Ajoene is a chemical compound available from garlic (Allium sativum). It is found as a mixture of four isomers, 4,5,9-trithiadodeca-1,6,11-triene 9-oxide. Two isomers of ajoene based on carbon chirality (designated E- and Z-) were early identified and isolated, and, more recently, the chirality of the sulfoxide was also identified, meaning that there are in fact four isomers of the compound, with optical isomerism associated with the sulfoxide isomers.
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 has shown potential virucidal properties against a number of viruses including vesicular stomatitis, vaccinia, human rhinovirus parainfluenza, and herpes simplex. In the infected cell system of a human immunodeficiency virus (HIV), it is shown to block the integrin-dependent processes. Ajoene is also known to have effective broad-spectrum antimicrobial (antibacterial and antifungal) properties, Ajoene has been investigated as an anti-leukemia agent for acute myeloid leukemia therapy. Ajoene has been found to decrease basal-cell carcinoma tumor size by inducing apoptosis while it has also been shown effective in inhibiting tumor cell growth by targeting the microtubule cytoskeleton of such cells and by other mechanisms. In 2012 it was reported that ajoene inhibits genes controlled by quorum sensing.
