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Chemical Compound Review

diallylsulfide     3-prop-2-enylsulfanylprop-1- ene

Synonyms: Garlic oil, Oil garlic, Allyl sulfide, CHEMBL170458, CCRIS 3252, ...
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Disease relevance of Dially monosulfide

  • Mechanisms of inhibition of chemical toxicity and carcinogenesis by diallyl sulfide (DAS) and related compounds from garlic [1].
  • In contrast, GSH reductase and GST activities in the DAS group, either 20 or 80 mg/kg body weight, were similar to the control group [2].
  • These results suggest that while reduction of EROD activity may, at least in part, contribute to the DAS-mediated inhibition of BP-induced lung cancer, anticarcinogenic effects of OSCs against BP-induced forestomach carcinogenesis seems to be independent of this mechanism [3].
  • The induction of BaP and CP induced chromosomal aberrations, micronuclei formation, and sister chromatid exchanges (SCEs) were found to be inhibited in a dose-dependent manner by DAS, I3C, CUR, and BTP [4].

High impact information on Dially monosulfide

  • We describe the different effects of DAS and DADS on hepatic CYP2B1/2, CYP3A and epoxide hydrolase (EpH) mRNAs in rats, in terms of activation profile, doses and kinetics [5].
  • The aim of this work was to describe the effect of DAS and DADS on xenobiotic-related gene expressions and to study molecular mechanisms relaying DAS effect [5].
  • Finally, we demonstrated that antibodies raised against rGSTA5 strongly reduced the antimutagenic activity of cytosols from DAS- and DADS-treated rats against AFBO [6].
  • Western blot analysis showed that DADS is a potent inducer of glutathione S-transferase A5 (rGSTA5) and AFB(1) aldehyde reductase 1 (rAFAR1), while DAS is a weak inducer of these enzymes [6].
  • In order to study the mechanisms involved in this protection, we have examined the ability of liver microsomes and cytosols from DAS- and DADS-treated rats to modulate the mutagenicity and the metabolism of AFB(1) [6].

Chemical compound and disease context of Dially monosulfide


Biological context of Dially monosulfide

  • In this study, diallyl sulfide (DAS), diallyl disulfide (DADS) and diallyl trisulfide (DATS), which are major organosulfur compounds (OSCs) of garlic, were used as experimental materials to investigate their modulation effects on cell viability and cell cycle in human liver tumor cells (J5) [8].

Anatomical context of Dially monosulfide

  • According to the results of lactate dehydrogenase (LDH) leakage and microscopic examination, 0.5 or 1 mM DAS treatment did not have any adverse effects on the viability of hepatocytes [9].
  • Dosing for 8 weeks with 200 mg/kg DAS, but not AMS or lower doses of DAS, induced bile duct obstruction and focal areas of necrosis [7].
  • Administration of DAS and DADS enhanced the weight of vital organs such as the spleen and thymus [10].
  • Diallyl sulfide (DAS) and diallyl disulfide (DADS) at 25 microg ml(-1)decreased the benzo[a]pyrene (B[a]P)-induced colony growth inhibition of human epidermal keratinocytes [11].

Associations of Dially monosulfide with other chemical compounds

  • In addition, DADS and DATS were much more potent inducers of forestomach NQO activity than DAS, which is a weak inhibitor of BP-induced forestomach tumorigenesis than the former compounds [12].
  • Diallyl sulfide (DAS), diallyl disulfide (DADS), dipropyl sulfide (DPS) and dipropyl disulfide (DPDS), were administered by gavage (1mmol/kg) to male SPF Wistar rats for 4 consecutive days [13].
  • DADS also increased the mEH levels in the liver, intestine, and kidney, while DAS and DPS moderately induced mEH level in the liver [14].
  • We found DADS and DATS, but not DAS, could be activated by the versatile epoxide-forming oxidant dimethyldioxirane (DMDO) and could strongly inhibit nuclear RNA synthesis in vitro [15].
  • 4. Both DAS and DADS increased the activity of GST and p-nitrophenol UDP-glucuronyltransferase (UDPGT 1), whereas UDPGT 2 activity was enhanced only by DAS [16].

Gene context of Dially monosulfide

  • GO and DADS inhibited glutathione peroxidase activity (p < 0.05), and DADS and DAS enhanced glutathione reductase activity (p < 0.05) [17].
  • We also found that both CYP2A5 and CYP2G1 are inhibitable by DAS in vitro [18].
  • For example, treatment of mice with DAS, which is a potent inhibitor of BP-induced pulmonary tumorigenesis, resulted in about 3.2-fold increase in pulmonary NQO activity [12].
  • QR activity, total and mu GST activities were also increased by DAS and DPDS whereas DPS increased only mu GST activity and QR activity [13].
  • Immunoblot assay showed that the protein contents of cytochrome P450 1A1, 2B1, and 3A1 were increased by garlic oil and each of three allyl sulfides, and the change among the allyl sulfides was in the order of DAS > DADS > DATS [19].

Analytical, diagnostic and therapeutic context of Dially monosulfide

  • The assay revealed a significant reduction in MN induction after treatment of cells with 5 microM but not with 10 microM DAS in mesothelial cells [20].


  1. Mechanisms of inhibition of chemical toxicity and carcinogenesis by diallyl sulfide (DAS) and related compounds from garlic. Yang, C.S., Chhabra, S.K., Hong, J.Y., Smith, T.J. J. Nutr. (2001) [Pubmed]
  2. Effects of organosulfur compounds from garlic oil on the antioxidation system in rat liver and red blood cells. Wu, C.C., Sheen, L.Y., Chen, H.W., Tsai, S.J., Lii, C.K. Food Chem. Toxicol. (2001) [Pubmed]
  3. Mechanism of differential efficacy of garlic organosulfides in preventing benzo(a)pyrene-induced cancer in mice. Srivastava, S.K., Hu, X., Xia, H., Zaren, H.A., Chatterjee, M.L., Agarwal, R., Singh, S.V. Cancer Lett. (1997) [Pubmed]
  4. Antigenotoxic potential of certain dietary constituents. Shukla, Y., Arora, A., Taneja, P. Teratog., Carcinog. Mutagen. (2003) [Pubmed]
  5. Different activation patterns of rat xenobiotic metabolism genes by two constituents of garlic. Zhang, P., Noordine, M.L., Cherbuy, C., Vaugelade, P., Pascussi, J.M., Du??e, P.H., Thomas, M. Carcinogenesis (2006) [Pubmed]
  6. Mechanisms of protection against aflatoxin B(1) genotoxicity in rats treated by organosulfur compounds from garlic. Guyonnet, D., Belloir, C., Suschetet, M., Siess, M.H., Le Bon, A.M. Carcinogenesis (2002) [Pubmed]
  7. Modulation of cytochrome P450 enzymes by organosulfur compounds from garlic. Davenport, D.M., Wargovich, M.J. Food Chem. Toxicol. (2005) [Pubmed]
  8. Differential effects of allyl sulfides from garlic essential oil on cell cycle regulation in human liver tumor cells. Wu, C.C., Chung, J.G., Tsai, S.J., Yang, J.H., Sheen, L.Y. Food Chem. Toxicol. (2004) [Pubmed]
  9. Effect of the active principle of garlic--diallyl sulfide--on cell viability, detoxification capability and the antioxidation system of primary rat hepatocytes. Sheen, L.Y., Lii, C.K., Sheu, S.F., Meng, R.H., Tsai, S.J. Food Chem. Toxicol. (1996) [Pubmed]
  10. Immunomodulatory effect of some naturally occuring sulphur-containing compounds. Kuttan, G. Journal of ethnopharmacology. (2000) [Pubmed]
  11. Inhibition of the benzo[a]pyrene-induced toxicity by allyl sulfides in human epidermal keratinocytes. Chun, H.S., Kim, H.J., Kim, Y., Chang, H.J. Biotechnol. Lett. (2004) [Pubmed]
  12. Differential induction of NAD(P)H:quinone oxidoreductase by anti-carcinogenic organosulfides from garlic. Singh, S.V., Pan, S.S., Srivastava, S.K., Xia, H., Hu, X., Zaren, H.A., Orchard, J.L. Biochem. Biophys. Res. Commun. (1998) [Pubmed]
  13. Antimutagenic activity of organosulfur compounds from Allium is associated with phase II enzyme induction. Guyonnet, D., Belloir, C., Suschetet, M., Siess, M.H., Le Bon, A.M. Mutat. Res. (2001) [Pubmed]
  14. Modulation of phase II enzymes by organosulfur compounds from allium vegetables in rat tissues. Guyonnet, D., Siess, M.H., Le Bon, A.M., Suschetet, M. Toxicol. Appl. Pharmacol. (1999) [Pubmed]
  15. Prevention of chemical carcinogen DNA binding and inhibition of nuclear RNA polymerase activity by organosulfur compounds as the possible mechanisms for their anticancer initiation and proliferation effects. Yu, F.L., Bender, W., Fang, Q., Ludeke, A., Welch, B. Cancer Detect. Prev. (2003) [Pubmed]
  16. Modification of hepatic drug-metabolizing enzymes in rat fed naturally occurring allyl sulphides. Haber, D., Siess, M.H., de Waziers, I., Beaune, P., Suschetet, M. Xenobiotica (1994) [Pubmed]
  17. Effects of garlic oil and its organosulfur compounds on the activities of hepatic drug-metabolizing and antioxidant enzymes in rats fed high- and low-fat diets. Sheen, L.Y., Chen, H.W., Kung, Y.L., Liu, C.T., Lii, C.K. Nutrition and cancer. (1999) [Pubmed]
  18. Role of CYP2A5 and 2G1 in acetaminophen metabolism and toxicity in the olfactory mucosa of the Cyp1a2(-/-) mouse. Genter, M.B., Liang, H.C., Gu, J., Ding, X., Negishi, M., McKinnon, R.A., Nebert, D.W. Biochem. Pharmacol. (1998) [Pubmed]
  19. Differential effects of garlic oil and its three major organosulfur components on the hepatic detoxification system in rats. Wu, C.C., Sheen, L.Y., Chen, H.W., Kuo, W.W., Tsai, S.J., Lii, C.K. J. Agric. Food Chem. (2002) [Pubmed]
  20. Diallylsulfide attenuates asbestos-induced genotoxicity. Lohani, M., Yadav, S., Schiffmann, D., Rahman, Q. Toxicol. Lett. (2003) [Pubmed]
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