Investigation of new products of quercetin formed in boiling water via UPLC-Q-TOF-MS-MS analysis

Shiye Lin; Haolin Zhang; Jesus Simal-Gandara; Ka-Wing Cheng; Mingfu Wang; Hui Cao; Jianbo Xiao

doi:10.1016/j.foodchem.2022.132747

Investigation of new products of quercetin formed in boiling water via UPLC-Q-TOF-MS-MS analysis

Food Chem. 2022 Aug 30:386:132747. doi: 10.1016/j.foodchem.2022.132747. Epub 2022 Mar 19.

Authors

Shiye Lin¹, Haolin Zhang², Jesus Simal-Gandara³, Ka-Wing Cheng⁴, Mingfu Wang⁵, Hui Cao⁶, Jianbo Xiao⁷

Affiliations

¹ College of Food Science and Technology, Guangdong Ocean University, Zhanjiang 524088, China.
² Institute of Chinese Medical Sciences, University of Macau, Macao, China. Electronic address: yc07501@umac.mo.
³ Universidade de Vigo, Nutrition and Bromatology Group, Department of Analytical and Food Chemistry, Faculty of Sciences, 32004 Ourense, Spain. Electronic address: Spainjsimal@uvigo.es.
⁴ Institute for Innovative Development of Food Industry, Shenzhen University, Shenzhen 518060, China; Institute for Advanced Study, Shenzhen University, Shenzhen 518060, China. Electronic address: kwcheng@szu.edu.cn.
⁵ Institute for Innovative Development of Food Industry, Shenzhen University, Shenzhen 518060, China; Institute for Advanced Study, Shenzhen University, Shenzhen 518060, China. Electronic address: mfwang@szu.edu.cn.
⁶ College of Food Science and Technology, Guangdong Ocean University, Zhanjiang 524088, China; Universidade de Vigo, Nutrition and Bromatology Group, Department of Analytical and Food Chemistry, Faculty of Sciences, 32004 Ourense, Spain. Electronic address: hui.cao@uvigo.es.
⁷ Institute of Food Safety and Nutrition, Jinan University, Guangzhou, China. Electronic address: jianboxiao@jnu.edu.cn.

PMID: 35339090
DOI: 10.1016/j.foodchem.2022.132747

Abstract

Quercetin is one of most important flavonoids in foods with multi-benefits for human health. The thermal processing is the main food processing approach. Here, the stability of quercetin in boiling water (100 °C) was investigated by UPLC-Q-TOF-MS-MS. With the increasing boiling time, quercetin gradually degraded, and the initial degradation time is 17.57 min and the half-degradation time is 169.72 min. The degradation mechanisms included oxidation, hydroxylation and nucleophilic attack cleavage. Combining the retention time and characteristic fragment ion information of the corresponding standards, the degraded products of quercetin in boiling water were identified as 3,4-dihydroxyphenylglyoxylate, 1,3,5-trihydroxybenzene, 3,4,5-trihydroxybenzoic acid and 2,4,6-trihydroxybenzoic acid. Moreover, 2,3-dihydro-2,3',4',5,7-pentahydroxy-3-oxoflavone, quercetin dimers and quinones were also formed.

Keywords: Degradation; Dimer; Oxidation; Quercetin; Stability.

MeSH terms

Chromatography, High Pressure Liquid
Flavonoids
Humans
Quercetin* / metabolism
Tandem Mass Spectrometry*
Water

Substances

Flavonoids
Water
Quercetin