Antimicrobial pentacyclic triterpenoids from Terminalia superba.

ABSTRACT

Antibacterial bioassay-guided fractionation of the methanol extract of the stem bark of Terminalia superba led to the isolation of four new triterpene glucosides (1-4) which were characterized as 2 alpha,3 beta-dihydroxyolean-12-en-28-oic acid 28-O-beta-D-glucopyranoside (1), 2 alpha,3 beta, 21 beta-trihydroxyolean-12-en-28-oic acid 28-O-beta-D-glucopyranoside (2), 2 alpha,3 beta, 29-trihydroxyolean-12-en-28-oic acid 28-O-beta-D-glucopyranoside (3) and 2 alpha,3 beta,23,27-tetrahydroxyolean-12-en-28-oic acid 28-O-beta-D-glucopyranoside (4) together with the known triterpene 2 alpha,3 beta,23-trihydroxyolean-12-en-28-oic acid (5). Structures were established by spectroscopic methods including one- and two-dimensional NMR, EI-MS and HR-EI-MS. The antibacterial activity of 1-5 was also investigated against two gram-positive (Bacillus subtilis, Staphylococcus aureus), and four gram-negative (Escherichia coli, Shigella flexenari, Pseudomonas aeruginosa, Salmonella typhi) bacterial strains.