Biological Activity of Pulcherrimin from the Meschnikowia pulcherrima Clade

Kręgiel, Dorota; Nowacka, Maria; Rygała, Anna; Vadkertiová, Renáta

doi:10.3390/molecules27061855

Cited by 22 publications

(18 citation statements)

References 39 publications

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“…Pulcherrimin is known to be an iron chelator. Previous studies have shown that secreted pulcherrimin caused localized iron depletion in the media (17,44). Results from our transcriptome pro ling show that many iron homeostasis genes were downregulated in the pulcherrimin mutant, including the entire bacillibactin biosynthetic operon (dhbABCEF), bacillibactin transport genes (feuABC, fhuBCG) and the bacillibactin esterase gene besA (Fig.…”

Section: Resultsmentioning

confidence: 69%

Pulcherrimin protects Bacillus subtilis against oxidative stress during biofilm development

Chai

Angelini

Santos

et al. 2023

Preprint

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Pulcherrimin is an iron-binding reddish pigment produced by various bacterial and yeast species. In the soil bacterium Bacillus subtilis, this pigment is first synthesized intracellularly as the colorless pulcherriminic acid by using two molecules of tRNA-charged leucine as the substrate; pulcherriminic acid molecules are then secreted and bind to ferric iron extracellularly to form the red-colored pigment pulcherrimin. The biological importance of pulcherrimin is not well understood. A previous study showed that secretion of pulcherrimin caused iron depletion in the surroundings and growth arrest on cells located at the edge of a B. subtilis colony biofilm. In this study, we identified that pulcherrimin is primarily produced under biofilm conditions and provides protection to cells in the biofilm against oxidative stress. We presented molecular evidence on how pulcherrimin lowers the level of reactive oxygen species (ROS) and alleviates oxidative stress and DNA damage caused by ROS accumulation in a mature biofilm. We also performed global transcriptome profiling to identify differentially expressed genes in the pulcherrimin-deficient mutant compared to wild type, and further characterized the regulation of genes by pulcherrimin that are related to iron homeostasis, DNA damage response (DDR), and oxidative stress response. Based on our findings, we propose pulcherrimin as an important antioxidant as well as a signal modulating B. subtilis biofilm development.

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Section: Resultsmentioning

confidence: 69%

Pulcherrimin protects Bacillus subtilis against oxidative stress during biofilm development

Chai

Angelini

Santos

et al. 2023

Preprint

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show abstract

“…Pulcherrimin is known to be an iron chelator. Previous studies have shown that secreted pulcherrimin caused localized iron depletion in the media 21,51 . Results from our transcriptome profiling show that many iron homeostasis genes were downregulated in the pulcherrimin mutant, including the entire Fig.…”

Section: Synthesis Of Pulcherriminic Acid Remains Constitutive Upon C...mentioning

confidence: 98%

Pulcherrimin protects Bacillus subtilis against oxidative stress during biofilm development

Angelini

Santos

Fox

et al. 2023

npj Biofilms Microbiomes

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Pulcherrimin is an iron-binding reddish pigment produced by various bacterial and yeast species. In the soil bacterium Bacillus subtilis, this pigment is synthesized intracellularly as the colorless pulcherriminic acid by using two molecules of tRNA-charged leucine as the substrate; pulcherriminic acid molecules are then secreted and bind to ferric iron extracellularly to form the red-colored pigment pulcherrimin. The biological importance of pulcherrimin is not well understood. A previous study showed that secretion of pulcherrimin caused iron depletion in the surroundings and growth arrest on cells located at the edge of a B. subtilis colony biofilm. In this study, we identified that pulcherrimin is primarily produced under biofilm conditions and provides protection to cells in the biofilm against oxidative stress. We presented molecular evidence on how pulcherrimin lowers the level of reactive oxygen species (ROS) and alleviates oxidative stress and DNA damage caused by ROS accumulation in a mature biofilm. We also performed global transcriptome profiling to identify differentially expressed genes in the pulcherrimin-deficient mutant compared with the wild type, and further characterized the regulation of genes by pulcherrimin that are related to iron homeostasis, DNA damage response (DDR), and oxidative stress response. Based on our findings, we propose pulcherrimin as an important antioxidant that modulates B. subtilis biofilm development.

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“…In this way, Fertinagro Biotech has found an extract from the natural yeast Metschnikowia pulcherrima that exhibits urease inhibitory capacity . In the literature, the antifungal and antimicrobial properties of M. pulcherrima have been described. − According to the literature, these properties are caused by the characteristic red pigment found in this yeast, named pulcherrimin. Pulcherrimin ( 1 ) is a polymeric Fe(III) chelate of pulcherriminic acid ( 2 ). , M. pulcherrima biosynthesizes pulcherriminic acid from the cyclic dipeptide of l -leucine ( 3 ).…”

Section: Introductionmentioning

confidence: 99%

Origin of the Urease Inhibition of Metschnikowia pulcherrima Extracts: Comparative Assays with Synthetic Pulcherriminic Acid and Cyclo-dileucine

Aligué,

Atarés,

Dorado

et al. 2024

ACS Agric. Sci. Technol.

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The objective of this work was to determine whether pulcherriminic acid was responsible for the urease inhibition activity of the extracts of the yeast Metschnikowia pulcherrima. Pulcherriminic acid was synthesized through a seven-step pathway from L-leucine, starting with the thermal cyclodimerization of L-leucine to the corresponding 2,5-diketopiperazine, followed by oxidation to the 2,5-dichloropyrazine through three consecutive steps without purification of the intermediates, oxidation to the corresponding di-N-oxide, dechlorination by nucleophilic aromatic substitution with benzyloxide, and deprotection with trifluoroacetic acid without isolation of an intermediate. The urease inhibition assay showed 57 ± 2.3% inhibition of the urease activity at 500 ppm of pulcherriminic acid, much lower than the percent inhibition obtain with the extract, in which pulcherriminic acid was not detected. The cyclic dimer of L-leucine was present in the extract, and its inhibitory capacity was also tested, showing a percent inhibition of 56.1 ± 6.11% of the urease activity at 400 ppm, again much lower than the percent inhibition of the extract. This work demonstrates that the inhibitory capacity of the extracts of the yeast M. pulcherrima is not due to either only pulcherriminic acid or only its cyclic dipeptide precursor.

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Biological Activity of Pulcherrimin from the Meschnikowia pulcherrima Clade

Cited by 22 publications

References 39 publications

Pulcherrimin protects Bacillus subtilis against oxidative stress during biofilm development

Pulcherrimin protects Bacillus subtilis against oxidative stress during biofilm development

Pulcherrimin protects Bacillus subtilis against oxidative stress during biofilm development

Origin of the Urease Inhibition of Metschnikowia pulcherrima Extracts: Comparative Assays with Synthetic Pulcherriminic Acid and Cyclo-dileucine

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