Nordihydroguaiaretic acid

Manufactured by Merck Group

Sourced in United States, Germany

Nordihydroguaiaretic acid is a chemical compound that can be used as a laboratory reagent. It is a naturally occurring plant-derived compound with antioxidant properties. The core function of nordihydroguaiaretic acid is to serve as a research tool in biochemical and chemical studies.

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Lab products found in correlation

Indomethacin, by Merck Group (4 mentions) Ascorbic acid, by Merck Group (4 mentions) 2 2 diphenyl 1 picrylhydrazyl (dpph), by Merck Group (3 mentions) Linoleic acid sodium salt, by Merck Group (3 mentions) Arachidonic acid, by Merck Group (3 mentions) Xanthine oxidase, by Merck Group (3 mentions) Xanthine, by Merck Group (3 mentions) Dimethyl sulfoxide (dmso), by Merck Group (2 mentions) Trolox, by Merck Group (2 mentions) Caffeic acid, by Merck Group (2 mentions) Neurobasal medium, by Thermo Fisher Scientific (2 mentions) R deprenyl hydrochloride, by Merck Group (2 mentions) Arachidonic acid, by Cayman Chemical (2 mentions) Isp 1, by Merck Group (2 mentions) Apigenin, by Thermo Fisher Scientific (2 mentions) Ajamaline, by MP Biomedicals (2 mentions) Bw755c, by Bio-Techne (2 mentions) Neurobasal medium, by Merck Group (2 mentions) Creatine, by Merck Group (2 mentions) Nitroblue tetrazolium, by Merck Group (2 mentions)

Spelling variants of this product

Nordihydroguaiaretic acid (NDGA, (7 citations)

25 protocols using nordihydroguaiaretic acid

Inhibition Assay of Bioactive Compounds

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Cinnamtannin B-1 was purchased from Enzo Life Sciences, Inc., (New York, NY, USA). The target-verified inhibitors including LOPAC1280 used in the inhibition assay were obtained from Sigma-Aldrich Corp., (St. Louis, MO, USA). The PI3K and PKC inhibitors (LY294002 and Gö6983, respectively) were purchased from EMD Millipore Corp., (Billerica, MA, USA). The phospholipase C (PLC), lipoxygenase (LOX), and purine inhibitors (U-73343, nordihydroguaiaretic acid, and azathioprine, respectively) were obtained from Sigma-Aldrich Corp., (St. Louis, MO, USA).
The biflavonoids used were procyanidins and biflavonoids from Cupressus and Garcinia [25 ,26 ], which are similar to the procyanidins. Procyanidin A2, procyanidin B1, and cupressuflavone were obtained from Extrasynthese (Genay, France). For the monomeric flavonoids and polyphenols, (+)-catechin was purchased from Nagara Science Co., Ltd., (Gifu, Japan). Genistein was purchased from Sigma-Aldrich Corp., (St. Louis, MO, USA). Caffeic and gallic acids were obtained from LKT Laboratories, Inc., (St. Paul, MN, USA).

Fujita K., Kuge K., Ozawa N., Sahara S., Zaiki K., Nakaoji K., Hamada K., Takenaka Y., Tanahashi T., Tamai K., Kaneda Y, & Maeda A. (2015). Cinnamtannin B-1 Promotes Migration of Mesenchymal Stem Cells and Accelerates Wound Healing in Mice. PLoS ONE, 10(12), e0144166.

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Modulating Inflammatory Signaling in Ventricular Myocytes

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Isoproterenol (Sigma) and TNFα (R&D) were respectively used at 100 nM and 50 ng/mL, as previously reported^{26 (link)}. Neutralizing anti-TNFR₁ or anti-TNFR₂ antibodies (R&D) were preincubated 1 hour at 37 °C at a final concentration of 2.5 µg/mL. All pharmacological inhibitors were preincubated for 10 min. Orai pharmacological inhibitors YM58483 (Tocris) and Synta66 (Servier) were added at 1 µM. PLA₂ activating peptide (R&D) and the _cPLA₂ inhibitor, methyl arachidonylfluorophosphonate (MAFP) (Sigma), were respectively used at 20 µg/mL and 4 µg/mL. Lipoxygenase and cycloxygenase inhibitors, nordihydroguaiaretic acid (NDGA) and indomethacin (Sigma), were used at 1 µM. Montelukast (Sigma) was used at 2 µM. To explore ventricular myocyte resistance to oxidative stress, we applied 100 µM of H₂O₂ (Sigma). Semapimod (MedKoo) was used in vitro on CD11b/c cells at 10 µM.

Keck M., Flamant M., Mougenot N., Favier S., Atassi F., Barbier C., Nadaud S., Lompré A.M., Hulot J.S, & Pavoine C. (2019). Cardiac inflammatory CD11b/c cells exert a protective role in hypertrophied cardiomyocyte by promoting TNFR2- and Orai3- dependent signaling. Scientific Reports, 9, 6047.

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Compound Library Screening for Metabolic Enzymes

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A chemical library of 480 compounds was obtained from National Development Institute of Korean Medicine (NIKOM). Antibodies for glyceraldehyde 3-phosphate dehydrogenase (GAPDH) were purchased from Santa Cruz Biotechnology (sc-32233, Dallas, TX, USA). The anti-LDHA antibody was obtained from Santa Cruz Biotechnology (sc-137243). All chemicals and reagents, including NADH, pyruvate, Cibacron Blue agarose, 1,3-benzodioxole, piperonyl alcohol, and nordihydroguaiaretic acid were obtained from Sigma-Aldrich (St. Louis, MO, USA).

Chung T.W., Kim E.Y., Han C.W., Park S.Y., Jeong M.S., Yoon D., Choi H.J., Jin L., Park M.J., Kwon Y.J., Lee H., Kim K.J., Park K.H., Kim S., Jang S.B, & Ha K.T. (2019). Machilin A Inhibits Tumor Growth and Macrophage M2 Polarization Through the Reduction of Lactic Acid. Cancers, 11(7), 963.

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Reagents for Ion Channel Studies

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AA, Cs-methanesulfonate, Na-methanesulfonate, and nordihydroguaiaretic acid (NDGA) were purchased from Sigma-Aldrich. LTC₄, N-methyl LTC₄ (NMLTC₄), and eicosatetraynoic acid (ETYA) were from Cayman. 2-Aminoethoxydiphenyl borate (2-APB) was purchased from EMD Millipore. Cs-1,2-bis-(2-aminophenoxy)ethane-N,N,N′,N′-tetraacetic acid (Cs-BAPTA) was purchased from Invitrogen. GdCl₃ was from Acros Organics. All small interference RNAs (siRNAs) were purchased from Dharmacon and have been described previously (Abdullaev et al., 2008 (link); González-Cobos et al., 2013 (link); Motiani et al., 2013 (link); Shinde et al., 2013 (link); see also Table S1). The transfection kits (VCA-1003 for HEK293 cells and VPI-1004 for VSMCs) were from Lonza. All other chemicals were from Thermo Fisher Scientific.

Zhang X., Zhang W., González-Cobos J.C., Jardin I., Romanin C., Matrougui K, & Trebak M. (2014). Complex role of STIM1 in the activation of store-independent Orai1/3 channels. The Journal of General Physiology, 143(3), 345-359.

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Cytotoxicity and CYP3A4 Enzymatic Assays

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Human hepatoma HuH-7 cells were purchased from Health Science Research Resources Bank, Japan Health Sciences Foundation (Osaka, Japan). HepG2/C3A cells were obtained from ATCC (Manassas, VA). HepaRG cells were purchased from Life Technologies (Grand Island, NY). Cell culture medium and medium supplements were obtained from Life Technologies. Fetal bovine serum was purchased from Atlanta Biologicals (Lawrenceville, GA). The following compounds (all ≥ 97% purity) were obtained from Sigma-Aldrich (St. Louis, MO): dimethyl sulfoxide (DMSO), ketoconazole, nifedipine, troleandomycin, rifampicin, dexathemasone, nordihydroguaiaretic acid (NDGA), nitrofurantoin, desipramine hydrochloride, troglitazone, nefazodone hydrochloride, bicinchoninic acid, and copper sulfate. P450-Glo CYP3A4 assay (luciferin-IPA substrate), CellTiter-Fluor, and CellTiter-Glo cell viability assays were purchased from Promega (Madison, WI). Supersomes human CYP3A4 plus reductase and b5, NADPH regenerating system, and rat tail collagen type I were obtained from Corning (Corning, NY). RNeasy mini Kit and QIA shredder were purchased from QIAGEN (Valencia, CA). High-capacity cDNA reverse transcription kits, TaqMan gene expression assays (beta-actin, 18S and human CYP3A4), and NucRed Live 647 fluorescent dye were purchased from Life Technologies.

Liu Y., Flynn T.J., Xia M., Wiesenfeld P.L, & Ferguson M.S. (2015). Evaluation of CYP3A4 inhibition and hepatotoxicity using DMSO-treated human hepatoma HuH-7 cells. Cell biology and toxicology, 31(4-5), 221-230.

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Antioxidant and Redox Activity Assays

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Thiobarbituric acid (TBA); lipoxygenase from soybean; nitroblue tetrazolium (NBT); reduced form of nicotinamide adenine dinucleotide (NADH) and N-phenylmethazonium methosulfate (PMS) were purchased from Fluka, Biochemika, Sigma-Aldrich, Steinheim, Germany. Linoleic acid sodium salt; 2,2’-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) diammonium salt (ABTS); 2,2-diphenyl-1-picrylhydrazyl (DPPH); nordihydroguaiaretic acid (NDGA) and 2-deoxyribose were purchased from Sigma-Aldrich, Steinheim, Germany. Trichloro acetic acid was purchased from VWR, Leuven, Belgium. Ferrozine iron reagent hydrate; ethylenediaminetetra acetic acid (EDTA); FeCl₂.4H₂O, FeCl₃; and potassium persulfate were purchased from Acros organics, New Jersey, USA. L(+)-Ascorbic acid and boric acid were purchased from Merck, Darmstadt, Germany. KH₂PO₄-K₂HPO₄; FeSO₄.7H₂O were purchased from Panreac, Barcelona, Spain. H₂O₂ was purchased from Fisher Scientific, New Jersey, USA. L-α-lecithin of soybean was purchased from CALBIOCHEM, Darmstadt, Germany. Chloroform was purchased from lab-scan, Dublin; Folin Ciocalteu's phenol reagent, was purchased from Panreac Química SA (Barcelona, Spain). Gallic acid; Na₂CO₃; acetic acid; acetic acid; sodium dodecyl sulfate (SDS); KCl; butanol; butylated hydroxytoluene (BHT); mannitol KCl were purchased from Riedel de Haen (Seelze, Germany).

Ben-Nasr S., Aazza S., Mnif W, & Miguel M.D. (2015). Antioxidant and anti-lipoxygenase activities of extracts from different parts of Lavatera cretica L. grown in Algarve (Portugal). Pharmacognosy Magazine, 11(41), 48-54.

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Fatty Acid and Oxidative Stress Biomarkers

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Arachidonic Acid (AA), nordihydroguaiaretic acid (NDGA) and Xylenol Orange tetrasodium salt were purchased from Sigma-Aldrich® (USA). Fish oil containing 35% eicosapentaenoic acid (EPA) and 40% docosahexaenoic acid (DHA) from Natufarma Labs (Buenos Aires, Argentina). Blood glucose and glycated haemoglobin (HbA1c) were determined by rapid test Accu-check by Roche (Switzerland). Total cholesterol (Chol), TG, C-Reactive Protein (CRP), enzymes: transaminases, pyruvic oxaloacetic, glutamic oxaloacetic and gamma glutamyltranspeptidase (GGTP) diagnostic kits were purchased from Wiener Lab® (Argentina). Rabbit polyclonal anti-synaptophysin (SYN) antibody was purchased from Dako Biotechnology (Denmark). IL-6 plasma levels were measured by immuno-ELISA OptEIA™ system and apoptosis determined by Flow Cytometry (Annexin V: PE) both detection kits were provided by BD Biosciences® (USA). Fatty acids methyl ester (FAME) were identified using a commercial standard Nu-check® (USA) [12 (link)]. Hippocampal IL-6 levels were determined by RT-PCR, supplies was purchased from Life Technologies (USA). Apoptotic cells in histological slides were identified by TunelS7100 ApopTag® Peroxidase in situ Apoptosis Detection Kit (Germany).

Díaz-Gerevini G.T., Daín A., Pasqualini M.E., López C.B., Eynard A.R, & Repossi G. (2019). Diabetic encephalopathy: beneficial effects of supplementation with fatty acids ω3 and nordihydroguaiaretic acid in a spontaneous diabetes rat model. Lipids in Health and Disease, 18, 43.

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Quantification of Bioactive Compounds

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The following compounds of the purity ≥98% were purchased from Sigma-Aldrich (Saint Louis, MO, USA): ethyl 4-hydroxybenzoate (E-4-OH-BA), ethyl vanillate (EV), gallic acid (GA), gentisic acid (GNA), homogentisic acid (HGA), homo vanillic acid (HVA), 3-hydroxybenzoic acid (3-OH-BA), 4-hydroxybenzoic acid (4-OH-BA), 4-hydroxyphenylacetic acid (4-OH-PA), 4-hydroxyphenylpyruvic acid (4-OH-PP), nordihydroguaiaretic acid (NDGA), protocatechuic acid (PCA), salicylic acid (SA), sinapic acid (SNA), syringic acid (SRA), vanillic acid (VA), acetylthiocholine iodide (ACh), and Acetylcholinesterase from Electrophorus electricus (electric eel) (AChE). Methyl syringate (MS) was purchased from Apin Chemicals Ltd., (Abingdon, UK).

Budryn G., Majak I., Grzelczyk J., Szwajgier D., Rodríguez-Martínez A, & Pérez-Sánchez H. (2022). Hydroxybenzoic Acids as Acetylcholinesterase Inhibitors: Calorimetric and Docking Simulation Studies. Nutrients, 14(12), 2476.

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Antioxidant Capacity Evaluation of Coumarin Derivatives

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1,1-diphenyl-picrylhydrazyl (DPPH), Trolox, nordihydroguaiaretic acid (NDGA), linoleic acid sodium salt, and lipoxidase Type I-B from Glycine max (soybean) were purchased from Sigma Chemical Co. (St. Louis, MO, USA); sodium phosphate monobasic monohydrate and sodium phosphate dibasic dehydrate were purchased from Merck KgaA, Merck Group (Darmstadt, Germany); boric acid, sodium tetraborate decahydrate, and tri-sodium phosphate hexahydrate were purchased from Honeywell Fluka^™ (Charlotte, NC, USA); ammonium heptamolybdate tetrahydrate was purchased from Kemika d.d. (Zagreb, Croatia); dimethyl sulfoxide and sulfuric acid were purchased from Gram-Mol d.o.o. (Zagreb, Croatia); and 2,2′-azobis(2-methylpropionamidine) dihydrochloride and coumarin were purchased from Acros Organics B.V.B.A. (Geel, Belgium).
The coumarin derivatives (1–39) were synthesized and characterized as previously reported [28 (link)].

Lončarić M., Strelec I., Pavić V., Šubarić D., Rastija V, & Molnar M. (2020). Lipoxygenase Inhibition Activity of Coumarin Derivatives—QSAR and Molecular Docking Study. Pharmaceuticals, 13(7), 154.

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Protein Binding Assay Protocol

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Essentially globulin and fatty acid free Human serum albumin (A1887), Bovine serum albumin (A7030), Nordihydroguaiaretic acid (N5023), Warfarin (A2250) and Phenylbutazone (P8386) were procured from Sigma Aldrich. Diazepam was obtained from Ranbaxy Laboratories Ltd. All other reagents were of analytical grade. Double distilled water free from any fluorescent contaminants was used.

Nusrat S., Siddiqi M.K., Zaman M., Zaidi N., Ajmal M.R., Alam P., Qadeer A., Abdelhameed A.S, & Khan R.H. (2016). A Comprehensive Spectroscopic and Computational Investigation to Probe the Interaction of Antineoplastic Drug Nordihydroguaiaretic Acid with Serum Albumins. PLoS ONE, 11(7), e0158833.

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