Brazilian green propolis (EPP-AF®) extract and gel were evaluated using an HPLC/DAD system (Shimadzu apparatus equipped with a CBM-20 A controller, a LC-20AT quaternary pump, an SPD-M 20 A diode-array detector, and Shimadzu LC solution software, version 1.21 SP1) coupled to a Shimadzu Shim-Pack CLC-ODS column (4.6 mm × 250 mm, 5 µm particle diameter, 100 Å pore diameter). The mobile phase consisted of methanol (HPLC grade) and a water-formic acid solution (0.1% v/v), pH 2.7 (A). The method consisted of a linear gradient of 20%–95% methanol over a period of 77 min at a flow rate of 0.8 mL/min. Detection was set at 275 nm, in accordance with a previously published protocol (Berretta et al., 2012 (link)). Samples were diluted in 5 mL of methanol in 10 mL volumetric flasks, subjected to sonication for 10 min and filled to volume with Milli-Q water. All samples were filtered through a 0.45 µm filter before analysis. The chemical references used were caffeic acid (Sigma-Aldrich, L: SLBZ6416), p-coumaric acid (Sigma-Aldrich, L: 091M119V), 3,5 dicaffeoylquinic acid (Phytolab, L. 3215), 4,5–dicaffeoylquinic acid (Phytolab, L. 9943), galangin (Sigma-Aldrich: BCCG2648), artepillin C (Phytolab, L: 111674647), as well as aromadendrin-4′-O-methyl ether, drupanin and baccharin previously isolated by De Sousa et al. (2007) (link).
3 5 dicaffeoylquinic acid
Manufactured by Phytolab
Sourced in Germany
3,5-dicaffeoylquinic acid is a chemical compound found in various plant species. It is a type of chlorogenic acid, which is a group of esters formed between caffeic acid and quinic acid. This compound can be used as a reference standard or analytical standard in laboratory research and analysis.
Automatically generated - may contain errors
Lab products found in correlation
Caffeic acid, by Merck Group (6 mentions)
4 5 dicaffeoylquinic acid, by Phytolab (5 mentions)
1 5 dicaffeoylquinic acid, by Phytolab (4 mentions)
Formic acid, by Merck Group (4 mentions)
5 caffeoylquinic acid, by Merck Group (4 mentions)
Ferulic acid, by Merck Group (4 mentions)
Quercetin, by Merck Group (3 mentions)
Rutin, by Merck Group (3 mentions)
4 hydroxyphenylacetic acid, by Merck Group (3 mentions)
3 4 dihydroxyphenylacetic acid, by Merck Group (3 mentions)
Formic acid, by ITW Reagents (3 mentions)
Acetonitrile, by ITW Reagents (3 mentions)
P coumaric acid, by Merck Group (2 mentions)
Gallic acid, by Merck Group (2 mentions)
Catechin, by Merck Group (2 mentions)
Chlorogenic acid, by Merck Group (2 mentions)
Epicatechin, by Merck Group (2 mentions)
Cryptochlorogenic acid, by Phytolab (2 mentions)
Milli q purification system, by Merck Group (2 mentions)
Apigenin, by Merck Group (2 mentions)
13 protocols using 3 5 dicaffeoylquinic acid
1
HPLC/DAD Analysis of Brazilian Green Propolis
2
Quantification of Polyphenolic Compounds in Medicinal Plants
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From Sigma-Aldrich (St. Louis, MO, USA): Amberlite® XAD7HP, gallic acid, vanillic acid, salicylic acid, 5-O-caffeoylquinic acid, pinocembrin, dimethyl sulfoxide (DMSO), and acetylcholinesterase (AChE) from Electrophorus electricus (electric eel), and butyrylcholinesterase (BChE) from equine serum. From PhytoLab (Vestenbergsgreuth, Germany): p-hydroxybenzoic acid, 3-O-caffeoylquinic acid, trans-caffeic acid, 1,5-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, (+)-catechin, B-type procyanidin dimer ((epi)catechin-(epi)catechin), naringin, naringenin, luteolin-7-O-glucuronide, myricetin-3-O-glucoside, luteolin-7-O-glucoside, quercetin-3-O-glucuronide, quercetin-3-O-galactoside, quercetin-3-O-rutinoside, quercetin-3-O-glucoside, quercetin-3-O-arabinoside, kaempferol-3-O-glucoside, isorhamnetin-3-O-rutinoside, quercetin-3-O-rhamnoside, isorhamnetin-3-O-glucoside, apigenin-7-O-glucoside, luteolin, quercetin, isorhamnetin, and pelargonidin chloride. From Merck (Darmstadt, Germany): HPLC-grade methanol, acetonitrile, formic acid, and ethanol. Ultrapure water was obtained using a Barnstead EasyPure water filter (Thermo Scientific, Waltham, MA, USA).
3
Enzymatic Digestion Protocol for Phytochemical Analysis
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Intestinal Acetone powder from a rat source of α-glucosidase (EC 3.2.1.20), α-amylase from porcine pancreas type VI-B (EC 3.2.1.1), pancreatin from porcine pancreas, pepsin from the gastric mucosa of pigs, bile from bovine and ovine, TRIS-HCl, acarbose, caffeic acid, chlorogenic acid, (+)-catechin, cinchonine, (+)-catechin, (−)-epicatechin, kaempferol 3-glucoside, naringin, sodium chloride, maltose, formic acid, methanol, and acetonitrile were obtained from Sigma Aldrich (Steinheim, Germany). Acetone, ethanol, ethyl acetate, hydrochloric acid, sodium hydroxide, sodium bicarbonate, iodine, potassium iodide, disodium phosphate, and monosodium phosphate were purchased from Chempur (Piekary Śląskie, Poland). Potato starch and calcium chloride were purchased from POCH (Gliwice, Poland) and glucose test from Biomaxima SA (Lublin, Poland). Quercetin 3-glucoside, quercetin 3-rutinoside, quercetin 3-rhamnoside, and isorhamnetin 3-glucoside were obtained from Extrasynthese (Lyon, France). Procyanidin C1, procyanidin B1, procyanidin B2, neochlorogenic acid, cryptochlorogenic acid, and 3,5-dicaffeoylquinic acid were purchased from PhytoLab (Vestenbergsgreuth, Germany). Kaempferol was purchased from ICN Biomedicals (Costa Mesa, CA, USA). Ultrapurity water was prepared in the laboratory using a Simplicity Water Purification System (Millipore, Marlborough, MA, USA).
4
Phytochemical Analysis of Plant Extracts
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Formic acid (>98% purity), acetonitrile (LC-MS grade), methanol, rutin, quercetin, apigenin and kaempferol were purchased from Merck (Darmstadt, Germany). apigenin 7-O-glucoside, quercetin 3-O-glucoside, kaempferol 3-O-rutinoside and luteolin were purchased from Extrasynthese (Genay Cedex, France). Cynarin, chlorogenic acid, 1,5-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid, luteolin 7-O-glucuronide, apigenin, 7-O-glucoside, luteolin 7-O-glucoside and diosmetin were purchased from Phytolab (Vestenbergsgreuth, Germany). Bond Elut Jr 500 mg SPE-C18 cartridge was from Agilent (Santa Clara, California, USA). A Milli-Q purification system (Millipore, Bedford, MA, USA) was used to obtain the deionised water (18.2 MΩ cm). All chemicals used for biological assays were obtained as pure commercial products from Sigma Chemical Co (St. Louis, USA) and used without further purification. Spectrophotometric determinations were obtained with an Ultrospec 2100 spectrophotometer (Biochrom Ltd, Cambridge, England) using a 1 cm length path cell.
5
Quantification of Polyphenol Metabolites
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Ascorbic, 5-caffeoylquinic acid, 3′,4′-dihydroxycinnamic acid, 4′-hydroxy-3′-methoxycinnamic acid, 4′-hydroxycinnamic acid; hippuric acid, 3-(3′,4′-dihydroxyphenyl)propanoic acid, 3-(4′-hydroxy-3′-methoxyphenyl)propanoic acid, 3-(4′-hydroxyphenyl)propanoic acid, 3-(3′-hydroxyphenyl)propanoic acid, 3′,4′-dihydroxyphenylacetic acid, 4′-hydroxy-3′-methoxyphenylacetic acid, 4′-hydroxyphenylacetic acid, 3′-hydroxyphenylacetic acid, 3,4-dihydroxybenzoic acid, 4-hydroxy-3-methoxybenzoic acid, 4-hydroxybenzoic acid, and 3-hydroxybenzoic acid were purchased from Sigma-Aldrich (Madrid, Spain). 3,5-dicaffeoylquinic acid was purchased from PhytoLab (Vestenbergsgreuth, Germany). HPLC-grade solvents were acquired from Panreac (Madrid, Spain). Ultrapure water from MilliQ system (Millipore, Bedford, MA, USA) was used throughout the experiment.
6
Quantification of Caffeic Acid Derivatives and Flavonols
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Authentic standards of caffeic acid-derived chlorogenic acids (3-caffeoylquinic acid; 4-caffeoylquinic acid; 5-caffeoylquinic acid; 1,3-di-caffeoylquinic acid; 1,5-di-caffeoylquinic acid; 3,4-di-caffeoylquinic acid; 3,5-di-caffeoylquinic acid and 4,5-di-caffeoylquinic acid) and flavonols (quercetin-3-O-glycoside; quercetin-4-O-glycoside; quercetin-7-O-glycoside and rutin) were purchased from Phytolab (Vestenbergsgreuth, Germany). Analytical-grade acetonitrile was obtained from Romil (Cambridge, UK). Formic acid and diatomaceous earth were obtained from Sigma-Aldrich (St. Louis, MO, USA).
7
Formulation of a Nutraceutical Blend
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B-Can™ 70% Oat Beta-Glucan purchased in Garuda International, Inc. (California, United States), and a decaffeinated phenol-rich (45%) green coffee extract acquired from Quimifarma Laboratorios S.L. (Toledo, Spain), were selected for the design of the nutraceutical. The mixture of 3.57 g BG and 0.66 g of GCPE (considering their purity) was flavoured (vanilla and chocolate) to increase its acceptability and was presented in single-dose sachets for dispersion in water (Quimifarma Laboratorios S.L. Toledo, Spain).
All solvents and reagents were of analytical grade unless otherwise stated. Ascorbic; 5caffeoylquinic acid; 3´,4´-dihydroxycinnamic acid; 4´-hydroxy-3´-methoxycinnamic acid; 4´hydroxycinnamic acid; hippuric acid; 3-(3´,4´-dihydroxyphenyl)propanoic acid; 3-(4´-hydroxy-3´methoxyphenyl)propanoic acid;
3-(4´-hydroxyphenyl)propanoic acid;
3-(3´hydroxyphenyl)propanonic acid; 3´,4´-dihydroxyphenylacetic acid; 4´-hydroxy-3´methoxyphenylacetic acid; 4´-hydroxyphenylacetic acid; 3´-hydroxyphenylacetic acid; 3,4dihydroxybenzoic acid; 4-hydroxy-3-methoxybenzoic acid; 4-hydroxybenzoic acid and 3hydroxybenzoic acid were from Sigma-Aldrich (Madrid, Spain). 3,5-dicaffeoylquinic acid was purchased from PhytoLab (Vestenbergsgreuth, Germany). Methanol, formic acid and acetonitrile (HPLC grade) were acquired from Panreac (Madrid, Spain).
All solvents and reagents were of analytical grade unless otherwise stated. Ascorbic; 5caffeoylquinic acid; 3´,4´-dihydroxycinnamic acid; 4´-hydroxy-3´-methoxycinnamic acid; 4´hydroxycinnamic acid; hippuric acid; 3-(3´,4´-dihydroxyphenyl)propanoic acid; 3-(4´-hydroxy-3´methoxyphenyl)propanoic acid;
3-(4´-hydroxyphenyl)propanoic acid;
3-(3´hydroxyphenyl)propanonic acid; 3´,4´-dihydroxyphenylacetic acid; 4´-hydroxy-3´methoxyphenylacetic acid; 4´-hydroxyphenylacetic acid; 3´-hydroxyphenylacetic acid; 3,4dihydroxybenzoic acid; 4-hydroxy-3-methoxybenzoic acid; 4-hydroxybenzoic acid and 3hydroxybenzoic acid were from Sigma-Aldrich (Madrid, Spain). 3,5-dicaffeoylquinic acid was purchased from PhytoLab (Vestenbergsgreuth, Germany). Methanol, formic acid and acetonitrile (HPLC grade) were acquired from Panreac (Madrid, Spain).
8
Phytochemical Characterization of Plant Extracts
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HPLC-grade acetonitrile (LC-MS grade), formic acid (>98% purity), chlorogenic acid, rutin, apigenin 7-O-glucoside, apigenin, diosmin and kaempferol were from Sigma Aldrich (Bellefonte, USA). Deionized water (18.2 MΩ cm) was obtained from a Milli-Q purification system (Millipore, Bedford, MA, USA). Luteolin, quercetin 3-O-glucoside, kaempferol 3-O-rutinoside and kaempferol 3-Oglucoside were from Extrasynthese (Genay Cedex, France). Cryptochlorogenic acid, 1,5dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid, Luteolin 7-O-glucoside, Luteolin 7-O-glucuronide, apigenin 7-O-glucuronide, kaempferol 3-O-rhamnoside, diosmetin and tricin were from Phytolab (Vestenbergsgreuth, Germany).
9
Comparative Analysis of Yerba Mate Brands
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Four different commercial brands (A-D) of yerba mate (Ilex paraguariensis), selected among the most widely consumed brands in Argentina, were purchased in a local supermarket in Madrid (Spain). The four brands were elaborated from selected Ilex paraguariensis leaves that had been slightly roasted for short time at temperatures under 100 °C, dried, minced, and stored at ambient temperature ("estacionado natural") during 12 months before packaging; the specific elaboration procedures are protected proprietary information. The four mate brands contained minor amounts of stems ("palo") and were produced in Argentina, two in the state of Misiones (brands A and B) and the other two in Corrientes (brands C and D). 3,5-dicaffeoylquinic acid was acquired from PhytoLab (Vestenbergsgreuth, Germany). 2,4,6-tripyridyl-s-triazine (TPTZ), caffeine and potassium persulfate were from Fluka (Madrid, Spain). Caffeic acid, 5-caffeoylquinic acid, ferulic acid, gallic acid, rutin, theobromine, theophylline, 2,2'-azinobis-3ethylbenzothiazoline-6-sulphonic acid (ABTS), 2,2'-azobis(2-amidinopropane) dihydrochloride (AAPH), 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox), fluorescein sodium salt, were obtained from Sigma-Aldrich (Madrid, Spain).
Folin-Cicalteau reagent was from Panreac (Madrid, Spain). All other reagents were of analytical or chromatographic grade.
Folin-Cicalteau reagent was from Panreac (Madrid, Spain). All other reagents were of analytical or chromatographic grade.
10
Phenolic Compounds Analysis in Roasted Coffee
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A commercial brand of soluble green/roasted coffee blend (Nescafe Green Blend©) was purchased in a local supermarket in Madrid (Spain). All solvents and reagents were of analytical grade unless otherwise stated. Ascorbic acid, 5-caffeoylquinic acid, p-coumaric acid, ferulic acid, caffeic acid, 3,4-dihydroxyphenylpropionic acid, 4-hydroxyphenylpropionic acid, 4hydroxy-3-metoxyphenylpropionic acid, 3,4-dihydroxyphenylacetic acid, 4hydroxyphenylacetic acid, 3,4-dihydroxyphenylbenzoic acid and 4-hydroxyphenylbenzoic acid were from Sigma-Aldrich (Madrid, Spain). 3,5-dicaffeoylquinic acid was purchased from PhytoLab (Vestenbergsgreuth, Germany). Methanol, formic acid, and acetonitrile (HPLC grade)
were acquired from Panreac (Madrid, Spain).
were acquired from Panreac (Madrid, Spain).
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