Preparative Isolation of Anthocyanins by High-Speed Countercurrent Chromatography and Application of the Color Activity Concept to Red Wine

Abstract

Red pigments were isolated from wine and grape-skin extracts using preparative high-speed countercurrent chromatography (HSCCC) and identified by NMR and MS techniques. Four solvent systems were developed in order to separate anthocyanins with different polarities. Malvidin-3-glucoside was the major component present in young red wines, and up to 500 mg of pure malvidin-3-glucoside could be obtained from a single bottle of a red wine. Other isolated pigments were the malvidin- and peonidin-3,5-diglucosides, as well as acetyl-, coumaroyl-, and caffeoyl-derivatives of anthocyanins. Furthermore, condensed red wine pigments formed from malvidin-3-glucoside (vitisin A and acetylvitisin A) were isolated on a preparative scale. Isolated compounds were used as standards for quantification of anthocyanins in a range of red wines. The "color activity concept" was applied to red wine, and visual detection thresholds were determined for some of the isolated anthocyanins. Mono-glucosides were found to exhibit lower visual detection thresholds than di-glucosides and acylated anthocyanins.

Cyanidin and Malvidin from Oryza sativa cv. Heugjinjubyeo Mediate Cytotoxicity against Human Monocytic Leukemia Cells by Arrest of G2/M Phase and Induction of Apoptosis

“…Cyanidin ( [M + 1] + (2.8); 1 H NMR and 13 C NMR data were consistent with those in the literature (20), described in Table 1.…”

“…Complete identification of isolated compounds made use of a variety of physical and chemical methods, which includes MS spectrometry, UV-vis, IR, and 1 H and 13 C NMR spectroscopy. The structures of these compounds (Figure 1) were identified by comparing spectra with published data (19,20). The isolated cytotoxic compounds were determined as cyanidin (1) and malvidin (2), and detailed data are described as follows.…”

Phenolics in cereals, fruits and vegetables: Occurrence, extraction and analysis

“…Degenhart et al [373] used HSCCC for preparative isolation of anthocyanins from red wines and grape skins. Anthocyanins were fractionated based on their polarities into four solvents systems.…”

Preparative separation of grape skin polyphenols by high-speed counter-current chromatography

“…Degenhardt, Hofmann, Knapp, and Winterhalter (2000) used firstly HSCCC technique for preparative isolation of anthocyanins from grape skins of red varieties.…”