Redox Modulation at Work: Natural Phytoprotective Polysulfanes From Alliums Based on Redox-Active Sulfur

Ali, Anwar; Gould, Emma; Tinson, Ryan; Iqbal, Javaid; Hamilton, Chris J.

doi:10.1007/s40495-018-0153-2

Cited by 8 publications

(5 citation statements)

References 85 publications

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“…Garlic oils are known to exhibit broad spectrum antimicrobial activitiy [1,2,3,4,5,6]. When garlic is crushed the rapid conversion of alliin to allicin is catalysed by the enzyme alliinase ( Fig.…”

Section: Introduction1mentioning

confidence: 99%

Antimicrobial garlic-derived diallyl polysulfanes: Interactions with biological thiols in Bacillus subtilis

Arbach

Santana

Moxham

et al. 2019

Biochimica et Biophysica Acta (BBA) - General Subjects

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Background: Diallylpolysulfanes are the key constituents of garlic oils, known to exhibit broad spectrum anticancer and antimicrobial activity. Studies in vitro, and in mammalian cells, have shown they react, via thiolpolysulfane exchange, with their major low molecular weight thiol, glutathione. However, there are no detailed reports of diallylpolysulfane effects on other common thiol metabolites (cysteine and coenzyme A) or major thiol cofactors (e.g. bacillithiol) that many Gram positive bacteria produce instead of glutathione. Methods: Diallylpolysulfanes were individually purified then screened for antimicrobial activity against Bacillus subtilis. Their impact on thiol metabolites (bacillithiol, cysteine, coenzyme A, protein thiols allyl thiols//persulfides) in B. subtilis cultures were analysed, by HPLC. Results: Diallylpolysulfane bioactivity increased with increasing chain length up to diallyltetrasulfane, but then plateaued. Within two minutes of treating B. subtilis with diallyltrisulfane or diallyltetrasulfane intracellular bacillithiol levels decreased by ~90%. Cysteine and CoA were also affected but to a lesser degree. This was accompanied by the accumulation of allyl thiol and allyl persulfide. A significant level of proteinS -allylation was also detected. Conclusions: In addition to the major low molecular weight thiol, diallylpolysulfanes can also have an impact on other thiol metabolites and protein thiols. General Significance: This study shows the rapid parallel impact of polysulfanes on different biological thiols inside Bacillus subtilis alongside the concomitant generation of allyl thiols and persulfides.

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Section: Introduction1mentioning

confidence: 99%

Antimicrobial garlic-derived diallyl polysulfanes: Interactions with biological thiols in Bacillus subtilis

Arbach

Santana

Moxham

et al. 2019

Biochimica et Biophysica Acta (BBA) - General Subjects

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“…The compounds found in plants of the Allium genus have traditionally been used as plant protection products for both humans and crops [12]. This characteristic is believed to be related to the presence of polysulfides and polysulfanes in large quantities, 1.4% of fresh weight [93]. The reduced forms of polysulfanes can mitigate the impact of ROS such as superoxide and bind metal ions, decreasing oxidative stress in proteins and cell membranes [90].…”

Section: Absorption and Assimilation Of Sulfur In Plantsmentioning

confidence: 99%

From Elemental Sulfur to Hydrogen Sulfide in Agricultural Soils and Plants

et al. 2019

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Sulfur is an essential element in determining the productivity and quality of agricultural products. It is also an element associated with tolerance to biotic and abiotic stress in plants. In agricultural practice, sulfur has broad use in the form of sulfate fertilizers and, to a lesser extent, as sulfite biostimulants. When used in the form of bulk elemental sulfur, or micro- or nano-sulfur, applied both to the soil and to the canopy, the element undergoes a series of changes in its oxidation state, produced by various intermediaries that apparently act as biostimulants and promoters of stress tolerance. The final result is sulfate S+6, which is the source of sulfur that all soil organisms assimilate and that plants absorb by their root cells. The changes in the oxidation states of sulfur S0 to S+6 depend on the action of specific groups of edaphic bacteria. In plant cells, S+6 sulfate is reduced to S−2 and incorporated into biological molecules. S−2 is also absorbed by stomata from H2S, COS, and other atmospheric sources. S−2 is the precursor of inorganic polysulfides, organic polysulfanes, and H2S, the action of which has been described in cell signaling and biostimulation in plants. S−2 is also the basis of essential biological molecules in signaling, metabolism, and stress tolerance, such as reactive sulfur species (RSS), SAM, glutathione, and phytochelatins. The present review describes the dynamics of sulfur in soil and plants, considering elemental sulfur as the starting point, and, as a final point, the sulfur accumulated as S−2 in biological structures. The factors that modify the behavior of the different components of the sulfur cycle in the soil–plant–atmosphere system, and how these influences the productivity, quality, and stress tolerance of crops, are described. The internal and external factors that influence the cellular production of S−2 and polysulfides vs. other S species are also described. The impact of elemental sulfur is compared with that of sulfates, in the context of proper soil management. The conclusion is that the use of elemental sulfur is recommended over that of sulfates, since it is beneficial for the soil microbiome, for productivity and nutritional quality of crops, and also allows the increased tolerance of plants to environmental stresses.

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“…Allicin decomposition occurs rapidly during heating or distillation resulting in various diallyl polysulfanes, with 2-6 sulfur atoms organized as sulfur chains, including diallyl di-, tri-, tetra-, penta-, and hexa polysulfanes (DAS2-6) [3,4]. DAS2 and DAS3 are the most frequently observed sulfur compounds present in garlic oils [12][13][14].…”

Section: Introductionmentioning

confidence: 99%

“…The mode of action of garlic sulfur compounds was attributed to S-thioallylation of LMW and protein thiols, causing rapid depletion of the reduced thiol pool upon allicin and DAS4 stress [5,7,8,19,20]. Treatment of GSH with allicin and polysulfanes in vitro results in a thiol-disulfide exchange reaction and the formation of GSH conjugated S-thioallylated di-, tri-, and tetra-sulfanes, and allyl thiols or allyl persulfides [3,9,13]. The S-thioallylated di-and trisulfanes were the major GSH conjugates measured upon GSH exposure to DAS3-6 in vitro [9].…”

Section: Introductionmentioning

confidence: 99%

The Disulfide Stress Response and Protein S-thioallylation Caused by Allicin and Diallyl Polysulfanes in Bacillus subtilis as Revealed by Transcriptomics and Proteomics

et al. 2019

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Garlic plants (Allium sativum L.) produce antimicrobial compounds, such as diallyl thiosulfinate (allicin) and diallyl polysulfanes. Here, we investigated the transcriptome and protein S-thioallylomes under allicin and diallyl tetrasulfane (DAS4) exposure in the Gram-positive bacterium Bacillus subtilis. Allicin and DAS4 caused a similar thiol-specific oxidative stress response, protein and DNA damage as revealed by the induction of the OhrR, PerR, Spx, YodB, CatR, HypR, AdhR, HxlR, LexA, CymR, CtsR, and HrcA regulons in the transcriptome. At the proteome level, we identified, in total, 108 S-thioallylated proteins under allicin and/or DAS4 stress. The S-thioallylome includes enzymes involved in the biosynthesis of surfactin (SrfAA, SrfAB), amino acids (SerA, MetE, YxjG, YitJ, CysJ, GlnA, YwaA), nucleotides (PurB, PurC, PyrAB, GuaB), translation factors (EF-Tu, EF-Ts, EF-G), antioxidant enzymes (AhpC, MsrB), as well as redox-sensitive MarR/OhrR and DUF24-family regulators (OhrR, HypR, YodB, CatR). Growth phenotype analysis revealed that the low molecular weight thiol bacillithiol, as well as the OhrR, Spx, and HypR regulons, confer protection against allicin and DAS4 stress. Altogether, we show here that allicin and DAS4 cause a strong oxidative, disulfide and sulfur stress response in the transcriptome and widespread S-thioallylation of redox-sensitive proteins in B. subtilis. The results further reveal that allicin and polysulfanes have similar modes of actions and thiol-reactivities and modify a similar set of redox-sensitive proteins by S-thioallylation.

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Redox Modulation at Work: Natural Phytoprotective Polysulfanes From Alliums Based on Redox-Active Sulfur

Cited by 8 publications

References 85 publications

Antimicrobial garlic-derived diallyl polysulfanes: Interactions with biological thiols in Bacillus subtilis

Antimicrobial garlic-derived diallyl polysulfanes: Interactions with biological thiols in Bacillus subtilis

From Elemental Sulfur to Hydrogen Sulfide in Agricultural Soils and Plants

The Disulfide Stress Response and Protein S-thioallylation Caused by Allicin and Diallyl Polysulfanes in Bacillus subtilis as Revealed by Transcriptomics and Proteomics

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