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Allicin is an organosulfur compound obtained from garlic and leeks. [1] When fresh garlic is chopped or crushed, the enzyme alliinase converts alliin into allicin, which is responsible for the aroma of fresh garlic. [2] Allicin is unstable and quickly changes into a series of other sulfur-containing compounds such as diallyl disulfide. [3]
The sulfur compound allicin, produced by crushing or chewing fresh garlic, [10] produces other sulfur compounds: ajoene, allyl polysulfides, and vinyldithiins. [2] Aged garlic lacks allicin, but may have some activity due to the presence of S-allylcysteine. Some people suffer from allergies to garlic and other species of Allium. [2]
Alliin / ˈ æ l i. ɪ n / is a sulfoxide that is a natural constituent of fresh garlic. [1] It is a derivative of the amino acid cysteine.When fresh garlic is chopped or crushed, the enzyme alliinase converts alliin into allicin, which is responsible for the aroma of fresh garlic.
Allicin breaks down into additional organosulfur compounds. In the presence of oil or organic solvents, among the compounds formed are the isomeric vinyldithiins and ajoene . As shown in the Scheme, allicin ( 1 ) decomposes into 2-propenesulfenic acid ( 2 ) and thioacrolein ( 3 ).
Allicin, S-benzyl phenylmethanethiosulfinate, and related thiosulfinates show radical-trapping antioxidant activity associated with easy formation of sulfenic acids [12] The acyclic thiosulfinates from Allium and Brassica species possess antimicrobial, antiparasitic, antitumor and cysteine protease inhibitory activity while the natural 1,2-dithiolane-1-oxides are growth inhibitors.
In garlic, an alliinase enzyme acts on the chemical alliin converting it into allicin. The process involves two stages: elimination of 2-propenesulfenic acid from the amino acid unit (with dehydroalanine as a byproduct), and then condensation of two of the sulfenic acid molecules. Reaction scheme for the conversion: cysteine → alliin → allicin
[1] [2] [3] Various other sulfur compounds are also produced when allicin in garlic is broken down in the stomach and liver. Out of the many compounds, allyl methyl sulfide (AMS) does not break down quickly and remains in the body in significant amounts hours after consumption, resulting in an odor that can last for hours — or even for as ...
When crushed and then analyzed using a DART ion source, elephant garlic has been shown to produce both allicin, found in garlic, and syn-propanethial-S-oxide (onion lachrymatory factor), found in onion and leek, but absent in garlic, consistent with the classification of elephant garlic as a closer relative of leek than of garlic.