Reactivity of Allicin and its Transformation Products with Sulfhydryl Groups, Disulfide Groups, and Human Blood

Winkler, Georg; Iberl, Bernhard; Knobloch, Karl

doi:10.1055/s-2006-961678

Cited by 6 publications

(3 citation statements)

References 1 publication

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“…The reactivity of thiosulfinates towards thiol-groups is an important component of their antimicrobial activity 15 , 23 , 33 , 34 . The electron-withdrawing effect of the O -atom creates an electrophilic sulfur centre which reacts readily with thiols, or more specifically, with thiolate ions (Fig.…”

Section: Introductionmentioning

confidence: 99%

A Comparison of the Antibacterial and Antifungal Activities of Thiosulfinate Analogues of Allicin

Leontiev

Hohaus

Jacob

et al. 2018

Sci Rep

157

127

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Allicin (diallylthiosulfinate) is a defence molecule from garlic (Allium sativum L.) with broad antimicrobial activities in the low µM range against Gram-positive and -negative bacteria, including antibiotic resistant strains, and fungi. Allicin reacts with thiol groups and can inactivate essential enzymes. However, allicin is unstable at room temperature and antimicrobial activity is lost within minutes upon heating to >80 °C. Allicin’s antimicrobial activity is due to the thiosulfinate group, so we synthesized a series of allicin analogues and tested their antimicrobial properties and thermal stability. Dimethyl-, diethyl-, diallyl-, dipropyl- and dibenzyl-thiosulfinates were synthesized and tested in vitro against bacteria and the model fungus Saccharomyces cerevisiae, human and plant cells in culture and Arabidopsis root growth. The more volatile compounds showed significant antimicrobial properties via the gas phase. A chemogenetic screen with selected yeast mutants showed that the mode of action of the analogues was similar to that of allicin and that the glutathione pool and glutathione metabolism were of central importance for resistance against them. Thiosulfinates differed in their effectivity against specific organisms and some were thermally more stable than allicin. These analogues could be suitable for applications in medicine and agriculture either singly or in combination with other antimicrobials.

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Section: Introductionmentioning

confidence: 99%

A Comparison of the Antibacterial and Antifungal Activities of Thiosulfinate Analogues of Allicin

Leontiev

Hohaus

Jacob

et al. 2018

Sci Rep

157

127

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show abstract

“…Allicin from garlic is the most prominent sulfur-containing bioactive compound in freshly damaged garlic tissue [11,12]. It oxidizes thiol-groups in a thiol-disulfide-exchangelike manner, leading to S-thioallylated adducts [13][14][15][16][17]. Since allicin is a strongly antimicrobial compound with a broad-spectrum of activity, it has the potential for application in agricultural pest control [18][19][20][21][22].…”

Section: Introductionmentioning

confidence: 99%

Mode of Action of the Natural Product Allicin in a Plant Model: Influence on the Cytoskeleton and Subsequent Shift in Auxin Localization

et al. 2022

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Allicin is a defense substance produced by garlic cells when they are injured. It is a redox-active thiosulfinate showing redox-activity with a broad range of dose-dependent antimicrobial and biocidal activity. It is known that allicin efficiently oxidizes thiol-groups, and it has been described as a redox toxin because it alters the redox homeostasis in cells and triggers oxidative stress responses. Allicin can therefore be used as a model substance to investigate the action of thiol-specific prooxidants. In order to learn more about the effect of allicin on plants, we used pure synthetized allicin, and studied the influence of allicin on organelle movement in Tradescantia fluminensis as a cytoskeleton-dependent process. Furthermore, we investigated cytoplasmic streaming in sterile filaments of Tradescantia fluminensis, organelle movement using transgenic Arabidopsis with organelle-specifics GFP-tags, and effects on actin and tubulin in the cytoskeleton using GFP-tagged lines. Tubulin and actin were visualized by GFP-tagging in transgenic lines of Arabidopsis thaliana to visualize the influence of allicin on the cytoskeleton. Since auxin transport depends on recycling and turnover of the PIN protein involving cytoskeletal transport to and from the membrane localization sites, auxin distribution in roots was investigated using of transgenic PIN1–GFP, PIN3–GFP, DR5–GFP and DII–VENUS Arabidopsis reporter lines. Allicin inhibited cytoplasmic streaming in T. fluminensis, organelle movement of peroxi-somesperoxisomes, and the Golgi apparatus in a concentration-dependent manner. It also destroyed the correct root tip distribution of auxin, which probably contributed to the observed inhibition of root growth. These observations of the disruption of cytoskeleton-dependent transport processes in plant cells add a new facet to the mechanism of action of allicin as a redox toxin in cells.

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“…Allicin from garlic is the most prominent sulfur-containing bioactive compound in freshly damaged garlic tissue (Cavallito, 1944; Block 1992). It oxidizes thiol-groups in a thiol-disulfide-exchange-like manner leading to S-thioallylated adducts (Gruhlke et al 2011; Gruhlke et al 2010; Miron et al 2010; Pinto et al 2006; Winkler et al 1992). Since allicin is a strongly antimicrobial compound with a broad-spectrum of activity, it has the potential for application in agricultural pest control (Auger et al 2004; Freeman and Kodera 1995; Portz et al 2008; Slusarenko et al 2011; Slusarenko et al 2008).…”

Section: Introductionmentioning

confidence: 99%

Allicin From Garlic Disrupts the Cytoskeleton in Plants

Noll

Schreiber

Hermanns

et al. 2021

Preprint

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Allicin is a defence substance produced by garlic cells upon injury. It is a thiosulfinate showing redox-activity and a broad range of antimicrobial and biocidal activity. It is known that allicin efficiently oxidizes thiol-groups and it has been described as a redox toxin. In order to learn more about the effect of allicin on plants we used pure synthetized allicin, and investigated cytoplasmic streaming in sterile filaments of Tradescantia fluminensis, organelle movement using transgenic Arabidopsis with organelle-specifics GFP-tags, and effects on actin and tubulin in the cytoskeleton using GFP-tagged lines. Auxin distribution in roots was investigated using PIN1:GFP, PIN3:GFP, DR5:GFP and DII-VENUS Arabidopsis reporter lines. Allicin inhibited cytoplasmic streaming in T. fluminensis and organelle movement of peroxisomes and the golgi-apparatus in a concentration-dependent manner, inhibited root growth and destroyed the correct root tip distribution of auxin. We speculate that the cytoskeleton can be a primary receptor for allicins oxidizing properties and as a consequence cytoskeleton-dependent cellular processes are disrupted.

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Reactivity of Allicin and its Transformation Products with Sulfhydryl Groups, Disulfide Groups, and Human Blood

Cited by 6 publications

References 1 publication

A Comparison of the Antibacterial and Antifungal Activities of Thiosulfinate Analogues of Allicin

A Comparison of the Antibacterial and Antifungal Activities of Thiosulfinate Analogues of Allicin

Mode of Action of the Natural Product Allicin in a Plant Model: Influence on the Cytoskeleton and Subsequent Shift in Auxin Localization

Allicin From Garlic Disrupts the Cytoskeleton in Plants

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