Cyanidin 3 o glucoside

HPLC grade methanol, acetonitrile, formic acid, Folin-Ciocalteu reagent and dimethylcinnamaldehyde were purchased from Sigma-Aldrich (Oakville, ON, Canada). The liquid chromatography standards were purchased as follows: Cyanidin-3-O-glucoside from Extrasynthese (Genay Cedex, France); phloridzin, phloretin, chlorogenic acid, ferulic acid and caffeic acid from Sigma-Aldrich; catechin, epicatechin, quercetin, quercetin-3-O-galactoside and quercitin-3-O-glucoside from ChromaDex, Inc. (Santa Ana, CA, USA); quercitin-3-O-rhamnoside, quercitin-3-O-galactoside and anthocyanin standards from Indofine Chemical Company (Hillsborough, NJ, USA). Hydrochloric acid, sulfuric acid, and 96-well microplates were purchased from Fisher Scientific (Ottawa, ON, Canada). Phorbol 12-myristate 13-acetate, diclofenac sodium salt, nimesulide and lipopolysaccharide were obtained from Sigma-Aldrich. COX-2 human ELISA kit was purchased from Enzo Life Sciences, Inc. (Farmingdale, NY, USA). Prostaglandin E₂ EIA kit and nitric oxide quantification kit was purchased from Cayman Chemical Company (Ann Arbor, MI, USA). The TNF-α and IL-6 ELISA kits were purchased from BD Biosciences (San Diego, CA, USA).

The compounds 2,2′-Azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox), 2,4,6-tri(2-pyridyl)-s-triazine (TPTZ), methanol acetic acid, phloroglucinol, β-cyclodextrin, and K₂S₂O₅ were purchased from Sigma-Aldrich (Steinheim, Germany). On the other hand, (−)-epicatechin, (+)-catechin, procyanidin B2, chlorogenic acid, neochlorogenic acid, cryptochlorogenic acid, caffeic acid, dicaffeoylquinic acid, p-coumaric acid, myricetin, isoquercitrin, cyanidin-3-O-galactoside, and cyanidin-3-O-glucoside were purchased from Extrasynthese (Lyon, France). Acetonitrile for ultra-performance liquid chromatography (UPLC; Gradient grade) and ascorbic acid were from Merck (Darmstadt, Germany). Yeasts S. cerevisiae and S. bayanus were purchased from Eaton company (Sandomierz, Poland).

All used chemicals were of high-performance liquid chromatography analytical grade. Phenolic standards of delphinidin-3-O-glucoside, cyanidin-3-O-glucoside, peonidin-3-O-glucoside, malvidin-3-O-glucoside, epigallocatechin, procyanidin B1, procyanidin B2, rutin (quercetin 3-O-rutinoside) and myricetin were purchased from Extrasynthese (Lyon, France). The standard of caftaric, caffeic, p-coumaric, vanillic, syringic and gallic acid and trans-resveratrol, (–)-epicatechin, (+)-catechin and (–)-epicatechin-gallate were obtained from Sigma-Aldrich (St. Louis, MO, USA). Kaempferol, quercetin and isorhamnetin were obtained from Fluka (Steinheim, Germany) and quercetin-3-O-glucoside from Sigma (St. Louis, MO, USA). Acetonitrile was purchased from J. T. Baker (Deventer, Netherlands). Formic acid and orthophosphoric acid (85% w/w) were purchased from Fluka (Buchs, Switzerland) and ethanol from Kemika (Zagreb, Croatia). Milli-Q water was used for the high-performance liquid chromatography.

(2-¹⁴C)-Malonyl-coenzyme A (55 mCi/mmol) was purchased from New England Nuclear Corp. GmbH (Vienna, Austria). (¹⁴C)-Labeled flavonoids naringenin, DHK, DHQ, and DHM were synthesized as previously described [16 (link), 17 (link)] using recombinant F3’5’H from Sollya heterophylla and recombinant F3′H from Arabidopsis thaliana.
Pelargonidin-3-O-glucoside chloride, pelargonidin-3-O-rutinoside chloride, and, cyanidin-3-O-galactoside chloride available from Carbosynth (Berkshire, UK), cyanidin-3-O-glucoside was purchased from Extrasynthese (Genay, France) and cyanidin-3-O-rutinoside was obtained from Roth (Karlsruhe, Germany).