A fluorescence-based bioassay for antibacterials and its application in screening natural product extracts

Michels, Katharina; Heinke, Ramona; Schöne, Pia; Kuipers, Oscar P.; Arnold, Norbert; Wessjohann, Ludger A.

doi:10.1038/ja.2015.71

Cited by 10 publications

(7 citation statements)

References 25 publications

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“…To gain insight into the antibiotic potential of the products, single compound dimers 8a–j were subjected to a preliminary evaluation against Bacillus subtilis ( Fig. 3 ) [ 35 – 36 ]. The active compounds inhibited bacterial growth in a range from 29% to 44% at 1 μM concentration, while erythromycin as the standard led to a growth inhibition of 71% under the same assay conditions.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of antibacterial 1,3-diyne-linked peptoids from an Ugi-4CR/Glaser coupling approach

Brauer¹,

Filho²,

Westermann³

et al. 2015

Beilstein J. Org. Chem.

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SummaryA library of ten 1,3-diyne-linked peptoids has been synthesized through an Ugi four-component reaction (U-4CR) followed by a copper-catalysed alkyne homocoupling (Glaser reaction). The short and chemoselective reaction sequence allows generating diverse (pseudo) dimeric peptoids. A combinatorial version allows the one-pot preparation of, e.g., six-compound-libraries of homo- and heterodimers verified by ESI-MS and HPLC. In a preliminary evaluation, some compounds display moderate activity against the Gram-positive bacterium Bacillus subtilis.

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Section: Resultsmentioning

confidence: 99%

Synthesis of antibacterial 1,3-diyne-linked peptoids from an Ugi-4CR/Glaser coupling approach

Brauer¹,

Filho²,

Westermann³

et al. 2015

Beilstein J. Org. Chem.

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“…Many publications often state a multitude of unrelated activities, for example from antiviral to antidiabetic properties, for the same plant extract. Commonly, this is related to a detection of general toxicity (e.g., through redox system disturbance) or tanning properties (e.g., of unspecific polyphenol-protein interactions), or the effects are only observed at very high concentrations (80,81). In a chemoinformatic survey, such false positive effects cannot (yet) easily be separated from specific effects useful for drug development.…”

Section: Methodsmentioning

confidence: 99%

Evaluation of plant sources for antiinfective lead compound discovery by correlating phylogenetic, spatial, and bioactivity data

Holzmeyer

Hartig

Franke

et al. 2020

Proc. Natl. Acad. Sci. U.S.A.

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Antibiotic resistance and viral diseases are rising around the world and are becoming major threats to global health, food security, and development. One measure that has been suggested to mitigate this crisis is the development of new antibiotics. Here, we provide a comprehensive evaluation of the phylogenetic and biogeographic patterns of antiinfective compounds from seed plants in one of the most species-rich regions on Earth and identify clades with naturally occurring substances potentially suitable for the development of new pharmaceutical compounds. Specifically, we combine taxonomic and phylogenetic data for >7,500 seed plant species from the flora of Java with >16,500 secondary metabolites and 6,255 georeferenced occurrence records to 1) identify clades in the phylogeny that are characterized by either an overrepresentation (“hot clades”) or an underrepresentation (“cold clades”) of antiinfective compounds and 2) assess the spatial patterns of plants with antiinfective compounds relative to total plant diversity across the region. Across the flora of Java, we identify 26 “hot clades” with plant species providing a high probability of finding antibiotic constituents. In addition, 24 “cold clades” constitute lineages with low numbers of reported activities but which have the potential to yield novel compounds. Spatial patterns of plant species and metabolite diversity are strongly correlated across Java, indicating that regions of highest species diversity afford the highest potential to discover novel natural products. Our results indicate that the combination of phylogenetic, spatial, and phytochemical information is a useful tool to guide the selection of taxa for efforts aimed at lead compound discovery.

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“…The leaf disc was 591 subsequently covered with moist filter paper (Whatman) and sealed with Parafilm® measurements. In this case the fluorescence could be used indirectly as a "benchmark" for the 604 growth inhibition induced by the test compounds (Michels et al, 2015). The Bacillus subtilis 605 168 strain was grown on TY media with 1% tryptone, 0.5% yeast extract, 1% NaCl and 606 chloramphenicol (5 ug/ml) for selection.…”

Section: Computational Methods For the Calculation Of CD Spectra 535mentioning

confidence: 99%

Two novel 7-epi-zingiberene derivatives with biological activity fromSolanum habrochaitesare produced by a single cytochrome P450 monooxygenase

Zabel

Brandt

Porzel

et al. 2020

Preprint

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13Secretions from glandular trichomes potentially protect the plant against a variety of 14 aggressors. In the tomato genus, wild species constitute a rich source of chemical diversity 15 produced at the leaf surface by glandular trichomes. Previously, 7-epi-zingiberene produced 16 in several accessions of Solanum habrochaites was found to confer resistance to whiteflies 17 (Bemisia tabaci) and other insect pests. Here, we identify two derivatives of 7-epi-zingiberene 18 from S. habrochaites that had not been reported as yet. We identified them as 9-hydroxy-19 zingiberene and 9-hydroxy-10,11-epoxyzingiberene. Using a combination of genetics and 20 transcriptomics we identified a single cytochrome P450 oxygenase, ShCYP71D184 that 21 carries out two successive oxidations to generate the two sesquiterpenoids. Bioactivity assays 22 showed that only 9-hydroxy-10,11-epoxyzingiberene exhibits substantial toxicity against B. 23tabaci. In addition, both 9-hydroxy-zingiberene and 9-hydroxy-10,11-epoxyzingiberene display 24 substantial growth inhibitory activities against a range of microorganisms, including Bacillus 25 subtilis, Phytophtora infestans and Botrytis cinerea. Our work shows that trichome secretions 26 from wild tomato species can provide protection against a wide variety of organisms. In 27 addition, the availability of the genes encoding the enzymes for the pathway of 7-epi-28 zingiberene derivatives makes it possible to introduce this trait in cultivated tomato by precision 29 breeding. 30 sesquiterpene synthases able to convert Z,Z-FPP have been identified in S. habrochaites. The 59 santalene and bergamotene synthase (ShSBS) is a multiproduct cyclase which makes (+)-α-60

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A fluorescence-based bioassay for antibacterials and its application in screening natural product extracts

Cited by 10 publications

References 25 publications

Synthesis of antibacterial 1,3-diyne-linked peptoids from an Ugi-4CR/Glaser coupling approach

Synthesis of antibacterial 1,3-diyne-linked peptoids from an Ugi-4CR/Glaser coupling approach

Evaluation of plant sources for antiinfective lead compound discovery by correlating phylogenetic, spatial, and bioactivity data

Two novel 7-epi-zingiberene derivatives with biological activity fromSolanum habrochaitesare produced by a single cytochrome P450 monooxygenase

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