Ajoene
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Ajoene
| Ajoene | |
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| Identifiers | |
| CAS number | 92285-01-3  |
| PubChem | 5386591 |
| ChemSpider | 4533332 |
| ChEMBL | CHEMBL122890 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C9H14OS3 |
| Molar mass | 234.4 g/mol |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Ajoene (
/ˈɑːhoʊ.iːn/) is a chemical compound available from garlic (Allium sativum). It was first isolated and studied in the laboratory in 1984 by Eric Block, Mahendra K. Jain, Rafael Apitz-Castro and coworkers.[1][2][3][4] The name (and pronunciation) is derived from "ajo", the Spanish word for garlic. It is found as a mixture of two isomers, E-, and Z- 4,5,9-trithiadodeca-1,6,11-triene 9-oxide.
Ajoene, an unsaturated disulfide, is formed from a chemical reaction involving two allicin molecules. Allicin is a sulfinyl compound that gives garlic its strong odor and flavor. The release of allicin occurs after a garlic clove is crushed or finely chopped. Subsequent formation of ajoene occurs when allicin is dissolved in various solvents including edible oils. Ajoene is also found in garlic extract. Ajoene is most stable and most abundant in macerate of garlic (chopped garlic in edible oil).
Scientists have found that ajoene has many properties of interest to current medicine. It functions as an antioxidant, by inhibiting the release of superoxide. Ajoene also has antithrombotic (anti-clotting) properties, which helps prevent platelets in the blood from forming blood clots, potentially reducing the risk of heart disease and stroke in humans. Ajoene is also known to have effective broad-spectrum antimicrobial (antibacterial and antifungal) properties,[5][6] helpful in preventing yeast infection (Candida albicans) and treating athlete's foot (tinea pedis), for example. Ajoene has been investigated as an anti-leukaemia agent for acute myeloid leukaemia therapy.[7] Ajoene has even been shown effective in inhibiting tumor cell growth by targeting the microtubule cytoskeleton of such cells and by other mechanisms.[8] In 2012 it was reported that ajoene inhibits genes controlled by quorum sensing.[9]
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References
- ^ Block E, Ahmad S, Jain MK, Crecely R, Apitz-Castro R, Cruz MR (1984). "(E,Z)-Ajoene: A potent antithrombotic agent from garlic". Journal of the American Chemical Society 106: 8295–8296. doi:10.1021/ja00338a049.
- ^ Block, Eric (1985). "The chemistry of garlic and onions". Scientific American 252 (March): 114–119. doi:10.1038/scientificamerican0385-114. PMID 3975593.
- ^ Block E, Ahmad S, Catalfamo JL, Jain MK, Apitz-Castro R (1986). "The chemistry of alkyl thiosulfinate esters. 9. Antithrombotic organosulfur compounds from garlic: structural, mechanistic, and synthetic studies". Journal of the American Chemical Society 108: 7045–7055. doi:10.1021/ ja00282a033.
- ^ Block, Eric (2010). Garlic and Other Alliums: The Lore and the Science. Royal Society of Chemistry. ISBN 978-0-85404-190-9.
- ^ Torres J, Romero H (2012). "In vitro antifungal activity of ajoene on five clinical isolates of Histoplasma capsulatum var. capsulatum". Revista Iberoamericana de Micologia 29 (1): 24–28. PMID 21635962.
- ^ Ledezma E, Apitz-Castro R (2006). "Ajoene the main active compound of garlic (Allium sativum): a new antifungal agent". Revista Iberoamericana de Micologia 23 (2): 75–80. PMID 16854181.
- ^ Hassan HT (2004). "Ajoene (natural garlic compound): a new anti-leukaemia agent for AML therapy". Leukemia Research 28 (7): 667–671. PMID 15158086.
- ^ Terrasson J, Xu B, Li M, Allart S, Davignon JL, Zhang LH, Wang K, Davrinche C (2007). "Activities of Z-ajoene against tumour and viral spreading in vitro". Fundamental & Clinical Pharmacology 21 (3): 281–289. PMID 17521297.
- ^ Givskov M, et al. (2012). "Ajoene, a sulfur rich molecule from garlic, inhibits genes controlled by quorum sensing". Antimicrobial Agents and Chemotherapy. doi:10.1128/AAC.05919-11. PMID 22314537.
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