Allixin
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Preferred IUPAC name
3-Hydroxy-5-methoxy-6-methyl-2-pentyl-4H-pyran-4-one | |
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UNII | |
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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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.
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
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]
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Bis(allixinato)oxovanadium(IV)
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Bis(allixinato)zinc(II)
References
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- PMID 11911208.
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- ^ PMID 9335231.
- ^ Nishino, H.; Nishino, A.; Takayasu, J.; Iwashima, A.; Itakura, Y.; Kodera, Y.; Matsuura, H.; Fuwa, T. (1990). "Antitumor-promoting activity of allixin, a stress compound produced by garlic". Cancer Journal. 3 (1): 20–21.
- PMID 1909211.
- PMID 8439494.
- S2CID 20891167.
- S2CID 44533555.
- PMID 16722643.
- S2CID 11210678.
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