Canarimoic acid: new tirucallane triterpene with antisalmonellal activity from the stem bark of Canarium schweinfurthii Engl.

One new tirucallane triterpene named as canarimoic acid (1), and three known analogues: 3ß-hydroxytirucalla-8,24-dien-21-oic acid (2), 3α-acetyltirucalla-8,24-diene-21oic acid (3) and 3-oxotirucalla-8,24-dien-21-oic (4) were isolated from the hydro-ethanolic crude extract of Canarium schweinfurthii. Their structures were established by extensive analysis of 1 D and 2 D NMR data in conjunction with mass spectrometry and by comparison with those reported in the literature. The evaluation of their antisalmonellal activity using broth microdilution method showed that compound 3 was the most active (MIC =16 µg/mL) against Salmonella Typhi and Salmonella Typhimurium followed by compound 1 (MIC= 32 µg/mL) against Salmonella Typhi and Salmonella Enteritidis.

Isolation, characterization and in vitro anti-salmonellal activity of compounds from stem bark extract of Canarium schweinfurthii.

BACKGROUND: Bacteria belonging to the Salmonella genus are major concern for health, as they are widely reported in many cases of food poisoning. The use of antibiotics remains a main stream control strategy for avian salmonellosis as well as typhoid and paratyphoid fevers in humans. Due to the growing awareness about drug resistance and toxicities, the use of antibiotics is being discouraged in many countries whilst advocating potent benign alternatives such as phyto-based medicine. The objective of this work was to isolate, characterise the bioactive compounds of Canarium schweinfurthii; and evaluate their anti-salmonellal activity. METHODS: The hydro-ethanolic extract of Canarium schweinfurthii was fractionated and tested for their anti-salmonellal activity. The most active fractions (i.e. chloroform and ethyl acetate partition fractions) were then explored for their phytochemical constituents. Fractionation on normal phase silica gel column chromatography and size exclusion chromatography on Sephadex LH-20 led to the isolation of four compounds (maniladiol, scopoletin, ethyl gallate and gallic acid) reported for the first time in Canarium schweinfurthii. RESULTS: Result indicated that scopoletin and gallic acid had greater activity than the crude extracts and partition fractions. Among the isolated compounds, scopoletin showed the highest inhibitory activity with a MIC of 16 µg/ml against Salmonella Typhimurium and Salmonella Enteritidis. CONCLUSIONS: The overall results of this study indicates that the hydro-ethanolic extract as well as some of isolated compounds have interesting anti-salmonellal activities that could be further explored for the development of potent therapy for salmonellosis. Furthermore, the study adds credence to the folkloric applications of the plant.

Antimicrobial activities of saponins from Melanthera elliptica and their synergistic effects with antibiotics against pathogenic phenotypes.

BACKGROUND: Resistance of bacteria and fungi to antibiotics is one of the biggest problems that faces public health. The present work was designated to evaluate the antimicrobial activities of saponins from Melanthera elliptica and their synergistic effects with standard antibiotics against pathogenic phenotypes. The plant extract was prepared by maceration in methanol. The methanol extract was partitioned into ethyl acetate and n-butanol extracts. Column chromatography of the n-butanol extract followed by purification of different fractions led to the isolation of four saponins. Their structures were elucidated on the basis of spectra analysis, and by comparison with those from the literature. The antimicrobial activities of the extracts/compounds alone and their combinations with tetracycline and fluconazole were evaluated using the broth microdilution method through the determination of minimum inhibitory concentration (MIC) and minimum microbicidal concentration. RESULTS: Four compounds: 3-O-ß-D-glucuronopyranosyl-oleanolic acid (1), 3-O-ß-D-glucuronopyranosyloleanolic acid 28-O-ß-D-glucopyranosyl ester (2), 3-O-ß-D-glucopyranosyl(1 → 2)-ß-D-glucuronopyranosyl oleanolic acid (3) and 3-O-ß-D-glucopyranosyl(1 → 2)-ß-D-glucuronopyranosyl oleanolic acid 28-O-ß-D-glucopyranosyl ester (4) were isolated. Compounds 1, 2 and 3 showed the largest antibacterial activities (MIC = 8-128 µg/mL) whereas compound 4 displayed the highest antifungal activities (MIC = 8-16 µg/mL). The antibacterial activities of compounds 1 and 2 (MIC = 16-32 µg/mL) against multi-drug-resistant Escherichia coli S2 (1) and Shigella flexneri SDINT are equal to those of vancomycin (MIC = 16-32 µg/mL) used as reference antibiotic. CONCLUSIONS: The present study showed significant antimicrobial activity of compounds 1, 2, 3 and 4 against the tested microorganisms. The saponins act in synergy with the tested standard antibiotics. This synergy could lead to new options for the treatment of infectious diseases and emerging drug resistance.

Antimicrobial activities of flavonoid glycosides from Graptophyllum grandulosum and their mechanism of antibacterial action.

BACKGROUND: The search for new antimicrobials should take into account drug resistance phenomenon. Medicinal plants are known as sources of potent antimicrobial compounds including flavonoids. The objective of this investigation was to evaluate the antimicrobial activities of flavonoid glycosides from Graptophyllum grandulosum, as well as to determine their mechanism of antibacterial action using lysis, leakage and osmotic stress assays. METHODS: The plant extracts were prepared by maceration in organic solvents. Column chromatography of the n-butanol extract followed by purification of different fractions led to the isolation of five flavonoid glycosides. The antimicrobial activities of extracts/compounds were evaluated using the broth microdilution method. The bacteriolytic activity was evaluated using the time-kill kinetic method. The effect of extracts on the red blood cells and bacterial cell membrane was determined by spectrophotometric methods. RESULTS: Chrysoeriol-7-O-ß-D-xyloside (1), luteolin-7-O-ß-D-apiofuranosyl-(1 → 2)-ß-D-xylopyranoside (2), chrysoeriol-7-O-ß-D-apiofuranosyl-(1 → 2)-ß-D-xylopyranoside (3), chrysoeriol-7-O-α-L-rhamnopyranosyl-(1 → 6)-ß-D-(4"-hydrogeno sulfate) glucopyranoside (4) and isorhamnetin-3-O-α-L-rhamnopyranosyl-(1 → 6)-ß-D-glucopyranoside (5) were isolated from G. grandulosum and showed different degrees of antimicrobial activities. Their antibacterial activities against multi-drug-resistant Vibrio cholerae strains were in some cases equal to, or higher than those of ciprofloxacin used as reference antibiotic. The antibacterial activities of flavonoid glycosides and chloramphenicol increased under osmotic stress (5% NaCl) whereas that of vancomycin decreased under this condition. V. cholerae suspension treated with flavonoid glycosides, showed a significant increase in the optical density at 260 nm, suggesting that nucleic acids were lost through a damaged cytoplasmic membrane. A decrease in the optical density of V. cholerae NB2 suspension treated with the isolated compounds was observed, indicating the lysis of bacterial cells. The tested samples were non-toxic to normal cells highlighting their good selectivity index. CONCLUSIONS: The results of the present study indicate that the purified flavonoids from G. glandulosum possess antimicrobial activities. Their mode of antibacterial activity is due to cell lysis and disruption of the cytoplasmic membrane upon membrane permeability.