allyl compounds


Summary: Alkenes with the general formula H2C=CH-CH2-R.

Top Publications

  1. Das A, Banik N, Ray S. Garlic compounds generate reactive oxygen species leading to activation of stress kinases and cysteine proteases for apoptosis in human glioblastoma T98G and U87MG cells. Cancer. 2007;110:1083-95 pubmed
    ..Garlic compounds induced apoptosis in glioblastoma cells due toproduction of ROS, increase in ER stress, decrease in Delta psi(m), and activation of stress kinases and cysteine proteases. ..
  2. Cherng J, Tsai K, Perng D, Wang J, Wei C, Lin J. Diallyl sulfide protects against ultraviolet B-induced skin cancers in SKH-1 hairless mouse: analysis of early molecular events in carcinogenesis. Photodermatol Photoimmunol Photomed. 2011;27:138-46 pubmed publisher
    ..Diallyl sulfide (DAS) has been shown to have a preventive effect against various cancers...
  3. Brozek L, Ardolino M, Morken J. Diastereocontrol in asymmetric allyl-allyl cross-coupling: stereocontrolled reaction of prochiral allylboronates with prochiral allyl chlorides. J Am Chem Soc. 2011;133:16778-81 pubmed publisher
  4. Park H, Kim G, Choi I, Kim N, Hwang H, Choi Y, et al. Inhibition of matrix metalloproteinase activities and tightening of tight junctions by diallyl disulfide in AGS human gastric carcinoma cells. J Food Sci. 2011;76:T105-11 pubmed publisher
    ..Although further studies are needed, these results suggest that DADS treatment may inhibit tumor cell motility and invasion and, therefore, act as a dietary source to decrease the risk of cancer metastasis...
  5. Choi Y, Park H. Apoptosis induction of U937 human leukemia cells by diallyl trisulfide induces through generation of reactive oxygen species. J Biomed Sci. 2012;19:50 pubmed publisher
    ..However, the mechanisms of antiproliferative activity in leukemia cells are not fully understood. In this study, the apoptotic effects of DATS were investigated in human leukemia cells...
  6. Lu X, Rasco B, Jabal J, Aston D, Lin M, Konkel M. Investigating antibacterial effects of garlic (Allium sativum) concentrate and garlic-derived organosulfur compounds on Campylobacter jejuni by using Fourier transform infrared spectroscopy, Raman spectroscopy, and electron microscopy. Appl Environ Microbiol. 2011;77:5257-69 pubmed publisher
  7. Borkowska A, Sielicka Dudzin A, Herman Antosiewicz A, Halon M, Wozniak M, Antosiewicz J. P66Shc mediated ferritin degradation--a novel mechanism of ROS formation. Free Radic Biol Med. 2011;51:658-63 pubmed publisher
    ..DATS induced G2/M arrest in WT MEFs but had no effect in the p66Shc(-/-) cell line. Moreover, increases in LIP and ROS formation were significantly attenuated in p66Shc(-/-) MEFs treated with DATS...
  8. Li W, Tian H, Li L, Li S, Yue W, Chen Z, et al. Diallyl trisulfide induces apoptosis and inhibits proliferation of A549 cells in vitro and in vivo. Acta Biochim Biophys Sin (Shanghai). 2012;44:577-83 pubmed publisher
    ..All the evidence both in vitro and in vivo suggested that DATS could be an ideal anti-cancer drug...
  9. Deng C, Rao F, Kuang S, Wu S, Shan Z, Li X, et al. Allitridi inhibits transient outward potassium currents in human atrial myocytes. Clin Exp Pharmacol Physiol. 2011;38:323-7 pubmed publisher
    ..4. The results of the present study indicate that allitridi inhibits I(to), but not I(Kur) and I(Ca), and prolongs the action potential duration in human atrial myocytes. ..

More Information


  1. Lee B, Park B, Kim S, Lee Y. Role of Bim in diallyl trisulfide-induced cytotoxicity in human cancer cells. J Cell Biochem. 2011;112:118-27 pubmed publisher
    ..Our results indicate that the cytotoxicity caused by DATS is mediated by the generation of ROS and subsequent activation of the ASK1-JNK-Bim signal transduction pathway in human breast carcinoma MDA-MB-231 cells. ..
  2. Hornillos V, Perez M, Fañanás Mastral M, Feringa B. Copper-catalyzed enantioselective allyl-allyl cross-coupling. J Am Chem Soc. 2013;135:2140-3 pubmed publisher
    ..This transformation tolerates a large variety of functionalized substrates. The versatility of this new reaction is illustrated in the catalytic asymmetric synthesis of the Martinelline alkaloids chromene derivative core...
  3. Wu P, Liu K, Huang W, Chueh F, Ko Y, Chiu T, et al. Diallyl trisulfide (DATS) inhibits mouse colon tumor in mouse CT-26 cells allograft model in vivo. Phytomedicine. 2011;18:672-6 pubmed publisher
    ..These findings indicated that DATS inhibits tumor growth in an allograft animal model. Thus, DATS may represent a colon cancer preventive agent and can be used in the future. ..
  4. Na H, Kim E, Choi M, Park J, Kim D, Surh Y. Diallyl trisulfide induces apoptosis in human breast cancer cells through ROS-mediated activation of JNK and AP-1. Biochem Pharmacol. 2012;84:1241-50 pubmed publisher
    ..These results suggest that DATS-induced apoptosis is mediated through ROS generation and subsequent activation of JNK and AP-1...
  5. Lai K, Kuo C, Ho H, Yang J, Ma C, Lu H, et al. Diallyl sulfide, diallyl disulfide and diallyl trisulfide affect drug resistant gene expression in colo 205 human colon cancer cells in vitro and in vivo. Phytomedicine. 2012;19:625-30 pubmed publisher
    ..05) in the colo 205 xenograft mice. Based on our in vitro and in vivo results, diallyl polysulfides (DAS, DADS and DATS) affected the gene expression of the multidrug resistance in colo 205 human colon cancer cells in vitro and in vivo...
  6. Zhang C, Zeng T, Zhao X, Yu L, Zhu Z, Xie K. Protective effects of garlic oil on hepatocarcinoma induced by N-nitrosodiethylamine in rats. Int J Biol Sci. 2012;8:363-74 pubmed publisher
    ..These data suggest that GO exhibited significant protection against NDEA-induced hepatocarcinogenesis, which might be related with the enhancement of the antioxidant activity and the induction of apoptosis. ..
  7. Zhang P, Le H, Kyne R, Morken J. Enantioselective construction of all-carbon quaternary centers by branch-selective Pd-catalyzed allyl-allyl cross-coupling. J Am Chem Soc. 2011;133:9716-9 pubmed publisher
    ..Strategies for distinguishing the product alkenes and application to the synthesis of (+)-?-cuparenone are also described. ..
  8. Zeng T, Zhang C, Song F, Zhao X, Xie K. Garlic oil alleviated ethanol-induced fat accumulation via modulation of SREBP-1, PPAR-?, and CYP2E1. Food Chem Toxicol. 2012;50:485-91 pubmed publisher
    ..These results suggested that GO had the potential to ameliorate alcoholic steatosis which might be related to its modulation on SREBP-1c, PPAR-?, and CYP2E1...
  9. Antony M, Singh S. Molecular mechanisms and targets of cancer chemoprevention by garlic-derived bioactive compound diallyl trisulfide. Indian J Exp Biol. 2011;49:805-16 pubmed
    ..This article reviews mechanisms and targets of cancer chemoprevention by DATS...
  10. Sieber J, Morken J. Asymmetric Ni-catalyzed conjugate allylation of activated enones. J Am Chem Soc. 2008;130:4978-83 pubmed publisher
    ..Enantioselectivities range from 91 to 94% ee for a range of substrates when chiral ligand 14 is employed. ..
  11. Zeng T, Zhang C, Zhu Z, Yu L, Zhao X, Xie K. Diallyl trisulfide (DATS) effectively attenuated oxidative stress-mediated liver injury and hepatic mitochondrial dysfunction in acute ethanol-exposed mice. Toxicology. 2008;252:86-91 pubmed publisher
    ..The increase of the hepatic and mitochondrial GSH levels and the elevation of the antioxidant enzymes activities should account for the preventive effects. ..
  12. Liu K, Chen H, Wang R, Lei Y, Sheen L, Lii C. DATS reduces LPS-induced iNOS expression, NO production, oxidative stress, and NF-kappaB activation in RAW 264.7 macrophages. J Agric Food Chem. 2006;54:3472-8 pubmed
    ..The inhibitory effect of DATS on LPS-induced iNOS expression is likely attributed to its antioxidant potential to inhibit NF-kappaB activation. ..
  13. Shrotriya S, Kundu J, Na H, Surh Y. Diallyl trisulfide inhibits phorbol ester-induced tumor promotion, activation of AP-1, and expression of COX-2 in mouse skin by blocking JNK and Akt signaling. Cancer Res. 2010;70:1932-40 pubmed publisher
    ..Taken together, the inhibitory effects of DATS on TPA-induced AP-1 activation and COX-2 expression through modulation of JNK or Akt signaling may partly account for its antitumor-promoting effect on mouse skin carcinogenesis...
  14. Guyonnet D, Belloir C, Suschetet M, Siess M, Le Bon A. Mechanisms of protection against aflatoxin B(1) genotoxicity in rats treated by organosulfur compounds from garlic. Carcinogenesis. 2002;23:1335-41 pubmed
    ..The induction of rGSTA5 and rAFAR1 is probably the main mechanism by which allyl sulfides give protection against AFB(1)-induced carcinogenesis. ..
  15. Lan H, Lu Y. Allitridi induces apoptosis by affecting Bcl-2 expression and caspase-3 activity in human gastric cancer cells. Acta Pharmacol Sin. 2004;25:219-25 pubmed
    ..The expression and activity of caspase-3 started to increase after allitridi treatment for 72 h. Allitridi induced apoptosis through down-regulation of Bcl-2, and increased caspase-3 expression and its activity. ..
  16. Arora A, Shukla Y. Induction of apoptosis by diallyl sulfide in DMBA-induced mouse skin tumors. Nutr Cancer. 2002;44:89-94 pubmed
    ..These observations suggest that induction of apoptosis may be the major contributing factor for antitumorigenic properties of DAS. ..
  17. Xiao D, Singh S. Diallyl trisulfide, a constituent of processed garlic, inactivates Akt to trigger mitochondrial translocation of BAD and caspase-mediated apoptosis in human prostate cancer cells. Carcinogenesis. 2006;27:533-40 pubmed
    ..In conclusion, the present study demonstrates that DATS-induced apoptosis in human prostate cancer cells is mediated, at least in part, by inactivation of Akt signaling axis. ..
  18. Kwon K, Yoo S, Ryu D, Yang J, Rho H, Kim J, et al. Induction of apoptosis by diallyl disulfide through activation of caspase-3 in human leukemia HL-60 cells. Biochem Pharmacol. 2002;63:41-7 pubmed
    ..The induction of apoptosis by DADS may be the pivotal mechanism by which its chemopreventative action against cancer is based. ..
  19. Wang Y, Qin J, Zheng X, Bai Y, Yang K, Xie L. Diallyl trisulfide induces Bcl-2 and caspase-3-dependent apoptosis via downregulation of Akt phosphorylation in human T24 bladder cancer cells. Phytomedicine. 2010;17:363-8 pubmed publisher
    ..These findings suggest that DATS may be an effective way for treating human bladder and other types of cancers. ..
  20. Xiao D, Zeng Y, Singh S. Diallyl trisulfide-induced apoptosis in human cancer cells is linked to checkpoint kinase 1-mediated mitotic arrest. Mol Carcinog. 2009;48:1018-29 pubmed publisher
  21. Germain E, Auger J, Ginies C, Siess M, Teyssier C. In vivo metabolism of diallyl disulphide in the rat: identification of two new metabolites. Xenobiotica. 2002;32:1127-38 pubmed
    ..Only AMSO and AMSO(2) are significantly excreted in urine. 4. These potential metabolites are thought to be active in the target tissues. Our data warrant further studies to check this hypothesis. ..
  22. Filomeni G, Aquilano K, Rotilio G, Ciriolo M. Reactive oxygen species-dependent c-Jun NH2-terminal kinase/c-Jun signaling cascade mediates neuroblastoma cell death induced by diallyl disulfide. Cancer Res. 2003;63:5940-9 pubmed
  23. Seki T, Hosono T, Hosono Fukao T, Inada K, Tanaka R, Ogihara J, et al. Anticancer effects of diallyl trisulfide derived from garlic. Asia Pac J Clin Nutr. 2008;17 Suppl 1:249-52 pubmed
    ..These results suggest that diallyl trisulfide is responsible, at least in part, for the epidemiologically proven anticancer effect for garlic eaters. ..
  24. Nigam N, Shukla Y. Preventive effects of diallyl sulfide on 7,12-dimethylbenz[a]anthracene induced DNA alkylation damage in mouse skin. Mol Nutr Food Res. 2007;51:1324-8 pubmed
    ..49% protection, at an intermittent period of 48 h, against DMBA-induced DNA strand breakage. These findings suggest that DAS can effectively check the mutations induced by environmental toxicants. ..
  25. Morris C, Chen S, Zhou L, Schopfer L, Ding X, Mirvish S. Inhibition by allyl sulfides and phenethyl isothiocyanate of methyl-n-pentylnitrosamine depentylation by rat esophageal microsomes, human and rat CYP2E1, and Rat CYP2A3. Nutr Cancer. 2004;48:54-63 pubmed
    ..7-70 microM for inhibition by DADS. With PEITC, Ki for MPN depentylation by REM, rat CYP2E1, and rat CYP2A3 was 0.4-4.6 microM. These low Ki and IC50 values may help explain how garlic and Cruciferae inhibit carcinogenesis. ..
  26. Fisher C, Augustine L, Maher J, Nelson D, Slitt A, Klaassen C, et al. Induction of drug-metabolizing enzymes by garlic and allyl sulfide compounds via activation of constitutive androstane receptor and nuclear factor E2-related factor 2. Drug Metab Dispos. 2007;35:995-1000 pubmed
    ..These studies indicate that GO constituents, particularly DAS, activate CAR and Nrf2 to induce drug-metabolizing enzymes. ..
  27. Lu H, Sue C, Yu C, Chen S, Chen G, Chung J. Diallyl disulfide (DADS) induced apoptosis undergo caspase-3 activity in human bladder cancer T24 cells. Food Chem Toxicol. 2004;42:1543-52 pubmed
    ..DADS also increased cyclin E and decreased CDK2 gene expression which may lead to the G2/M arrest of T24 cells. ..
  28. Jeong H, Lee Y. Protective effects of diallyl sulfide on N-nitrosodimethylamine-induced immunosuppression in mice. Cancer Lett. 1998;134:73-9 pubmed
    ..The results show that the protective effects of DAS against the NDMA-induced immunotoxicity may, at least in part, be due to its ability to block bioactivation of NDMA mainly by the inhibition of cytochrome P450 2E1. ..
  29. Hui C, Jun W, Ya L, Ming X. Effect of Allium sativum (garlic) diallyl disulfide (DADS) on human non-small cell lung carcinoma H1299 cells. Trop Biomed. 2008;25:37-45 pubmed
    ..These results indicated that diallyl disulfide could induce apoptosis in human non-small cell lung carcinoma H1299 cells via, at least partly, G2/M-phase block of the cell cycle, related to a rise in MAPK phosphorylation. ..
  30. Pedraza Chaverri J, Maldonado P, Barrera D, Cerón A, Medina Campos O, Hernandez Pando R. Protective effect of diallyl sulfide on oxidative stress and nephrotoxicity induced by gentamicin in rats. Mol Cell Biochem. 2003;254:125-30 pubmed
    ..The mechanism by which DAS has a protective effect on GM-induced nephrotoxicity may be related, at least in part, to the decrease in oxidative stress in renal cortex. ..
  31. Wen J, Zhang Y, Chen X, Shen L, Li G, Xu M. Enhancement of diallyl disulfide-induced apoptosis by inhibitors of MAPKs in human HepG2 hepatoma cells. Biochem Pharmacol. 2004;68:323-31 pubmed
  32. Hassan H, El Agmy S, Gaur R, Fernando A, Raj M, Ouhtit A. In vivo evidence of hepato- and reno-protective effect of garlic oil against sodium nitrite-induced oxidative stress. Int J Biol Sci. 2009;5:249-55 pubmed
    ..However, garlic oil supplementation showed a remarkable amelioration of these abnormalities. Our data indicate that garlic is a phytoantioxidant with powerful chemopreventive properties against chemically-induced oxidative stress. ..
  33. Zeng T, Zhang C, Song F, Han X, Xie K. The modulatory effects of garlic oil on hepatic cytochrome P450s in mice. Hum Exp Toxicol. 2009;28:777-83 pubmed publisher
    ..The CYP2E1 and 1A2 suppression might contribute to its hepatoprotection, and data about CYP3A indicated that GO was unlikely to alter the metabolism of the concomitantly used drugs. ..
  34. Liu S, Sun Y, Li W, Yu H, Li X, Liu Z, et al. The antibacterial mode of action of allitridi for its potential use as a therapeutic agent against Helicobacter pylori infection. FEMS Microbiol Lett. 2010;303:183-9 pubmed publisher
    ..Our investigations on the antibacterial mode of action of allitridi provide an insight into the potential use of allitridi as a therapeutic agent against H. pylori infection. ..
  35. Zhang P, Brozek L, Morken J. Pd-catalyzed enantioselective allyl-allyl cross-coupling. J Am Chem Soc. 2010;132:10686-8 pubmed publisher
    ..In the presence of appropriate chiral ligands, this reaction is rendered enantioselective and applies to both aromatic and aliphatic allylic carbonates. ..
  36. Sener G, Sakarcan A, Yegen B. Role of garlic in the prevention of ischemia-reperfusion injury. Mol Nutr Food Res. 2007;51:1345-52 pubmed
    ..Future studies should focus on post ischemia reperfusion administration of garlic to explore its rescue potential rather than prophylactic impact. Bench research findings should be translated into clinical use through human studies. ..
  37. Park E, Kwon K, Park K, Park B, Jhee E. Role of Ca(2+) in diallyl disulfide-induced apoptotic cell death of HCT-15 cells. Exp Mol Med. 2002;34:250-7 pubmed
    ..Collectively, our data demonstrate that DADS can induce apoptosis in HCT-15 cells through the sequential mechanism of Ca(2+) homeostasis disruption, accumulation of H(2)O(2), and resulting caspase-3 activation. ..
  38. Keith J, Behenna D, Mohr J, Ma S, Marinescu S, Oxgaard J, et al. The inner-sphere process in the enantioselective Tsuji allylation reaction with (S)-t-Bu-phosphinooxazoline ligands. J Am Chem Soc. 2007;129:11876-7 pubmed
  39. Kim Y, Xiao D, Xiao H, Powolny A, Lew K, Reilly M, et al. Mitochondria-mediated apoptosis by diallyl trisulfide in human prostate cancer cells is associated with generation of reactive oxygen species and regulated by Bax/Bak. Mol Cancer Ther. 2007;6:1599-609 pubmed
    ..In conclusion, the present study reveals that the mitochondria-mediated cell death by DATS is associated with ROS generation and regulated by Bax/Bak but independent of Bcl-2 or Bcl-xL. ..
  40. Agarwal M, Iqbal M, Athar M. Garlic oil ameliorates ferric nitrilotriacetate (Fe-NTA)-induced damage and tumor promotion: implications for cancer prevention. Food Chem Toxicol. 2007;45:1634-40 pubmed
  41. Arora A, Kalra N, Shukla Y. Regulation of p21/ras protein expression by diallyl sulfide in DMBA induced neoplastic changes in mouse skin. Cancer Lett. 2006;242:28-36 pubmed
    ..Thus, one mechanism of the growth inhibitory properties of DAS is through the suppression of development of tumors that harbor ras mutations by inhibiting the membrane association of oncogenic p21/ras protein. ..
  42. Nissbrandt H, Bergquist F, Jonason J, Engberg G. Inhibition of cytochrome P450 2E1 induces an increase in extracellular dopamine in rat substantia nigra: a new metabolic pathway?. Synapse. 2001;40:294-301 pubmed
    ..Other mechanisms, such as the influence on the DA transporter or the release process cannot, however, be ruled out. ..
  43. Xiao D, Choi S, Johnson D, Vogel V, Johnson C, Trump D, et al. 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. Oncogene. 2004;23:5594-606 pubmed
    ..In conclusion, our data point towards important roles for Bcl-2, JNK and ERK in DATS-induced apoptosis in human prostate cancer cells. ..
  44. Xiao D, Herman Antosiewicz A, Antosiewicz J, Xiao H, Brisson M, Lazo J, et al. Diallyl trisulfide-induced G(2)-M phase cell cycle arrest in human prostate cancer cells is caused by reactive oxygen species-dependent destruction and hyperphosphorylation of Cdc 25 C. Oncogene. 2005;24:6256-68 pubmed
    ..In conclusion, the results of the present study indicate that DATS-induced G(2)-M phase cell cycle arrest in human prostate cancer cells is caused by ROS-mediated destruction and hyperphosphorylation of Cdc 25 C. ..
  45. Wu X, Kassie F, Mersch Sundermann V. The role of reactive oxygen species (ROS) production on diallyl disulfide (DADS) induced apoptosis and cell cycle arrest in human A549 lung carcinoma cells. Mutat Res. 2005;579:115-24 pubmed
    ..Treatment of A549 cells with N-acetyl cysteine (NAC) completely abrogated DADS-induced cell cycle arrest and apoptosis. The result indicated that oxidative stress modulates cell proliferation and cell death induced by DADS. ..
  46. Milner J. Preclinical perspectives on garlic and cancer. J Nutr. 2006;136:827S-831S pubmed publisher
    ..Likewise, additional studies are needed that incorporate transgenic and knockout models to assist in the identification of molecular targets for garlic and its associated allyl sulfur components. ..
  47. Druesne Pecollo N, Pagniez A, Thomas M, Cherbuy C, Duée P, Martel P, et al. Diallyl disulfide increases CDKN1A promoter-associated histone acetylation in human colon tumor cell lines. J Agric Food Chem. 2006;54:7503-7 pubmed
  48. Hosono T, Fukao T, Ogihara J, Ito Y, Shiba H, Seki T, et al. Diallyl trisulfide suppresses the proliferation and induces apoptosis of human colon cancer cells through oxidative modification of beta-tubulin. J Biol Chem. 2005;280:41487-93 pubmed
    ..1 Da. The potent antitumor activity of DATS was also demonstrated in nude mice bearing HCT-15 xenografts. This is the first paper describing intracellular target molecules directly modified by garlic components. ..
  49. Liu C, Hse H, Lii C, Chen P, Sheen L. Effects of garlic oil and diallyl trisulfide on glycemic control in diabetic rats. Eur J Pharmacol. 2005;516:165-73 pubmed
    ..Both garlic oil and diallyl trisulfide improve glycemic control in diabetic rats through increased insulin secretion and increased insulin sensitivity. ..
  50. Chen C, Pung D, Leong V, Hebbar V, Shen G, Nair S, et al. Induction of detoxifying enzymes by garlic organosulfur compounds through transcription factor Nrf2: effect of chemical structure and stress signals. Free Radic Biol Med. 2004;37:1578-90 pubmed
  51. Xiao D, Lew K, Kim Y, Zeng Y, Hahm E, Dhir R, et al. Diallyl trisulfide suppresses growth of PC-3 human prostate cancer xenograft in vivo in association with Bax and Bak induction. Clin Cancer Res. 2006;12:6836-43 pubmed
    ..The present study indicates that DATS administration inhibits growth of PC-3 xenografts in vivo in association with induction of Bax and Bak. ..
  52. Gayathri R, Gunadharini D, Arunkumar A, Senthilkumar K, Krishnamoorthy G, Banudevi S, et al. Effects of diallyl disulfide (DADS) on expression of apoptosis associated proteins in androgen independent human prostate cancer cells (PC-3). Mol Cell Biochem. 2009;320:197-203 pubmed publisher
    ..Bcl-2 protein has significantly decreased in DADS treated cells. Therefore, the present investigation serves as evidence that DADS may be a therapeutic drug in the treatment of prostate cancer. ..
  53. Malki A, El Saadani M, Sultan A. Garlic constituent diallyl trisulfide induced apoptosis in MCF7 human breast cancer cells. Cancer Biol Ther. 2009;8:2175-85 pubmed
    ..Together, the results of the present study show, for the first time, that DATS administration might offer a novel strategy for the treatment of human breast cancer. ..