1/30/2019

Ajoene(in Garlic)

(amy.cheng@cimasci.com)




Garlic (Allium Satirum L.) is a perennial herb of the family Liliaceae. 
Garlic could be classified into purple garlic and white garlic, large garlic, and small garlic.
Garlic is rich in vitamins, amino acids, proteins, sugars, inorganic salts, and other nutrients. In addition, it contains selenium, barium and other trace elements, vitamin B1, vitamin A, vitamin C, SOD and other natural ingredients with obvious pharmacological activities.

The main active ingredients: Alliin, Allicin, research shows that these sulfur compounds have significant effects in reducing blood fat, improving immunity, bactericidal and antibacterial, anti-aging, promoting blood flow, anti-cancer and anti-cancer.

Black garlic has a soft, non-sticky taste, moderate sweetness, and sourness, no spicy or odor. Moreover, the content of sulfur compounds such as Ajoene and S-allyl-cysteine (SAC) is increased. Therefore, the physiological function of black garlic is greatly improved compared with fresh garlic.

Ajoene



Product name: Ajoene 
Other name:4,5,9-trithiadodeca-1,6,11-triene-9-oxide)
Molecular formula:C9H14OS3
Molar mass:234.4g/mol
Two isomers:(E)-Ajoene;(Z)-Ajoene
Z-ajoene is more active than E-ajoene due to the presence of cis-carbon double bonds



The production process of ajoene in garlic:

Fresh garlic contains alliin (C6H11O3NS) and alliinase, which are present in the cytoplasm and vacuole, respectively. When garlic is broken, alliin is converted to allyl sulfenic acid (C3H6OS) and dehydroalanine (C3H5O2N) by the action of alliinase. Allyl sulfonic acid is produced allicin (ie, two Allyl thiosulfinate, C6H10OS2)by disproportionation reaction. Allicin is extremely unstable and will be further decomposed into diallyl sulfide compounds (C6H10Sn, n=1~6), dithiane (C6H8S2) and ajoene (C9H14OS3, E, and Z). Therefore, it can be said that ajoene in garlic is the second degradation product of alliin.



Factors affecting the production of ajoene:
  
 Enzymatic hydrolysis time 5-30min
 pH5.0-6.5
 Temperature 4—35°C
 Solvent type Use:non-polar or weakly polar solvents (such as n-hexane, vegetable oil, etc.), polar solvents (such as methanol, ethanol, etc.)

The physiological function of ajoene

Ajoene is a highly biologically active sulfide that has the effects of preventing cardiovascular disease, anti-oxidation, anti-thrombosis, lowering blood pressure, reducing the incidence of Alzheimer's disease, resisting pathogenic bacteria, anti-virus, and improving immunity.

Ajoene has no spicy odor of garlic and is more biologically active than ether sulfur compounds and dithiene. Therefore, ajoene is easily accepted by people and has greater application potential in the production of medicines and health products.


Reference:The production process of ajoene in black garlic and its anti-hypertensive effect,by Guangyong Zhou,Prof.Yelian Miao

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