Structural features of tannic acid important for DNA degradation in the presence of Cu(II)

Tannic acid has numerous food and pharmacological applications. It is an additive in medicinal products and is used as a flavouring agent and as an antioxidant in various foods and beverages. However, there are reports of its mutagenicity and carcinogenicity in bacterial and animal test systems. Tannic acid and its structural monomer gallic acid are also capable of inducing apoptosis in animal cells. We have earlier shown that tannic acid in the presence of Cu(II) causes DNA degradation through generation of reactive oxygen species such as hydroxyl radicals. In order to understand the chemical basis of the various biological properties of tannic acid we have studied the structure-activity relationship between tannic acid and gallic acid using the DNA cleavage assay. Results in the present paper indicate that gallic acid is considerably more active than tannic acid. However, if two of the three hydroxyl groups of gallic acid are methylated (syringic acid) the DNA degrading capacity declines sharply. Further, decarboxylation of gallic acid (pyrogallol) leads to enhancement of its activity. In conclusion, the results indicate that the DNA cleavage activity of tannic acid is due to its digalloyl moeity and that free hydroxyl groups are essential for cleavage.