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18 protocols using formic

1

Antioxidant Compound Quantification Protocol

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The Folin–Ciocalteu reagent was purchased from BIO-RAD (Milano, Italy). Chlorogenic, gallic, caffeic, ferulic, p-coumaric acids, epicatechin, rutin, quercetin, 2,2-diphenyl-1-picrylhydrazyl (DPPH), ascorbic acid, β-carotene, HPLC-grade methanol, metaphosphoric, sulphuric, formic and acetic and acids, acetonitrile, petroleum ether, ethanol and acetone were acquired from Sigma-Aldrich (Milano, Italy). Apigenin was bought from Extrasynthese (Genay, France). Distilled water was obtained from a Milli-Q apparatus (Millipore, Milano, Italy).
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2

Quantitative Analysis of Bioactive Compounds

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Authentic standards of L-carnosine, inosinic acid (IMP), acetylcholine (ACh), and L-carnitine were purchased from Sigma-Aldrich. HPLC-grade solvents (acetonitrile, methanol, formic) were purchased from Sigma Aldrich (St. Louis, MO, USA). Purified water was obtained from a Millipore Elix (Millipore, Bedford, MA, USA) system. All other chemicals used for experiments were analytical reagent or HPLC grade of commercial resource.
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3

Comprehensive Lipid and Carbohydrate Analysis

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Hexane, methanol and dimethylformamide were HPLC grade (VWR Chemicals, West Chester, PA, USA). Lactic acid (≥90%) was also purchased from VWR. Sulfuric acid was obtained from Honeywell Fluka (Charlotte, NC, USA), while sodium methoxide and methyl acetate were obtained from Acros Organics (Geel, Belgium). GLC-Nestlé36 FAME mix was obtained from Nu-Chek Prep, Inc. (Elysian, MN, USA) and butterfat CRM-164 (EU Commission; Brussels, Belgium) from Fedelco Inc. (Madrid, Spain). Undecanoic acid (98.0%) was obtained from Alfa Aesar (Haverhill, MA, USA) while glyceryl tritridecanoate (>99.0%) was obtained from Larodan (Solna, Sweden). Galactose (≥98%) and acetic acid (100%) were obtained from Merck (Darmstadt, Germany). Sodium hydroxide was procured from LabChem (LaborSpirit Lda, Loures, Portugal) and phenolphthalein from José M. Vaz Pereira S.A. (Santarém, Portugal). Supelco 37 FAME mix, methyl tricosanoate (≥99.0%), α-lactose monohydrate (≥99%, total lactose basis), glucose (≥99.5%), Candida rugosa (CRL) type VII lipase and formic (≥95%), propionic (99%) and citric (99%) acids were purchased from Sigma-Aldrich (St. Louis, MO, USA). Pasteurized semi-skimmed cows’ milk and flaxseed oil (FSO) were bought in local markets (Porto, Portugal).
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4

Quantitative Analysis of Organic Acids

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The reagents used were all of analytical grade (purity > 98%): DL-lactic acid and butyric acid purchased from Fluka (Buchs, Switzerland), acetic acid from Riedel-de-Haën (Seelze, Germany), L-(+)-tartaric acid, formic, citric acid, benzoic acid, succinic acid, malic acid, propionic acid, DL-p-hydroxyphenyllactic acid (HO-PLA), sodium hydroxide, sodium chloride, glycerol, and phenyllactic acid (PLA) bought from Sigma-Aldrich (Germany). Phosphoric acid 85% and oxalic acid were supplied by Merck (Hamburg, Germany), cetyltrimethylammonium bromide (CTAB) from LOBA Chemie (Fischamend, Austria), HPLC-grade water and 0.1 and 1 N sodium hydroxide solutions were purchased from Agilent Technologies (USA). All solvents (Merck, Darmstadt, Germany) and solutions were filtered through 0.2-μm membranes (Millipore, Bedford, MA, USA). Peptone water and MRS broth media were purchased from Oxoid Ltd. (Hampshire, UK).
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5

Quantification of Urolithin Metabolites in Urine

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All solvents were HPLC grade from Fisher Scientific. Ellagic, formic and phosphoric acid were purchased from Sigma-Aldrich (St Louis, MO). Pure punicalagin A/B was purchased from ChromaDex (Irvine, CA) and urolithin A was purchased from Jinan Feiteng Technology (Jinan Shandon, China). The composition of the pomegranate extract was analyzed by HPLC and diode array detection. To determine the concentration of urolithin A glucuronide and dimethylEllagic acid glucuronide in urine, samples (1 mL) were diluted with 1 ml of 2% formic acid MeOH, vortexed for 30 s and centrifuged at 20,000xg for 10 min at 4 °C. The supernatant was analyzed by LC-MS/MS8 (link). The concentration was estimated based on urolithin A standard. The conversion of urolithin A glucuronide to urolithin was estimated by using β-glucuronidase to catalyze hydrolysis of β-D-glucuronic acid residues from urolithin A glucuronide in human urine samples.
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6

Comparative Analysis of Traditional and Balsamic Vinegar Metabolites

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A total of 57 samples of both TBVM and BVM have been analyzed. The 36 samples of TBVM were of different ages from 12 to over 25 years (14 old and 22 extra-old). Among the 21 samples of BVM, 13 were defined as aged. All kinds of vinegar samples were provided by private producers. Each sample belonged to a different set of barrels. Pyridoxine, dimethyl sulphoxide-d6 (DMSO-d6), and 3-(Trimethylsilyl)propionic-2,2,3,3-d4 acid sodium salt (TSP) for internal referencing were purchased from Sigma-Aldrich (Milan, Italy). Citric, malic, succinic, lactic, acetic, formic, and tartaric acids, ethyl acetate, glucose, fructose, 6-O-acetyl glucose, acetyl fructose, 5-hydroxymethylfurfural (5-HMF), leucine, valine, 2,3-butanediol, and ethanol were provided by Sigma-Aldrich (Milan, Italy).
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7

Quantification of Phytochemicals in Allium Vegetables

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HPLC-grade methanol, metaphosphoric, formic, methanesulfonic acid, acetonitrile, ethanol were purchased from Sigma-Aldrich (St. Louis, MO, USA). NaOH, sodium carbonate, and sodium bicarbonate were purchased from Merck KGaA (Darmstadt, Germany).
Standards for phenolic (caffeic acid, caftaric acid, quercetin 3-ß-d-glucoside, quercetin, rutin, hyperoside) and volatile (di-allyl-sulphide-DAS; di-allyl-disulphide-DADS; di-allyl-trisulphide-DATS, di-methyl-sulphide, crotonaldehyde, pelargonaldehyde) compounds were purchased from Sigma-Aldrich (MO, USA).
Glucose, fructose, and sucrose standards were purchased from Chem Service (West Chester, USA); all the other standards were purchased from Sigma-Aldrich (MO, USA). Ultrapure water (18.2 MΩ cm resistivity at 25 °C) was obtained from a water purification system Milli Q (Millipore, Germany).
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8

Synthesis and Characterization of Lignoceryl Acetate

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Formic, acetic, propionic, butyric, valeric, and hexanoic acids, hexane, lignoceryl alcohol, acetic anhydride, pyridine, and anhydrous sodium sulfate were purchased from Sigma-Aldrich (Milwaukee, WI). Anhydrous dichloromethane (DCM) was acquired from ACROS (New Jersey, US). An aliquot of 11 mg of lignoceryl acetate was prepared in two batches, one starting with 10.2 mg and the other with 7 mg of lignocerol dissolved in anhydrous DCM. A pyridine/DCM solution was added stepwise; the reactions were left at room temperature for 5 h. Then, 0.5 M HCl was added, the organic phase was extracted and washed with brine, and anhydrous sodium sulfate was added. After reducing the volume by evaporation, the crude material was subjected to flash column chromatography (see above). An aliquot (1 mg) was used to make a hexane solution for GC-MS analysis and comparison of retention times. The rest of the sample was used for indoor behavioral assays and field tests in Brazil.
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9

Organic acids and their analytical standards

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The organic acids used were of analytical standard grade. Caproic and valeric acids were obtained from Fluka (Steinheim, Germany); succinic acid from Lancaster (Morecambe, UK); 95% formic, thiocyanic, nitric, pyruvic and ascorbic acids, as well as monohydrate citric acid, plus oxalic, propionic, butyric, 85% ortho-phosphoric acids from Sigma-Aldrich (Saint-Quentin-Fallavier, France) and 80% D,L-lactic acid from Avantor Performance Materials Poland S.A. (Gliwice, Poland). A 36–38% hydrochloric acid was delivered by Baker Analyzed and methylhydroxyethylcellulose (M-HEC) by HERCULES (Prague, Czech Republic), β-alanine by Merck (Darmstadt, Germany) and L-histidine by Serva (Heidelberg, Germany); 99.5% acetic acid was obtained from Chempur (Piekary Śląskie, Poland). Deionized water of 18 MΩcm was obtained from Milli Ro & Q water purification system (Merck-Millipore, Billerica, MA, USA).
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10

Quantification of Biogenic Amines and Sugars

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Standards of biogenic amines (tyramine, putrescine, cadaverine, spermine, and spermidine), mono- and disaccharides (lactose, glucose, and galactose), and organic acids (formic, citric, and lactic acids), all ≥ 98%, were purchased from Sigma-Aldrich (St. Louis, MO, USA). Acetonitrile (HPLC grade) and all analytical-grade chemicals were obtained from Tedia (São Paulo, Brazil). A Millipore Milli-Q water system was also used (Millipore, Bedford, MA, USA).
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