Folin ciocalteu s phenol reagent

The following reagents were obtained from Sigma Co. (St. Louis, MO, USA): catechin, kaempferol, isorhamnetin, naringenin, quercetin, butylated hydroxytoluene (BHT), Folin–Ciocalteu’s phenol reagent, copper sulfate, ethylenediaminetetraacetic acid (EDTA), β-glucuronidase type H-2 (containing sulfatase from Helix pomatia), glutathione reductase (type III), nicotinamide adenine dinucleotide phosphate (NADP), sodium 1-octanesulfonate monohydrate, reduced glutathione, oxidized glutathione, sodium azide, sodium chloride, sodium phosphate monobasic, sodium phosphate dibasic, 1,1,3,3-tetraethoxypropane, 2’,3’,4’-trihydroxyacetophenone, Tris buffer, magnesium chloride, triphenylphosine, and α-tocopherol. Diisopropylethylamine (DIPEA), O-bis (trimethylsilyl) trifluoroacetamide (BSTFA), and pentafluorobenzyl bromide (PFBBr) were purchased from Thermo (Boston, MA, USA). Deuterated prostaglandin (PG) F_2α (internal standard), PGF_2β, and 8-iso-PGF_2α were purchased from Cayman (Ann Arbor, MI, USA). All organic solvents, glacial acetic acid, and potassium bromide were purchased from Fisher Co. (Fair Lawn, NJ, USA).

The following chemicals and reagents were purchased from Sigma-Aldrich Italia (Milan, Italy): Folin–Ciocalteu’s phenol reagent, 6-hydroxyl-2,5,7,8-tetramethyl-chroman-2-carboxylic acid (Trolox), 2,2-azinobis (3-ethylbenzothiazoline-6-sulfonic acid; ABTS), AlCl₃, NaNO₂, FeCl₂, FeCl₃, FerroZine^®, fluorescein, 2,2-azobis(2-amidinopropane) dihydrochloride (AAPH), phosphoric acid (85–87%, w/w), hydrochloric acid (37%, w/w), monobasic sodium phosphate (>98%), sodium hydroxide beads (>98%), and HPLC-grade solvents. Pure standards of phenolic acids (4-hydroxybenzoic, gallic, caffeic, chlorogenic, ferulic, p-coumaric, sinapic, syringic, trans-cinnamic, and vanillic acids) and flavonoids (quercetin, quercetin-3-O-glucoside, quercetin-3-O-rutinoside, quercetin-3-O-galactoside, kaempferol, kaempferol-3-O-rutinoside, catechin, epicatechin, daidzein, and genistein) were purchased from Extrasynthese (Genay Cedex, France). The IUPAC names for these compounds are indicated in Table S1. All standards (>99.5% purity in powder form) were prepared as stock solutions at 1 mg/mL in methanol and stored in the dark at −18 °C for less than three months.

2,2-Diphenyl-1-picrylhydrazyl (DPPH), 6-hydroxyl-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox), 5,5-dimethyl-1-pyrroline N-oxide (DMPO), riboflavin, hydrogen peroxide (30%, H₂O₂), dimethyl sulfoxide (DMSO), 2,2′-azobis(2-methylpropionamidine) dihydrochloride (AAPH), fluorescein, Folin–-Ciocalteu’s phenol reagent, quercetin, gallic acid, chloroform-d, acetone-d₆ and methanol-d were purchased from Sigma Aldrich (St. Louis, MO, USA). pBR322 plasmid DNA was purchased by Thermo Fisher Scientific (Waltham, MA, USA). Silica gel (230–400 mesh), NP F254 and RP-18 F254 TLC plates were obtained from Merck (Darmstadt, Germany). Spherical C18 100 Å reversed phase silica gel (particle size: 20–40 μm) was obtained from SILICYCLE (Ville de Québec, QC, Canada). Sodium hydroxide, ethylenediamine tetraacetic acid, disodium dehydrate (EDTA), iron (II) sulfate heptahydrate (FeSO₄), sodium nitrite (NaNO₂), sodium carbonate anhydrous (Na₂CO₃), aluminium chloride (AlCl₃), methanol, acetone, ethylacetate, chloroform and n-hexane were purchased from Duksan Co. (Gyenggi, Korea).

The following chemicals were purchased from Sigma-Aldrich (Steinheim, Germany): 1,1-diphenyl-2-picrylhydrazyl (DPPH), Trolox (TE), Folin-Ciocalteu’s phenol reagent, sodium carbonate, sodium nitrate, ammonium nitrate, hydrochloric acid, aluminum chloride, sodium hydroxide, glucose, acetic acid, acetonitrile, methanol, gallic acid, quercetin, chlorogenic acid, rutin, and cyanidin chloride.

Coriander (Coriandrum sativum L.) seeds were purchased from a local food store in Warsaw, Poland, whereas almonds (Prunus dulcis) and hazelnuts (Corylis avellana L.) were obtained from the Hebar Company, Poland. The yeast strain of Y. lipolytica W29 (ATCC20460) was obtained from the culture collection of the Food and Microbiology Processing and Engineering Laboratory (GPMA) at the University of Burgundy/AgroSup, France. The strain was stored in 10% glycerol in freezing conditions (−80 °C). All medium ingredients (agar–agar, yeast extract, peptone, and glucose) were obtained from BTL Łódź, Poland. Sodium chloride, methyl and ethyl alcohol (99.8%), chloroform, ethyl acetate, n-hexane, toluene, and anhydrous magnesium sulfate were purchased from POCH, Poland, a division of Avantor Performance Products (Center Valley, PA, USA). Trolox (6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid), DPPH (2,2-diphenyl-1-picrylhydrazyl), Folin-Ciocalteu’s phenol reagent, and gallic acid were obtained from Sigma-Aldrich Chemicals, Poznan, Poland. p-Nitrophenyl laurate was synthesized at our laboratory from lauroyl chloride (Sigma-Aldrich) and p-nitrophenol (POCH), according to a method described by Vogel et al. [12 ]. All reagents used were of analytical grade.

Methanol, Folin Ciocalteu’s phenol reagent, gallic acid, 2,2-diphenyl-1-picrylhydrazyl (DPPH), and 2,4,6-trimethylpyridine were purchased from Sigma-Aldrich Co. (Saint Louis, MO, USA). R. oligosporus was from the Indonesian Culture Collection, Research Center for Biology, the Indonesian Institute of Science, Cibinong Indonesia. Black CI rice (Bogor, West Java, Indonesia) and IPR30 rice was from the Indonesian Center for Rice Research, Indonesian Agency for Agricultural Research and Development, Ministry of Agriculture, Subang, West Java, Indonesia.