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Food Chem Toxicol. 2017 Jul;105:223-240. doi: 10.1016/j.fct.2017.04.021. Epub 2017 Apr 18.

Galloylation of polyphenols alters their biological activity.

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Department of Medical Chemistry and Biochemistry, Faculty of Medicine and Dentistry, Palacký University, Hněvotínská 3, CZ-775 15 Olomouc, Czech Republic; Institute of Molecular and Translational Medicine, Faculty of Medicine and Dentistry, Palacký University, Hněvotínská 3, CZ-775 15 Olomouc, Czech Republic.
Institute of Microbiology, Laboratory of Biotransformation, Czech Academy of Sciences, Vídeňská 1083, Prague 4, CZ-142 20, Czech Republic. Electronic address:


Polyphenols form one of the largest groups of natural compounds and possess a wide range of biological properties. These activities can be influenced by the galloyl moiety within their structures. A multitude of galloylated polyphenolic compounds occurs in nature, but galloylated phenols are also produced synthetically to influence their biological properties. This review provides a comprehensive summary of current knowledge about natural (galloylated catechins, theaflavins and proanthocyanidins, penta-O-galloyl-β-d-glucose, gallotannins, ellagitannins, ellagic acid and flavonols) and semisynthetic gallates with a focus on their biological activity and toxicity issues. The effects of tea catechins (epicatechin, epigallocatechin, epicatechin gallate, and epigallocatechin gallate) and semisynthetic galloyl esters of the flavonolignans silybin and 2,3-dehydrosilybin from the milk thistle (Silybum marianum) on angiogenesis were used as examples of the structure-activity relationship (SAR) study.


Angiogenesis; Gallic acid; Galloylation; Natural gallates; Polyphenols; Synthetic galloyl esters

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