Allicin

Catalog No.S3860 Synonyms: diallyl thiosulfinate

For research use only.

Allicin (Diallyl Thiosulfinate), the main biologically active component of the freshly crushed garlic extracts, possesses various biological activities including antibacterial, antifungal and antiparasitic effects.

Allicin Chemical Structure

CAS No. 539-86-6

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Biological Activity

Description Allicin (Diallyl Thiosulfinate), the main biologically active component of the freshly crushed garlic extracts, possesses various biological activities including antibacterial, antifungal and antiparasitic effects.
In vitro

Allicin is readily permeable through phospholipid membranes aiding its biological activity. It inhibits the growth of cancer cells of murine and human origin. Allicin induces the formation of apoptotic bodies, nuclear condensation and a typical DNA ladder in cancer cells. Furthermore, activation of caspases-3, -8 and -9 and cleavage of poly(ADP-ribose) polymerase are induced by allicin[1]. Allicin is highly reactive with thiol-groups but under certain conditions it also reacts with itself forming further compounds which can also be bioactive, such as vinyl-dithiins, ajoene and polysulfanes. Since allicin is able to oxidize biomolecules such as glutathione or protein cysteine residues under physiological conditions, it fulfils the definition of a Reactive Sulfur Species (RSS). Allicin certainly acts as a “physiological antioxidant” by inducing the cellular “phase II detoxification system”. Allicin activates the redox-dependent mammalian transcription factor Nrf-2 the localization of which depends upon the Keap1 protein (Kelch-like ECH1-associated protein), presumably by oxidizing the regulatory cysteine-residues, as demonstrated for the YAP1-transcription factor which is a functional homologue of the Nrf-2 system in yeast[1]. In vitro studies show that allicin inhibits TNF-α-mediated T cell adhesion to extracellular matrix components and to endothelial cells. Allicin also inhibits TNF-α-mediated intercellular adhesion molecule-1 and vascular cell adhesion molecule-1 expression on human vascular endothelial cells.

In vivo Allicin has a protective effect on immune-mediated, Con A-induced hepatitis in mice[2].

Protocol (from reference)

Cell Research:[1]
  • Cell lines: L-929, SW480 and HeLa cells
  • Concentrations: 0-100 μM
  • Incubation Time: 24 or 48 h
  • Method: Cell viability assays are carried out as described with slight modifications. Briefly, cells are seeded at a density of 3×104 cells/well into 24-well plates. After 24 h, allicin is added to the medium at various concentrations and incubated for 24 or 48 h as indicated. At the end of the incubation, 50 μl of MTT (2 mg/ml) per well is added, and the formazan crystals formed are solubilized in acidified isopropanol after aspirating the medium. The extent of MTT reduction is measured spectrophotometrically at 570 nm, and the cell survival is expressed as percentage over the untreated control.
  • (Only for Reference)
Animal Research:[2]
  • Animal Models: Balb/c male mice
  • Dosages: 8-20 mg/kg/day
  • Administration: by oral gavage
  • (Only for Reference)

Chemical Information

Molecular Weight 162.27
Formula

C6H10OS2

Density 1.109 g/mL
CAS No. 539-86-6
Storage 2 years -20°C(in the dark) liquid
Smiles C=CCSS(=O)CC=C

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