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Chemical Compound Review

Alliosan     3-prop-2- enylsulfinylsulfanylprop-1- ene

Synonyms: Allicin, Allimed, DADSO, CHEMBL359965, CPD-9275, ...
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Disease relevance of C07600

  • We also tested allicin on erythrocytic stages and found that a 4-day regimen of allicin administered either orally or intravenously significantly decreased parasitemias and increased the survival of infected mice by 10 days [1].
  • CONCLUSIONS: These favourable results, despite the short half-life of this compound in vivo, support further studies of controlled sustained release or more prolonged administration of allicin as a treatment for aspergillosis [2].
  • Allicin (5 mg/kg body weight) was administered iv once daily for 5 days post-infection or orally (po) (9 mg/kg body weight) for 5 days pre-infection and 10 days post-infection [2].
  • Allicin in garlic protects against coronary endothelial dysfunction and right heart hypertrophy in pulmonary hypertensive rats [3].
  • Multiple administration (i.p.) of allicin elicited a marked antitumor effect in mice inoculated with B-16 melanoma and MCA-105 fibrosarcoma [4].

High impact information on C07600

  • Moreover, allicin and DADS activate the cloned TRPA1 channel when expressed in heterologous systems [5].
  • Garlic belongs to the Allium family of plants that produce organosulfur compounds, such as allicin and diallyl disulfide (DADS), which account for their pungency and spicy aroma [5].
  • Intriguingly, allicin and DADS share structural similarities with allyl isothiocyanate, the pungent ingredient in wasabi and other mustard plants that induces pain and inflammation by activating TRPA1, an excitatory ion channel on primary sensory neurons of the pain pathway [5].
  • When sporozoites were treated with allicin before injection into mice, malaria infection was completely prevented [1].
  • The effects of DADS and allicin on GST expression were especially prominent in stomach and small intestine, where there were major coordinate changes in GST subunit profiles [6].

Chemical compound and disease context of C07600


Biological context of C07600


Anatomical context of C07600


Associations of C07600 with other chemical compounds

  • Various components of garlic and aged garlic extract, including allicin, S-allylcysteine (SAC) and volatile metabolites of allicin were determined in breath, plasma and simulated gastric fluids by HPLC, gas chromatography (GC) or HPLC- and GC-mass spectrometry (MS) [17].
  • The failure of five recent clinical trials to show significant reduction in elevated serum cholesterol by a single brand of allicin-standardized garlic powder tablets is in contrast to many prior positive studies with the same brand [18].
  • Enhancement of the Fungicidal Activity of Amphotericin B by Allicin, an Allyl-Sulfur Compound from Garlic, against the Yeast Saccharomyces cerevisiae as a Model System [19].
  • All dipropenyl thiosulfinates (allicin, 1-propenyl allyl, and allyl 1-propenyl) were formed at an optimum pH of 4.5-5 [20].
  • The new stable compound allylmercaptocaptopril combines the beneficial properties of captopril and allicin and is a potential candidate for antihypertensive drug therapy [21].

Gene context of C07600


Analytical, diagnostic and therapeutic context of C07600


  1. Antimalarial activity of allicin, a biologically active compound from garlic cloves. Coppi, A., Cabinian, M., Mirelman, D., Sinnis, P. Antimicrob. Agents Chemother. (2006) [Pubmed]
  2. Efficacy of allicin, the reactive molecule of garlic, in inhibiting Aspergillus spp. in vitro, and in a murine model of disseminated aspergillosis. Shadkchan, Y., Shemesh, E., Mirelman, D., Miron, T., Rabinkov, A., Wilchek, M., Osherov, N. J. Antimicrob. Chemother. (2004) [Pubmed]
  3. Allicin in garlic protects against coronary endothelial dysfunction and right heart hypertrophy in pulmonary hypertensive rats. Sun, X., Ku, D.D. Am. J. Physiol. Heart Circ. Physiol. (2006) [Pubmed]
  4. Allicin stimulates lymphocytes and elicits an antitumor effect: a possible role of p21ras. Patya, M., Zahalka, M.A., Vanichkin, A., Rabinkov, A., Miron, T., Mirelman, D., Wilchek, M., Lander, H.M., Novogrodsky, A. Int. Immunol. (2004) [Pubmed]
  5. Pungent products from garlic activate the sensory ion channel TRPA1. Bautista, D.M., Movahed, P., Hinman, A., Axelsson, H.E., Sterner, O., Högestätt, E.D., Julius, D., Jordt, S.E., Zygmunt, P.M. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  6. Selective expression of glutathione S-transferase genes in the murine gastrointestinal tract in response to dietary organosulfur compounds. Andorfer, J.H., Tchaikovskaya, T., Listowsky, I. Carcinogenesis (2004) [Pubmed]
  7. The effects of allicin on weight in fructose-induced hyperinsulinemic, hyperlipidemic, hypertensive rats. Elkayam, A., Mirelman, D., Peleg, E., Wilchek, M., Miron, T., Rabinkov, A., Oron-Herman, M., Rosenthal, T. Am. J. Hypertens. (2003) [Pubmed]
  8. Induction of total insensitivity to capsaicin and hypersensitivity to garlic extract in human by decreased expression of TRPV1. Park, J.J., Lee, J., Kim, M.A., Back, S.K., Hong, S.K., Na, H.S. Neurosci. Lett. (2007) [Pubmed]
  9. Inhibition of GSH-dependent PGH2 isomerase in mammary adenocarcinoma cells by allicin. Shalinsky, D.R., McNamara, D.B., Agrawal, K.C. Prostaglandins (1989) [Pubmed]
  10. Caspase-independent cell death by allicin in human epithelial carcinoma cells: involvement of PKA. Park, S.Y., Cho, S.J., Kwon, H.C., Lee, K.R., Rhee, D.K., Pyo, S. Cancer Lett. (2005) [Pubmed]
  11. In vitro mechanism of inhibition of bacterial cell growth by allicin. Feldberg, R.S., Chang, S.C., Kotik, A.N., Nadler, M., Neuwirth, Z., Sundstrom, D.C., Thompson, N.H. Antimicrob. Agents Chemother. (1988) [Pubmed]
  12. Allicin from garlic strongly inhibits cysteine proteinases and cytopathic effects of Entamoeba histolytica. Ankri, S., Miron, T., Rabinkov, A., Wilchek, M., Mirelman, D. Antimicrob. Agents Chemother. (1997) [Pubmed]
  13. Ajoene, the antiplatelet compound derived from garlic, specifically inhibits platelet release reaction by affecting the plasma membrane internal microviscosity. Rendu, F., Daveloose, D., Debouzy, J.C., Bourdeau, N., Levy-Toledano, S., Jain, M.K., Apitz-Castro, R. Biochem. Pharmacol. (1989) [Pubmed]
  14. Suppression of Mycobacterium tuberculosis induced reactive oxygen species (ROS) and TNF-alpha mRNA expression in human monocytes by allicin. Hasan, N., Yusuf, N., Toossi, Z., Islam, N. FEBS Lett. (2006) [Pubmed]
  15. Effect of allicin and ajoene, two compounds of garlic, on inducible nitric oxide synthase. Dirsch, V.M., Kiemer, A.K., Wagner, H., Vollmar, A.M. Atherosclerosis (1998) [Pubmed]
  16. Allicin, a naturally occurring antibiotic from garlic, specifically inhibits acetyl-CoA synthetase. Focke, M., Feld, A., Lichtenthaler, K. FEBS Lett. (1990) [Pubmed]
  17. Determination of allicin, S-allylcysteine and volatile metabolites of garlic in breath, plasma or simulated gastric fluids. Rosen, R.T., Hiserodt, R.D., Fukuda, E.K., Ruiz, R.J., Zhou, Z., Lech, J., Rosen, S.L., Hartman, T.G. J. Nutr. (2001) [Pubmed]
  18. Allicin release under simulated gastrointestinal conditions from garlic powder tablets employed in clinical trials on serum cholesterol. Lawson, L.D., Wang, Z.J., Papadimitriou, D. Planta Med. (2001) [Pubmed]
  19. Enhancement of the Fungicidal Activity of Amphotericin B by Allicin, an Allyl-Sulfur Compound from Garlic, against the Yeast Saccharomyces cerevisiae as a Model System. Ogita, A., Fujita, K., Taniguchi, M., Tanaka, T. Planta Med. (2006) [Pubmed]
  20. Characterization of the formation of allicin and other thiosulfinates from garlic. Lawson, L.D., Hughes, B.G. Planta Med. (1992) [Pubmed]
  21. Allylmercaptocaptopril: a new antihypertensive drug. Miron, T., Rabinkov, A., Peleg, E., Rosenthal, T., Mirelman, D., Wilchek, M. Am. J. Hypertens. (2004) [Pubmed]
  22. Metabolism of diallyl disulfide by human liver microsomal cytochromes P-450 and flavin-containing monooxygenases. Teyssier, C., Guenot, L., Suschetet, M., Siess, M.H. Drug Metab. Dispos. (1999) [Pubmed]
  23. Allicin inhibits SDF-1alpha-induced T cell interactions with fibronectin and endothelial cells by down-regulating cytoskeleton rearrangement, Pyk-2 phosphorylation and VLA-4 expression. Sela, U., Ganor, S., Hecht, I., Brill, A., Miron, T., Rabinkov, A., Wilchek, M., Mirelman, D., Lider, O., Hershkoviz, R. Immunology (2004) [Pubmed]
  24. Allicin characterization and its determination by HPLC. Jansen, H., Müller, B., Knobloch, K. Planta Med. (1987) [Pubmed]
  25. Quantitative determination of allicin in garlic: supercritical fluid extraction and standard addition of alliin. Rybak, M.E., Calvey, E.M., Harnly, J.M. J. Agric. Food Chem. (2004) [Pubmed]
  26. Hypocholesterolemic effect of an enteric-coated garlic supplement. Kannar, D., Wattanapenpaiboon, N., Savige, G.S., Wahlqvist, M.L. Journal of the American College of Nutrition. (2001) [Pubmed]
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