From Fisher Scientific (Fairlawn, OH, USA), anhydrous sodium acetate and solvents (diethyl ether, formic acid, acetonitrile, methanol, and water) which were HPLC-grade or higher were purchased. Lyophilized glucuronidase/sulfatase from Helix pomatia, dimethyl sulfoxide, and equol were obtained from Sigma-Aldrich (St. Louis, MO, USA). Daidzein, genistein, glycitein, daidzin, genistin, glycitin, acetyl daidzin, malonyl genistin, and acetyl genistin were obtained from LC laboratories division (PKC Pharmaceuticals, Inc., Woburn, MA, USA), and malonyl daidzin and malonyl glycitin from Wako Chemicals USA, Inc., (Richmond, VA, USA). Isoflavone metabolites (dihydroDaidzein DHD, dihydrogenistein DHG, ODMA, and 6-OH-ODMA) were acquired from Plantech (Reading, UK). The following authenticated isoflavone standards were purchased from Sigma-Aldrich (St. Louis, MO, USA): Daidzein, genistein, glycitein, and equol. Food isoflavone standards (daidzin, genistin, glycitin, acetyl daidzin, malonyl genistin, and acetyl genistin) were obtained from LC Laboratories division (PKC Pharmaceuticals, Inc., Woburn, MA, USA).
Equol
Manufactured by Merck Group
Sourced in United States
Equol is a lab equipment product manufactured by Merck Group. It is a chemical compound that is used as a standard reference material in analytical and biomedical research applications. Equol is a metabolite of the isoflavone daidzein, which is found in certain plant-based foods.
Automatically generated - may contain errors
Lab products found in correlation
Daidzein, by Merck Group (12 mentions)
Genistein, by Merck Group (10 mentions)
P coumaric acid, by Merck Group (6 mentions)
Resveratrol, by Merck Group (6 mentions)
Gallic acid, by Merck Group (6 mentions)
Chlorogenic acid, by Merck Group (5 mentions)
Quercetin, by Merck Group (5 mentions)
Rutin, by Merck Group (5 mentions)
Epicatechin, by Merck Group (5 mentions)
Glycitein, by Merck Group (4 mentions)
Protocatechuic acid, by Merck Group (4 mentions)
Ferulic acid, by Merck Group (3 mentions)
Coffeic acid, by Merck Group (3 mentions)
Epigallocatechin, by Merck Group (3 mentions)
Epicatechin gallate, by Merck Group (3 mentions)
Folin ciocalteu s phenol reagent, by Merck Group (3 mentions)
Caffeic acid, by Merck Group (3 mentions)
Anhydrous sodium acetate, by Thermo Fisher Scientific (2 mentions)
Dimethyl sulfoxide (dmso), by Merck Group (2 mentions)
Lyophilized glucuronidase sulfatase from helix pomatia, by Merck Group (2 mentions)
15 protocols using equol
1
Isoflavone Quantification Protocol
2
Phenolic Compounds Antioxidant Assay
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The Folin–Ciocalteu’s phenol reagent, standard phenolic compounds (2-hydrocinnamic acid, rutin, daidzein, equol, coffeic acid, p-coumaric acid, epigallocatechin, quercetin, ferulic acid, epicatechin, glycitein, resveratrol, chlorogenic acid, gallic acid, epicatechin gallate, genistein, and protocatechuic acid), ABTS (2,2’-azinobis(3-ethyl-benothiazoline-6-sulphonic acid) diammonium salt), and Trolox (6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Potassium acetate, potassium persulphate, aluminum chloride hexahydrate, and sodium carbonate were purchased from Tianjin Chemical Factory (Tianjin, China). The formic acid and methanol of HPLC grade were used for the UPLC-MS/MS analysis. Besides, all other chemicals and reagents used in this work were of analytical grade, and deionized water was used in all the experiments.
3
Antioxidant Compound Characterization
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Trolox (6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid), ABTS (2,2′-azinobis(3-ethyl-benothiazoline-6-sulphonic acid) diammonium salt), Folin-Ciocalteu’s phenol reagent, and phenolic compound standards (rutin, 2-hydrocinnamic acid, daidzein, equol, epigallocatechin, p-coumaric acid, glycitein, resveratrol, chlorogenic acid, quercetin, epicatechin, gallic acid, coffeic acid, epicatechin gallate, genistein, ferulic acid, and protocatechuic acid) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Sodium carbonate, potassium persulphate, potassium acetate, and aluminum chloride hexahydrate were purchased from Tianjin Chemical Factory (Tianjin, China). Ethanol of analytical grade was used during the extraction process, and the formic acid and methanol of chromatographically pure grade were used in the UPLC-MS/MS analysis. All the other chemicals and reagents applied in this study were analytically pure, and deionized water was used.
4
Isoflavone and Metabolite Quantification
5
Chemical Standards for Analytical Assays
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Analytical standards of BPA (≥97%), enterolactone (95%), enterodiol (95%), daidzein (98%), equol (99%), genistein (98%), creatinine (99%) and β-glucuronidase (145700 units/mL β-glucuronidase and 887 units/mL sulfatase) were purchased from Sigma-Aldrich (St. Louis, MO, USA). O-DMA (98%) was purchased from Plantech (Reading, UK). Stable isotope-labeled standards, 13C12-BPA, D3-daidzein and D4-genistein were purchased from Cambridge Isotope Laboratories (Andover, MA, USA). D3-creatinine (99%) was purchased from CDN Isotopes (Pointe-Claire, QC, Canada).
6
Antioxidant Potential of Fruit Vinegars
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The chemicals for the determination of ferric-reducing antioxidant power (FRAP), Trolox equivalent antioxidant capacity (TEAC), TPC, TFC and phenol analysis were bought according to the paper [17 (link)] we published previously. Eighteen standard phenolic compounds, including gallic acid, protocatechuic acid, gallo catechin, chlorogenic acid, cyanidin-3-glucoside, caffeic acid, epicatechin, catechin gallate, p-coumaric acid, ferulaic acid, melatonin, 2-hydroxycinnamic acid, rutin, resveratrol, daidzein, equol, quercetin, and genistein were purchased from Sigma-Aldrich (St. Louis, MO, USA). Standard organic acids, including ascorbic acid, lactic acid, citric acid, and succinic acid, were obtained from Sigma-Aldrich, and oxalic acid, tartaric acid, and malic acid were bought from National Institutes for Food and Drug Control (Beijing, China). Phosphoric acid and potassium phosphate monobasic used for organic acid analysis were of analytical grade and bought from Damao Chemical Factory (Tianjin, China) and Yongda Chemical Reagent Company (Tianjin, China), respectively. Double-distilled water was used in all the experiments. The 23 fruit vinegars (Table 1 ) were bought from online shopping platforms and local markets in Guangzhou, China, and were stored at 4 °C before use.
7
Analytical Characterization of Bioactive Compounds
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The 2,2′-azinobis(3-ethylbenothiazoline-6-sulphonic acid) diammonium salt (ABTS), 6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid (Trolox), 2,4,6-tri(2-pyridyl)-s-triazine (TPTZ), Folin-Ciocalteu’s phenol reagent, and the standard compounds (gallic acid, protocatechuic acid, gallo catechin, chlorogenic acid, cyanidin-3-glucoside, caffeic acid, epicatechin, catechin gallate, p-coumaric acid, ferulaic acid, melatonin, 2-hydroxycinnamic acid, rutin, resveratrol, daidzein, equol, quercetin and genistein) were provided by Sigma-Aldrich (St. Louis, MO, USA). Tetrahydrofuran, methanol, formic acid, diethyl ether and ethyl acetate were provided by Kermel Chemical Factory (Tianjin, China). Acetic acid, sodium acetate, potassium acetate, sodium hydroxide, hydrochloric acid, ethylenediaminetetraacetic acid (EDTA), ascorbic acid, iron (III) chloride hexahydrate (FeCl3·6H2O), iron(II) sulphate heptahydrate (FeSO4·7H2O), potassium persulphate, sodium carbonate, aluminum chloride hexahydrate (AlCl3·6H2O), ethanol and n-hexane were provided by Damao Chemical Factory (Tianjin, China). All chemical reagents used in the tests were of analytical or chromatographic grade, and the water used was double distilled.
8
Bioconversion of Genistein to Orobol
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Orobol was produced as described in our previous study31 (link) via the bioconversion of genistein using tyrosinase which leads to ∂-hydroxylation42 (link),58 (link) in Bacillus megaterium. Polyethylene glycol 200 (PEG 200), 3-isobutyl-1-methylcanthine (IBMX), dexamethasone (DEX), human insulin, genistin, genistein, daidzin, daidzein, and equol were purchased from Sigma-Aldrich (St. Louis, MO). 6,7,4′-Trihydroxyisoflavone (6-ODI) was obtained from Chromadex™ (Irvine, CA). 7,3′,4′-Trihydroxyisoflavone (3′-ODI) and 7,8,4′-trihydroxyisoflavone (8-ODI) were purchased from Indofine Chemical (Hillsborough, NJ). 3-[4,5-Diethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT) was purchased from USB (Cleveland, OH). CK1ε and eIF4E antibodies were purchased from Santa Cruz Biotechnology (Dallas, TX). Antibodies against phosphorylated 4E-BP1 and 4E-BP1 were purchased from Cell Signaling Biotechnology (Danvers, MA). The antibody against phosphorylated eIF4E was purchased from EPITOMICS (Burlingame, CA).
9
Vascular Smooth Muscle Contractility Assay
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After moving the vascular smooth muscle flap in the experimental container of 25 mL capacity, connet it to a isometric tension transducer (isometric force transducer 52-9545, Harvard, UK) and the contraction and relaxation of the vascular smooth muscle were measured by using a physiological recorder (physiograph, 50-8630, Harvard, UK). The preferred method of the test was the same as in previous tests.[20 ,21 ]
The test conditions were as given state of the resting tension of 2 g in a constant temperature of 37℃ and 100% oxygen was supplied. The surgery-induced damage was repaired while the contractile force was measured after resting for an hour or more, changing physiological saline as test solution in every 30 min in order to avoid the accumulation of metabolites.
The composition of the physiological solution was made with NaCl 140 mM, KCl 5 mM, CaCl2 2 mM, MgCl2 1 mM, and glucose 11 mM, and the pH was adjusted to 7.4 by using NaOH. All sampled chemicals including equol and those used in this test was purchased from Sigma Chemical Company.
Every test was repeated eight times and more, and the most representative illustration was used for the results.
The test conditions were as given state of the resting tension of 2 g in a constant temperature of 37℃ and 100% oxygen was supplied. The surgery-induced damage was repaired while the contractile force was measured after resting for an hour or more, changing physiological saline as test solution in every 30 min in order to avoid the accumulation of metabolites.
The composition of the physiological solution was made with NaCl 140 mM, KCl 5 mM, CaCl2 2 mM, MgCl2 1 mM, and glucose 11 mM, and the pH was adjusted to 7.4 by using NaOH. All sampled chemicals including equol and those used in this test was purchased from Sigma Chemical Company.
Every test was repeated eight times and more, and the most representative illustration was used for the results.
10
Soybean Bioactives and Cell Culture
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Genistein, daidzein, glycitein, genistin, daidzin, glycitin, equol, soyasaponin, β-sitosterol, Bowman-birk trypsin inhibitor (BBI), lectin and insulin were purchased from Sigma-Aldrich (St. Louis, MO, USA). Lunasin was synthesized by the American Peptide Company (Sunnyvale, CA, USA). 2-(4-(2-hydroxyethyl)-1-piperazinyl)-ethanesulphonic acid (HEPES), Hank’s balancedsalt solution (HBSS), fetal bovine serum (FBS), penicillin-streptomycin, phosphate-buffered saline (PBS) and α-minimum essential medium (α-MEM) were purchased from Gibco BRL Life Technologies (Grand Island, NY, USA). Methylene blue was purchased from BBL (Cockeysville, MD, USA). All reagents are of analytical grade.
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