The hydrolyzable gallotannin, penta-O-galloyl-β-D-glucopyranoside, inhibits the formation of advanced glycation endproducts by protecting protein structure

Molecular BioSystems
Hang MaNavindra P Seeram

Abstract

Glycation is a spontaneous process initiated by a condensation reaction between reducing sugars and proteins that leads to the formation of advanced glycation endproducts (AGEs). The in vivo accumulation of AGEs is associated with several chronic human diseases and, thus, the search for AGE inhibitors is of great research interest. Hydrolyzable tannins (gallotannins and ellagitannins) are bioactive plant polyphenols which show promise as natural inhibitors of glycation and AGE formation. Notably, the gallotannin, 1,2,3,4,6-penta-O-galloyl-β-D-glucose (PGG), is a key intermediate involved in the biosynthesis of hydrolyzable tannins in plants. Herein, we investigated the effects of PGG on the individual stages of protein glycation and on protein structure (using bovine serum albumin; BSA). MALDI-TOF data demonstrated that PGG inhibited early glycation by 75% while the synthetic AGE inhibitor, aminoguanidine (AG), was not active (both at 50 μM). In addition, PGG reduced the formation of middle and late stage AGEs by 90.1 and 60.5%, respectively, which was superior to the positive control, AG. While glycation induced conformational changes in BSA from α-helix to β-sheets (from circular dichroism and congo red binding studies), PGG ...Continue Reading

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Citations

Nov 10, 2015·Journal of Agricultural and Food Chemistry·Yan ZhangNavindra P Seeram
May 18, 2016·Pharmacology & Therapeutics·Mary E Reyland, David N M Jones
Jul 31, 2019·Phytotherapy Research : PTR·Alessandra DurazzoAntonello Santini
May 16, 2018·Journal of Agricultural and Food Chemistry·Lijun YangQiang Dong

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