Abstract
Many filamentous fungi produce compounds that adversely affect the growth and development of plants. Determining the importance of these phytotoxic compounds in plant/fungal interactions has proven to be an extremely difficult task. Although research on fungal phytotoxins spans almost a century, it is only within the past few years that their role in plant disease has been unambiguously demonstrated. This chapter will focus on recent progress in characterizing the maromolecular aspects of fungal phytotoxin biosynthesis, which, together with advances in fungal molecular genetics, have provided powerful new approaches for investigating the significance of phytotoxins in plant/fungal interactions. A number of reviews covering phytotoxin biosynthesis, isolation, structure, and mechanism of action have been published over the past 15 years (Scheffer 1983; Mitchell 1984; Knoche and Duvick 1987). The reader is directed to the excellent review by Stoessl (1984) for a comprehensive account of fungal phytotoxin biosynthesis.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Aducci P, Ballio A, Federico R, Marra M, Graniti A (1983) Translocation of fusicoccin within almond plants infected by Fusicoccum amygadali Del. Phytopathol Mediterr 22: 100–102
Arntzen CJ (1972) Inhibition of photophosphorylation by tentoxin, a cyclic tetrapeptide. Biochim Biophys Acta 283: 539
Ashby MN, Spear DH, Edwards PA (1990) Prenyltransferases: From yeast to man. In: Attie AD (ed) Molecular biology of atherosclerosis. Elsevier, Amsterdam, pp 27–34
Avni A, Anderson JD, Holland N, Rochaix J-D, GrometElhanan Z, Edelman M (1992) Tentoxin sensitivity of chloroplasts determined by codon 83 of b subunit of proton-ATPase. Science 257: 1245–1247
Back K, Chappell J (1995) Cloning and bacterial expression of a sesquiterpene cyclase from Hyoscyamus muticus and its molecular comparison to related terpene cyclases. J Biol Chem 270: 7375–7381
Beck J, Pipka S, Siegner A, Schlitz E, Schweizer E (1990) The multifunctional 6-methylsalicylic acid synthase gene of Penicillium patulum: its gene structure relative to that of other polyketide synthases. Eur J Biochem 192: 487–498
Beremand MN (1987) Isolation and characterization of mutants blocked in T-2 toxin biosynthesis. Appl Environ Microbiol 53: 1855–1859
Bernadini M, Carilli A, Pacioni G, Santurbano B (1975) Isolation of beauvericin from Paecilomyces fumosoroseus. Phytochemistry 14: 18–65
Billich A, Zocher R (1991) Formation of N-methylated peptide bonds in peptides anf peptidols. In: Kleinkauf H, von Dohren H (eds) Biochemistry of peptide antibiotics. de Gruyter, Berlin, pp 57–79
Billich A, Zocher R, Kleinkauf H, Braun DG, Lavanchy D, Hochkeppel HK (1987) Monoclonal antibodies to the multienzyme enniatin synthetase. Production and use in structural studies. Biol Chem Hoppe-Seyler 368: 521–529
Bronson CR (1991) The genetics of phytotoxin production by plant pathogenic fungi. Experientia 47: 771–776
Bunkers GJ, Strobel GA (1991) A proposed mode of action for green island induction by the eremophilane phytotoxins produced by Drechslera gigantea. Physiol Mol Plant Pathol 38: 313–323
Burmeister HR, Plattner RD (1987) Enniatin production by Fusarium tricinctum and its effect on germinating wheat seeds. Phytopathology 77: 1483–1487
Calpouzos L, Stalknecht GF (1967) Symptomas of Cercospora leaf spot of sugar beets influenced by light intensity. Phytopathology 57: 799–800
Cane DE (1990) Enzymatic formation of sesquiterpenes. Chem Rev 90: 1089–1103
Cane DE, Rawlings BJ, Yang C-C (1987) Isolation of (—)g-cadinene and aristolochene from Aspergillus terreus. J Antibiot 40: 1331–1334
Cane DE, Sohng JK, Lamberson CR, Rudnicki SM, Wu Z, Lloyd MD, Oliver JS, Hubbard BR (1994) Pentalenene synthase. Purification, molecular cloning, sequencing, and high-level expression in Escherichia coli of a terpenoid cyclase from Streptomyces ÚC5319. Biochemistry 33: 5846–5857
Casale WL, Hart LP (1988) Inhibition of 3H-leucine incorporation by trichothecene mycotoxins in maize and wheat tissue. Phytopathology 78: 1673–1677
Chang PK, Cary JW, Yu JJ, Bhatnagar D, Cleveland TE (1995) The Aspergillus parasiticus polyketide synthase gene pksA, a homolog of Aspergillus nidulans wA, is required for aflatoxin B-1 biosynthesis. Mol Gen Genet 248: 270–277
Colby SM, Alonso WR, Katahira EJ, McGarvey DJ, Croteau R (1993) 4S-Limonene synthase from the oil glands of spearmint (Mentha spicata). cDNA isolation, characterization, and bacterial expression of the catalytically active monoterpene cyclase. J Biol Chem 268: 23016–23024
Croteau R (1987) Biosynthesis and catabolism of monoterpenoids. Chem Rev 87: 929–954
Cundliffe E (1989) How antibiotic-producing organisms avoid suicide. Annu Rev Microbial 43: 207–233
Cutler HG (1988) Trichothecenes and their role in the expression of plant disease. Biotechnology of crop protection. ACS Symp Ser 379: 50–72
Daub ME (1982) Cercosporin, a photosensitizing toxin from Cercospora species. Phytopathology 72: 370–374
Daub ME, Ehrenshaft M (1993) The photoactivated toxin cercosporin as a tool in fungal photobiology. Physiol Plant 89: 227–236
Deol BD, Ridley DD, Singh P (1978) Isolation of cyclodepsipeptides from plant pathogenic fungi. Aust J Chem 31: 1397–1399
Desjardins AE, Plattner RD, VanMiddlesworth F (1986) Trichothecene biosynthesis in Fusarium sporotrichioides: origin of the oxygen atoms of T-2 toxin. Appl Environ Microbiol 51: 493–497
Desjardins AE, Spencer GF, Plattner RD, Beremand MN (1989) Furanocoumarin phytoalexins, trichothecene toxins and infection of Pastinaca sativa by Fusarium sporotrichioides. Phytopathology 79: 170–175
Desjardins AE, Hohn TM, McCormick SP (1992) The effect of gene disruption of trichodiene synthase (Tox5) on the virulence of Gibberella pulicaris. Mol Plant-Microbe Interact 5: 214–222
Desjardins AE, Hohn TM, McCormick SP (1993) Trichothecene biosynthesis in Fusarium species: chemistry, genetics, and significance. Microbiol Rev 57: 595–604
Donadio S, Stayer MJ, McAlpine JB, Swanson SJ, Katz L (1991) Modular organization of genes required for complex polyketide biosynthsis. Science 252: 675–679
Durbin RD, Graniti A (1989) Possible applications of phytotoxins. In: Graniti A, Durbin RD, Ballio A (eds) Phytotoxins and plan pathogenesis. Springer, Berlin Heidelberg New York, pp 337–355
Durbin RD, Uchytil TF (1977) A survey of plant insensitivity to tentoxin. Phytopathology 67: 602–603
Edwards JV, Lax AR, Lillehoj EB, Boudreaux GJ (1987) Structure-activity relationships of cyclic and acyclic analogues of the phytotoxic peptide tentoxin. J Agric Food Chem 35: 451–456
Ehrenshaft M, Upchurch RG (1991) Isolation of light-enhanced cDNAs of Cercospora kikuchii. Appl Environ Microbiol 57: 2671–2676
Facchini PJ, Chappell J (1992) A gene family for an elicitor-induced sesquiterpene cyclase in tobacco. Proc Natl Acad Sci USA 89: 11088–11092
Fajola AO (1978) Cercosporin, a phytotoxin of Cercospora spp. Physiol Plant Pathol 13: 157–164
Feng GH, Leonard TJ (1995) Characterization of the polyketide synthase gene (pksLl) required for aflatoxin biosynthesis in Aspergillus parasiticus. J Bacteriol 177: 6246–6254
Fincham JRS (1989) Transformation in fungi. Microbiol Rev 53: 148–170
Gäumann E, Naef-Roth S, Kern H (1960) Zur phytotoxischen Wirksamkeit der Enniatine. Phytopathology 40: 45–51
Greenhalgh R, Fielder DA, Morrison LA et al. (1989) Apotrichothecenes: Minor metabolites of the Fusarium species. In: Natori S, Hashimoto K, Ueno Y (eds) Mycotoxins and phycotoxins ‘88. Elsevier, Amsterdam, pp 223–232
Haese A, Schubert M, Herrmann M, Zocher R (1993) Molecular characterization of the enniatin synthetase gene encoding a multifunctional enzyme catalyzing Nmethyldepsipeptide formation in Fusarium scirpi. Mol Microbiol 7: 905–914
Hamill RL, Higgens CE, Boaz HE, Gorman M (1969) The structure of beauvericin, a new depsipeptide antibiotic toxic to Artemia salina. Tetrahedron Lett 4255–4258
Hermann M, Zocher R, Haese A (1996a) Enniatin production by Fusarium strains and its effect on potato tuber tissue. Appl Environ Microbiol 62: 393–398
Hermann M, Zocher R, Haese A (1996b) Effect of disruption of the enniatin synthetase gene on the virulence of Fusarium avenaceum. Mol Plant-Microbe Interact 9: 226–232
Hohn TM, Beremand PD (1989) Isolation and nucleotide sequence of a sesquiterpene cyclase gene from the trichothecene-producing fungus Fusarium sporotrichioides. Gene 79: 131–138
Hohn TM, Desjardins AE (1992) Isolation and gene disruption of the Tox5 gene encoding trichodiene synthase in Gibberella pulicaris. Mol Plant-Microbe Interact 5: 249–256
Hohn TM, VanMiddlesworth F (1986) Purification and characterization of the sesquiterpene cyclase trichodiene synthetase from Fusarium sporotrichioides. Arch Biochem Biophys 251: 756–761
Hohn TM, McCormick SP, Desjardins AE (1993) Evidence for a gene cluster involving trichothecene pathway biosynthetic genes in Fusarium sporotrichioides. Curr Genet 24: 291–295
Hohn TM, Desjardins AE, McCormick SP (1995a) The Tri4 gene of Fusarium sporotrichioides encodes a cytochrome P450 monooxygenase involved in trichothecene biosynthesis. Mol Gen Genet 248: 95–102
Hohn TM, Desjardins AE, McCormick SP, Proctor RH (1995b) Biosynthesis of trichothecenes, genetic and molecuar aspects. In: Eklund M, Richard JL, Katsutoshi M (eds) Molecular approaches to food safety. Alaken, Fort Collins, Colorado, pp 239–247
Hopwood DA, Sherman DH (1990) Molecular genetics of polyketides and its comparison to fatty acid biosynthesis. Annu Rev Genet 24: 37–60
Jarvis BB (1991) Macrocyclic trichothecenes. In: Sharma RP, Salunkhe DK (eds) Mycotoxins and phytoalexins. CRC Press, Boca Raton, pp 361–421
Jarvis BB (1992) Macrocyclic trichothecenes from Brazilian Baccharis species: from microanalysis to large scale isolation. Phytochem Anal 3: 241–249
Jeker N, Tamm C (1988) Synthesis of new, unnatural macrocyclic trichothecenes: 4-epiverrucarin A. Helv Chim Acta 71: 1904–1913
Katz L, Donadio S (1993) Polyketide synthesis: prospects for hybrid antibiotics. Annu Rev Microbiol 47: 875–912
Kenfield D, Bunkers G, Strobel G et al. (1989a) Fungal phytotoxins: potential new herbicides. In: Graniti A, Durbin RD, Ballio A (eds) Phytotoxins and plant pathogenesis. Springer, Berlin Heidelberg New York, pp 319–335
Kenfield D, Bunkers G, Wu Y-H, Strobel G, Sugawara F, Hallock Y, Clardy J (1989b) Gigantenone, a novel sesquiterpene phytohormone mimic Experientia 45: 900–902
Kleinkauf H, von Döhren H (1990a) Bioactive peptides: Recent advances and trends. In: Kleinkauf H, von Döhren H (eds) Biochemistry of peptide antibiotics. deGruyter, Berlin, pp 1–31
Kleinkauf H, von Döhren H (1990b) Nonribosomal biosynthesis of peptide antibiotics. Eur J Biochem 192: 1–15
Klotz MG (1988) The action of tentoxin on membrane processes in plants. Physiol Plant 74: 575–582
Knoche HW, Duvick JP (1987) The role of fungal toxins in plant disease. In: Pegg GF, Ayers PG (eds) Fungal infection of plants. Cambridge University Press, Cambridge, pp 158–191
Kuti JO, Ng TJ, Bean GA (1989) Possible pathogen-produced trichothecene metabolite in Myrothecium leafspot of muskmelon. Physiol Mol Plant Pathol 34: 41–54
Kuyama S, Tamura T (1957) A pigment of Cercospora kikuchii (Matsumoto et Tomoyasu). 1. Cultivation of the fungus, isolation and purification of pigment. J Am Chem Soc 79: 5725–5726
Lax AR, Shepherd HS, Edwards JV (1988) Tentoxin, a chlorosis-inducing toxin from Alternaria as a potential herbicide. Weed Technol J Weed Sci Soc Am 2: 540–544
Liebermann B, Ramm K (1991) N-methylation in the biosynthesis of the phytotoxin tentoxin. Phytochemistry 30: 1815–1817
Marre E (1979) Fusicoccin: a tool in plant physiology. Annu Rev Plant Physiol 30: 273–288
Mayorga ME, Timberlake WE (1992) The developmentally regulated Aspergillus nidulans wA gene encodes a polypeptide homologous to polyketide and fatty acid synthases. Mol Gen Genet 235: 205–212
McCormick SP, Hohn TM, Desjardins AE (1996) Isolation and characterization of Tri3, a gene encoding 15–0acetyltransferase from Fusarium sporotrichioides. Appl Environ Microbiol 62: 353–359
Mitchell RE (1984) The relevance of non-host-specific toxins in the expression of virulence by pathogens. Annu Rev Phytopathol 22: 215–245
Okubo A, Yamazaki S, Fuwa K (1975) Biosynthesis of cercosporin. Agric Biol Chem 39: 1173–1175
Panaccione DG, Scott-Craig JS, Pocard J-A, Walton JD (1992) A cyclic peptide synthetase gene required for pathogenicity of the fungus Cochliobolus carbonum on maize. Proc Natl Acad Sci USA 89: 6590–6594
Payne GA, Nystrom GJ, Bhatnagar D, Cleveland TE, Woloshuk CP (1993) Cloning of the afl-2 gene involved in aflatoxin biosynthesis from Aspergillus flavus. Appl Environ Microbiol 59: 156–162
Peeters H, Zocher R, Kleinkauf H (1988) Synthesis of beauvericin by a multifunctional enzyme. J Antibiol 41: 352–359
Plattner RD, Nelson PE (1994) Production of beauvericin by a strain of Fusarium proliferatum isolated from corn fodder for swine. Appl Environ Microbiol 60: 3894–3896
Proctor RH, Hohn TM (1993) Aristolochene synthase. Isolation, characteriztion, and bacterial expression of a sesquiterpenoid biosynthetic gene (Aril) from Penicillium roqueforti. J Biol Chem 268: 4543–4548
Proctor RH, Hohn TM, McCormick SP (1995a) Reduced virulence of Gibberella zeae caused by disruption of a trichothecene toxin biosynthetic gene. Mol Plant-Microbe Interact 8: 593–601
Proctor RH, Hohn TM, McCormick SP, Desjardins AE (1995b) Tri6 encodes an unsual zinc finger protein involved in the regulation of trichothecene biosynthesis in Fusarium sporotrichioides. Appl Environ Microbiol 61: 1923–1930
Scheffer RP (1983) Toxins as chemical determinants of plant disease. In: Daly JM, Deverall BJ (eds) Toxins and plant pathogenesis. Academic Press, New York, pp 1–40
Schoner B, Geistlich M, Rosteck P Jr, Rao RN, Seno E, Reynolds P, Cox K, Burgett S, Hershberger C (1992) Sequence similarity between macrolide-resistance determinants and ATP-binding transport proteins. Gene 115: 93–96
Scott-Craig JS, Panaccione DG, Pocard J-A, Walton JD (1992) The cyclic peptide synthetase catalyzing HC-toxin production in the filamentous fungus Cochliobolus carbonum is encoded by a 15.7-kilobase open reading frame. J Biol Chem 267: 26044–26049
Skory CD, Chang P-K, Cary J, Linz JE (1992) Isolation and characterization of a gene from Aspergillus parasiticus associated with the converison of versicolorin A to sterigmastocystin in aflatoxin biosynthesis. Appl Environ Microbiol 58: 3527–3537
Smith DA (1982) Toxicity of phytoalexins. In: Bailey JA, Mansfield JW (eds) Phytoalexins. Halstead Press, New York, pp 218–252
Smith DJ, Earl AJ, Turner G (1990) The multifunctional peptide synthetase performing the first step of penicilin biosythesis in Penicillium chrysogenum is a 421 073 Balton protein similar to Bacillus brevis peptide antibiotic sythetases. EMBO J 9: 2743–2750
Steele JA, Uchytil TF, Durbin RD, Bhatnagar P, Rich DH (1976) Chloroplast coupling factor 1: a species-specific receptor for tentoxin. Proc Natl Acad Sci USA 73: 2245–2248
Stoessl A (1981) Structure and biogentic relations: fungal nonhost-specific. In: Durbin RD (ed) Toxins in plant disease. Academic Press, New York, pp 109–219
Sugawara F, Strobel G, Fisher LE, Van Duyne GD, Clardy J (1985) Bipolaroxin, a selective phytotoxin produced by Bipolaris cynodontis. Proc Natl Acad Sci USA 82: 8291–8294
Tanaka S, Wada K, Marumo S, Hattori H (1984) Structure of sporogen-AO 1, a sporogenic substance of Aspergillus oryzae. Tetrahedron Lett 25: 5907–5910
Tanaka Y, Omura S (1993) Agroactive compounds of microbial origin. Annu Rev Microbiol 47: 57–87
Trail F, Mahanti N, Linz J (1995) Molecular biology of aflatoxin biosynthesis. Microbiology-Uk 141: 755–765
Upchurch RG, Walker DC, Rollins JA, Ehrenshaft M, Daub ME (1991) Mutants of Cercospora kikuchii altered in cercosporin synthesis and pathogenicity. Appl Environ Microbiol 57: 2940–2945
Walton JD, Panaccione DG (1993) Host-selective toxins and disease specificity: perspectives and progress. Annu Rev Phytopathol 31: 275–303
Wang I-K, Reeves C, Gaucher CM (1991) Isolation and sequencing of a genomic DNA clone containing the 3’ terminus of the 6-methylsalicylic acid polyketide synthetase gene of Penicillium urticae. Can J Microbiol 37: 86–95
Wang YZ, Miller JD (1988) Effects of Fusarium graminearum metabolites of wheat tissue in relation to Fusarium head blight resistance. J Phytopathol 122: 118–125
Whitehead IM, Threlfall DR, Ewing DF (1989) 5-epiaristolochene is a common precursor of the sesquiterpenoid phytoalexins capsidiol and debneyol. Phytochemistry 28: 775–779
Yoder OC (1980) Toxins in pathogenesis. Annu Rev Phytopathol 18: 103–129
Yu JH, Leonard TJ (1995) Sterigmatocystin biosynthesis in Aspergillus nidulans requires a novel type I polyketide synthase. J Bacteriol 177: 4792–4800
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1997 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Hohn, T.M. (1997). Fungal Phytotoxins: Biosynthesis and Activity. In: Carroll, G.C., Tudzynski, P. (eds) Plant Relationships. The Mycota, vol 5. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-10370-8_8
Download citation
DOI: https://doi.org/10.1007/978-3-662-10370-8_8
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-662-10372-2
Online ISBN: 978-3-662-10370-8
eBook Packages: Springer Book Archive