A Comparison of the Antibacterial and Antifungal Activities of Thiosulfinate Analogues of Allicin
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...
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| Published in: | Scientific reports Vol. 8; no. 1; pp. 6763 - 19 |
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| Main Authors: | , , , , |
| Format: | Journal Article |
| Language: | English |
| Published: |
London
Nature Publishing Group UK
30-04-2018
Nature Publishing Group Nature Portfolio |
| Subjects: | |
| Online Access: | Get full text |
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| Summary: | 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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| Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| ISSN: | 2045-2322 2045-2322 |
| DOI: | 10.1038/s41598-018-25154-9 |