In vitro evaluation of the antioxidant and antimicrobial activity of DIMBOA [2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one]

Gleńsk, Michał; Gajda, Beata; Franiczek, Roman; Krzyżanowska, Barbara; Biskup, Izabela; Włodarczyk, Maciej

doi:10.1080/14786419.2015.1054284

Cited by 18 publications

(20 citation statements)

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“…BXs were also analysed for antimicrobial properties against the model organisms for human pathogens Escherichia coli (Migula 1895) Castellani & Chalmers 1919, Staphylococcus aureus Rosenbach, 1884, and Candida albicans (C.P.Robin) Berkhout, as well as the yeast Saccharomyces cerevisiae Meyen ex E.C. Hansen [85][86][87]. Antimicrobial activity required concentrations above the millimolar range.…”

Section: Interactions With Microbesmentioning

confidence: 99%

Plant Protection by Benzoxazinoids—Recent Insights into Biosynthesis and Function

et al. 2018

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Benzoxazinoids (BXs) are secondary metabolites present in many Poaceae including the major crops maize, wheat, and rye. In contrast to other potentially toxic secondary metabolites, BXs have not been targets of counter selection during breeding and the effect of BXs on insects, microbes, and neighbouring plants has been recognised. A broad knowledge about the mode of action and metabolisation in target organisms including herbivorous insects, aphids, and plants has been gathered in the last decades. BX biosynthesis has been elucidated on a molecular level in crop cereals. Recent advances, mainly made by investigations in maize, uncovered a significant diversity in the composition of BXs within one species. The pattern can be specific for single plant lines and dynamic changes triggered by biotic and abiotic stresses were observed. Single BXs might be toxic, repelling, attractive, and even growth-promoting for insects, depending on the particular species. BXs delivered into the soil influence plant and microbial communities. Furthermore, BXs can possibly be used as signalling molecules within the plant. In this review we intend to give an overview of the current data on the biosynthesis, structure, and function of BXs, beyond their characterisation as mere phytotoxins.2 of 24 by the producing plant. In the so-called two-component defence systems, reactivity is reduced by chemical modification, mostly glycosylation, and simultaneously a reactivating enzyme, e.g., a glycosidase, is provided. The stabilised metabolite (component one) and activating enzyme (component two) are physically separated in different organelles or tissues but meet in case of cell damage, thereby liberating the toxin. Examples are alkaloid glucosides, benzoxazinoid glucosides, cyanogenic glucosides, glucosinolates, iridoid glucosides, and salicinoids (see [7] for review).Advances in chemical analysis and well-developed genetic resources, especially in maize, have revealed distinct functions for different BXs in defence. Furthermore, in planta signalling is a matter of debate [8]. Within maize populations, diversity in the quality and quantity of different BXs has been revealed. Recent reviews summarise the role of BXs on plant-plant allelopathy [9], deal with the interaction between BXs and insects [10], and describe the BX structure diversity and function in maize [8]. Here we aim to give an overview on the present knowledge of the biosynthesis, distribution, and biological function of different BXs. The available data on BX-mediated interactions are summarised in Table 1, providing a guide through the literature.

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Section: Interactions With Microbesmentioning

confidence: 99%

Plant Protection by Benzoxazinoids—Recent Insights into Biosynthesis and Function

et al. 2018

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“…12,13,23 In addition to the defensive effect against phytopathogens, Bex-derived compounds have also shown activity against microorganisms of medical interest. [14][15][16][17] Bravo et al 15 reported that the Bexs benzoxazolin-2-one (BOA), 2-hydroxy-1,4-benzoxazin-3-one (HBOA) and 2,4-dihydroxy-1,4-benzoxazin-3-one (DIBOA) exhibit antibacterial effects against Staphylococcus aureus and Streptococcus mutans at concentrations of 500 μg/mL, and against Escherichia coli at a concentration of 1,000 μg/mL according to microdilution broth assays. The compound, 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA; at a concentration of 2 mg/disk), is active against the bacteria Enterococcus faecalis, Klebsiella pneumoniae, Pseudomonas aeruginosa, Bacillus subtilis, S. aureus methicillin-resistant and E. coli extended-spectrum β-lactamases produced by disc diffusion.…”

Section: Resultsmentioning

confidence: 99%

“…The compound, 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA; at a concentration of 2 mg/disk), is active against the bacteria Enterococcus faecalis, Klebsiella pneumoniae, Pseudomonas aeruginosa, Bacillus subtilis, S. aureus methicillin-resistant and E. coli extended-spectrum β-lactamases produced by disc diffusion. 17 In addition, the antifungal activity of Bex-derived compounds and their metabolites have been recognized against the yeasts Candida albicans, Candida glabrata, and Saccharomyces cerevisae, and also against molds, Penicillium chrysogenum, Monilia Formosa, Phanerochaete chrysosporium and Trichoderma reesei. 12,14,17 Wang and Ng 16 showed that Bexs also have antiviral properties; 6-methoxy-benzoxazolin-2-one (MBOA) is able to inhibit reverse transcriptase from human immunodeficiency virus (HIV).…”

Section: Resultsmentioning

confidence: 99%

“…17 In addition, the antifungal activity of Bex-derived compounds and their metabolites have been recognized against the yeasts Candida albicans, Candida glabrata, and Saccharomyces cerevisae, and also against molds, Penicillium chrysogenum, Monilia Formosa, Phanerochaete chrysosporium and Trichoderma reesei. 12,14,17 Wang and Ng 16 showed that Bexs also have antiviral properties; 6-methoxy-benzoxazolin-2-one (MBOA) is able to inhibit reverse transcriptase from human immunodeficiency virus (HIV). Thus, Bexs have proven to be potential sources for the development of novel anti-infective agents.…”

Section: Resultsmentioning

confidence: 99%

“…12,13 Moreover, recent work has uncovered a critical antimicrobial activity for the compounds, covering bacteria, yeast, molds, and retroviruses of great medical importance. [14][15][16][17] Our group has previously developed and synthesized a series of new Bex analogs that have shown antimicrobial activity against microorganisms of high medical relevance such as Enterococcus faecalis, Staphylococcus aureus, Acinetobacter baumannii, Candida albicans, C. tropicalis and C. glabrata. 18 Here, we aimed to evaluate potential antileishmanial effects of these compounds against promastigotes of Leishmania (V.) braziliensis and Leishmania (L.) infantum and also aim determine the cytotoxicity of these analogs against hamster spleen cells.…”

Section: Introductionmentioning

confidence: 99%

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Toxicity and Anti-promastigote Activity of Benzoxazinoid Analogs Against Leishmania (Viannia) braziliensis and Leishmania (Leishmania) infantum

et al. 2019

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Purpose: Here, we aim to evaluate the antileishmanial activity of compounds with a benzoxazinoid (BX) skeleton, previously synthesized by our group, against Leishmania (Viannia) braziliensis and Leishmania (Leishmania) infantum promastigotes. Methods: Anti-promastigote activity, as well as cytotoxicity, were determined using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) colorimetric assays. The selectivity index (SI) for each compound was calculated using a ratio of the cytotoxicity of compounds and the geometric mean (GM) of antileishmanial concentrations to each species tested. The comparisons between groups were carried out using a t test or analysis of variance (one-way ANOVA). A P value of less than 0.05 was considered significant. Results: All the compounds tested were active, with IC50 falling between 92±6.19 µg/mL and 238±6.57 µg/mL for L. braziliensis, and 89±6.43 µg/mL and 188±3.58 µg/mL against L. infantum. Bex2, Bex3, Pyr1, Pyr2, and Pyr4 were compounds that showed activity similar to the drug Glucantime®, exhibited low cytotoxicity against splenic hamster cells (CC50 raging between >400 and 105.7±2.26 µg/mL) and had favorable selectivity indices (SI 1.12 to 3.96). Conclusion: The analogs in question are promising prototypes for the pharmaceutical development of novel, safer and more effective leishmanicidal agents.

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Neopolyploidy has variable effects on the diversity and composition of the wild strawberry microbiome

Anneberg,

Cullen,

O'Neill

et al. 2024

American J of Botany

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PremiseWhole‐genome duplication (neopolyploidy) can instantly differentiate the phenotype of neopolyploids from their diploid progenitors. These phenotypic shifts in organs such as roots and leaves could also differentiate the way neopolyploids interact with microbial species. While some studies have addressed how specific microbial interactions are affected by neopolyploidy, we lack an understanding of how genome duplication affects the diversity and composition of microbial communities.MethodsWe performed a common garden experiment with multiple clones of artificially synthesized autotetraploids and their ancestral diploids, derived from 13 genotypes of wild strawberry, Fragaria vesca. We sequenced epiphytic bacteria and fungi from roots and leaves and characterized microbial communities and leaf functional traits.ResultsAutotetraploidy had no effect on bacterial alpha diversity of either organ, but it did have a genotype‐dependent effect on the diversity of fungi on leaves. In contrast, autotetraploidy restructured the community composition of leaf bacteria and had a genotype‐dependent effect on fungal community composition in both organs. The most differentially abundant bacterial taxon on leaves belonged to the Sphingomonas, while a member of the Trichoderma was the most differentially abundant fungal taxon on roots. Ploidy‐induced change in leaf size was strongly correlated with a change in bacterial but not fungal leaf communities.ConclusionsGenome duplication can immediately alter aspects of the plant microbiome, but this effect varies by host genotype and bacterial and fungal community. Expanding these studies to wild settings where plants are exposed continuously to microbes are needed to confirm the patterns observed here.

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In vitro evaluation of the antioxidant and antimicrobial activity of DIMBOA [2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one]

Cited by 18 publications

References 10 publications

Plant Protection by Benzoxazinoids—Recent Insights into Biosynthesis and Function

Plant Protection by Benzoxazinoids—Recent Insights into Biosynthesis and Function

Toxicity and Anti-promastigote Activity of Benzoxazinoid Analogs Against Leishmania (Viannia) braziliensis and Leishmania (Leishmania) infantum

Neopolyploidy has variable effects on the diversity and composition of the wild strawberry microbiome

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