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Thiosulfinates, Organic Polysulfanes, and Related Compounds: From an Unusual Chemistry Toward a Wealth of Potential Applications

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Recent Advances in Redox Active Plant and Microbial Products

Abstract

The study of and interest in thiosulfinates, polysulfanes, and other related sulfur-containing secondary metabolites derived from Alliums and other plants is steadily on the increase. This is hardly surprising given their fascinating and unusual chemistry, the ever-widening circle of uses to which these compounds could be put and, understandably, the economic importance which they have quickly come to assume. Here, we review some specific chemistry, biochemical processes, biological activities, and potential applications of certain selected members of this individually- distinct but biosynthetically- related group of compounds.

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References

  • Adamu I, Joseph PK, Augusti KT (1982) Hypolipidemic action of onion and garlic unsaturated oils in sucrose fed rats over a two-month period. Experientia 38(8):899–901

    CAS  PubMed  Google Scholar 

  • Agarwal KC (1996) Therapeutic actions of garlic constituents. Med Res Rev 16(1):111–124

    CAS  PubMed  Google Scholar 

  • Amarawardana L, Bandara P, Kumar V, Pettersson J, Ninkovic V, Glinwood R (2007) Olfactory response of Myzus persicae (Homoptera: Aphididae) to volatiles from leek and chive: potential for intercropping with sweet pepper. Acta Agr Scand B-S P 57(1):87–91

    Google Scholar 

  • Ankri S, Mirelman D (1999) Antimicrobial properties of allicin from garlic. Microbes Infect 1(2):125–129

    CAS  PubMed  Google Scholar 

  • Antosiewicz J, Herman-Antosiewicz A, Marynowski SW, Singh SV (2006) C-Jun NH2-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(10):5379–5386

    CAS  PubMed  Google Scholar 

  • Apitz-Castro R, Cabrera S, Cruz MR, Ledezma E, Jain MK (1983) Effects of garlic extract and of three pure components isolated from it on human platelet aggregation, arachidonate metabolism, release reaction and platelet ultrastructure. Thromb Res 32(2):155–169

    CAS  PubMed  Google Scholar 

  • Apitz-Castro R, Ledezma E, Escalante J, Jain MK (1986) The molecular basis of the antiplatelet action of ajoene: direct interaction with the fibrinogen receptor. Biochem Biophys Res Commun 141(1):145–150

    CAS  PubMed  Google Scholar 

  • Apitz-Castro R, Badimon JJ, Badimon L (1994) A garlic derivative, ajoene, inhibits platelet deposition on severely damaged vessel wall in an in vivo porcine experimental-model. Thromb Res 75(3):243–249

    CAS  PubMed  Google Scholar 

  • Ariga T, Oshiba S, Tamada T (1981) Platelet aggregation inhibitor in garlic. Lancet 1(8212):150–151

    CAS  PubMed  Google Scholar 

  • Arya A, Chauhan RCA (1995) Effect of allicin and extracts of garlic and bignonia on two fungi. Indian J Mycol Plant Pathol 25:316–318

    Google Scholar 

  • Assis FA, Moraes JC, Assis GA (2007) Effect of the aqueous extract of garlic bulbs on the aphid Myzus persicae (Sulzer) (Hemiptera: Aphididae) on potato. Ecossistema 32(1–2):63–66

    Google Scholar 

  • Bakker J, Gommers FJ, Nieuwenhuis I, Wynberg H (1979) Photoactivation of the nematicidal compound alpha-terthienyl from roots of marigolds (Tagetes species). A possible singlet oxygen role. J Biol Chem 254(6):1841–1844

    CAS  PubMed  Google Scholar 

  • Bat-Chen W, Golan T, Peri I, Ludmer Z, Schwartz B (2010) Allicin purified from fresh garlic cloves induces apoptosis in colon cancer cells via Nrf2. Nutr Cancer 62(7):947–957

    CAS  PubMed  Google Scholar 

  • Bayer T, Wagner H, Block E, Grisoni S, Zhao SH, Neszmelyi A (1989) Zwiebelanes—novel biologically-active 2,3-dimethyl-5,6-dithiabicyclo[2.1.1]hexane 5-oxides from onion. J Am Chem Soc 111(8):3085–3086

    CAS  Google Scholar 

  • Bianchi A, Zambonelli A, DAulerio AZ, Bellesia F (1997) Ultrastructural studies of the effects of Allium sativum on phytopathogenic fungi in vitro. Plant Dis 81(11):1241–1246

    CAS  Google Scholar 

  • Block E (1992) The organosulfur chemistry of the genus Allium—implications for the organic-chemistry of sulfur. Angew Chem Int Edit 31(9):1135–1178

    Google Scholar 

  • Block E (2010) Garlic and other Alliums: the lore and the science

    Google Scholar 

  • Block E, Deorazio R (1994) Chemistry in a salad bowl—comparative organosulfur chemistry of garlic, onion and shiitake mushrooms. Pure Appl Chem 66(10–11):2205–2206

    CAS  Google Scholar 

  • Block E, Ahmad S, Jain MK, Crecely RW, Apitzcastro R, Cruz MR (1984) (E, Z)-ajoene—a potent antithrombotic agent from garlic. J Am Chem Soc 106(26):8295–8296

    CAS  Google Scholar 

  • Block E, Bayer T, Naganathan S, Zhao SH (1996) Allium chemistry: Synthesis and sigmatropic rearrangements of alk(en)yl 1-propenyl disulfide S-oxides from cut onion and garlic. J Am Chem Soc 118(12):2799–2810

    CAS  Google Scholar 

  • Block E, Dane AJ, Thomas S, Cody RB (2010) Applications of direct analysis in real time mass spectrometry (DART-MS) in allium chemistry. 2-propenesulfenic and 2-propenesulfinic acids, diallyl trisulfane S-oxide, and other reactive sulfur compounds from crushed garlic and other Alliums. J Agr Food Chem 58(8):4617–4625

    CAS  Google Scholar 

  • Bowman GT, Clement JJ, Davidson DE Jr, Eswarakrishnan V, Field L, Hoch JM, Musallam HA, Pick RO, Ravichandran R, Srivastava PK (1986) Potential antiradiation drugs containing no nitrogen, and related compounds. Chem Biol Interact 57(2):161–174

    CAS  PubMed  Google Scholar 

  • Brzostowska EM, Greer A (2003) The role of amine in the mechanism of pentathiepin (polysulfur) antitumor agents. J Am Chem Soc 125(2):396–404

    CAS  PubMed  Google Scholar 

  • Busch C, Jacob C, Anwar A, Burkholz T, Ba LA, Cerella C, Diederich M, Brandt W, Wessjohann L, Montenarh M (2010) Diallylpolysulfides induce growth arrest and apoptosis. Int J Oncol 36(3):743–749

    CAS  PubMed  Google Scholar 

  • Castiglioni A (1985) A history of medicine. Jason Aronson, New York

    Google Scholar 

  • Cavallito CJ, Bailey JH (1944) Allicin, the antibacterial principle of Allium sativum. I. Isolation, physical properties and antibacterial action. J Am Chem Soc 66(11):1950–1951

    CAS  Google Scholar 

  • Cavallito CJ, Buck JS, Suter CM (1944) Allicin, the antibacterial principle of Allium sativum. II. Determination of the chemical structure. J Am Chem Soc 66(11):1952–1954

    CAS  Google Scholar 

  • Cerella C, Scherer C, Cristofanon S, Henry E, Anwar A, Busch C, Montenarh M, Dicato M, Jacob C, Diederich M (2009) Cell cycle arrest in early mitosis and induction of caspase-dependent apoptosis in U937 cells by diallyltetrasulfide (Al2S4). Apoptosis 14(5):641–654

    CAS  PubMed  Google Scholar 

  • Curtis H, Noll U, Stoermann J, Slusarenko AJ (2004) Broad-spectrum activity of the volatile phytoanticipin allicin in extracts of garlic (Allium sativum L.) against plant pathogenic bacteria, fungi and oomycetes. Physiol Mol Plant 65(2):79–89

    CAS  Google Scholar 

  • Davidson BS, Molinski TF, Barrows LR, Ireland CM (1991) Varacin—a novel benzopentathiepin from Lissoclinum-Vareau that is cytotoxic toward a human colon-tumor. J Am Chem Soc 113(12):4709–4710

    CAS  Google Scholar 

  • Davis SR (2005) An overview of the antifungal properties of allicin and its breakdown products—the possibility of a safe and effective antifungal prophylactic. Mycoses 48(2):95–100

    CAS  PubMed  Google Scholar 

  • Dicke M (1999) Are herbivore-induced plant volatiles reliable indicators of herbivore identity to foraging carnivorous arthropods? Entomol Exp Appl 91(1):131–142

    CAS  Google Scholar 

  • Dirsch VM, Gerbes AL, Vollmar AM (1998) Ajoene, a compound of garlic, induces apoptosis in human promyeloleukemic cells, accompanied by generation of reactive oxygen species and activation of nuclear factor kappa B. Mol Pharmacol 53(3):402–407

    CAS  PubMed  Google Scholar 

  • Doering M, Ba LA, Lilienthal N, Nicco C, Scherer C, Abbas M, Zada AA, Coriat R, Burkholz T, Wessjohann L, Diederich M, Batteux F, Herling M, Jacob C (2010) Synthesis and selective anticancer activity of organochalcogen based redox catalysts. J Med Chem 53(19):6954–6963

    CAS  PubMed  Google Scholar 

  • Egen-Schwind C, Eckard R, Jekat FW, Winterhoff H (1992) Phamacokinetics of vinyldithiins, transformation products of allicin. Planta Med 58(1):8–13

    CAS  PubMed  Google Scholar 

  • Ford PW, Davidson BS (1993) Synthesis of varacin, a cytotoxic naturally-occurring benzopentathiepin isolated from a marine ascidian. J Org Chem 58(17):4522–4523

    CAS  Google Scholar 

  • Gardner CD, Lawson LD, Chatterjee LM, Kiazand A, Balise RR, Kraemer HC (2007) Effect of raw garlic vs commercial garlic supplements on plasma lipid concentrations in adults with moderate hypercholesterolemia—a randomized clinical trial. Arch Intern Med 167(4):346–353

    CAS  PubMed  Google Scholar 

  • Giles GI, Tasker KM, Jacob C (2001) Hypothesis: the role of reactive sulfur species in oxidative stress. Free Radical Bio Med 31(10):1279–1283

    CAS  Google Scholar 

  • 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

    CAS  PubMed Central  PubMed  Google Scholar 

  • Gmelin R, Susilo R, Fenwick GR (1981) Cyclic polysulfides from parkia-speciosa. Phytochemistry 20(11):2521–2523

    CAS  Google Scholar 

  • Gruhlke MCH, Portz D, Stitz M, Anwar A, Schneider T, Jacob C, Schlaich NL, Slusarenko AJ (2010) Allicin disrupts the cell’s electrochemical potential and induces apoptosis in yeast. Free Radical Bio Med 49(12):1916–1924

    CAS  Google Scholar 

  • Hardy G (2000) Nutraceuticals and functional foods: introduction and meaning. Nutrition 16(7–8):688–689

    CAS  PubMed  Google Scholar 

  • Hirsch K, Danilenko M, Giat J, Miron T, Rabinkov A, Wilchek M, Mirelman D, Levy J, Sharoni Y (2000) Effect of purified allicin, the major ingredient of freshly crushed garlic, on cancer cell proliferation. Nutr Cancer 38(2):245–254

    CAS  PubMed  Google Scholar 

  • Höfle G, Gmelin R, Luxa HH, Galamulumetreves MN, Hatanaka SI (1976) Structure of lentinic acid—2-(Gamma-Glutamylamino)-4,6,8,10,10-pentaoxo-4,6,8,10-tetrathiaundecanoic acid. Tetrahedron Lett 36:3129–3132

    Google Scholar 

  • Horev-Azaria L, Eliav S, Izigov N, Pri-Chen S, Mirelman D, Miron T, Rabinkov A, Wilchek M, Jacob-Hirsch J, Amariglio N, Savion N (2009) Allicin up-regulates cellular glutathione level in vascular endothelial cells. Eur J Nutr 48(2):67–74

    CAS  PubMed  Google Scholar 

  • Huang Y, Chen SX, Ho SH (2000) Bioactivities of methyl allyl disulfide and diallyl trisulfide from essential oil of garlic to two species of stored-product pests, Sitophilus zeamais (Coleoptera: Curculionidae) and Tribolium castaneum (Coleoptera: Tenebrionidae). J Econ Entomol 93(2):537–543

    CAS  PubMed  Google Scholar 

  • Hudson JB, Graham EA, Rossi R, Carpita A, Neri D, Towers GHN (1993) Biological-activities of terthiophenes and polyynes from the Asteraceae. Planta Med 59(5):447–450

    CAS  PubMed  Google Scholar 

  • Iberl B, Winkler G, Knobloch K (1990) Products of allicin transformation: ajoenes and dithiins, characterization and their determination by HPLC. Planta Med 56(2):202–211

    CAS  PubMed  Google Scholar 

  • Iciek M, Bilska A, Ksiazek L, Srebro Z, Wlodek L (2005) Allyl disulfide as donor and cyanide as acceptor of sulfane sulfur in the mouse tissues. Pharmacol Rep 57(2):212–218

    CAS  PubMed  Google Scholar 

  • Imai S, Tsuge N, Tomotake M, Nagatome Y, Sawada H, Nagata T, Kumagai H (2002) Plant biochemistry: an onion enzyme that makes the eyes water. Nature 419(6908):685

    CAS  PubMed  Google Scholar 

  • Jacob C (2006) A scent of therapy: pharmacological implications of natural products containing redox-active sulfur atoms. Nat Prod Rep 23(6):851–863

    CAS  PubMed  Google Scholar 

  • Jacob C, Anwar A (2008) The chemistry behind redox regulation with a focus on sulphur redox systems. Physiol Plant 133(3):469–480

    CAS  PubMed  Google Scholar 

  • Jain MK, Apitz-Castro R (1987) Garlic: molecular basis of the putative ‘vampire-repellant’ action and other matters related to heart and blood. Trends Biochem Sci 12:252–254

    CAS  Google Scholar 

  • Jamaluddin MP, Krishnan LK, Thomas A (1988) Ajoene inhibition of platelet aggregation: possible mediation by a hemoprotein. Biochem Biophys Res Commun 153(1):479–486

    CAS  PubMed  Google Scholar 

  • Jones MG (2010) The biosynthesis of volatile sulfur flavour compounds. In: Herrmann A (ed) The chemistry and biology of volatiles. Wiley, West Sussex, United Kingdom

    Google Scholar 

  • Kelkel M, Cerella C, Mack F, Schneider T, Jacob C, Schumacher M, Dicato M, Diederich M (2012) ROS-independent JNK activation and multisite phosphorylation of Bcl-2 link diallyl tetrasulfide-induced mitotic arrest to apoptosis. Carcinogenesis 33(11):2162–2171

    CAS  PubMed  Google Scholar 

  • Kensler TW, Curphey TJ, Maxiutenko Y, Roebuck BD (2000) Chemoprotection by organosulfur inducers of phase 2 enzymes: dithiolethiones and dithiins. Drug Metab Drug Interact 17(1–4):3–22

    CAS  Google Scholar 

  • Keusgen M (2008) Unusual cystine lyase activity of the enzyme alliinase: direct formation of polysulphides. Planta Med 74(1):73–79

    CAS  PubMed  Google Scholar 

  • Kim S, Kubec R, Musah RA (2006) Antibacterial and antifungal activity of sulfur-containing compounds from Petiveria alliacea L. J Ethnopharmacol 104(1–2):188–192

    CAS  PubMed  Google Scholar 

  • Kjaer A, Larsen PO (1977) Non-protein amino acids, cyanogenic glycosides and glucosinolates. In: Bulock JD (ed) Biosynthesis, specialist periodical reports, vol 2., Royal Society of ChemistryCambridge, United Kingdom, pp 121–122

    Google Scholar 

  • Koch HP, Lawson LD (1996) Garlic: the science and therapeutic application of Allium sativum L and related species. Williams and Wilkins, Baltimore, Md

    Google Scholar 

  • Kouokam JC, Jahns T, Becker H (2002) Antimicrobial activity of the essential oil and some isolated sulfur-rich compounds from Scorodophloeus zenkeri. Planta Med 68(12):1082–1087

    CAS  PubMed  Google Scholar 

  • Kubec R, Cody RB, Dane AJ, Musah RA, Schraml J, Vattekkatte A, Block E (2010) Applications of direct analysis in real time-mass spectrometry (DART-MS) in allium chemistry. (Z)-Butanethial S-oxide and 1-butenyl thiosulfinates and their S-(E)-1-butenylcysteine S-oxide precursor from Allium siculum. J Agr Food Chem 58(2):1121–1128

    CAS  Google Scholar 

  • Kupiecki FP, Virtanen AI (1960) Cleavage of alkyl cysteine sulphoxides by an enzyme in onion (Allium-Cepa). Acta Chem Scand 14(9):1913–1918

    CAS  Google Scholar 

  • Lancaster JE, Shaw ML, Walton EF (2000) S-alk(en)yl-L-cysteine sulfoxides, alliinase and aroma in Leucocoryne. Phytochemistry 55(2):127–130

    CAS  PubMed  Google Scholar 

  • Lawson LD, Wood SG, Hughes BG (1991) Hplc analysis of allicin and other thiosulfinates in garlic clove homogenates. Planta Med 57(3):263–270

    CAS  PubMed  Google Scholar 

  • Lawson LD, Ransom DK, Hughes BG (1992) Inhibition of whole-blood platelet-aggregation by compounds in garlic clove extracts and commercial garlic products. Thromb Res 65(2):141–156

    CAS  PubMed  Google Scholar 

  • Ledezma E, Apitz-Castro R (2006) [ajoene the main active compound of garlic (Allium sativum): a new antifungal agent]. Revista iberoamericana de micologia 23(2):75–80

    Google Scholar 

  • Li M, Ciu JR, Ye Y, Min JM, Zhang LH, Wang K, Gares M, Cros J, Wright M, Leung-Tack J (2002) Antitumor activity of Z-ajoene, a natural compound purified from garlic: antimitotic and microtubule-interaction properties. Carcinogenesis 23(4):573–579

    CAS  PubMed  Google Scholar 

  • Liu P, Guo JH, Liu HM, Cheng YJ, Wang BQ, Long CA, Deng BX (2009) Diallyl trisulfide (DATS) effectively induced apoptosis of postharvest disease Penicillium expansum of citrus. Ann Microbiol 59(4):675–679

    CAS  Google Scholar 

  • Liu C, Cao F, Tang QZ, Yan L, Dong YG, Zhu LH, Wang L, Bian ZY, Li HL (2010) Allicin protects against cardiac hypertrophy and fibrosis via attenuating reactive oxygen species-dependent signaling pathways. J Nutr Biochem 21(12):1238–1250

    CAS  PubMed  Google Scholar 

  • Makarieva TN, Stonik VA, Dmitrenok AS, Grebnev BB, Isakov VV, Rebachyk NM, Rashkes YW (1995) Varacin and three new marine antimicrobial polysulfides from the far-eastern ascidian Polycitor sp. J Nat Prod 58(2):254–258

    CAS  PubMed  Google Scholar 

  • Makheja AN, Bailey JM (1990) Antiplatelet constituents of garlic and onion. Agents Actions 29(3–4):360–363

    CAS  PubMed  Google Scholar 

  • Medicine TFfI (1992) The nutraceutical initiative—a proposal for economic and regulatory reform. Food Technol Chicago 46(4):77–79

    Google Scholar 

  • Miron T, Wilehek M, Sharp A, Nakagawa Y, Naoi M, Nozawa Y, Akao Y (2008) Allicin inhibits cell growth and induces apoptosis through the mitochondrial pathway in HL60 and U937 cells. J Nutr Biochem 19(8):524–535

    CAS  PubMed  Google Scholar 

  • Morita K, Kobayash S (1966) Isolation and synthesis of lenthionine an odorous substance of shiitake an edible mushroom. Tetrahedron Lett 6:573

    Google Scholar 

  • Morita K, Kobayash S (1967) Isolation structure and synthesis of lenthionine and its analogs. Chem Pharm Bull 15(7):988

    CAS  PubMed  Google Scholar 

  • Mueller AL, Virtanen AI (1966) Synthesis of S-(buten-1-yl)-L-cysteine sulfoxide and its enzymic cleavage to 1-butenylsulfenic acid. Acta Chem Scand B 20(4):1163–1165

    CAS  Google Scholar 

  • Munchberg U, Anwar A, Mecklenburg S, Jacob C (2007) Polysulfides as biologically active ingredients of garlic. Org Biomol Chem 5(10):1505–1518

    PubMed  Google Scholar 

  • 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 Radical Bio Med 34(9):1200–1211

    CAS  Google Scholar 

  • Musah RA, He Q, Kubec R (2009) Discovery and characterization of a novel lachrymatory factor synthase in Petiveria alliacea and its influence on alliinase-mediated formation of biologically active Organosulfur compounds. Plant Physiol 151(3):1294–1303

    CAS  PubMed Central  PubMed  Google Scholar 

  • Naganawa R, Iwata N, Ishikawa K, Fukuda H, Fujino T, Suzuki A (1996) Inhibition of microbial growth by ajoene, a sulfur-containing compound derived from garlic. Appl Environ Microb 62(11):4238–4242

    CAS  Google Scholar 

  • Nishikawa T, Yamada N, Hattori A, Fukuda H, Fujino T (2002) Inhibition by ajoene of skin-tumor promotion in mice. Biosci Biotech Bioch 66(10):2221–2223

    CAS  Google Scholar 

  • O’Gara EA, Hill DJ, Maslin DJ (2000) Activities of garlic oil, garlic powder, and their diallyl constituents against Helicobacter pylori. Appl Environ Microb 66(5):2269–2273

    Google Scholar 

  • Oommen S, Anto RJ, Srinivas G, Karunagaran D (2004) Allicin (from garlic) induces caspase-mediated apoptosis in cancer cells. Eur J Pharmacol 485(1–3):97–103

    CAS  PubMed  Google Scholar 

  • Pari L, Murugavel P, Sitasawad SL, Kumar KS (2007) Cytoprotective and antioxidant role of diallyl tetrasulfide on cadmium induced renal injury: an in vivo and in vitro study. Life Sci 80(7):650–658

    CAS  PubMed  Google Scholar 

  • Park SY, Cho SJ, Kwon HC, Lee KR, Rhee DK, Pyo S (2005) Caspase-independent cell death by allicin in human epithelial carcinoma cells: involvement of PKA. Cancer Lett 224(1):123–132

    CAS  PubMed  Google Scholar 

  • Paterson I, Anderson EA (2005) The renaissance of natural products as drug candidates. Science 310(5747):451–453

    PubMed  Google Scholar 

  • Perez HA, De la Rosa M, Apitz R (1994) In vivo activity of ajoene against rodent malaria. Antimicrob Agents Chemother 38(2):337–339

    CAS  PubMed Central  PubMed  Google Scholar 

  • Portz D, Koch E, Slusarenko AJ (2008) Effects of garlic (Allium sativum) juice containing allicin on Phytophthora infestans and downy mildew of cucumber caused by Pseudoperonospora cubensis. Eur J Plant Pathol 122(1):197–206

    CAS  Google Scholar 

  • Rabinkov A, Miron T, Mirelman D, Wilchek M, Glozman S, Yavin E, Weiner L (2000) S-Allylmercaptoglutathione: the reaction product of allicin with glutathione possesses SH-modifying and antioxidant properties. Bba-Mol Cell Res 1499(1–2):144–153

    CAS  Google Scholar 

  • Romagnoli C, Mares D, Fasulo MP, Bruni A (1994) Antifungal effects of alpha-terthienyl from tagetes-patula on 5 dermatophytes. Phytother Res 8(6):332–336

    CAS  Google Scholar 

  • Russell PE, Mussa AEA (1977) Use of garlic (Allium sativum) extracts to control foot rot of phaseolus-vulgaris caused by fusarium-solani fsp phaseoli. Ann Appl Biol 86(3):369–372

    Google Scholar 

  • Scharfenberg K, Wagner R, Wagner KG (1990) The cytotoxic effect of ajoene, a natural product from garlic investigated differ cell-lines. Cancer Lett 53(2–3):103–108

    CAS  PubMed  Google Scholar 

  • Schneider T, Ba LA, Khairan K, Zwergel C, Bach ND, Bernhardt I, Brandt W, Wessjohann L, Diederich M, Jacob C (2011) Interactions of polysulfanes with components of red blood cells. Medchemcomm 2(3):196–200

    CAS  Google Scholar 

  • Seki T, Hosono T, Hosono-Fukao T, Inada K, Tanaka R, Ogihara J, Ariga T (2008) Anticancer effects of diallyl trisulfide derived from garlic. Asia Pac J Clin Nutr 17:249–252

    CAS  PubMed  Google Scholar 

  • Sendl A, Schliack M, Loser R, Stanislaus F, Wagner H (1992) Inhibition of cholesterol synthesis in vitro by extracts and isolated compounds prepared from garlic and wild garlic. Atherosclerosis 94(1):79–85

    CAS  PubMed  Google Scholar 

  • Shibuya T, Shimada S, Sakurai H, Kumagai H (2005) Mechanism of inhibition of platelet aggregation by lenthionine, a flavour component from shiitake mushroom. In: IFT annual meeting, New Orleans, LA, 15–20 July 2005

    Google Scholar 

  • Shimada S, Komamura K, Kumagai H, Sakurai H (2004) Inhibitory activity of shiitake flavor against platelet aggregation. Bio Factors 22(1–4):177–179

    CAS  Google Scholar 

  • 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

    Google Scholar 

  • Slusarenko AJ, Patel A, Portz D (2008) Control of plant diseases by natural products: allicin from garlic as a case study. Eur J Plant Pathol 121(3):313–322

    Google Scholar 

  • Small LD, Bailey JH, Cavallito CJ (1947) Alkyl thiolsulfinates. J Am Chem Soc 69(7):1710–1713

    CAS  PubMed  Google Scholar 

  • Small LD, Bailey JH, Cavallito CJ (1949) Comparison of some properties of thiosulfinates and thiosulfonates. J Am Chem Soc 71(10)

    Google Scholar 

  • Steudel R (2002) The chemistry of organic polysulfanes R-S-n-R (n > 2). Chem Rev 102(11):3905–3945

    CAS  PubMed  Google Scholar 

  • Tatarintsev AV, Vrzheshch PV, Schegolev AA, Yershov DE, Turgiev AS, Varfolomeyev SD, Kornilayeva GV, Makarova TV, Karamov EV (1992) Ajoene antagonizes integrin-dependent processes in HIV-infected T-lymphoblasts. Aids 6(10):1215–1217

    CAS  PubMed  Google Scholar 

  • Tilli CMLJ, Stavast-Kooy AJW, Vuerstaek JDD, Thissen MRTM, Krekels GAM, Ramaekers FCS, Neumann HAM (2003) The garlic-derived organosulfur component ajoene decreases basal cell carcinoma tumor size by inducing apoptosis. Arch Dermatol Res 295(3):117–123

    CAS  PubMed  Google Scholar 

  • Tsao SM, Yin MC (2001) In vitro antimicrobial activity of four diallyl sulphides occurring naturally in garlic and Chinese leek oils. J Med Microbiol 50(7):646–649

    CAS  PubMed  Google Scholar 

  • Urbina JA, Marchan E, Lazardi K, Visbal G, Apitz-Castro R, Gil F, Aguirre T, Piras MM, Piras R (1993) Inhibition of phosphatidylcholine biosynthesis and cell proliferation in trypanosoma cruzi by ajoene, an antiplatelet compound isolated from garlic. Biochem Pharmacol 45(12):2381–2387

    CAS  PubMed  Google Scholar 

  • Vaidya V, Ingold KU, Pratt DA (2009) Garlic: source of the ultimate antioxidants-sulfenic acids. Angew Chem-Int Ed 48(1):157–160

    CAS  Google Scholar 

  • Van Etten HD, Mansfield JW, Bailey JA, Farmer EE (1994) Two classes of plant antibiotics: phytoalexins versus “phytoanticipins”. Plant Cell 6(9):1191–1192

    Google Scholar 

  • Voigt M, Wolf E (1986) Knoblauch: HPLC-Bestimmung von Knoblauchwirkstoffen in Extrakten, Pulver und Fertigarzneimitteln. Deutsche Apotheker Zeitung 126:591–593

    Google Scholar 

  • Wills ED (1956) Enzyme inhibition by allicin, the active principle of garlic. Biochem J 63(3):514–520

    CAS  PubMed Central  PubMed  Google Scholar 

  • Wratten SJ, Faulkner DJ (1976) Cyclic polysulfides from the red alga Chondria Californica. J Org Chem 41(14):2465–2467

    CAS  PubMed  Google Scholar 

  • Xiao D, Zeng Y, Hahm ER, Kim YA, Ramalingam S, Singh SV (2009) Diallyl trisulfide selectively causes Bax- and Bak-mediated apoptosis in human lung cancer cells. Environ Mol Mutagen 50(3):201–212

    CAS  PubMed Central  PubMed  Google Scholar 

  • Yang JS, Chen GW, Hsia TC, Ho HC, Ho CC, Lin MW, Lin SS, Yeh RD, Ip SW, Lu HF, Chung JG (2009) Diallyl disulfide induces apoptosis in human colon cancer cell line (COLO 205) through the induction of reactive oxygen species, endoplasmic reticulum stress, caspases casade and mitochondrial-dependent pathways. Food Chem Toxicol 47(1):171–179

    CAS  PubMed  Google Scholar 

  • Yasumoto K, Iwami K, Mitsuda H (1971) Studies on shiitake flavor 1, new sulfur-containing peptide from lentinus-edodes acting as a precursor for lenthionine. Agr Biol Chem Tokyo 35(13):2059

    Google Scholar 

  • Yoshida S, Kasuga S, Hayashi N, Ushiroguchi T, Matsuura H, Nakagawa S (1987) Antifungal activity of ajoene derived from garlic. Appl Environ Microb 53(3):615–617

    CAS  Google Scholar 

  • Zhang WL, Ha MW, Gong YH, Xu Y, Dong NA, Yuan YA (2010) Allicin induces apoptosis in gastric cancer cells through activation of both extrinsic and intrinsic pathways. Oncol Rep 24(6):1585–1592

    CAS  PubMed  Google Scholar 

  • Zheng DX, Zhang SQ, Zhao S, Min JM, Wang K, Liu SL (1998) Z-ajoene induces tumor cells to die by apoptosis. Chinese Sci Bull 43(13):1135–1140

    CAS  Google Scholar 

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Acknowledgment

Ifeanyi D. Nwachukwu was supported by funding from the European Community’s 7th Framework Programme [FP7/2007-2013] under grant agreement No: 215009.

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Authors and Affiliations

  1. Department of Plant Physiology (Bio III), RWTH Aachen University, 52056, Aachen, Germany

    Ifeanyi D. Nwachukwu & Alan J. Slusarenko

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  1. Ifeanyi D. Nwachukwu
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  2. Alan J. Slusarenko
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Correspondence to Alan J. Slusarenko .

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Editors and Affiliations

  1. Bioorganic Chemistry/School of Pharmacy, University of Saarland, Saarbrücken, Saarland, Germany

    Claus Jacob

  2. SRSMC UMR 7565, Université de Lorraine, Metz, Moselle, France

    Gilbert Kirsch

  3. Plant Physiology (Bio III), RWTH Aachen University, Aachen, Germany

    Alan Slusarenko

  4. Medical School, University of Exeter, Exeter, United Kingdom

    Paul G. Winyard

  5. Bioorganic Chemistry/School of Pharmacy, University of Saarland, Saarbrücken, Saarland, Germany

    Torsten Burkholz

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Nwachukwu, I.D., Slusarenko, A.J. (2014). Thiosulfinates, Organic Polysulfanes, and Related Compounds: From an Unusual Chemistry Toward a Wealth of Potential Applications. In: Jacob, C., Kirsch, G., Slusarenko, A., Winyard, P., Burkholz, T. (eds) Recent Advances in Redox Active Plant and Microbial Products. Springer, Dordrecht. https://doi.org/10.1007/978-94-017-8953-0_10

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