The isolation of anthocyanin monomers from blueberry pomace and their radical-scavenging mechanisms in DFT study. (30th August 2023)

• Record Type: Journal Article
• Authors: Gui, Hailong; Dai, Jian; Tian, Jinlong; Jiang, Qiao; Zhang, Ye; Ren, Guangyu; Song, Baoge; Wang, Mingshuang; Saiwaidoula, Mihereban; Dong, Wenjiang; Li, Bin
• Is Part Of: Food chemistry. Volume 418(2023)
• Publication Date: 2023-08-30
• Subjects: Blueberry pomace -- Anthocyanin monomer -- Isolation and identification -- Density functional theory -- Scavenge free radical capacity; ABTS 2, 2′-azino-bis-3-ethylbenzothiazoline-6-sulphonic acid -- BDE the dissociation enthalpy of phenolic hydroxyl bond -- DFT density functional theory -- Dp3G delphinidin-3-O-glucoside -- Dp3Ga delphinidin-3-O-galactoside -- DPPH 1, 1-diphenyl-2-picrylhydrazyl -- EA electron affinity -- ESP electrostatic potential surface -- EtOH ethanol -- HOMO the highest occupied molecular orbital -- HPLC-MS/MS high performance liquid chromatography tandem mass spectrometry -- IEF-PCM integral equation formalism polarizable continuum model -- IP the ionization potential -- LUMO the lowest unoccupied molecular orbital -- M3G malvidin-3-O-glucoside -- M3Ga malvidin-3-O-galactoside -- MeOH methanol -- Mva malvidin-3-O-arabinoside -- MvaceG malvidin-3-O-(6-O-acetyl)-glucoside. -- NMR nuclear magnetic resonance -- Semi-HPLC semi-preparative high-performance liquid chromatography -- SET the single electron transfer -- TFA trifluoroacetic acid; Food -- Analysis -- Periodicals; Food -- Composition -- Periodicals; 664
• DOI: 10.1016/j.foodchem.2023.135872
• Languages: English
• ISSNs: 0308-8146

Abstract

Highlights: Anthocyanin monomers were obtained from blueberry pomace in a new isolation method. The identification of anthocyanins was completed by LC-MS and 1 H NMR spectra. Scavenge free radical capacity of anthocyanins was evaluated in DPPH and ABTS. The DFT analysis of anthocyanins was consistent with the in vitro experiment. Abstract: This study explored the isolation of anthocyanin monomers using a medium- and high-pressure separation technique as a means to increase the added value of a by-product of the blueberry juice industry. Six anthocyanin monomers were isolated with a purity of 95% and identified as mono-galactoside, glucoside, and isomers of delphinidin, malvidin, and even malvidin-3-O-arabinoside, malvidin-3-(6″-acetyl)-O-glucoside by LC-MS and 1 H NMR. Following the conformation search, the computer calculation manifested the active sites of six anthocyanins (C4′ -OH) and their stabilities based on the structural and energy parameters. The DPPH tests demonstrated that delphinidin glycoside's free radical scavenging ability (89.93 ± 2.03 % and 86.50 ± 3.16 %) was significantly higher than that of malvidin (80.39 ± 1.30 % and 81.02 ± 0.45 %), and that malvidin's capacity was improved by conjugation arabinoside (87.48 ± 2.39 %) and acetylated glucoside (88.39 ± 1.37 %), which was compatible with the computer calculation.