Allixin
Chemical compound
From Wikipedia, the free encyclopedia
Allixin is a phytoalexin found in garlic (Allium sativum) bulbs. It was first isolated and characterized in 1989.[1] When garlic is stored for long periods of time, it can form visible accumulations of crystalline allixin on its surface, particularly in areas where tissue has become necrotic.[2] After 2 years of storage, the amount of allixin accumulated can approach 1% of the dry weight of the cloves. Since allixin has weak antimicrobial activity,[1] these high concentrations are thought to be produced by the garlic bulb to protect itself from further damage from microorganisms.
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| Preferred IUPAC name
3-Hydroxy-5-methoxy-6-methyl-2-pentyl-4H-pyran-4-one | |
| Identifiers | |
3D model (JSmol) |
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CompTox Dashboard (EPA) |
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| Properties | |
| C12H18O4 | |
| Molar mass | 226.272 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Since allixin is found in high concentrations in garlic, there has been scientific interest in determining if it is responsible for any of the known health benefits of garlic. As a result of ongoing research, a variety of biological activities have been attributed to allixin. Pharmaceutical drug discovery research based on derivatives of allixin has followed.[3]
Laboratory synthesis
Two laboratory syntheses of allixin have been developed. In the first method, reported in 1997, allixin was synthesized in 22 steps starting from D-mannose.[4] A shorter synthesis was developed in 1998 which involved only 5 steps, starting from 5-methylfurfural.[5]
Biological activities
In in vitro studies, allixin demonstrates neurotrophic activity, but at high concentrations it has cytotoxic effects.[6] Simple chemical analogs of allixin were found to have more potent neurotrophic activity, but without the cytotoxic effects.[6] Allixin may therefore be a useful starting point for the development of pharmaceutical drugs for the treatment of neurodegenerative disorders or for neuronal regeneration in the brain.[6]
Pharmacological studies have demonstrated that allixin exerts an anti-promoting activity against skin tumors induced by the chemical 12-O-tetradecanoylphorbol-13-acetate (TPA)[7] and an inhibitory effect on aflatoxin B1-induced mutagenesis.[8] Allixin may therefore be responsible, at least in part, for the tumor-preventative effects of garlic extract.[9][10]
Allixin has also been shown to have a radical scavenging effect.[11]
Metal complexes
Metal complexes with allixin have been shown to have beneficial pharmacological effects in animal models of diabetes.[3] A complex with vanadium, bis(allixinato)oxovanadium(IV), is a potent anti-diabetic agent. In studies in streptozotocin-induced diabetic mice, this vanadium complex was shown to be an insulin mimetic with hypoglycemic effects.[12] Similarly, a zinc-allixin complex, bis(allixinato)zinc(II), shows the same insulin mimetic effects.[13][14] The mechanism of action by which these complexes regulate insulin signaling pathways is unclear.[3]
Bis(allixinato)oxovanadium(IV)
Bis(allixinato)zinc(II)
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