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A new hemisynthetic oleanane saponin: 4',2",3",4",6"-penta-O-acetyl-6'-O- methyl-3-O-β-D-glucopyranosyl-(1→2)-β-D-glucuronopyranosyl oleanolic acid (2) was obtained after acetylation and methylation reaction on 3-O-β-D- glucopyranosyl-(1→2)-β-D-glucuronopyranosyl oleanolic acid (1). Its structure was established by extensive analysis of 1D-(1H, 13C), 2D-(COSY, HSQC and HMBC) NMR data in conjunction with mass spectrometry (HR- TOFESIMS). The evaluation of antimicrobial activities using microdilution method showed that, reaction product (2) presented the lowest values of MIC against E. coli (MIC = 16 μg/mL), S. aureus (MIC = 8 μg/mL), C. tropicalis (MIC = 16 μg/mL) C. albicans (MIC = 8 μg/mL) compare to the substrate (1) against the same microbial strains: E. coli (MIC = 32 μg/mL), S. aureus (MIC = 16 μg/mL), C. tropicalis (MIC = 32 μg/mL), C. albicans (MIC = 16 μg/mL). These results indicate that, acetylation and methylation reactions of compound 1 increase its antimicrobial activities against the tested microorganisms.

One new tirucallane triterpene named as canarimoic acid (1), and three known analogues: 3β-hydroxytirucalla-8,24-dien-21-oic acid (2), 3α-acetyltirucalla-8,24-diene-21oic acid (3) and 3-oxotirucall...

One new tirucallane triterpene named as canarimoic acid (

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.

International audience; Five new pentacyclic triterpenoids, Melantheraside A–E (1–5) together with eleven known compounds (6-16) were isolated from the methanol extract of the aerial parts of Melanthera elliptica O. Hoffm. Their structures were established by extensive analysis of 1D- (1H, 13C), 2D- (COSY, ROESY, HSQC and HMBC) NMR data experiments in conjunction with mass spectrometry (TOFESIMS and HR-TOFESIMS) and by comparison with data reported in the literature. The structures of the new compounds were established as: 12α-chloro-3β-hydroxyoleanan-28,13β-olide (1), 3β-acetoxy-12α-hydroxytaraxer-14-en-28-oic acid (2), 3β-hydroxy-12-oximetaraxeran-28,14β-olide (3), 3β-acetoxy-12-oximetaraxeran-28,14β-olide (4) and 2β-carboxyamino-12α-chloro-3-oxo-1-nor-oleanan-28,13β-olide (5). The 3β-acetoxy-12α-chloro-oleanan-28,13β-olide (6) was isolated for the first time as natural product.

International audience; 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-β-D-xyloside (1), luteolin-7-O-β-D-apiofuranosyl-(1 → 2)-β-D-xylopyranoside (2), chrysoeriol-7-O-β-D-apiofuranosyl-(1 → 2)-β-D-xylopyranoside (3), chrysoeriol-7-O-α-L-rhamnopyranosyl-(1 → 6)-β-D-(4"-hydrogeno sulfate) glucopyranoside (4) and isorhamnetin-3-O-α-L-rhamnopyranosyl-(1 → 6)-β-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.

International audience; Grandulosides A-C, three new flavonoid glycosides, were isolated from the aerial parts of Graptophyllum grandulosum Turill and identified as chrysoeriol-7-O-β-d-apiofuranosyl-(1 → 2)-β-d-xylopyranoside (1), chrysoeriol-7-O-[4′′′-O-acetyl-β-d-apiofuranosyl-(1 → 2)]-β-d-xylopyranoside (2) and 7-O-α-l-rhamnopyranosyl-(1 → 6)-β-d-(4′′-Sodium hydrogeno sulfate) glucopyranoside (3). Four known compounds, chrysoeriol-7-O-β-d-xyloside (4), isorhamnetin-3-O-α-l-rhamnopyranosyl-(1 → 6)-β-d-glucopyranoside (5), luteolin-7-O-β-d-apiofuranosyl-(1 → 2)-β-d-xylopyranoside (6) and sucrose (7) were also obtained. The structures of these compounds were established by interpretation of their spectral data, mainly HR-TOFESIMS, 1D-NMR (1H, 13C) and 2D-NMR (COSY, NOESY, HSQC and HMBC) and by comparison with the literature data.