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

Abstract 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 e...

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Autores principales:	Roman Leontiev, Nils Hohaus, Claus Jacob, Martin C. H. Gruhlke, Alan J. Slusarenko
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2018
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/ef14f614f2c74399ad101e6e03db8467
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spelling	oai:doaj.org-article:ef14f614f2c74399ad101e6e03db84672021-12-02T11:40:26ZA Comparison of the Antibacterial and Antifungal Activities of Thiosulfinate Analogues of Allicin10.1038/s41598-018-25154-92045-2322https://doaj.org/article/ef14f614f2c74399ad101e6e03db84672018-04-01T00:00:00Zhttps://doi.org/10.1038/s41598-018-25154-9https://doaj.org/toc/2045-2322Abstract 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.Roman LeontievNils HohausClaus JacobMartin C. H. GruhlkeAlan J. SlusarenkoNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 8, Iss 1, Pp 1-19 (2018)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Roman Leontiev Nils Hohaus Claus Jacob Martin C. H. Gruhlke Alan J. Slusarenko A Comparison of the Antibacterial and Antifungal Activities of Thiosulfinate Analogues of Allicin
description	Abstract 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.
format	article
author	Roman Leontiev Nils Hohaus Claus Jacob Martin C. H. Gruhlke Alan J. Slusarenko
author_facet	Roman Leontiev Nils Hohaus Claus Jacob Martin C. H. Gruhlke Alan J. Slusarenko
author_sort	Roman Leontiev
title	A Comparison of the Antibacterial and Antifungal Activities of Thiosulfinate Analogues of Allicin
title_short	A Comparison of the Antibacterial and Antifungal Activities of Thiosulfinate Analogues of Allicin
title_full	A Comparison of the Antibacterial and Antifungal Activities of Thiosulfinate Analogues of Allicin
title_fullStr	A Comparison of the Antibacterial and Antifungal Activities of Thiosulfinate Analogues of Allicin
title_full_unstemmed	A Comparison of the Antibacterial and Antifungal Activities of Thiosulfinate Analogues of Allicin
title_sort	comparison of the antibacterial and antifungal activities of thiosulfinate analogues of allicin
publisher	Nature Portfolio
publishDate	2018
url	https://doaj.org/article/ef14f614f2c74399ad101e6e03db8467
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A Comparison of the Antibacterial and Antifungal Activities of Thiosulfinate Analogues of Allicin

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