E

Buckingham, J.

doi:10.1007/978-1-4899-3316-4_5

Cited by 3 publications

(5 citation statements)

References 361 publications

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“…The resulting crude reaction mixture was profiled by UHPLC-high resolution mass spectrometry (HRESIMS) in negative (NI) electrospray ionization (ESI) modes (Figure S1, Supporting Information). A comparison between the photodiode array (PDA) and MS data was obtained, and those compounds that were described in the Dictionary of Natural Products database from previous isolations from the Vitis genus were identified. The formation of dimeric stilbene analogues was suspected from the mass range observed for the various peaks occurring after biotransformation ([M – H] − : m / z 347–471).…”

Section: Resultsmentioning

confidence: 99%

Generation of Antifungal Stilbenes Using the Enzymatic Secretome of Botrytis cinerea

et al. 2017

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The protein secretome of Botrytis cinerea was used to perform the biotransformation of resveratrol, pterostilbene, and a mixture of both. Metabolite profiling by UHPLC-HRMS revealed the presence of compounds with unusual molecular formula, suggesting the existence of new products. To isolate these products, the reactions were scaled-up, and 21 analogues were isolated and fully characterized by NMR and HRESIMS analyses. The reaction with pterostilbene afforded five new compounds, while the reaction with a mixture of pterostilbene and resveratrol afforded seven unusual stilbene dimers. The antifungal properties of these compounds were evaluated using in vitro bioassays against Plasmopara viticola. The cytological effects of the isolated antifungal compounds on the ultrastructure of P. viticola were also evaluated.

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Section: Resultsmentioning

confidence: 99%

Generation of Antifungal Stilbenes Using the Enzymatic Secretome of Botrytis cinerea

et al. 2017

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“…Metabolite profiling by UHPLC-HRESIMS revealed that the molecular formula of peak 17 was C 14 H 13 NO 2 (HRESIMS [M + H] + at m / z 228.1019, calcd for C 14 H 14 NO 2 , 228.1019; Δppm = 0.02) and that of 18 was C 15 H 15 NO 3 (HRESIMS [M + H] + at m / z 258.1126, calcd for C 15 H 16 NO 3 , 257.1125; Δppm = 0.54). A cross search of these molecular formulas in the Dictionary of Natural Products within the genus Conchocarpus did not yield any proposed compound identification, while many isomers for both molecular formulas were found to have been reported for other genera in the Rutaceae family. The identification of these active principles thus required their targeted isolation, and they were purified in one step by semipreparative HPLC from the leaf CH 2 Cl 2 fraction, which contained them in high yields (Figure ).…”

Section: Resultsmentioning

confidence: 89%

“…Data treatment and the dereplication process were performed using mzMine 2.14.2 . The Dictionary of Natural Products was used as the database for the dereplication () . The conversion of the proprietary files to open MS format (.mzXML) was performed using ProteoWizzard .…”

Section: Methodsmentioning

confidence: 99%

Targeted Isolation of Indolopyridoquinazoline Alkaloids from Conchocarpus fontanesianus Based on Molecular Networks

et al. 2016

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A dichloromethane-soluble fraction of the stem bark of Conchocarpus fontanesianus showed antifungal activity against Candida albicans in a bioautography assay. Off-line high-pressure liquid chromatography activity-based profiling of this extract enabled a precise localization of the compounds responsible for the antifungal activity that were isolated and identified as the known compounds flindersine (17) and 8-methoxyflindersine (18). As well as the identification of the bioactive principles, the ultra-high-pressure liquid chromatography-high-resolution mass spectrometry metabolite profiling of the dichloromethane stem bark fraction allowed the detection of more than 1000 components. Some of these could be assigned putatively to secondary metabolites previously isolated from the family Rutaceae. Generation of a molecular network based on MS(2) spectra indicated the presence of indolopyridoquinazoline alkaloids and related scaffolds. Efficient targeted isolation of these compounds was performed by geometric transfer of the analytical high-pressure liquid chromatography profiling conditions to preparative medium-pressure liquid chromatography. This yielded six new indolopyridoquinazoline alkaloids (5, 16, 19-22) that were assigned structurally. The medium-pressure liquid chromatography separations afforded additionally 16 other compounds. This work has demonstrated the usefulness of molecular networks to target the isolation of new natural products and the value of this approach for dereplication. A detailed analysis of the constituents of the stem bark of C. fontanesianus was conducted.

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“…Dereplication of the metabolites eluting in the active zones was performed by complementary UHPLC-high-resolution mass spectrometry (HRESIMS) metabolite profiling of the crude extract in both the positive (PI) and negative (NI) electrospray ionization (ESI) modes (Figure C). A peak list of the relevant features ( m / z at a given t R ; Table S1, Supporting Information) was compared to a comprehensive list of all the molecular formulas of chemical constituents reported in the Swartzia genus extracted from the Dictionary of Natural Products database . This led to the tentative identification of 23 compounds within a 3 ppm tolerance (Table S1, Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

“…Data treatment and dereplication processes were performed using mzMine 2.10, a modular framework for processing, visualizing, and analyzing mass spectrometry-based molecular profile data . The Dictionary of Natural Products was used as a database for the dereplication () …”

Section: Methodsmentioning

confidence: 99%

Anti-Candida Cassane-Type Diterpenoids from the Root Bark of Swartzia simplex

et al. 2015

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A dichloromethane extract of the roots from the Panamanian plant Swartzia simplex exhibited a strong antifungal activity in a bioautography assay against a genetically modified hypersusceptible strain of Candida albicans. At-line HPLC activity based profiling of the crude extract enabled a precise localization of the antifungal compounds, and dereplication by UHPLC-HRESIMS indicated the presence of potentially new metabolites. Transposition of the HPLC reversed-phase analytical conditions to medium-pressure liquid chromatography (MPLC) allowed an efficient isolation of the major constituents. Minor compounds of interest were isolated from the MPLC fractions using semipreparative HPLC. Using this strategy, 14 diterpenes (1-14) were isolated, with seven (5-10, 14) being new antifungal natural products. The new structures were elucidated using NMR spectroscopy and HRESIMS analysis. The absolute configurations of some of the compounds were elucidated by electronic circular dichroism spectroscopy. The antifungal properties of these compounds were evaluated as their minimum inhibitory concentrations in a dilution assay against both hypersusceptible and wild-type strains of C. albicans and by assessment of their antibiofilm activities. The potential cytological effects on the ultrastructure of C. albicans of the antifungal compounds isolated were evaluated on thin sections by transmission electron microscopy.

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E

Cited by 3 publications

References 361 publications

Generation of Antifungal Stilbenes Using the Enzymatic Secretome of Botrytis cinerea

Generation of Antifungal Stilbenes Using the Enzymatic Secretome of Botrytis cinerea

Targeted Isolation of Indolopyridoquinazoline Alkaloids from Conchocarpus fontanesianus Based on Molecular Networks

Anti-Candida Cassane-Type Diterpenoids from the Root Bark of Swartzia simplex

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