Perspective on recent developments on sulfur-containing agents and hydrogen sulfide signaling

Planta Medica

Volumn 74, Issue 13, 2008, Pages 1580-1592

  Jacob, Claus ^a   Anwar, Awals ^a   Burkholz, Torsten ^a  

^a SAARLAND UNIVERSITY   (Germany)

Author keywords

Garlic; Hydrogen sulfide; Natural sulfur products; Polysulfides; Vascular homeostasis

Indexed keywords

ALLICIN; ALLYL SULFIDE; CARBON MONOXIDE; CYSTATHIONINE BETA SYNTHASE; CYSTATHIONINE GAMMA LYASE; DIALLYL DISULFIDE; DIALLYL TRISULFIDE; DISULFIDE; HYDROGEN SULFIDE; NITRIC OXIDE; S ALLYLCYSTEINE; SULFIDE; THIOL DERIVATIVE; THIONINE;

BEAN; BRAIN TISSUE; DIET; FOOD PROCESSING; FRUIT; GARLIC; GAS TRANSPORT; HEALTH STATUS; HEART PROTECTION; HUMAN; LIVER; MOLECULAR MECHANICS; MUSHROOM; ONION; REVIEW; SMOOTH MUSCLE; VASCULAR SMOOTH MUSCLE;

ALLIUM; ANTICARCINOGENIC AGENTS; HYDROGEN SULFIDE; MOLECULAR STRUCTURE; PLANT EXTRACTS; SIGNAL TRANSDUCTION; SULFUR; SULFUR COMPOUNDS;

ALLIUM SATIVUM; BASIDIOMYCOTA;

EID: 56249132709     PISSN: 00320943     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0028-1088299     Document Type: Review

References (52)

1. Jacob C. A scent of therapy: pharmacological implications of natural products containing redox-active sulfur atoms. Nat Prod Rep 2006; 23: 851-63
2. Das DK. Hydrogen sulfide preconditioning by garlic when it starts to smell. Am J Physiol Heart Circ Physiol 2007; 293: H2629-H30
3. Block E. The organosulfur chemistry of the genus Allium-implications for the organic chemistry of sulfur. Angew Chem Int Ed Engl 1992; 31: 1135-78
4. Biteau B, Labarre J, Toledano MB. ATP-dependent reduction of cysteine-sulphinic acid by S-cerevisiae sulphiredoxin. Nature 2003; 425: 980-4
5. Giles CI, Tasker KM, Jacob C. Hypothesis: The role of reactive sulfur species in oxidative stress. Free Radic Biol Med 2001; 31: 1279-83
6. Munday R, Munday J, Munday CM. Comparative effects of mono-, di-, tri-, and tetrasulfides derived from plants of the allium family: Redox cycling in vitro and hemolytic activity and phase 2 enzyme induction in vivo. Free Radic Biol Med 2003; 34: 1200-11
7. Xiao D, Herman-Antosiewicz A, Antosiewicz J, Xiao H, Brisson M, Lazo JS et al. Dialiyl 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 Cdc25C Oncogene 2005; 24: 6256-68
8. Hosono T, Fukao T, Ogihara J, Ito Y, Shiba H, Seki T et al. Dialiyl 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
9. Ha MW, Ma R, Shun LP, Gong YH, Yuan Y. Effects of allitridi on cell cycle arrest of human gastric cancer cells. World J Gastroenterol 2005; 11: 5433-7
10. Jakubíková J, Sedlák J. Garlic-derived organosulfides induce cytotoxicity, apoptosis, cell cycle arrest and oxidative stress in human colon carcinoma cell lines. Neoplasma 2006; 53: 191-9
11. Anwar A, Burkholz T, Scherer C, Abbas M, Lehr CM, Diederich M et al. Naturally occurring reactive sulfur species, their activity against Caco-2 cells, and possible modes of biochemical action. J Sulfur Chem 2008; 29: 251-68
12. Jacob C, Anwar A. The chemistry behind redox regulation with a focus on sulphur redox systems. Physiol Plant 2008; 133: 469-80
13. Steudel R. The chemistry of organic polysulfanes R-S-n-R(n > 2). Chem Rev 2002; 102: 3905-45
14. Muenchberg U, Anwar A, Mecklenburg S, Jacob C. Polysulfides as biologically active ingredients of garlic. Org Biomol Chem 2007; 5: 1505-18
15. Benavides GA, Squadrito GL, Mills RW, Patel HD, Isbell TS, Patel RP et al. Hydrogen sulfide mediates the vasoactivity of garlic. Proc Natl Acad Sci USA 2007; 104: 17977-82
16. Benavides GA, Mills RW, Squadrito GL, Doeller JE, Kraus DW. Effectiveness of garlic-derived sulfur compounds in H2S-Mediated vasoactivity. Free Radic Biol Med 2006; 41: S19-S20
17. Chuah SC, Moore PK, Zhu YZ. S-Allylcysteine mediates cardioprotection in an acute myocardial infarction rat model via a hydrogen sulfide-mediated pathway. Am J Physiol Heart Circ Physiol 2007; 293: H2693-H701
18. Li L, Moore PK. An overview of the biological significance of endogenous gases: new roles for old molecules. Biochem Soc Trans 2007; 35: 1138-41
19. Fiorucci S, Distrutti E, Cirino G, Wallace JL. The emerging roles of hydrogen sulfide in the gastrointestinal tract and liver. Gastroenterology 2006; 131: 259-71
20. Durazo-Quiroz F, Pastelâin-Hemâandez G, del Valle-Mondragâon L, Tenorio-Lâopez FA, Torres-Narvâaez JC, Rubio-Donnadieu F et al. El âoxido nâitrico en medicina. Gac Med Mex 2007; 143: 401-14
21. Coburn RF, Blakemore WS, Forster RE. Endogenous carbon monoxide production in man. J Clin Invest 1963; 42: 1172-8
22. Abe K, Kimura H. The possible role of hydrogen sulfide as an endogenous neuromodulator. J Neurosci 1996; 16: 1066-71
23. Szabo C. Hydrogen sulphide and its therapeutic potential. Nat Rev Drug Discov 2007; 6: 917-35
24. Wallace JL. Hydrogen sulfide-releasing anti-inflammatory drugs. Trends Pharmacol Sci 2007; 28: 501-5
25. 2S) - the third gas for interest for pharmacologists. Pharmacol Rep 2007; 59: 4-24
26. Chen CQ, Xin H, Zhu YZ. Hydrogen sulfide: third gaseous transmitter, but with great pharmacological potential. Acta Pharmacol Sin 2007; 28: 1709-16
27. Kraus JP, Janosik M, Kozich V, Mandell R, Shih V, Sperandeo MP et al. Cystathionine beta-synthase mutations in homocystinuria. Hum Mutat 1999; 13: 362-75
28. 2S as a novel endogenous gaseous K-ATP channel opener. Embo J 2001; 20: 6008-16
29. Li L, Whiteman M. Guan YY, Neo KL, Cheng Y, Lee SW et al. Characterization of a novel, water-soluble hydrogen sulfide-releasing molecule (GYY4137): New insights into the biology of hydrogen sulfide. Circulation 2008; 117: 2351-60
30. Coleman JE. Mechanism of action of carbonic anhydrase-substrate sulfonamide and anion binding. J Biol Chem 1967; 242: 5212-9
31. Leffler C, Parfenova H, Jaggar JH, Wang R. Carbon monoxide and hydrogen sulfide: gaseous messengers in cerebrovascular circulation. J Appl Physiol 2006; 100: 1065-76
32. 2S be the third endogenous gaseous transmitter? FASEB J 2002; 16: 1792-8
33. 2S-releasing enzymes of higher plants - From the field to the test tube and back. Plant Biol 2007; 9: 582-8
34. Kopriva S. Regulation of sulfate assimilation in Arabidopsis and beyond. Ann Bot 2006; 97: 479-95
35. Rodrigue R, Jordan JW, Mollis JP. Nematodes - biological control in rice fields - role of hydrogen sulfide. Science 1965; 148: 524-6
36. Miller DL, Roth MB. Hydrogen sulfide increases thermotolerance and lifespan in Caenorhabditis elegans. Proc Natl Acad Sci USA 2007; 104: 20618-22
37. Blachier F, Mariotti F, Huneau JF, Tome D. Effects of amino acid-derived luminal metabolites on the colonie epithelium and physiopathological consequences. Amino Acids 2007; 33: 547-62
38. Levine J, Ellis CJ, Furne JK, Springfield J, Levitt MD. Fecal hydrogen sulfide production in ulcerative colitis. Am J Gastroenterol 1998; 93: 83-7
39. Suarez F, Fume J, Springfield J, Levin M. Production and elimination of sulfur-containing gases in the rat colon. Am J Physiol Gastrointest Liver Physiol 1998; 37: G727-G33
40. Washio J, Sato T, Koseki T, Takahashi N. Hydrogen sulfide-producing bacteria in tongue biofilm and their relationship with oral malodour. J Med Microbiol 2005; 54: 889-95
41. Mendes-Ferreira A, Mendes-Faia A, Leao C. Survey of hydrogen sulphide production by wine yeasts. J Food Protect 2002; 65: 1033-7
42. Mahattanatawee K. Perez-Cacho PR, Davenport T, Rouseff R. Comparison of three lychee cultivar odor profiles using gas chromatography- olfactometry and gas chromatography-sulfur detection. J Agric Food Chem 2007; 55: 1939-44
43. Miyazawa M, Osman F. Headspace constituents of Parkia speciosa seeds. Nat Prod Lett 2001; 15: 171-6
44. Chatterji T, Keerthi K, Gates KS. Generation of reactive oxygen species by a persulfide (BnSSH). Bioorg Med Chem Lett 2005; 15: 3921-4
45. Jansson EA, Huang L, Malkey R, Covoni M, Nihlén C, Olsson A et al. A mammalian functional nitrate reductase that regulates nitrite and nitric oxide homeostasis. Nat Chem Biol 2008; 4:411-7
46. Kamoun P. Endogenous production of hydrogen sulfide in mammals. Amino Acids 2004; 26: 243-54
47. Ashby MT, Aneetha H. Reactive sulfur species: Reactions of hypothiocyanite. J lnorg Biochem 2003; 96: 96-
48. Ashby MT, Aneetha H. Reactive sulfur species: aqueous chemistry of sulfenyl thiocyanates. J Am Chem Soc 2004; 126: 10216-7
49. Nagy P, Ashby MT. Reactive sulfur species: Kinetics and mechanisms of the oxidation of cysteine by hypohalous acid to give cysteine sulfenic acid. J Am Chem Soc 2007; 129: 14082-91
50. Whiteman M, Li L, Kostetski I, Chu SH, Siau JL, Bhatia M, Moore PK. Evidence for the formation of a novel nitrosothiol from the gaseous mediators nitric oxide and hydrogen sulphide. Biochem Biophys Res Commun 2006; 343: 303-10
51. AH MY, Ping CY, Mok YYP, Ling L, Whiteman M, Bhatia M, Moore PK. Regulation of vascular nitric oxide in vitro and in vivo; a new role for endogenous hydrogen sulphide? Br J Pharmacol 2006; 149: 625-34
52. Sun X, Guo T, He J, Zhao MH, Yan M, Cui FD et al. Determination of the concentration of diallyl trisulfide in rat whole blood using gas chromatography with electron-capture detection and identification of its major metabolite with gas chromatography mass spectrometry. Yakugaku Zasshi 2006; 126: 521-7