Galloylation of polyphenols alters their biological activity
Daniel Karas1, Jitka Ulrichová1, Kateřina Valentová2
1Department 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.
Abstract:
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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