RESUMO
From the leaves and bark of Zanthoxylum monophyllum, a new lignan, 3-methoxy-3',4'-methylenedioxylignan-4,8,9,9'-tetraol (1), has been isolated along with 22 known compounds (2- 23), fifteen of them reported for the first time from Z. monophyllum. Their chemical structures were elucidated using detailed spectroscopic studies and chemical analysis. All compounds were evaluated for antimicrobial and antiprotozoal activities. Alkaloids BIS-[6-(5,6-dihydro-chelerythrinyl)] ether (2) and 6-ethoxy-chelerythrine (4) exhibited strong activity against Aspergillus fumigatus and methicillin-resistant Staphylococcus aureus (MRSA). Compound 4-methoxy-N-methyl-2-quinolone (9) exhibited significant activity against MRSA (IC50 value of 8.0 µM) while compound 5,8,4'-trihydroxy-3,7,3'-trimethoxyflavone (10) showed weak activity against Plasmodium falciparum.
Assuntos
Alcaloides/farmacologia , Anti-Infecciosos/farmacologia , Lignanas/farmacologia , Extratos Vegetais/química , Zanthoxylum/química , Alcaloides/química , Aspergillus fumigatus/efeitos dos fármacos , Benzodioxóis/química , Benzodioxóis/farmacologia , Benzofenantridinas/química , Benzofenantridinas/farmacologia , Flavonas/química , Flavonas/farmacologia , Concentração Inibidora 50 , Lignanas/química , Staphylococcus aureus Resistente à Meticilina/efeitos dos fármacos , Casca de Planta/química , Folhas de Planta/química , Plasmodium falciparum/efeitos dos fármacos , Quinolinas/química , Quinolinas/farmacologiaRESUMO
Phytochemical evaluation of Zanthoxylum monophyllum has led to the isolation of the alkaloid 4-methoxy-N-methyl-2-quinolone (1) with a significant activity against methicillin-resistant Staphylococcus aureus (MRSA), with an IC50 value of 1.5 microg/mL. Xenobiotic biotransformation of 1 has been conducted with the general goal of increasing the bioactivity of the compound and contributing new leads for further pharmacological research. Twenty-nine microorganisms were used for screening and two (Aspergillus flavus and Cunninghamella echinulata var. echinulata) were able to transform compound 1 to 4-methoxy-2-quinolone (2). Structural identification of the compounds was based on NMR, IR, and MS data.
Assuntos
Alcaloides/metabolismo , Quinolonas/metabolismo , Xenobióticos/metabolismo , Zanthoxylum/química , Aspergillus flavus/metabolismo , Biotransformação , Cunninghamella/metabolismoRESUMO
Bioassay-guided fractionation of the EtOH extract of Artocarpus sepicanus Diels leaves has led to the isolation of a new geranyl flavanone (1), along with the known compounds, afzelechin-3-O-α-L-rhamnopyranoside and ß-sitosterol glucoside. The structure of the new compound was established by UV, IR, HRESIMS, 1D and 2D NMR experiments. Antimicrobial testing of the three compounds indicated that 1 displayed a significant selective antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) with IC50 and MIC values of 1.4 and 2.9 µM, respectively.
RESUMO
Bioassay-guided fractionation of a root extract of Sorocea muriculata led to the isolation and identification of two new oxygen heterocyclic Diels-Alder-type adducts, sorocenols G (1) and H (2), along with lupeol-3-(3' R-hydroxytetradecanoate) and oxyresveratrol. The structures of 1 and 2 were elucidated using 1D and 2D NMR spectroscopic and HRMS data and by comparison with reported values. The absolute configurations of 1 and 2 were established by analysis of their experimental and theoretically calculated CD spectra. Compounds 1 and 2 showed significant and selective activity against methicillin-resistant Staphylococcus aureus with IC50 values of 1.5 and 0.5 microM, respectively. Compound 2 also displayed antifungal activity against Candida albicans, Cryptococcus neoformans, and Aspergillus fumigatus, with IC 50 values of 5.4, 5.4, and 10.0 microM, respectively.
