Antithrombotic and anticancer effects of garlic-derived sulfur compounds: A review

BioFactors

Volumn 26, Issue 2, 2006, Pages 93-103

  Ariga, Toyohiko ^a   Seki, Taiichiro ^a  

^a NONE

Author keywords

Alliinase; Allyl sulfides; Cancer; Garlic; Thrombosis

Indexed keywords

ALLIIN LYASE; ALLYL SULFIDE; CASPASE 3; GARLIC EXTRACT; GLUTATHIONE TRANSFERASE; ORGANOSULFUR DERIVATIVE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE (PHOSPHATE) DEHYDROGENASE (QUINONE);

ABSORPTION; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; APOPTOSIS; CANCER; CANCER PREVENTION; CELL CYCLE; CELL GROWTH; CHEMICAL STRUCTURE; DETOXIFICATION; DNA DAMAGE; ENZYME INDUCTION; GARLIC; GROWTH INHIBITION; HUMAN; LEUKEMIA CELL; LIPID PEROXIDATION; NONHUMAN; PHYTOCHEMISTRY; PLANT; PRIORITY JOURNAL; REVIEW; THROMBOSIS; THROMBOSIS PREVENTION; TUMOR CELL LINE;

ALLYL COMPOUNDS; ANIMALS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; ANTIOXIDANTS; CARBON-SULFUR LYASES; CASPASE 3; CASPASES; CHEMOPREVENTION; CYTOCHROME P-450 ENZYME SYSTEM; FIBRINOLYTIC AGENTS; GARLIC; HUMANS; INTESTINAL ABSORPTION; PHYTOTHERAPY; SULFIDES;

ALLIUM SATIVUM;

EID: 33745541339     PISSN: 09516433     EISSN: None     Source Type: Journal    
DOI: 10.1002/biof.5520260201     Document Type: Review

References (73)

1. S.V. Amonkar and A. Banerj, Isolation and characterization of larvicidal principle of garlic, Science 174 (1971), 1343-1344.
2. S.V. Amonkar and E.L. Reeves, Mosquito control with active principle of garlic, Allium sativum, J. Econ. Entomol. 63 (1970), 1172-1175.
3. R. Apitz-Castro, J.J. Badimon and L. Badimon, Effect of ajoene, the major antiplatelet compound from garlic, on platelet thrombus formation, Thromb. Res. 68 (1992), 145-155.
4. R. Apitz-Castro, S. Cabrera, M.R. Cruz, E. Ledezma and M.K. Jain, Effect of garlic extract and of three pure components isolated from it on human platelet aggregation, arachidonate metabolism. Release reaction, and platelet ultra structure, Thromb. Res. 32 (1983), 155-169.
5. T. Ariga, H. Kumagai, M. Yoshikawa, H. Kawakami, T. Seki, H. Sakurai, I. Hasegawa, T. Etoh, H. Sumiyoshi, T. Tsuneyoshi, S. Sumi and K. Iwai, Garlic-like but odorless plant Allium ampeloprasum 'Mushuu-ninniku', J. Japan Soc. Hort. Sci. 71 (2002), 362-369.
6. T. Ariga, S. Oshiba and T. Tamada, Platelet aggregation inhibitor in garlic, Lancet 1 (1981), 150-151.
7. T. Ariga and T. Seki, Functional foods from garlic and onion, in: Asian Functional Foods, J. Shi, Chi-Tang Hoo and F. Shahidi, eds, CRC Press, 2005, pp. 433-489.
8. T. Ariga, T. Seki, K. Ando, S. Teramoto and H. Nishimura, Anti-platelet principle found in the essential oil of garlic (Allium sativum) and its inhibition mechanism, in: Developments in Food Engineering, eds, T. Yano, R. Matsuno and K. Nakamura, Tokyo: Blackey A & P, 1994, pp. 1056-1058.
9. T. Ariga, A. Takeda, S. Teramoto and T. Seki, Inhibition site of methylallyl trisulfide: A volatile oil component of garlic, in the platelet arachidonic acid cascade, in: Food Factors for Cancer Prevention, H. Ohigashi, T. Osawa, J. Terao, S. Watanabe and T. Yoshikawa, eds, Tokyo: Springer-Verlag, 1997, pp. 231-234.
10. T. Ariga, K. Tsuji, T. Seki, T. Moritomo and J. Yamamoto, Antithrombotic and antineoplastic effects of phyto-organosulfur compounds, BioFactors 13 (2000), 251-255.
11. S. Balasenthil, C.R. Ramachandran and S. Nagini, S-allylcysteine, a garlic constituent, inhibits 7,12-dimethylbenz[a] anthracene-induced hamster buccal pouch carcinogenesis, Nutr. Cancer 40 (2001), 165-172.
12. S. Balasenthil, K.S. Rao and S. Nagini, Apoptosis induction by S-allylcysteine, a garlic constituent, during 7,12-dimethylbenz[a]anthracene- induced hamster buccal pouch carcinogenesis, Cell Biochem. Funct. 20 (2002), 263-268.
13. E. Block, The chemistry of garlic and onions, Scid. Am. 252 (1985), 114-119.
14. E. Block, The organosulfur chemistry of the genus Allium: implication for organic chemistry of sulfur, Angew. Chem. Ed. Engl. 31 (1992), 1135-1178.
15. B. Challier, J.M. Peramau and J.F Viel, Garlic, onion and cereal fibre as protective factors for breast cancer: a French case-control study, Eur. J. Epidemiol. 14 (1998), 737-747.
16. G.S. Ellmore and R.S. Feldberg, Alliin lyase localization in bundle sheaths of the garlic clove (Allium sativum), Am. J. Bot. 81 (1994), 89-94.
17. T. Fukao, T. Hosono, S. Misawa, T. Seki and T. Ariga, Chemoprotective effect of diallyl trisulfide from garlic against carbon tetrachloride-induced acute liver injury of rats, Biofactors 21 (2004), 171-174.
18. T. Fukao, T. Hosono, S. Misawa, T. Seki and T. Ariga, The effects of allyl sulfides on the induction of phase II detoxification enzymes and liver injury by carbon tetrachloride, Food Chem. Toxicol. 42 (2004), 743-749.
19. T. Fukumoto, N. Sato, Y. Kato, F. Tsunashima, H. Kumagai, H. Sakurai, T. Oowada, A. Ozaki and T. Mizutani, Decomposition of S-allyl-L-cysteine sulfoxide, a precursor of garlic odors, in germ-free rats, 2nd Intl Conf. Food Factors (Japan). 1999. Abst. p. 186.
20. E.V. Goryachenkova, Enzyme in garlic which forms allycine (allyinase), a protein with phosphopyridoxal, Chem. Abst. 47 (1953), 4928, (Russian).
21. D. Guyonnet, R. Berges, M.H. Siess, M.F. Pinnert, M.C. Chagnon, M. Suschetet and A.M. Le Bon, Post-initiation modulating effects of allyl sulfides in rat hepatocarcinogenesis, Food Chem. Toxicol. 42 (2004), 1479-1485.
22. D. Haber-Mignard, M. Suschetet, R. Berges, P. Astorg and M.H. Siess, Inhibition of aflatoxin B1- and N-nitrosodiethylamine-induced liver preneoplastic foci in rats fed naturally occurring allyl sulfides, Nutr. Cancer 25 (1996), 61-70.
23. K. Hara, T. Hosono, T. Seki and T. Ariga, Diallyl trisulfide-induced apoptosis in HL-60 cells, Annual Meeting of Japan Soc. Biosci. Biotechnol. Agrochem., 2005, Abst. 106.
24. A. Herman-Antosiewicz and S.V. Singh, Checkpoint kinase 1 regulates diallyl trisulfide-induced mitotic arrest in human prostate cancer cells, J. Biol. Chem. 280 (2005), 28519-28528.
25. T. Hosono, T. Fukao, J. Ogihara, Y. Ito, H. Shiba, T. Seki and T. Ariga, Diallyl trisulfide suppresses the proliferation and induces apoptosis of human colon cancer cells through oxidative modification of β-tubulin, J. Biol. Chem. 280 (2005), 41487-41493.
26. A.W. Hsing, A.P. Chokkalingam, Y.T. Gao, M.P. Madigan, J. Deng, G. Gridley and J.F. Fraumeni Jr, Allium vegetables and risk of prostate cancer: a population-based study, J. Natl. Cancer Inst. 94 (2002), 1648-1651.
27. J. Hu, C.L. Vecchia, E. Negri, L. Chatenoud, C. Bosetti, X. Jia, R. Liu, G. Huang, D. Bi and C. Wang, Diet and brain cancer in adults: a case-control study in northeast China, Int. J. Cancer 81 (1999), 20-23.
28. B. Iberl, G. Winkler and K. Knobloch, Products of allicin transformation: ajoenes and dithiins, characterization and their determination by HPLC, Planta, Med. 56 (1990), 202-211.
29. H. Jansen, B. Mueller and K. Knobloch, Characterization of an alliin lyase preparation from garlic (Allium sativum), Planta. Med. 55 (1989), 434-439.
30. T.J. Key, P.B Silcocks, G.K. Davey, P.N. Appleby and D.T. Bishop, A case-control study of diet and prostate cancer, Br. J. Cancer 76 (1997), 678-687.
31. F. Khanum, K.R. Anilakumar and K.R. Viswanathan, Anticarcinogenic properties of garlic: a review, Crit. Rev. Food Sci. Nutr. 44 (2004), 479-488.
32. J.E. Lancaster and M.L. Shaw, Gamma-glutamyl peptides in the biosynthesis of S-alk(en)yl-L-cysteine sulphoxides (flavour precursors) in Allium, Phytochemistry 28 (1989), 455-460.
33. J.E. Lancaster and M.L. Shaw, Metabolism of gamma-glutamyl peptides during development, storage, and sprouting of onion bulbs, Phytochemistry 30 (1991), 2857-2859.
34. L.D. Lawson and B.G. Hughes, Characterization of the formation of allicin and other thiosulfinates from garlic, Planta. Med. 58 (1992), 345-350.
35. L.D. Lawson and Z.J. Wang, Allicin and allicin-derived garlic compounds increase breath acetone through allyl methyl sulfide: use in measuring allicin bioavailability, J. Agric. Food Chem. 53 (2005), 1974-1983.
36. L.D. Lawson, The composition and chemistry of garlic cloves and processed garlic, in: Garlic, (2nd ed.), H.P. Koch and L.D. Lawson, eds, Maryland: Williams & Wilkins, 1996, pp. 37-109.
37. L.D. Lawson, Z.J. Wang and B.G. Hughes, Identification and HPEC quantitation of the sulfides and dialk(en)yl thiosulfinates in commercial garlic products, Planta. Med. 57 (1991), 363-370.
38. F. Levi, C. Pasche, C.L. Vecchia, F. Lucchini and S. Franceschi, Food groups and colorectal cancer risk, Br. J. Cancer. 79 (1999), 1283-1287.
39. M. Li, J.R. Ciu, Y. Ye, J.M. Min, L.H. Zhang, K. Wang, M. Gares, J. Cros, M. Wright and J. Leung-Tack, Antitumor activity of Z-ajoene, a natural compound purified from garlic: antimitotic and microtubule-interaction properties, Carcinogenesis 23 (2002), 573-579.
40. G.B. Mahady, H. Matsuura and S.L. Pendland, Allixin, a phytoalexin from garlic, inhibits the growth of Helicobacter pylori in vitro, Am. J. Gastroenterol. 96 (2001), 3454-3455.
41. A.N. Makheja, J.Y. Vanderhoek and J.M. Bailey, Inhibition of platelet aggregation and thromboxane synthesis by onion and garlic, Lancet 1 (1979), 781.
42. M. Mazelis and L. Crews, Purification of the alliin lyase of garlic, Allium sativum L., Biochem. J. 108 (1968), 725-730.
43. J.A. Milner, Garlic: its anticarcinogenic and antitumorigenic properties, Nutr. Rev. 54 (1996), 82-86.
44. H. Nishimura and T. Ariga, Vinyldithiins in garlic and Japanese domestic Allium (A. victorialis). in: Food Phytochemicals for Cancer Prevention I, N.T. Huang, T. Osawa, C.T. Ho and R.T. Rosen, eds, ACS Symposium Series 546, Wasington, DC, 1994, pp. 128-143.
45. Y. Okada, K. Tanaka, I. Fujita, E. Sato and H. Okajima, Antioxidant activity of thiosulfinates derived from garlic, Redox Rep. 10 (2005), 96-102.
46. S. Orrenius, H. Thor and B. Jernstrom, The influence of inducers on drug-metabolizing enzyme activity and on formation of reactive drug metabolites in the liver, Ciba Found. Symp. 76 (1980), 25-42.
47. T. Otsuki, T. Seki and T. Ariga, Antinflammatory activity of allyl sulfides, 19th Japan Spice Soc. Annual meeting. (2004), Abst. 24, (Japanese).
48. K.A. Park, S. Kweon and H. Choi, Anticarcinogenic effect and modification of cytochrome P450 2E1 by dietary garlic powder in diethylnitrosamine-initiated rat hepatocarcinogenesis, J. Biochem. Mol. Biol. 35 (2002), 615-622.
49. A. Rabinkov, X.Z. Zhu, G. Grafi, G. Galili and D. Mirelman, Alliin lyase (alliinase) from garlic (Allium sativum). Biochemical characterization and cDNA cloning, Appl. Biochem. Biotechnol. 48 (1994), 149-171.
50. K. Sakamoto, L.D. Lawson and J.A. Milner, Allyl sulfides from garlic suppress the in vitro proliferation of human A549 lung tumor cells, Nutr. Cancer 29 (1997), 152-156.
51. H. Sakurai, N. Tsuchimoto, T. Fukumoto, H. Satsu, M. Shimizu and H. Kumagai, Decomposition and absorption of S-allyl-L-cysteine sulfoxide in the intestine and culture cells, Annual Meeting of Japan Soc. Biosci. Biotechnol. Agrochem. (2000), Abst. 139.
52. T. Seki, K. Tsuji, Y. Hayato, T. Moritomo and T. Ariga, Garlic and onion oils inhibit proliferation and induce differentiation of HL-60 cells, Cancer Lett. 160 (2000), 29-35.
53. K.N. Shashikanth, S.C. Basappa and V. Sreenivasamurthy, Allicin concentration in the gut of rats and its influence on the microflora, J. Food Sci. Technol. 22 (1985), 440-442.
54. L.Y. Sheen, H.W. Chen, Y.L. Kung, C.T. Liu and C.K. Lii, 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, Nutr. Cancer 35 (1999), 160-166.
55. L.Y. Sheen, H.W. Chen, S.J. Tsai and C.K. Lii, Effects of organosulfur compounds from garlic oil on the antioxidation system in rat liver and red blood cells, Food Chem. Toxicol. 39 (2001), 563-569.
56. L.Y. Sheen, C.C. Wu, C.K. Lii and S.J. Tsai, Effect of diallyl sulfide and diallyl disulfide, the active principles of garlic, on the aflatoxin B(1)-induced DNA damage in primary rat hepatocytes, Toxicol. Lett. 122 (2001), 45-52.
57. S.A. Sheweita, M. El-Gabar Abd and M. Bastawy, Carbon tetrachloride-induced changes in the activity of phase II drug-metabolizing enzyme in the liver of male rats: role of antioxidants, Toxicology 165 (2001), 217-224.
58. T.F. Slater, K.H. Cheeseman and K.U. Ingold, Carbon tetrachloride toxicity as a model for studying free-radical mediated liver injury, Philos. Trans. R. Soc. Lond. B. Biol. Sci. 311 (1985), 633-664.
59. K. Song and J.A. Milner, The influence of heating on the anticancer properties of garlic, J. Nutr. 131 (2001), 1054S-1057S.
60. K.A. Steinmetz, L.H. Kushi, R.M. Bostick, A.R. Folsom and J.D. Potter, Vegetables, fruit, and cancer prevention: a review, J. Am. Diet Assoc. 96 (1996), 1027-1039.
61. K.A. Steinmetz and J.D. Potter, Vegetables, fruit, and colon cancer in the Iowa's Women's Health Study, Am. J. Epidemiol. 139 (1994), 1-15.
62. A. Stoll and E. Sheebeck, Chemical investigation of alliin, the specific principle of garlic, Adv. Enzymol. 11 (1951), 377-400.
63. M. Sugii, T. Suzuki and S. Nagasawa, Isolation of (-)S-propenyl-L- cysteine from garlic, Chem. Pharm. Bull. 11 (1963), 548-549.
64. S.G. Sundaram and J.A. Milner, Diallyl disulfide inhibits the proliferation of human tumor cells in culture, Biochim. Biophys. Acta 1315 (1996), 15-20.
65. T. Suzuki, M. Sugii and T. Kakimoto, Metabolic incorporation of L-valine-[C14] into S-(2-carboxypropyl) glutathione and S-(2-carboxypropyl) cysteine in garlic, Chem. Pharm. Bull. 10 (1962), 328-331.
66. T. Suzuki, M. Sugii and T. Kakimoto, New gamma-glutamyl peptides in garlic, Chem. Pharm. Bull. 9 (1961), 77-78.
67. T. Suzuki, M. Sugii, T. Kakimoto and N. Tsuboi, Isolation of (-) S-allyl-L-cysteine from garlic, Chem. Pharm. Bull. 9 (1961), 251-252.
68. E.J.M. Van Damme, K. Smeets, S. Terrekens, F. Van Leuven and W.J. Peumans, Isolation and characterization of alliinase cDNA clones from garlic (Allium sativum L.) and related species, Eur. J. Biochem. 209 (1992), 751-757.
69. C.C. Wu, L.Y. Sheen, H.W. Chen, W.W. Kuo, S.J. Tsai and C.K. Lii, Differential effects of garlic oil and its three major organosulfur components on the hepatic detoxification system in rats, J. Agric. Food Chem. 50 (2002), 378-383.
70. C.C. Wu, L.Y. Sheen, H.W. Chen, S.J. Tsai and C.K. Lii, Effects of organosulfur compounds from garlic oil on the antioxidation system in rat liver and red blood cells, Food Chem. Toxicol. 39 (2001), 563-569.
71. D. Xiao, S. Choi, D.E. Johnson, V.G. Vogel, C.S. Johnson, D.L. Trump, Y.J. Lee and S.V. Singh, 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 23 (2004), 5594-5606.
72. D. Xiao, A. Herman-Antosiewicz, J. Antosiewicz, H. Xiao, M. Brisson, J.S. Lazo and S.V. Singh, Diallyl trisulfide-induced G2-M phase cell cycle arrest in human prostate cancer cells is caused by reactive oxygen species-dependent destruction and hyperphosphorylation of Cdc25C, Oncogene 24 (2005), 6256-6268.
73. C.S. Yang, S.K. Chhabra, J.Y. Hong and T.J. Smith, Mechanisms of inhibition of chemical toxicity and carcinogenesis by diallyl sulfide (DAS) and related compounds from garlic, J. Nutr. 131 (2001), 1041S-1045S.