S-allyl cysteine

Naturally occurring alliin, the major precursor to the garlic aroma, is (RcSs)-( I )-,S -allyl-[.-cysteine sulfoxide 26 (Scheme 10) with both a chiral carbon and chiral sulfur - probably the first such compound (note that sulforaphene - see earlier - was isolated more or less simultaneously with alliin). Hence there are four possible stereoisomers. The alliin level in garlic is significant 5-14 mg g 1 fresh weight. 

Garlic oil and S-allyl-cysteine sulfoxide (Alliin), a garlic compound, exhibited similar antioxidant properties. Aged garlic extract prevents ischemia and reperfusion injuries to the heart and brain. 

Alline S-Propenyl-cysteine sulfoxide 7-L-Glutamyl-S-allyl-cysteine... 

S-Allyl cysteine Allium sativum (Liliaceae) [bulb] FlypoGlc (ALL-DB rat), T insulin secretion (N rat P cells)... 

S-alkyl cysteines, such as S-allyl cysteine (SAC), S-methyl cysteine (SMC), and S-propyl cysteines are slowly formed during sprouting from the action of y-glutamyl transpeptidase on y-glutamyl cysteines. S-allyl cysteine is also rapidly formed in the body by hydrolysis of y-glutamyl cysteine particularly in the kidney which contains an abundant amount of Y-glutamyl transpeptidase activity [2]. 

Boiling of whole cloves inactivates the enzyme allinase and only 0.5-1% of alliin is converted to allicin which is rapidly converted to diallyl trisulfide. Also 12% of the y-glutamylcysteines are hydrolyzed to S-allyl cysteine (SAC) and S-l-propenyl cysteine. A similar loss of alliin is found [37]. Boiling of crushed or tiny chopped garlic enables tiie formation of allicin... 

S-allyl cysteine (SAC) neurotrophic, prevention of atherosclerosis, depression of liver carcinogenesis, blocking NMOR formation, blocking NF-kappa B activation, GST activiation, prevention of colon cancer, reduction of BaP-DNA adduct formation 71-73, 76-78. 

S-allyl cysteine (SAC) may be useful for prevention of aUierosclerosis and can protect vascular endothelial cells from injury caused by oxidized LDL. Pulmonary artery endothelial cells pre-incubated with S-allylcysteine (0.1, 1, 10 and 20 mM) at 37°C and 5% CO2 for 24 h, washed, and then exposed to 0.1 m ml oxidized LDL for 24 h, significantly prevented membrane damage, loss of cell viability and lipid peroxidation. This indicates that SAC can protect vascular endothelial cells from injury caused by oxidized LDL, and suggest tiiat it may be useful for prevention of atherosclerosis [72]. 

S-allyl cysteine (SAC), was found to protect bovine pulmonary artery endothelial cells from oxidant injury induced by hydrogen peroxide (H2O2). Also, SAC may act via antioxidant mechanisms to block NF-kappa B activation in Jurkat cells in which it consistently exhibited a dose-dependent inhibition of NF-kappa B activation induced by both TNF-alpha and H2O2. Supershift with specific antibodies to NF-kappa B subunits confirmed that the inducible retarded bands observed in the... 

Geng Z, Rong Y, Lau BH. S-Allyl cysteine inhibits activation of nuclear factor kappa B in human T cells. Free Radic Biol Med 1997 23 345-350. 

Takeyama H, Hoon DS, Saxton RE, Morton DL, Irie RF. Growth inhibition and modulation of cell markers of melanoma by S-allyl cysteine. Oncology 1993 50 63-69. 

Known active constituents of garlic (there are at least 35 other constituents whose actions are unknown) ajoene, allicin, aliin, allixin, allyl mercaptan, allyl methyl thiosulfmate, allyl methyl trisulfide, allyl propyl disulfide, diallyl disulfide, diallyl hepta sulfide, diallyl hexa sulfide, diallyl penta sulfide, diallyl sulfide, diallyl tetra sulfide, diallyl tri sulfide, dimethyl disulfide, dimethyl trisulfide, dirpopyl disulfide, methyl ajoene, methyl allyl thiosulfmate, propyline sulfide, 2-vinyl-4H-l, 3-tithiin, 3-vinyl-4H-1, 2dithiin, S-allyl cysteine sulfoxide, S-allyl mercapto, cysteine. 

Kim, K.M. et al.. Differential regulation of NO availability from macrophages and endothelial cells by the garlic component S-allyl cysteine. Free Radical Biol. Med., 30, 747,2001. 

Treatment of alloxan diabetic rats with S-allyl cysteine sulphoxide isolated from garlic Allium sativum L.), amehorated the diabetic condition almost to the same extent as did glibenclamide and insulin (Augusti and Sheela 1996). S-Allyl cysteine sulphoxide significantly stimulated in vitro in-... 

Ho SE, Ide N, Lau BH (2001) S-allyl cysteine reduces oxidant load in cells involved in the atherogenic process. Phytomedicine 8(l) 39-46... 

S-allyl cysteine sulfoxide ( S-2-Drooenvl cvsteine sulfoxide)... 

FIGURE 18.4. Formation of flavor compounds from S-allyl cysteine sulfoxide. 

Sheela, C.G. and August , K.T. 1992. Antidiabetic effects of S-allyl cysteine sulphoxide isolated from garlic Allium sativum Linn. Indian J Exp Biol 30 6) 523-526. 

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