The chemistry behind redox regulation with a focus on sulphur redox systems

Physiologia Plantarum

Volumn 133, Issue 3, 2008, Pages 469-480

  Jacob, Claus ^a   Anwar, Awais ^a  

^a SAARLAND UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

SULFUR; THIOL DERIVATIVE;

CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM; OXIDATION REDUCTION REACTION; REVIEW; SIGNAL TRANSDUCTION;

MODELS, CHEMICAL; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; SIGNAL TRANSDUCTION; SULFHYDRYL COMPOUNDS; SULFUR;

EID: 45249120583     PISSN: 00319317     EISSN: 13993054     Source Type: Journal    
DOI: 10.1111/j.1399-3054.2008.01080.x     Document Type: Review

References (45)

1. Antosiewicz J, Herman-Antosiewicz A, Marynowski SW, Singh SV (2006) c-Jun NH(2)-terminal kinase signaling axis regulates diallyl trisulfide-induced generation of reactive oxygen species and cell cycle arrest in human prostate cancer cells. Cancer Res 66 : 5379 5386
2. Arditti FD, Rabinkov A, Miron T, Reisner Y, Berrebi A, Wilchek M, Mirelman D (2005) Apoptotic killing of B-chronic lymphocytic leukemia tumor cells by allicin generated in situ using a rituximab-alliinase conjugate. Mol Cancer Ther 4 : 325 331
3. Benavides GA, Squadrito GL, Mills RW, Patel HD, Isbell TS, Patel RP, Darley-Usmar VM, Doeller JE, Kraus DW (2007) Hydrogen sulfide mediates the vasoactivity of garlic. Proc Natl Acad Sci USA 104 : 17977 17982
4. Bernardi R, Finiguerra MG, Rossi AA, Palmieri S (2003) Isolation and biochemical characterization of a basic myrosinase from ripe Crambe abyssinica seeds, highly specific for epi-progoitrin. J Agric Food Chem 51 : 2737 2744
5. Biteau B, Labarre J, Toledano MB (2003) ATP-dependent reduction of cysteine-sulphinic acid by S. cerevisiae sulphiredoxin. Nature 425 : 980 984
6. Block E (1992) The organosulfure chemistry of the genus Allium-implications for the organic chemistry of sulfur. Angew Chem Int Ed Engl 31 : 1135 1178
7. Brzostowska EM, Greer A (2003) The role of amine in the mechanism of pentathiepin (polysulfur) antitumor agents. J Am Chem Soc 125 : 396 404
8. Burmeister WP, Cottaz S, Rollin P, Vasella A, Henrissat B (2000) High resolution X-ray crystallography shows that ascorbate is a cofactor for myrosinase and substitutes for the function of the catalytic base. J Biol Chem 275 : 39385 39393
9. Chatterji T, Keerthi K, Gates KS (2005) Generation of reactive oxygen species by a persulfide (BnSSH). Bioorg Med Chem Lett 15 : 3921 3924
10. Choi MK, Chae KY, Lee JY, Kyung KH (2007) Antimicrobial activity of chemical substances derived from S-alk(en)yl-L-cysteine suffoxide (alllin) in garlic, Allium sativum L. Food Sci Biotechnol 16 : 1 7
11. Derbesy G, Harpp DN (1994) A simple method to prepare unsymmetrical disulfide trisulfide and tetrasulfide. Tetrahedron Lett 35 : 5381 5384
12. Fahey JW, Zalcmann AT, Talalay P (2001) The chemical diversity and distribution of glucosinolates and isothiocyanates among plants. Phytochemistry 56 : 5 51
13. Fimognari C, Nusse M, Cesari R, Iori R, Cantelli-Forti G, Hrelia P (2002) Growth inhibition, cell-cycle arrest and apoptosis in human T-cell leukemia by the isothiocyanate sulforaphane. Carcinogenesis 23 : 581 586
14. Fry FH, Jacob C (2006) Sensor/effector drug design with potential relevance to cancer. Curr Pharm Des 12 : 4479 4499
15. Fry FH, Okarter N, Baynton-Smith C, Kershaw MJ, Talbot NJ, Jacob C (2005) Use of a substrate/alliinase combination to generate antifungal activity in situ. J Agric Food Chem 53 : 574 580
16. Giles GI, Jacob C (2002) Reactive sulfur species: an emerging concept in oxidative stress. Biol Chem 383 : 375 388
17. Giles GI, Tasker KM, Jacob C (2001) Hypothesis: the role of reactive sulfur species in oxidative stress. Free Radic Biol Med 31 : 1279 1283
18. Giles GI, Tasker KM, Collins C, Giles NM, O'Rourke E, Jacob C (2002) Reactive sulphur species: an in vitro investigation of the oxidation properties of disulphide S-oxides. Biochem J 364 : 579 585
19. Giles NM, Watts AB, Giles GI, Fry FH, Littlechild JA, Jacob C (2003) Metal and redox modulation of cysteine protein function. Chem Biol 10 : 677 693
20. Greer A (2001) On the origin of cytotoxicity of the natural product varacin. A novel example of a pentathiepin reaction that provides evidence for a triatomic sulfur intermediate. J Am Chem Soc 123 : 10379 10386
21. Halliwell B, Gutteridge JMC (2007) Free Radicals in Biology and Medicine, 4th Edn. Oxford University Press, Oxford
22. Hanlon PR, Webber DM, Barnes DM (2007) Aqueous extract from spanish black radish (Raphanus sativus L. Var. niger) induces detoxification enzymes in the HepG2 human hepatoma cell line. J Agric Food Chem 55 : 6439 6446
23. Hosono T, Fukao T, Ogihara J, Ito Y, Shiba H, Seki T, Ariga T (2005) Diallyl trisulfide suppresses the proliferation and induces apoptosis of human colon cancer cells through oxidative modification of beta-tubulin. J Biol Chem 280 : 41487 41493
24. Iwami K, Yasumoto K, Mitsuda H (1975) Enzymatic cleavage of cysteine sulfoxide in Lentinus edodes. Agric Biol Chem 39 : 1947 1955
25. Jacob C (2006) A scent of therapy: pharmacological implications of natural products containing redox-active sulfur atoms. Nat Prod Rep 23 : 851 863
26. Jacob C, Giles GI, Giles NM, Sies H (2003) Sulfur and selenium: the role of oxidation state in protein structure and function. Angew Chem Int Ed Engl 42 : 4742 4758
27. Jacob C, Knight I, Winyard PG (2006) Aspects of the biological redox chemistry of cysteine: from simple redox responses to sophisticated signalling pathways. Biol Chem 387 : 1385 1397
28. Kazana E, Pope TW, Tibbles L, Bridges M, Pickett JA, Bones AM, Powell G, Rossiter JT (2007) The cabbage aphid: a walking mustard oil bomb. Proc R Soc B Biol Sci 274 : 2271 2277
29. Keusgen M, Junger M, Krest I, Schoning MJ (2003) Development of a biosensor specific for cysteine sulfoxides. Biosens Bioelectron 18 : 805 812
30. Kovacs JA, Brines LM (2007) Understanding how the thiolate sulfur contributes to the function of the non-heme iron enzyme superoxide reductase. Acc Chem Res 40 : 501 509
31. Lawson LD, Wang ZJ (2001) Low allicin release from garlic supplements: a major problem due to the sensitivities of alliinase activity. J Agric Food Chem 49 : 2592 2599
32. Lazzeri L, Curto G, Leoni O, Dallavalle E (2004) Effects of glucosinolates and their enzymatic hydrolysis products via myrosinase on the root-knot nematode Meloidogyne incognita. J Agric Food Chem 52 : 6703 6707
33. Leoni O, Iori R, Palmieri S (2000) Hydrolysis of glucosinolates using nylon-immobilized myrosinase to produce pure bioactive molecules. Biotechnol Bioeng 68 : 660 664
34. Milligan B, Saville B, Swan JM (1961) New syntheses of trisulphides. J Chem Soc 4850 4853
35. Miron T, Mironchik M, Mirelman D, Wilchek M, Rabinkov A (2003) Inhibition of tumor growth by a novel approach: in situ allicin generation using targeted alliinase delivery. Mol Cancer Ther 2 : 1295 1301
36. Munchberg U, Anwar A, Mecklenburg S, Jacob C (2007) Polysulfides as biologically active ingredients of garlic. Org Biomol Chem 5 : 1505 1518
37. Munday R, Munday JS, Munday CM (2003) 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 34 : 1200 1211
38. O'Gara EA, Hill DJ, Maslin DJ (2000) Activities of garlic oil, garlic powder, and their diallyl constituents against Helicobacter pylori. Appl Environ Microbiol 66 : 2269 2273
39. Ratzka A, Vogel H, Kliebenstein DJ, Mitchell-Olds T, Kroymann J (2002) Disarming the mustard oil bomb. Proc Natl Acad Sci USA 99 : 11223 11228
40. Shimon LJ, Rabinkov A, Shin I, Miron T, Mirelman D, Wilchek M, Frolow F (2007) Two structures of alliinase from Alliium sativum L.: apo form and ternary complex with aminoacrylate reaction intermediate covalently bound to the PLP cofactor. J Mol Biol 366 : 611 625
41. Steudel R (2002) The chemistry of organic polysulfanes R-S-n-R (n > 2). Chem Rev 102 : 3905 3945
42. Stoll A, Seebeck E (1951) Die Synthese des natürlichen Allins und seiner drei optisch aktiven Isomeren. Helv Chim Acta 34 : 481 486
43. Taipalensuu J, Falk A, Rask L (1996) A wound- and methyl jasmonate-inducible transcript coding for a myrosinase-associated protein with similarities to an early nodulin. Plant Physiol 110 : 483 491
44. Tierens KFMJ, Thomma BPH, Brouwer M, Schmidt J, Kistner K, Porzel A, Mauch-Mani B, Cammue BPA, Broekaert WF (2001) Study of the role of antimicrobial glucosinolate-derived isothiocyanates in resistance of arabidopsis to microbial pathogens. Plant Physiol 125 : 1688 1699
45. Xiao D, Herman-Antosiewicz A, Antosiewicz J, Xiao H, Brisson M, Lazo JS, Singh SV (2005) 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 24 : 6256 6268