文献类型：期刊文献

英文题名：Thermal degradation of (2R, 3R)-dihydromyricetin in neutral aqueous solution at 100 ℃

作者：Zhang, Haolin[1]; Lin, Shiye[2]; Xie, Ruiwei[3]; Zhong, Weizhi[4]; Wang, Hui[3]; Farag, Mohamed A.[5]; Hussain, Hidayat[6]; Arroo, Randolph R.J.[7]; Chen, Xiaojia[1]; Xiao, Jianbo[2]

机构：[1] Institute of Chinese Medical Sciences, University of Macau, China; [2] Universidade de Vigo, Department of Analytical and Food Chemistry, Faculty of Sciences, Ourense, 32004, Spain; [3] Guangdong Provincial Key Laboratory of Aquatic Product Processing and Safety, College of Food Science and Technology, Guangdong Ocean University, Zhanjiang, 524088, China; [4] Institute of Food Safety and Nutrition, Jinan University, Guangzhou, China; [5] Pharmacognosy Department, College of Pharmacy, Cairo University, Cairo, Egypt; [6] Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, Halle [Saale], D-06120, Germany; [7] Leicester School of Pharmacy, De Montfort University, The Gateway, Leicester, LE1 9BH, United Kingdom

年份：2024

卷号：435

外文期刊名：Food Chemistry

收录：EI(收录号：20234114849961)、Scopus(收录号：2-s2.0-85173134474)

语种：英文

外文关键词：Degradation - Dimers - Electrospray ionization - Flavonoids - Hydroxylation - Liquid chromatography - Mass spectrometry - Negative ions - Quinone - Reaction intermediates

外文摘要：In the field of thermal degradation of flavonoids, current studies mainly focused on flavonols. However, the thermal degradation of dihydroflavonols in aqueous solution has received limited attention compared to flavonols. The single C2-C3 bonds of dihydroflavonols, which differs from the C2-C3 double bond in flavonols, may cause different degradation mechanisms. Dihydromyricetin (DMY) is a typical dihydroflavonol with six hydroxyl groups, and possesses various health effects. We explored the thermal degradation of DMY in neutral aqueous solution (pH 7) at 100 ℃. Ultra-performance liquid chromatography combined with photodiode array and electrospray ionization quadrupole-time-of-flight tandem mass spectrometric detection (UPLC-PDA-ESI-QTOF–MS/MS) provided suitable platform for exploring DMY degradation pathways, and negative ion mode was applied. Thermal treatment led to a decline in DMY level with time, accompanied by the appearance of various degradation products of DMY. Degradation mechanisms of DMY included isomerization, oxidation, hydroxylation, dimerization and ring cleavage. The pyrogallol-type ring B of DMY might be initially oxidized into ortho-quinone, which could further attack another DMY to form dimers. In addition, hydroxylation is likely to occur at C-2, C-3 of DMY or DMY dimers, which then further yields ring-cleavage products via breakage of the O1-C2 bond, C2-C3 bond, or C3-C4 bond. The 3-hydroxy-5-(3,3,5,7-tetrahydroxy-4-oxochroman-2-yl) cyclohexa-3,5-diene-1, 2-dione (m/z 333.0244) and unknown compound m/z 435.0925 were annotated as key intermediates in DMY degradation. Four phenolic acids, including 3,4,5-trihydroxybenzoic acid (m/z 169.0136, RT 1.4 min), 2,4,6-trihydroxyphenylglyoxylic acid (m/z 197.0084, RT 1.7 min), 2-oxo-2-(2,4,6-trihydroxyphenyl) acetaldehyde (m/z 181.0132, RT 2.4 min), and 2,4,6-trihydroxybenzoic acid (m/z 169.0139, RT 2.5 min) were identified as the major end products of DMY degradation. In addition, 5-((3,5dihydroxyphenoxy) methyl)-3-hydroxycyclohexa-3,5-diene-1,2-dione (m/z 261.0399, RT 11.7 min) and unidentified compound with m/z 329.0507 (RT 1.0 min) were also suggested to be end products of DMY degradation. These results provide novel insights on DMY stability and degradation products. Moreover, the heat treatment of DMY aqueous solution was found to gradually reduce the antioxidant activities of DMY, and even destroy the beneficial effect of DMY on the gut microbiota composition. ? 2023 Elsevier Ltd