Penta-O-galloyl-β-d-glucose inhibits the formation of advanced glycation end-products (AGEs): A mechanistic investigation.

Penta-O-galloyl-β-d-glucose (PGG) was prepared from tannic acid methanolysis products based on HSCCC, and its protective effects and mechanism on the glucose-induced glycation were investigated for the first time. PGG was confirmed to exhibit strong anti-AGEs effects in bovine serum albumin (BSA)-glucose (Glu) and BSA-methylglyoxal (MGO) glycation systems. It was showed that PGG could inhibit the AGEs formation by blocking glycated intermediates (fructosamine and α-dicarbonyl compounds), eliminating radicals, and chelating metal-ions. In-depth mechanism analysis proved that PGG could prevent BSA from glycation by hindering the accumulation of amyloid fibrils, stabilizing the BSA secondary structures, and binding the partial glycation sites. Furthermore, PGG exhibited a prominent trapping capacities on the reactive intermediate MGO by generating PGG-mono-MGO adduct. This research indicated that PGG could be an effective agent to block Glu/MGO-triggered glycation and offered new insights into PGG as a functional ingredient in food materials for preventing diabetic syndrome.