N-hexane and methanol were purchased from Merck (Darmstadt, Germany). 1,1-Diphenyl-2-picrylhydrazyl (DPPH•), Phenolic standards: Catechin, 4-hydroxybenzoic acid, p-Coumaric acid, naringin, quercetin, p-Coumaric acid, and luteolin were purchased from Merck and Carl Roth GmbH (Karlsruhe, Germany). All other chemicals used were of analytical grade.
P coumaric acid
Manufactured by Merck Group
Sourced in United States, Germany, Italy, Spain, France, China, Poland, United Kingdom, Sao Tome and Principe, Switzerland, Canada, Ireland, India, Australia, Japan, Macao, Portugal
P-coumaric acid is a naturally occurring phenolic compound that can be utilized as a reference standard or an analytical reagent in various laboratory settings. It is a white to off-white crystalline solid that is soluble in organic solvents. P-coumaric acid is commonly used as a standard in analytical techniques, such as high-performance liquid chromatography (HPLC) and spectrophotometric measurements, to quantify and characterize similar compounds in sample matrices.
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Lab products found in correlation
Caffeic acid, by Merck Group (432 mentions)
Gallic acid, by Merck Group (347 mentions)
Ferulic acid, by Merck Group (337 mentions)
Quercetin, by Merck Group (289 mentions)
Chlorogenic acid, by Merck Group (259 mentions)
Vanillic acid, by Merck Group (220 mentions)
Catechin, by Merck Group (189 mentions)
Syringic acid, by Merck Group (180 mentions)
Rutin, by Merck Group (167 mentions)
Epicatechin, by Merck Group (152 mentions)
Kaempferol, by Merck Group (149 mentions)
Protocatechuic acid, by Merck Group (131 mentions)
Apigenin, by Merck Group (113 mentions)
Sinapic acid, by Merck Group (110 mentions)
Methanol, by Merck Group (102 mentions)
Luteolin, by Merck Group (100 mentions)
Naringenin, by Merck Group (100 mentions)
Formic acid, by Merck Group (97 mentions)
Acetonitrile, by Merck Group (94 mentions)
Myricetin, by Merck Group (85 mentions)
774 protocols using p coumaric acid
1
Antioxidant Capacity Determination
2
Ethanol-Induced Gastric Ulcer Amelioration by p-Coumaric Acid
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Following 18-h starvation, rats were divided into 4 groups. Rats were given 75% ethanol (ulcer and ulcer + p-coumaric acid groups) or saline (control and p-coumaric acid groups) by oral gavage under light isoflurane anesthesia. One hour before ethanol or saline administration, rats were treated with either 1 ml 10% tween-80 (ulcer and control groups) as vehicle or p-coumaric acid (Sigma-Aldrich C9008, Merck, Germany; 250 mg/kg; suspended in 10% tween-80) (p-coumaric acid and ulcer + p-coumaric acid groups) per oral (Table I). Barros, et al., showed that the dose of 250 mg/kg of p-coumaric acid reduced the macroscopic lesion index most compared to other doses [16] (link). Therefore, the dose of 250 mg/kg p-coumaric acid was used for treatment in the study. One hour after ulcer induction, all rats were euthanized by cutting the aorta and removing the heart under deep isoflurane anesthesia. Stomach samples were collected for macroscopic examination, histological evaluation, microscopic scoring and biochemical analyses. For histological evaluation the stomach samples were examined under light microscopy and for biochemical analyses tissue-associated myeloperoxidase (MPO) activity as the indicator of neutrophil infiltration, malondialdehyde (MDA) which is the end-product of lipid peroxidation and endogen antioxidant glutathione (GSH) levels were measured.
3
Evaluating Cognitive Performance in Bees
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For testing of cognitive performance, we collected and restrained bees as described above, and randomly allocated them to receive one of five feeding treatments, all dissolved to a final sucrose concentration of 1M: sucrose solution (Control, Invitrogen: 15503022), rutin 1 μM (Rut; Sigma-Aldrich: R5143, concentrations according to [14 (link), 42 ]; kaempferol 131 μM (Kaemp; Sigma-Aldrich: K0133, concentrations adapted from [6 (link)], p-coumaric acid 200 μM (p-CA; Sigma-Aldrich: C9008 concentrations following [8 (link)], rutin 1 μM + kaempferol 131 μM + p-coumaric acid 200 μM (Mix). In all cases, bees were fed six doses of 10 μL of the composition (two doses a day for three days). On the fourth day, bees were randomly assigned to one of two treatments three hours before training: 10 μL of 1M sucrose solution or 10 μL of fipronil 228.7 nM (Fip; 1ng/bee). Thus, bees belonged to one of ten treatments according to the composition administered: Control, Rut, Kaemp, p-CA, Mix, Fip, Rut+Fip, Kaemp+Fip, p-CA+Fip, Mix+Fip. These treatments were used for the evaluation of protection of learning and memory, motor activity, and sucrose sensitivity.
4
Krebs–Henseleit Buffer Preparation and Arterial Ring Viability Testing
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Chemicals used for Krebs–Henseleit buffer preparation and arterial ring viability testing in the pharmacological studies were purchased from Sigma-Aldrich® (St. Louis, MO, USA). The following commercial standards were used in the ITA assays: quercetin 3-O-glucoside (Sigma, 17793-10MG-F), quercetin (G Buchs SG. K148-/49/2), p-coumaric acid (Sigma, C9008) and tiliroside (Extrasynthese, 1001 S, 20316-62-5). The selective prostacyclin IP receptor antagonist Ro 1138452 hydrochloride (4268) was purchased from Tocris (Bristol, UK).
Chemicals used for phytochemical characterization were purchased from Merck® (Darmstadt, Germany) and correspond to the highest grade commercially available. The reference compounds used were: ellagic acid (Sigma, E2250-5G), p-coumaric acid (Sigma, C-9008, Lot: 22H0312), quercetin (G Buchs SG., Buchs, Switzerland, K148-/49/2), quercetin-3-O-glucoside (Sigma, 17793-10MG-F), tiliroside (Extrasynthese, Genay, France, 1001 S, Lot: 12080209), vitexin (Extrasynthese, 1232 S) and isovitexin (Extrasynthese, 1235 S).
Chemicals used for phytochemical characterization were purchased from Merck® (Darmstadt, Germany) and correspond to the highest grade commercially available. The reference compounds used were: ellagic acid (Sigma, E2250-5G), p-coumaric acid (Sigma, C-9008, Lot: 22H0312), quercetin (G Buchs SG., Buchs, Switzerland, K148-/49/2), quercetin-3-O-glucoside (Sigma, 17793-10MG-F), tiliroside (Extrasynthese, Genay, France, 1001 S, Lot: 12080209), vitexin (Extrasynthese, 1232 S) and isovitexin (Extrasynthese, 1235 S).
5
Rice Husk Antioxidant Potential and Cytotoxicity
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Rice husk was provided by the Rice Research Institute of Guangdong Academy of Agricultural Science, China. Folin-Ciocalteu reagent, fluorescein disodium salt, 2,2′-azobis (2-amidinopropane) dihydrochloride (ABAP), 2′,7′-Dichlorofluorescin diacetate (DCFH-DA), (+)-catechin, gallic acid, and chromatographic grade of p-coumaric acid, caffeic acid, p–coumaric acid, ferulic acid were purchased from Sigma-Aldrich Ltd. (St. Louis, MO, USA). Chromatographic grade of acetonitrile used for HPLC analysis was obtained from Anpel Ltd. (Shanghai, China). Human liver cancer cell line HepG2 (ATCC HB-8065) were purchased from ATCC company (Manassas, VA, USA). WME medium, fetal bovine serum (FBS), Hank’s balanced salt solution (HBSS), Trypsin-EDTA solution and other cell culture reagents were purchased from Gibco Life Technologies Co. (Grand Island, NY, USA).
6
Characterization of Antioxidant Compounds
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The 2-azinobis-3-ethylbenzothiazoline-6-sulphonic acid (ABTS), aluminum trichloride, ascorbic acid, 2,2-diphenyl-1-picrylhydrazyl (DPPH), food-grade ethanol (99%), gallic acid, α-glucosidase from S. cerevisiae, p-coumaric acid, trifluoroacetic acid, quercetin, sodium carbonate (Na2CO3), and Trolox were purchased from Sigma-Aldrich (Sintra, Portugal). Acetonitrile was purchased from Fischer Scientific (Oeiras, Portugal). Folin-Ciocalteu reagent and potassium persulfate (K2S2O8) were purchased from Merck (Algés, Portugal).
The standards of vitexin, diosmetin, isoschaftoside, orientin, viexin-2-O-rhamnoside (Extrasynthése, Genay, France), tricin, luteolin, protocatechuic acid, vanillic acid, p-coumaric acid, caffeic acid, ferulic acid, chlorogenic acid, gentisic acid, 4-hydroxybenzaldehyde, 4-hydroxybenzoic acid, and 3,4-dihydroxybenzalhedyde, syringic acid (Sigma-Aldrich) were used as external standards for calibration curves in LC-ESI-UHR-QqTOF-MS.
The standards of vitexin, diosmetin, isoschaftoside, orientin, viexin-2-O-rhamnoside (Extrasynthése, Genay, France), tricin, luteolin, protocatechuic acid, vanillic acid, p-coumaric acid, caffeic acid, ferulic acid, chlorogenic acid, gentisic acid, 4-hydroxybenzaldehyde, 4-hydroxybenzoic acid, and 3,4-dihydroxybenzalhedyde, syringic acid (Sigma-Aldrich) were used as external standards for calibration curves in LC-ESI-UHR-QqTOF-MS.
7
Yeast Naringenin Production from p-Coumaric Acid
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Yeast colonies of CENF09, CENFP01, CENFAA01, and CENFPAA01 were pre-cultured in 5-mL CM medium in 50-mL tubes overnight at 30 °C, 225 rpm, respectively. The pre-culture was then diluted into fresh 20-mL CM medium in 250-mL flasks to a final OD600 of 0.05, respectively. Fermentation was carried out at 30 °C, 225 rpm for 96 h, with substrate p-coumaric acid (Sigma-Aldrich, St. Louis, MO, USA) concentration at 0.5 mM. In addition, the best acetyl-CoA-producing strain was also tested at a series of p-coumaric acid concentration: 0.05, 0.1, 0.2, 0.3, 0.4, and 0.5 mM.
The fermentation broth was centrifuged at 12,000 rpm for 10 min. Samples from each supernatant were taken for HPLC analysis on a XDB-C18 column (Agilent, Santa Clara, USA). Compounds were separated by elution with acetonitrile–water gradient at 1.0 ml/min as described previously [21 (link)]. Naringenin standard (ACROS organics, New Jersey, USA) and naringenin from the samples were detected by its UV absorbance at 290 nm.
The fermentation broth was centrifuged at 12,000 rpm for 10 min. Samples from each supernatant were taken for HPLC analysis on a XDB-C18 column (Agilent, Santa Clara, USA). Compounds were separated by elution with acetonitrile–water gradient at 1.0 ml/min as described previously [21 (link)]. Naringenin standard (ACROS organics, New Jersey, USA) and naringenin from the samples were detected by its UV absorbance at 290 nm.
8
Extraction and Characterization of Phenolic Compounds
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Caffeic acid (CA ), ferulic acid (FA ), p-coumaric acid (PA ), and other reagents were purchased from Merck and used without further purification.
9
Extraction and Quantification of Polyphenols from Barley Spent Grain
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BSG L and D were provided by Diageo Ireland, Dublin. BSG Mix (light:dark, ~9:1 w/w) was obtained from the River Rye Brewing Company, Cellbridge, County Kildare, Ireland. The BSG samples were directly transported to the research centre within 30 min., oven-dried (Binder E28 oven, 72 h, 60 °C), milled (<1 mm) and vacuum packed until required.
The organic solvents (methanol, acetone, ethyl acetate (EtOAc), formic acid, acetonitrile), and sodium hydroxide (NaOH) were purchased from Merck (formerly Sigma Aldrich, Arklow, Co. Wicklow, Ireland). Polyphenol standards of gallic acid, p-coumaric acid, ferulic acid, sinapic acid, caffeic acid, protocatechuic acid, 4-hydroxybenzoic acid and +(-)catechin; and the chemicals FC reagent, hydrochloric acid and sodium carbonate were purchased from Merck (Arklow, Co. Wicklow, Ireland). Leucine-enkelphine was purchased from VWR International Ltd. (Blanchardstown, Dublin, Ireland).
The organic solvents (methanol, acetone, ethyl acetate (EtOAc), formic acid, acetonitrile), and sodium hydroxide (NaOH) were purchased from Merck (formerly Sigma Aldrich, Arklow, Co. Wicklow, Ireland). Polyphenol standards of gallic acid, p-coumaric acid, ferulic acid, sinapic acid, caffeic acid, protocatechuic acid, 4-hydroxybenzoic acid and +(-)catechin; and the chemicals FC reagent, hydrochloric acid and sodium carbonate were purchased from Merck (Arklow, Co. Wicklow, Ireland). Leucine-enkelphine was purchased from VWR International Ltd. (Blanchardstown, Dublin, Ireland).
10
Phytochemical Characterization and Bioassays
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The chemical compounds used in this study were analytical grade. The solvents (ethanol, methanol, ethyl acetate and distilled water), dimethyl sulfoxide (DMSO), p-coumaric acid (≥98%), ferulic acid (≥99%), quercetin (≥95%), and thiabendazole (≥98.0%) were purchased from Merck KGaA® (Darmstadt, Germany) and Sigma-Aldrich (St. Louis, MO, USA). Reagents for the bioassays (ovicidal activity) were purchased from Corning® (Corning, NY, USA). HPLC analyses were performed on a Waters 2695 Separation module system, equipped with a Waters 996 photodiode array detector and the Empower Pro software (Waters Corporation, Milford, MA, USA). Mass spectroscopy was performed on a Waters Xevo TQD mass spectrometer with an ESI ion source (Waters Milford, Milford, MA, USA). The ultraviolet (UV) spectra were obtained using a Waters array detector (Waters Co. 2996, Milford, MA, USA). Thin-layer chromatography (TLC) was performed using TLC Silica gel 60, F254 and 20 × 20-cm aluminium sheets (Merck KGaA®, Darmstadt, Germany).
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