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Cited by 212

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Tea Polyphenol (−)-Epigallocatechin-3-Gallate: A New Trapping Agent of Reactive Dicarbonyl Species

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Sang, Shengmin, Shao, Xi, Bai, Naisheng, Lo, Chih-Yu, Yang, Chung S., Ho, Chi-Tang·2007·Chemical Research in Toxicology

Abstract

Previous studies have demonstrated that reactive dicarbonyl compounds [e.g., methylglyoxal (MGO) and glyoxal (GO)] irreversibly and progressively modify proteins over time and yield advanced glycation end products (AGEs), which are thought to contribute to the development of diabetes mellitus and its subsequent complications. Thus, decreasing the levels of MGO and GO will be an effective approach to reduce the formation of AGEs and the development of diabetic complications. In our studies to find nontoxic trapping agents of reactive dicarbonyl species from dietary sources, we found that (-)-epigallocatechin-3-gallate (EGCG), the major bioactive green tea polyphenol, could efficiently trap reactive dicarbonyl compounds (MGO or GO) to form mono- and di-MGO or GO adducts under physiological conditions (pH 7.4, 37 degrees C). The products formed from EGCG and MGO (or GO), combined at different ratios, were analyzed using LC/MS. We also developed a method to purify the two major mono-MGO adducts of EGCG without derivatization, and their structures were identified as stereoisomers of mono-MGO adducts of EGCG based on their 1D and 2D NMR spectra. Our LC/MS and NMR data showed that positions 6 and 8 of the EGCG A-ring were the major active sites for trapping reactive dicarbonyl compounds. We also found that EGCG lost its trapping efficacy under acidic conditions (pH

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Metadata

Authors
Sang, S., Shao, X., Bai, N., Lo, C.-Y., Yang, C. S., & Ho, C.-T.
Venue
Chemical Research in Toxicology
Published
2007-11-15
Volume
20
Issue
12
Pages
1862-1870
ISSN
  • 0893-228X (ISSN-L)
  • 1520-5010
OpenAlex
W2007324558
Cited by
212
References
3
FWCI
2.60
Type
journal article
Language
en
Open access
green

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