Stability of Hydroxycinnamic Acid Derivatives, Flavonol Glycosides, and Anthocyanins in Black Currant Juice

: Leenamaija Mäkilä, Oskar Laaksonen, Aino-Liisa Alanne, Maaria Kortesniemi, Heikki Kallio, Baoru Yang

Publisher: AMER CHEMICAL SOC

: 2016

: Journal of Agricultural and Food Chemistry

: JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY

: J AGR FOOD CHEM

: 64

: 22

: 4584

: 4598

: 15

: 0021-8561

: 1520-5118

DOI: https://doi.org/10.1021/acs.jafc.6b01005

The stability of phenolic compounds was followed in black currant juice at ambient temperatures (in light and in dark, conditions) and at +4 degrees C for a year. Analyses were based on high-performance liquid chromatography diode-array detection-electrospray ionization-mass spectrometry (or tandem mass spectrometry) and high-performance liquid chromatography diode-array detection electrospray ionization quadrupole time-of-flight mass spectrometry methods supported by nuclear magnetic resonance after selective high-performance liquid chromatography isolation. Altogether, 43 metabolites were identified, of which 2-(Z)-p-coumaroyloxymethylene-4-beta-D-glucopyranosyloxy-2-(Z)-butenenitrile, 2-(E)-caffeoyloxymethylene-4-beta-D-glucopyranosyloxy-2-(Z)-butenenitrile, 1-O-(Z)-p-coumaroyl-beta-D-glucopyranose, (Z)-p-coumaric acid 4-O-beta-D-glucopyranoside, and (Z)-p-coumaric acid were novel findings in black currant juice. Hydroxycinnamic acid derivatives degraded 20-40% at room temperature during one year of storage, releasing free hydroxycinnamic acids. O-Glucosides of hydroxycinnamic acid compounds were the most stable, followed by O-acylquinic acids, acyloxymethyleneglucosyloxybutenenitriles, and O-acylglucoses. Light induced the isomerization of (E)-coumaric acid compounds into corresponding Z-isomers. Flavonol glycosides stayed fairly stable. Flavonol aglycones were derived mainly from malonylglucosides. Over 90% of anthocyanins were lost at room temperature in a year, practically independent of light. Storage at low temperatures, preferably excluding light, is necessary to retain the original composition of phenolic compounds.