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Chemical Compound Review

Alliin     (2S)-2-amino-3-prop-2- enylsulfinyl...

Synonyms: ACSO, CHEMBL464166, AG-E-28180, AG-F-94694, AC1L3DDL, ...
 
 
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Disease relevance of Alliin

  • Vitamins C and E significantly enhanced the anticancer efficacy of alliin in inhibiting colon and fibrosarcoma tumor growth [1].
  • Recombinant garlic alliin lyase was produced in Escherichia coli, Saccharomyces cerevisiae, and Pichia pastoris [2].
  • Considering that oxygen toxicity and the related free radical attack are involved in many pathophysiological conditions, and that Allium sativum (ASP) has been used therapeutically for many of them since antiquity, we examined the intervention of ASP and alliin in free radical processes [3].
 

High impact information on Alliin

  • CONCLUSIONS: Alliin lyase was found to be a major garlic allergen in a garlic-allergic group of patients in Taiwan. The wide distribution of alliin lyase in Allium suggests it may be a new cross-reactive allergen [4].
  • Comparison of the chemopreventive efficacies of garlic powders with different alliin contents against aflatoxin B1 carcinogenicity in rats [5].
  • Inhibition of carcinogen-induced DNA damage in rat liver and colon by garlic powders with varying alliin content [6].
  • Non-derivatized analysis of methiin and alliin in vegetables by capillary electrophoresis [7].
  • DNA damage induced by aflatoxin B1 in the liver or by 1,2-dimethylhydrazine in the colon were also decreased strongly by the three garlic powders but these decreases were not correlated to the alliin content of the garlic powders [6].
 

Biological context of Alliin

 

Anatomical context of Alliin

 

Associations of Alliin with other chemical compounds

  • Identification and immunologic characterization of an allergen, alliin lyase, from garlic (Allium sativum) [4].
  • High-performance ion-pair chromatography method for simultaneous analysis of alliin, deoxyalliin, allicin and dipeptide precursors in garlic products using multiple mass spectrometry and UV detection [13].
  • HPLC of S-Alk(en)yl-L-cysteine Derivatives in Garlic including Quantitative Determination of (+)-S-Allyl-L-cysteine Sulfoxide (Alliin) [14].
  • Natural antibodies to dietary proteins: the existence of natural antibodies to alliinase (Alliin lyase) and mannose-specific lectin from garlic (Allium sativum) in human serum [15].
  • Alliin Lyase from Garlic, Allium sativum: Investigations on Enzyme/Substrate, Enzyme/Inhibitor Interactions, and on a New Coenzyme [16].
 

Gene context of Alliin

  • The antioxidant vitamins C and E significantly (P < 0.001) enhanced the inhibitory efficacy of alliin on FGF2-induced EC tube formation and angiogenesis [1].
  • Alliin significantly inhibited both FGF2 and VEGF secretion from human fibrosarcoma cells in a concentration-dependent manner [1].
  • Additionally, alliin up-regulated the p53 production in FGF2-stimulated EC [1].
  • However, alliin and diallyl disulfide, organosulfur compounds from garlic, did not improve memory performance nor AChE inhibitory effect [17].
  • All the active substrates tested with onion alliin lyase were also active to the cysteine-S-conjugate beta-lyase of Mucor javanicus, but the catalytic activity of the Mucor enzyme was lower for all the substrates [18].
 

Analytical, diagnostic and therapeutic context of Alliin

References

  1. Anti-angiogenesis efficacy of the garlic ingredient alliin and antioxidants: role of nitric oxide and p53. Mousa, A.S., Mousa, S.A. Nutrition and cancer. (2005) [Pubmed]
  2. Recombinant expression of alliin lyase from garlic (Allium sativum) in bacteria and yeasts. Weik, R., Francky, A., Striedner, G., Raspor, P., Bayer, K., Mattanovich, D. Planta Med. (1998) [Pubmed]
  3. Effect on active oxygen species of alliin and Allium sativum (garlic) powder. Kourounakis, P.N., Rekka, E.A. Res. Commun. Chem. Pathol. Pharmacol. (1991) [Pubmed]
  4. Identification and immunologic characterization of an allergen, alliin lyase, from garlic (Allium sativum). Kao, S.H., Hsu, C.H., Su, S.N., Hor, W.T., Chang T, W.H., Chow, L.P. J. Allergy Clin. Immunol. (2004) [Pubmed]
  5. Comparison of the chemopreventive efficacies of garlic powders with different alliin contents against aflatoxin B1 carcinogenicity in rats. Bergès, R., Siess, M.H., Arnault, I., Auger, J., Kahane, R., Pinnert, M.F., Vernevaut, M.F., le Bon, A.M. Carcinogenesis (2004) [Pubmed]
  6. Inhibition of carcinogen-induced DNA damage in rat liver and colon by garlic powders with varying alliin content. Singh, V., Belloir, C., Siess, M.H., Le Bon, A.M. Nutrition and cancer. (2006) [Pubmed]
  7. Non-derivatized analysis of methiin and alliin in vegetables by capillary electrophoresis. Horie, H., Yamashita, K. Journal of chromatography. A. (2006) [Pubmed]
  8. Effect of purified allicin, the major ingredient of freshly crushed garlic, on cancer cell proliferation. Hirsch, K., Danilenko, M., Giat, J., Miron, T., Rabinkov, A., Wilchek, M., Mirelman, D., Levy, J., Sharoni, Y. Nutrition and cancer. (2000) [Pubmed]
  9. Effect of a garlic derivative (alliin) on peripheral blood cell immune responses. Salman, H., Bergman, M., Bessler, H., Punsky, I., Djaldetti, M. Int. J. Immunopharmacol. (1999) [Pubmed]
  10. Apoptotic killing of B-chronic lymphocytic leukemia tumor cells by allicin generated in situ using a rituximab-alliinase conjugate. Arditti, F.D., Rabinkov, A., Miron, T., Reisner, Y., Berrebi, A., Wilchek, M., Mirelman, D. Mol. Cancer Ther. (2005) [Pubmed]
  11. The antioxidant properties of garlic compounds: allyl cysteine, alliin, allicin, and allyl disulfide. Chung, L.Y. Journal of medicinal food. (2006) [Pubmed]
  12. The effect of a garlic preparation on the composition of plasma lipoproteins and erythrocyte membranes in geriatric subjects. Brosche, T., Platt, D., Dorner, H. British journal of clinical practice. Supplement. (1990) [Pubmed]
  13. High-performance ion-pair chromatography method for simultaneous analysis of alliin, deoxyalliin, allicin and dipeptide precursors in garlic products using multiple mass spectrometry and UV detection. Arnault, I., Christidès, J.P., Mandon, N., Haffner, T., Kahane, R., Auger, J. Journal of chromatography. A. (2003) [Pubmed]
  14. HPLC of S-Alk(en)yl-L-cysteine Derivatives in Garlic including Quantitative Determination of (+)-S-Allyl-L-cysteine Sulfoxide (Alliin). Ziegler, S.J., Sticher, O. Planta Med. (1989) [Pubmed]
  15. Natural antibodies to dietary proteins: the existence of natural antibodies to alliinase (Alliin lyase) and mannose-specific lectin from garlic (Allium sativum) in human serum. Tchernychev, B., Rabinkov, A., Mirelman, D., Wilchek, M. Immunol. Lett. (1995) [Pubmed]
  16. Alliin Lyase from Garlic, Allium sativum: Investigations on Enzyme/Substrate, Enzyme/Inhibitor Interactions, and on a New Coenzyme. Jansen, H., Müller, B., Knobloch, K. Planta Med. (1989) [Pubmed]
  17. Improvement of scopolamine-induced memory impairment by Z-ajoene in the water maze in mice. Yamada, N., Hattori, A., Hayashi, T., Nishikawa, T., Fukuda, H., Fujino, T. Pharmacol. Biochem. Behav. (2004) [Pubmed]
  18. Cysteine-S-conjugate beta-lyase activity and pyridoxal phosphate binding site of onion alliin lyase. Kitamura, N., Shimomura, N., Iseki, J., Honma, M., Chiba, S., Tahara, S., Mizutani, J. Biosci. Biotechnol. Biochem. (1997) [Pubmed]
  19. Changes in Contents of gamma-Glutamyl Peptides and Fructan during Growth of Allium sativum. Matsuura, H., Inagaki, M., Maeshige, K., Ide, N., Kajimura, Y., Itakura, Y. Planta Med. (1996) [Pubmed]
  20. Liquid chromatographic determination of alliin in garlic and garlic products. Mochizuki, E., Nakayama, A., Kitada, Y., Saito, K., Nakazawa, H., Suzuki, S., Fujita, M. J. Chromatogr. (1988) [Pubmed]
  21. Alliin lyase (alliinase) from garlic (Allium sativum): crystallization and preliminary X-ray characterization. Shimon, L.J., Rabinkov, A., Miron, T., Mirelman, D., Wilchek, M., Frolow, F. Acta Crystallogr. D Biol. Crystallogr. (2002) [Pubmed]
  22. 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]
 
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