Isolation and identification of pentagalloylglucose with broad-spectrum antibacterial activity from Rhus trichocarpa Miquel

Rhus trichocarpa Miguel has been utilised both as a food and for medicinal purposes. In this study, we determined that the methanol extracts of the stem and leaf portions of R. trichocarpa inhibited the growth of both Gram-negative and Gram-positive bacteria. The active constituent was isolated, and identified via mass spectrometry and NMR as 1,2,3,4,6-penta-O-galloyl-beta-d-glucose. The compound also evidenced a broad spectrum of antibacterial activity against both Gram-negative and Gram-positive bacteria including Staphylococcus aureus (both methicillin-resistant S. aureus and quinolone-resistant S. aureus), Bacillus subtilis, Streptococcus mutans, Escherichia coli, Salmonella typhimurium, and Pseudomonas aeruginosa with MRC values of 16-32 mu g/ml, whereas gallate failed to inhibit the growth of Gram-negative bacteria, even at a concentration of 1281 mu g/ml. The antibacterial activity of penta-O-galloylglucose was restored by the addition of Fe2+, whereas gallate was not, thereby indicating that its antibacterial activity could be attributable to the chelation of iron. The results of the time-kill study against S. aureus and E. coli revealed that penta-O-galloylglucose exhibited bacteriostatic activity. These findings indicate that the extracts of R. trichocarpa as well as its active component, penta-O-galloylglucose, may have profound potential for the control of both Gram-positive and negative pathogens. (C) 2010 Elsevier Ltd. All rights reserved.