Description
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. It reduces the survival of prostate cancer PC-3 cells (IC50 = 22 μM) and inhibits the growth of human colon adenocarcinoma HCT15 cells (IC50 = 11.5 μM). DATS suppresses the growth of PC-3 xenografts in vivo in mice and induces vascular smooth muscle relaxation. 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.
Chemical Properties
Diallyl trisulfide is a yellow liquid with a disagreeable odor. It is a stable transformation product of allicin. Insoluble in water and ethanol, miscible in ether. Natural products are found in onions, garlic, etc. Diallyl trisulfide (DATS) and diallyl disulfide (DADS) are the two major organosulfides in garlic oil.
Occurrence
Reported found in garlic oil.
Uses
Diallyl trisulfide (DATS) has been used to study its antimicrobial effects against
Campylobacter jejuni. It has also been used to test its effect on hepatic regeneration in partial hepatectomy (PHx) rats.
Uses
Diallyl Trisulfide, is an organosulfur garlic compound that induces neovasculogenesis and has preventive effects against ischemic injuries. Antiarrythmic effect.
Preparation
In nature, diallyl trisulfide is formed from alliin and allicin.
Definition
ChEBI: Diallyl trisulfide is an organic trisulfide that is trisulfane in which both of the hydrogens are replaced by allyl groups. A component of the essential oil of garlic and a major component of the traditional Chinese medicine allitridium, it exhibits antifungal, antitumour and antioxidant activity It has a role as an apoptosis inducer, an estrogen receptor antagonist, an antineoplastic agent, a vasodilator agent, an antioxidant, an anti-inflammatory agent, an insecticide, an antiprotozoal drug, a platelet aggregation inhibitor and an antilipemic drug.
General Description
Diallyl trisulfide (DATS) is one of the organosulfur compounds found in garlic (
Allium sativum), and other
Allium genera such as onions. This sulfur-rich compound is produced by the rapid disintegration of its metabolic precursor Allicin.
Biochem/physiol Actions
DATS is a potent anti-cancer and chemopreventive agent that regulates apoptosis, metastasis, cell cycle, and angiogenesis in cancer pathways. It is also an excellent neuroprotective agent. DATS elicits antioxidant and anti-inflammatory activities against doxorubicin (DOX)-induced rats brains. It may improve glycemic control, muscle glucose utilization, and insulin secretion in streptozotocin-induced diabetic rats.
References
[1] GLORIA A BENAVIDES. Hydrogen sulfide mediates the vasoactivity of garlic.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2007: 17977-17982. DOI:
10.1073/pnas.0705710104[2] DONG XIAO. 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[J]. Oncogene, 2004, 23 33: 5594-5606. DOI:
10.1038/sj.onc.1207747[3] TAKASHI HOSONO. Diallyl trisulfide suppresses the proliferation and induces apoptosis of human colon cancer cells through oxidative modification of beta-tubulin.[J]. The Journal of Biological Chemistry, 2005, 280 50: 41487-41493. DOI:
10.1074/jbc.m507127200[4] DONG XIAO. Diallyl trisulfide suppresses growth of PC-3 human prostate cancer xenograft in vivo in association with Bax and Bak induction.[J]. Clinical Cancer Research, 2006, 12 22: 6836-6843. DOI:
10.1158/1078-0432.ccr-06-1273[5] ZHE ZHOU. Microarray analysis of altered gene expression in diallyl trisulfide-treated HepG2 cells.[J]. Pharmacological Reports, 2005, 57 6: 818-823.
[6] GUPTA NISHA Porter T D. Garlic and Garlic-Derived Compounds Inhibit Human Squalene Monooxygenase[J]. Journal of Nutrition, 2001, 131 6: Pages 1662-1667. DOI:
10.1093/jn/131.6.1662
