The inhibition effects of chlorogenic acid on the formation of colored oxidation products of (-)-epigallocatechin gallate under enzymatic oxidation

被引:10
作者
Cui, Yuqing [1 ,2 ]
Han, Zisheng [3 ]
Lian, Li [1 ,2 ]
Zhang, Liang [1 ,2 ,4 ]
机构
[1] Anhui Agr Univ, State Key Lab Tea Plant Biol & Utilizat, Hefei 230036, Peoples R China
[2] Anhui Agr Univ, Int Joint Lab Tea Chem & Hlth Effects, Minist Educ, Hefei 230036, Peoples R China
[3] Rutgers State Univ, Dept Food Sci, New Brunswick, NJ 08901 USA
[4] 130 Changjiang West Rd, Hefei 230036, Anhui, Peoples R China
关键词
(-)-Epigallocatechin gallate; Enzymatic oxidation; Oolongtheanin; Color; Inhibition; BLACK TEA PIGMENT; THEAFLAVIN; THEANAPHTHOQUINONE; POLYPHENOL; STABILITY; MECHANISM; DIMERS;
D O I
10.1016/j.foodchem.2023.135895
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Untargeted Liquid chromatography tandem mass spectrometry (LC-MS) based metabolomics in combination with UV-visible and colorimeter was applied in identifying critical colored enzymatically oxidized products of (-)-epigallocatechin gallate (EGCG). Pearson correlation coefficient analysis between marker compounds and a* value was conducted, and then a series of colored oxidation products were targeted and subsequently identified by diode array detection and mass fragmentation ions. The quinone of oolongtheanin 3-O '-gallate degraded product with quasi-molecular mass ion at m/z 711 was identified as a critical colored oxidation product of single EGCG. To explore the effect of chlorogenic acid on the formation of colored EGCG enzymatic oxidation products, the variation of oxidation products on the oolongtheanin pathway was semi-quantitatively determined. The result showed chlorogenic acid significantly inhibited the formation of colored oxidation products, thus light-ened the color of EGCG oxidation mixture. The addition of chlorogenic acid influences the process of tea polyphenols' enzymatic oxidation.
引用
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页数:9
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共 30 条
[1]   Flavor Characteristics of Seven Grades of Black Tea Produced in Turkey [J].
Alasalvar, Cesarettin ;
Topal, Bahar ;
Serpen, Arda ;
Bahar, Banu ;
Pelvan, Ebru ;
Gokmen, Vural .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2012, 60 (25) :6323-6332
[2]   Isolation and structural elucidation of dimeric epigallocatechin-3-gallate autoxidation products and their antioxidant capacity [J].
Alfke, Julian ;
Kampermann, Uta ;
Kalinina, Svetlana ;
Esselen, Melanie .
EUROPEAN FOOD RESEARCH AND TECHNOLOGY, 2021, 247 (12) :2961-2975
[3]   Syntheses of methylated catechins and theaflavins using 2-nitrobenzenesulfonyl group to protect and deactivate phenol [J].
Asakawa, Tomohiro ;
Kawabe, Yusuke ;
Yoshida, Atsushi ;
Aihara, Yoshiyuki ;
Manabe, Tamiko ;
Hirose, Yoshitsugu ;
Sakurada, Asuka ;
Inai, Makoto ;
Hamashima, Yoshitaka ;
Furuta, Takumi ;
Wakimoto, Toshiyuki ;
Kan, Toshiyuki .
JOURNAL OF ANTIBIOTICS, 2016, 69 (04) :299-312
[4]   Identification of low-molecular-weight color contributors of black tea infusion by metabolomics analysis based on UV-visible spectroscopy and mass spectrometry [J].
Cui, Yuqing ;
Lai, Guoping ;
Wen, Mingchun ;
Han, Zisheng ;
Zhang, Liang .
FOOD CHEMISTRY, 2022, 386
[5]   Mechanism of oolongtheanin formation via three intermediates [J].
Hirose, Sayumi ;
Kamatari, Yuji O. ;
Yanase, Emiko .
TETRAHEDRON LETTERS, 2020, 61 (11-12)
[6]   Equilibrated structures of oolongtheanins [J].
Hirose, Sayumi ;
Ogawa, Kazuki ;
Yanase, Emiko .
TETRAHEDRON LETTERS, 2016, 57 (19) :2067-2069
[7]   Stability of black tea polyphenol, theaflavin, and identification of theanaphthoquinone as its major radical reaction product [J].
Jhoo, JW ;
Lo, CY ;
Li, SM ;
Sang, SM ;
Ang, CYW ;
Heinze, TM ;
Ho, CT .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2005, 53 (15) :6146-6150
[8]   Diverse Metabolite Variations in Tea (Camellia sinensis L.) Leaves Grown Under Various Shade Conditions Revisited: A Metabolomics Study [J].
Ji, Hyang-Gi ;
Lee, Yeong-Ran ;
Lee, Min-Seuk ;
Hwang, Kyeong Hwan ;
Park, Clara Yongjoo ;
Kim, Eun-Hee ;
Park, Jun Seong ;
Hong, Young-Shick .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2018, 66 (08) :1889-1897
[9]   Metabolomics for a Millenniums-Old Crop: Tea Plant (Camellia sinensis) [J].
Jiang, Chen-Kai ;
Ma, Jian-Qiang ;
Apostolides, Zeno ;
Chen, Liang .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2019, 67 (23) :6445-6457
[10]   Mass-spectrometric multi-omics linked to function - State-of-the-art investigations of mitochondria in systems medicine [J].
Kappler, Lisa ;
Lehmann, Rainer .
TRAC-TRENDS IN ANALYTICAL CHEMISTRY, 2019, 119