":"2007","journal-title":"J. Nat. Med."},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"1023","DOI":"10.1007\/BF02977395","article-title":"A New furofuran lignan with antioxidant and antiseizure activities from the leaves of Petasites japonicus","volume":"28","author":"Min","year":"2005","journal-title":"Arch. Pharm. Res."},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"307","DOI":"10.5264\/eiyogakuzashi.44.307","article-title":"Studies on product of browning reaction prepared from glucose amine","volume":"44","author":"Oyaizu","year":"1986","journal-title":"Jpn. J. Nutr."},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"397","DOI":"10.25135\/rnp.46.17.09.155","article-title":"Antioxidant activity of flaxseed (Linum usitatissimum L.) and analysis of its polyphenol contents by LC-MS\/MS","volume":"12","author":"Han","year":"2018","journal-title":"Rec. Nat. Prod."},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"e22006","DOI":"10.1002\/jbt.22006","article-title":"Synthesis of some novel pyridine compounds containing bis-1,2,4-triazole moiety and investigation of their antioxidant properties, carbonic anhydrase and acetylcholinesterase enzymes inhibition profiles","volume":"32","author":"Bulut","year":"2018","journal-title":"J. Biochem. Mol. Toxicol."},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"292","DOI":"10.1080\/09637480600798132","article-title":"The cupric ion reducing antioxidant capacity and polyphenolic content of some herbal teas","volume":"57","author":"Apak","year":"2006","journal-title":"Int. J. Food Sci. Nutr."},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"e06986","DOI":"10.1016\/j.heliyon.2021.e06986","article-title":"Antidiabetic, anticholinergic and antioxidant activities of aerial parts of shaggy bindweed (Convulvulus betonicifolia Miller subsp.)\u2014Profiling of phenolic compounds by LC-HRMS","volume":"7","author":"Bingol","year":"2021","journal-title":"Heliyon"},{"key":"ref_89","doi-asserted-by":"crossref","first-page":"e12776","DOI":"10.1111\/jfbc.12776","article-title":"Phytochemical content, antioxidant activity and enzyme inhibition effect of Salvia eriophora Boiss. & Kotschy against acetylcholinesterase, \u03b1-amylase, butyrylcholinesterase and \u03b1-glycosidase enzymes","volume":"43","author":"Bursal","year":"2019","journal-title":"J. Food Biochem."},{"key":"ref_90","doi-asserted-by":"crossref","first-page":"491","DOI":"10.1080\/09637480500450248","article-title":"The antioxidant and radical scavenging activities of black pepper (Piper nigrum) seeds","volume":"56","author":"Gulcin","year":"2005","journal-title":"Int. J. Food Sci. Nutr."},{"key":"ref_91","doi-asserted-by":"crossref","first-page":"6583","DOI":"10.1016\/j.bmc.2009.07.077","article-title":"Antioxidant activity of 5,10-dihydroindeno[1,2-b]indoles containing substituents on dihydroindeno part","volume":"17","author":"Talaz","year":"2009","journal-title":"Bioorg. Med. Chem."},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"685","DOI":"10.1080\/14756360601164903","article-title":"Synthesis of dimeric phenol derivatives and determination of in vitro antioxidant and radical scavenging activities","volume":"22","author":"Gulcin","year":"2007","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"ref_93","doi-asserted-by":"crossref","first-page":"7616791","DOI":"10.1155\/2017\/7616791","article-title":"Antioxidant and antiradical properties of some flavonoids and phenolic compounds","volume":"2017","author":"Huyut","year":"2017","journal-title":"Biochem. Res. Int."},{"key":"ref_94","doi-asserted-by":"crossref","first-page":"141","DOI":"10.1016\/j.sajb.2018.04.001","article-title":"In vitro antioxidant, antimicrobial, anticholinesterase and antidiabetic activities of Turkish endemic Achillea cucullata (Asteraceae) from ethanol extract","volume":"120","author":"Eruygur","year":"2019","journal-title":"S. Afr. J. Bot."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/23\/7099\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T07:35:03Z","timestamp":1760168103000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/23\/7099"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,11,24]]},"references-count":94,"journal-issue":{"issue":"23","published-online":{"date-parts":[[2021,12]]}},"alternative-id":["molecules26237099"],"URL":"https:\/\/doi.org\/10.3390\/molecules26237099","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,11,24]]}}}