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Alternaria Metabolites

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The Chemistry of Mycotoxins

Abstract

Metabolites of the genus Alternaria are apparently ubiquitous and have long been recognized as important plant pathogens, causing diverse diseases such as tobacco brown spot (453), potato and tomato blight (Fig. 11.1), and citrus seedling chlorosis (454). Although A. alternata has been regarded as the major mycotoxin-producing species, other species such as A. citri, A. longipes, A. solani, and the A. arborescens, A. infectoria, and A. tenuissima species groups also produce the characteristic Alternaria mycotoxins (455).

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References

  1. Kraus GA, Taschner MJ (1980) Model studies for the synthesis of quassinoids. 1. Construction of the BCE ring system. J Org Chem 45:1175

    Article  CAS  Google Scholar 

  2. Fürstner A, Thiel OR, Kindler N, Bartkowska B (2000) Total syntheses of (S)-(–)-zearalenone and lasiodiplodin reveal superior metathesis activity of ruthenium carbene complexes with imidazol-2-ylidene ligands. J Org Chem 65:7990

    Article  Google Scholar 

  3. Lucas GB (1959) Diseases of tobacco. Scarecrow Press, New York, p 228

    Google Scholar 

  4. Templeton GE (1972) Alternaria toxins related to pathogenesis in plants. Microb Toxins 8:169

    CAS  Google Scholar 

  5. . Barkai-Golan R, Paster N (2008) Alternaria mycotoxins. Mycotoxins Fruits Vegetables 185

    Google Scholar 

  6. Raistrick H, Stickings EC, Thomas R (1953) Studies in the biochemistry of microorganisms. 90. Alternariol and alternariol monomethyl ether, metabolic products of Alternaria tenuis. Biochem J 55:421

    CAS  Google Scholar 

  7. Freeman GG (1965) Isolation of alternariol and alternariol monomethyl ether from Alternaria dauci (kühn) groves and skolko. Phytochem istry 5:719

    Article  Google Scholar 

  8. Thomas R (1961) Studies in the biosynthesis of fungal metabolites. 2. The biosynthesis of alternariol and its relation to other fungal phenols. Biochem J 78:748

    CAS  Google Scholar 

  9. Cole RJ, Cox RH (eds) (1981) Handbook of toxic fungal metabolites. Academic, New York, p 614

    Google Scholar 

  10. http://www.growingproduce.com/articles/image/AVG/2009/March/Rotten%20Tomatoes%20No%20More/black_mold.jpgbyMikeDavis

  11. Griffin GF, Chu FS (1983) Toxicity of the Alternaria metabolites alternariol, alternariol methyl ether, altenuene, and tenuazonic acid in the chicken embryo assay. Appl Environ Microbiol 46:1420

    CAS  Google Scholar 

  12. Pero RW, Owens RG, Dale SW, Harvan D (1971) Isolation and identification of a new toxin, altenuene, from the fungus Alternaria tenuis. Biochim Biophys Acta 230:170

    Article  CAS  Google Scholar 

  13. McPhail AT, Miller RW, Harvan D, Pero RW (1973) X-ray crystal structure revision for the fungal metabolite (±)-altenuene. J Chem Soc Chem Commun 682

    Google Scholar 

  14. Visconti A, Bottalico A, Solfrizzo M, Palmisano F (1989) Isolation and structure elucidation of isoaltenuene, a new metabolite of Alternaria Alternata. Mycotoxin Res 5:69

    Article  CAS  Google Scholar 

  15. Nawaz S, Scudamore KA, Rainbird SC (1997) Mycotoxins in ingredients of animal feeding stuffs: I. Determination of Alternaria mycotoxins in oilseed rape meal and sunflower seed meal. Food Addit Contam 4:249

    Article  Google Scholar 

  16. Bradburn N, Coker RD, Blunden G, Turner CH, Crabb TA (1994) 5'-Epialtenuene and neoaltenuene, dibenzo-α-pyrones from Alternaria Alternata cultured on rice. Phytochem 35:665

    Article  CAS  Google Scholar 

  17. Nakanishi S, Toki S, Saitoh Y, Tsukuda E, Kawahara K, Ando K, Matsuda Y (1995) Isolation of myosin light chain kinase inhibitors from microorganisms: dehydroaltenusin, altenusin, atrovenetinone, and cyclooctasulfur. Biosci Biotech Biochem 59:1333

    Article  CAS  Google Scholar 

  18. Stinson EE (1985) Mycotoxins - their biosynthesis in Alternaria. J Food Prot 48:80

    CAS  Google Scholar 

  19. Murakami-Nakai C, Maeda N, Yonezawa Y, Kuriyama I, Kamisuki S, Takahashi S, Sugawara F, Yoshida H, Sakaguchi K, Mizushina Y (2004) The effects of dehydroaltenusin, a novel mammalian DNA polymerase-α-inhibitor, on cell proliferation and cell cycle progression. Biochim Biophys Acta 1674:193

    Article  CAS  Google Scholar 

  20. Pero RW, Posner H, Blois M, Harvan D, Spalding JW (1973) Toxicity of metabolites produced by the “Alternaria”. Environ Health Perspect :87

    Google Scholar 

  21. Scott PM, Stoltz DR (1979) Mutagens produced by Alternaria alternata. Mut Res-Genet Tox 78:33

    Article  Google Scholar 

  22. Stack ME, Prival MJ (1986) Mutagenicity of the Alternaria metabolites altertoxins I, II, and III. Appl Environ Microb 52:718

    CAS  Google Scholar 

  23. Stinson EE, Osman SF, Pfeiffer PE (1982) Structure of altertoxin 1, a mycotoxin from Alternaria. J Org Chem 47:4110

    Article  CAS  Google Scholar 

  24. Bringmann G, Günther C, Ochse M, Schupp O, Tasler S (2001) Biaryls in nature: a multi-facetted class of stereochemically, biosynthetically, and pharmacologically intriguing secondary metabolites. Prog Chem Org Nat Prod 82:1

    CAS  Google Scholar 

  25. Weidenbörner M (2001) Encyclopedia of food mycotoxins. Springer Verlag, Berlin

    Book  Google Scholar 

  26. Rosett R, Sankhala RH, Stickings CE, Taylor MEU, Thomas R (1957) Studies in the biochemistry of microorganism. 103. Metabolites of Alternaria tenuis auct.: culture filtrate products. Biochem J 67:390

    CAS  Google Scholar 

  27. Stickings CE (1959) Studies in the biochemistry of micro-organisms. 106. Metabolites of Alternaria tenuis auct.: the structure of tenuazonic acid. Biochem J 72:332

    CAS  Google Scholar 

  28. Gitterman CO (1965) Antitumor, cytotoxic, and antibacterial activities of tenuazonic acid and congeneric tetramic acids. J Med Chem 8:483

    Article  CAS  Google Scholar 

  29. Brian PW, Curtis PS, Hemming HG, Unwin CH, Wright JM (1949) Alternaric acid, a biologically active metabolic product of the fungus Alternaria solani. Nature 164:534

    Article  CAS  Google Scholar 

  30. Pero RW, Main CE (1970) Chlorosis of tobacco induced by alternariol monomethyl ether produced by Alternaria tenuis. Phytopathology 60:1570

    Article  CAS  Google Scholar 

  31. Templeton GE, Meyer WL, Groble CI, Sigel CW (1967) Factors affecting the amount and pattern of chlorosis caused by a metabolite of Alternaria tenuis. Phytopath 57:833

    Google Scholar 

  32. Christensen CM, Nelsen GH, Mirocha CJ, Bates F (1968) Toxicity to experimental animals of 943 isolates of fungi. Cancer Res 28:2293

    CAS  Google Scholar 

  33. Spalding JW, Pero RW, Owens RG (1970) Inhibition of the G2 phase of the mammalian cell cycle by the mycotoxin. Alternariol J Cell Biol 47:199

    Google Scholar 

  34. Liu G, Qian Y, Zhang P, Dong W, Qi Y, Guo H (1992) Etiological role of Alternaria alternata in human oesophageal cancer. Chin Med J 105:394

    CAS  Google Scholar 

  35. Liu GT, Qian YZ, Zhang P, Dong ZM, Shi ZY, Zhen YZ, Miao J, Xu YM (1991) Relationships between Alternaria alternata and oesophageal cancer. IARC Sci Publ :258

    Google Scholar 

  36. Dong ZG, Liu GT, Dong ZM, Qian YZ, An YH, Miao I, Zhen YZ (1987) Induction of mutagenesis and transformation by the extract of Alternaria alternata isolated from grains in linxian. China Carcinogenesis 8:989

    Article  CAS  Google Scholar 

  37. Zhen YZ, Xu YM, Liu GT, Miao J, Xing YD, Zhen QL, Ma YF, Su T, Wang XL, Lr R, Tian JF, Zhou G, Yang SL (1991) Mutagenicity of Alternaria alternata and Penicillium cyclopium isolated from grains in an area of high incidence of oesophageal cancer - linxian. IARC Sci Publ, China, 253

    Google Scholar 

  38. Stack ME, Mazzola EP, Page SW, Pohland AE (1986) Mutagenic perylenequinone metabolites of Alternaria alternata: altertoxins I, II, and III. J Nat Prod 49:866

    Article  CAS  Google Scholar 

  39. Schobert R, Schelnk A (2008) Tetramic and tetronic acids: an update on new derivatives and biological aspects. Bioorg Med Chem 16:4203

    Article  CAS  Google Scholar 

  40. Chelkowski J, Visconti A (1992) Alternaria: biology, Plant Diseases and Metabolites. Elsevier, Amsterdam

    Google Scholar 

  41. Steyn PS, Rabie CJ (1976) Characterization of magnesium and calcium tenuazonate from Phoma sorghina. Phytochemistry 15:1977

    Article  CAS  Google Scholar 

  42. Abell C, Bush BD, Staunton J (1986) Biomimetic syntheses of the polyketide fungal metabolites alternariol and rubrofusarin: models for cyclisation reactions catalyzed by polyketide synthase enzymes. J Chem Soc Perkin Trans 1:15

    Google Scholar 

  43. Leeper FJ, Staunton J (1984) Biomimetic syntheses of polyketide aromatics from reaction of an orsellinate anion with pyrones and a pyrylium salt. J Chem Soc Perkin Trans 1:1053

    Article  Google Scholar 

  44. Harris TM, Hay JV (1976) Biogenetically modeled syntheses of heptaacetate metabolites. Alternariol and lichexanthone. J Am Chem Soc 99:1631

    Article  Google Scholar 

  45. Koch K, Podlech J, Pfeiffer E, Metzler M (2005) Total synthesis of alternariol. J Org Chem 70:3275

    Article  CAS  Google Scholar 

  46. Bringmann G, Goetz R, Keller PA, Walter R, Boyd MR, Lang F, Garcia A, Walsh JJ, Tellitu I, Bhaskar KV, Kelly TR (1998) A convergent total synthesis of the michellamines. J Org Chem 63:1090

    Article  CAS  Google Scholar 

  47. Sargent MV (1982) Depsidone synthesis. Part 21. A new synthesis of grisa-2′,5′-diene-3,4′-diones. J Chem Soc Perkin Trans 1:403

    Article  Google Scholar 

  48. Altemöller M, Podlech J, Fenske D (2006) Total synthesis of altenuene and isoaltenuene. Eur J Org Chem:1678

    Google Scholar 

  49. Murray LM, O’Brien P, Taylor RJK (2003) Stereoselective reactions of a (−)-quinic acid-derived enone: application to the synthesis of the core of scyphostatin. Org Lett 5:1943

    Article  CAS  Google Scholar 

  50. Barros MT, Maycock CD, Ventura MR (2001) Approaches to the synthesis of (+)- and (–)-epibatidine. J Chem Soc Perkin Trans 1:166

    Article  Google Scholar 

  51. Kamisuki S, Takahashi S, Mizushina Y, Hanashima S, Kuramochi K, Kobayashi S, Sakaguchi K, Nakata T, Sugawara F (2004) Total synthesis of dehydroaltenusin. Tetrahedron 60:5695

    Article  CAS  Google Scholar 

  52. Barder TE, Walker SD, Martinelli JR, Buchwald SL (2005) Catalysts for Suzuki-Miyaura coupling processes: scope and studies of the effect of ligand structure. J Am Chem Soc 127:4685

    Article  CAS  Google Scholar 

  53. Walker SD, Barder TE, Martinelli JR, Buchwald SL (2004) A rationally designed universal catalyst for Suzuki-Miyaura coupling processes. Angew Chem Int Ed 43:1871

    Article  CAS  Google Scholar 

  54. Oh-e T, Miyaura N, Suzuki A (1990) Palladium-catalyzed cross-coupling reaction of aryl or vinylic triflates with organoboron compounds. Synlett:221

    Google Scholar 

  55. Cieplak AS (1999) Inductive and resonance effects of substituents on π-face selection. Chem Rev 99:1265

    Article  CAS  Google Scholar 

  56. Sha CK, Huang SJ (1995) Synthesis of β-substituted α-iodocycloalkenones. Tetrahedron Lett 36:6927

    Article  CAS  Google Scholar 

  57. Alves C, Barros MT, Maycock CD, Ventura MR (1999) An efficient transformation of quinic acid to shikimic acid derivatives. Tetrahedron 55:8443

    Article  CAS  Google Scholar 

  58. Altemöller M, Gehring T, Cudaj J, Podlech J, Goesmann H, Feldmann C, Rothenberger A (2009) Total Synthesis of graphislactones A, C, D, and H, of ulocladol, and of the originally proposed and revised structures of graphislactones E and F. Eur J Org Chem :2130

    Google Scholar 

  59. Suzuki A (2004) Organoborane coupling reactions (Suzuki coupling). Proc Jpn Acad 80:359

    Article  CAS  Google Scholar 

  60. Alonso F, Beletskaya IP, Yus M (2008) Non-conventional methodologies for transition-metal catalyzed carbon-carbon coupling: a critical overview. Part 2: The Suzuki reaction. Tetrahedron 64:3047

    Article  CAS  Google Scholar 

  61. Lebrun MH, Duvert P, Gaudemer F, Gaudemer A, Deballon C, Boucly P (1985) Complexation of the fungal metabolite tenuazonic acid with copper(II), iron(III), nickel(II), and magnesium(II) ions. J Inorg Biochem 24:167

    Article  CAS  Google Scholar 

  62. Harris SA, Fisher LV, Folkers K (1965) The synthesis of tenuazonic and congeneric tetramic acids. J Med Chem 8:478

    Article  CAS  Google Scholar 

  63. Schobert R, Jagusch C, Melanophy C, Mullen G (2004) Synthesis and reactions of polymer-bound Ph3P=C=C=O: a quick route to tenuazonic acid and other optically pure 5-substituted tetramates. Org Biomol Chem 2:3524

    Article  CAS  Google Scholar 

  64. Asam S (2011) Development of a stable isotope dilution assay for tenuazonic acid. J Agric Food Chem 59:2980

    Article  CAS  Google Scholar 

  65. Yang C, Sheng Q, Huang L, Zhang P, Zhu Z (2006) Method for preparation of tenuazonic acid. Patent No CN 1817859

    Google Scholar 

  66. Poncet J, Jouin P, Castro B (1990) Tetramic Acid Chemistry Part1. Reinvestigation of Racemisation during the Synthesis of Tetramic Acids via Dieckmann Cyclisation. J Chem Soc Perkin Trans 1:611

    Article  Google Scholar 

  67. Gossauer A (2003) Monopyrrolic natural products. Prog Chem Org Nat Prod 86:1

    Article  Google Scholar 

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Bräse, S. et al. (2013). Alternaria Metabolites. In: The Chemistry of Mycotoxins. Progress in the Chemistry of Organic Natural Products, vol 97. Springer, Vienna. https://doi.org/10.1007/978-3-7091-1312-7_11

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