Hydrogen sulfide (H2S) is an endogenously-produced gaseous second messenger that can regulate many physiological processes. Diallyl trisulfide (DATS) is an organic polysulfide compound found in garlic that acts as an H2S donor.1 It reduces the survival of prostate cancer PC-3 cells (IC50 = 22 μM)2 and inhibits the growth of human colon adenocarcinoma HCT-15 cells (IC50 = 11.5 μM).3 DATS suppresses the growth of PC-3 xenografts in vivo in mice4 and induces vascular smooth muscle relaxation.1 Garlic extracts also lower cholesterol and there is evidence that DATS can alter the expression of genes and inhibit enzymes that are relevant to cholesterol synthesis.5,6
1
Benavides, G.A., Squadrito, G.L., Mills, R.W., et al. Hydrogen sulfide mediates the vasoactivity of garlic. Proc Natl Acad Sci USA104(46)17977-17982(2007).
2
Xiao, D., Choi, S., Johnson, D.E., et al. Diallyl trisulfide-induced apoptosis in human prostate cancer cells involves c-jun N-terminal kinase and extracellular-signal regulated kinase-mediated phosphorylation of Bcl-2. Oncogene235594-5606(2004).
3
Hosono, T., Fukao, T., Ogihara, J., et al. Diallyl trisulfide supresses the proliferation and induces apoptosis of human colon cancer cells through oxidative modification of b-tubulin. J Biol Chem280(50)41487-41493(2005).
4
Xiao, D., Lew, K.L., Kim, Y., et al. Diallyl trisulfide suppresses growth of PC-3 human prostate cancer xenograft in vivo in association with bax and bak induction. Clin Cancer Res12(22)6836-6843(2006).
5
Zhou, Z., Tan, H., Xu, B., et al. Microarray analysis of altered gene expression in diallyl trisulfide-treated HepG2 cells. Pharmacol Rep57818-823(2005).
6
Gupta, N., and Porter, T.D. Garlic and garlic-derived compounds inhibit human squalene monooxygenase. J Nutr1311662-1667(2001).
Synonyms
DATS
NSC 651936
Formal Name
di-2-propen-1-yl trisdulfide
CAS Number
2050-87-5
Molecular Formula
C6H10S3
Formula Weight
178.3
Formulation
A solution in acetone
Purity
≥98%
Stability
1 year
Storage
-20°C
Shipping
Room temperature
in continental US; may vary elsewhere
SMILES
Copy SMILES to clipboard
C=CCSSSCC=C
Background Reading
Zhou, Z., Tan, H., Xu, B., et al. Microarray analysis of altered gene expression in diallyl trisulfide-treated HepG2 cells. Pharmacol Rep57818-823(2005).
Gupta, N., and Porter, T.D. Garlic and garlic-derived compounds inhibit human squalene monooxygenase. J Nutr1311662-1667(2001).
Benavides, G.A., Squadrito, G.L., Mills, R.W., et al. Hydrogen sulfide mediates the vasoactivity of garlic. Proc Natl Acad Sci USA104(46)17977-17982(2007).
Xiao, D., Choi, S., Johnson, D.E., et al. Diallyl trisulfide-induced apoptosis in human prostate cancer cells involves c-jun N-terminal kinase and extracellular-signal regulated kinase-mediated phosphorylation of Bcl-2. Oncogene235594-5606(2004).
Hosono, T., Fukao, T., Ogihara, J., et al. Diallyl trisulfide supresses the proliferation and induces apoptosis of human colon cancer cells through oxidative modification of b-tubulin. J Biol Chem280(50)41487-41493(2005).
Xiao, D., Lew, K.L., Kim, Y., et al. Diallyl trisulfide suppresses growth of PC-3 human prostate cancer xenograft in vivo in association with bax and bak induction. Clin Cancer Res12(22)6836-6843(2006).