Galloylation of polyphenols alters their biological activity

•Gallates occur in dicotyledon plants from Hamamelididae, Dilleniidae and Rosidae.•Natural polyphenols are often galloylated synthetically to improve bioactivities.•Galloylation affects physico-chemical properties of polyphenols.•Galloylated molecules are usually more biologically active.•Toxicity of gallates is slightly more pronounced only in vitro.

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.

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