Conformation of the tridimensional structure of 1,2,3,4,6‐pentagalloyl‐β‐D‐glucopyranose (PGG) by ¹H NMR, NOESY and theoretical study and membrane interaction in a simulated phospholipid bilayer: a first insight

Abstract

1,2,3,4,6-Penta-O-galloyl-β-D-glucopyranose (PGG) is a polyphenolic compound found in substantial amounts in a number of medicinal herbs. We report (i) its conformational analysis by solution NMR and molecular dynamics calculation and (ii) theoretical study of its interaction with a model membrane bilayer. The galloyl groups B and E appear to play important roles in the interaction with the phospholipid bilayer.

Inhibition of interaction between Staphylococcus aureus α-hemolysin and erythrocytes membrane by hydrolysable tannins: structure-related activity study

“…T4 is rather stiff in comparison with T2 due to the presence of the valoneoyl group at C4 and C6 positions in the molecule, which can limit its spatial reorganization and ability to interact with the membrane. Our assumption is in accordance with the work of Beretta et al 72 , which on the basis of studies of the interaction of PGG with liposomes by NMR and theoretical calculations, proposed a model that implied a gradual spatial reorientation of all of the 5 residues of PGG gallic acid interacting with lipids. The comparison of the activities of two tannins containing a valoneoyl group (T3 and T4) but differing in MM showed the strongest effect of the tannin having an additional gallic acid residue and, accordingly, 3-OH groups, i.e., of the tannin with a large MM.…”

Effects of Toona sinensis Leaf Extract and Its Chemical Constituents on Xanthine Oxidase Activity and Serum Uric Acid Levels in Potassium Oxonate-Induced Hyperuricemic Rats

“…Activity-guided fractionation of TSE gave five compounds, which were purified using Diaion, octadecyl-functionalized silica gel, and Sephadex LH-20 column chromatography. The isolated compounds ( 1 – 5 ) were identified as quercetin-3- O -rutinoside (rutin, 1 ) [16], quercetin-3- O -β- d -glucopyranoside (isoquercitrin, 2 ) [17], 1,2,3,4,6-penta- O -galloyl-β- d -glucopyranose (pentagalloyl glucose, 3 ) [18], quercetin-3- O -α- l -rhamnopyranoside (quercetrin, 4 ) [19], and kaempferol-3- O -α- l -rhamnopyranoside (afzelin, 5 ) [20], through analysis of our spectroscopic data ( 1 H- and 13 C-nuclear magnetic resonance (NMR) and high resolution electrospray ionization (HRESI)-MS, Supplementary Materials) and by comparison to previous literature. The structures of the compounds isolated from T. sinensis leaves are shown in Figure 1.…”

Structure elucidation of a new triterpene from Rhus trichocarpa roots

“…The known compounds, which were isolated, were identified as gallic acid (2), [15] 4-O-methylgallic acid (3), [16] and penta-O-galloyl glucose (4), [8,17] respectively, by comparison of their spectroscopic data to previously reported. Compounds 2-4 were major constituents of R. trichocarpa roots, and the contents of the compounds were 0.96 ± 0.00, 1.61 ± 0.01, 7.17 ± 0.09 mg/g, respectively (Figs.…”