Abstract
The trichothecenes are a group of naturally-occurring sesquiterpenoid epoxides which show a broad range of biological activity. They are powerful inhibitors of eukaryotic protein synthesis, are phytotoxic, insecticidal and toxic to animals, and some are among the most toxic nonnitrogenous compounds known to man. Several are commonly found in cereal grains, and the potential health risk from contaminated animal feed and human food is a major factor in stimulating research into this group of compounds. Since the isolation of the macrolide mixture, glutinosin t(1), was reported in 1946, the body of trichothecene literature has expanded to some 3000 publications
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References
Grove JF (1993) Macrocyclic Trichothecenes. Nat Prod Rep 10: 429
Grove JF (1988) Non-Macrocyclic Trichothecenes. Nat Prod Rep 5: 187
Grove JF (1996) Non-Macrocyclic Trichothecenes, Part 2. Prog Chem Org Nat Prod 69: 1
Godtfredsen WO, Grove JF, Tamm Ch (1967) Zur Nomenklatur einer neueren Klasse von Sesquiterpenen. Helv Chim Acta 50: 1666
Brian PW, Dawkins AW, Grove JF, Hemming HG, Lowe D, Norris GLF (1961) Phytotoxic Compounds Produced by Fusarium equiseti. J Exp Bot 12: 1
Jarvis BB, Stahly GP, Pavanasasivam G, Midiwo JO, DeSilva T, Holmlund CE, Mazzola EP, Geoghegan RF (1982) Isolation and Characterization of the Trichoverroids and New Roridins and Verrucarins. J Org Chem 47: 1117
Booth C (1971) The Genus Fusarium. CommonwealthMycological Institute, Kew, UK
Nelson PE, Toussoun TA, Marasas WFO (1983) Fusarium Species: An Illustrated Manual for Identification. Pennsylvania State University Press, University Park, PA
Marasas WFO, Nelson PE, Toussoun TA (1984) Toxigenic Fusarium Species. Identity and Mycotoxicology. Pennsylvania State University Press, University Park, PA
Kurata H (1984) Personal communication, in ref. 9, p. 128
Machida Y, Nozoe S (1972) Biosynthesis of Trichothecin and Related Compounds. Tetrahedron 28: 5113
Baldwin NCP, Bycroft BW, Dewick PM, Marsh DC, Gilbert J (1987) Trichothecene Mycotoxins from Fusarium culmorum Cultures. Z Naturforsch C42: 1043
Lauren DR, Sayer ST, di Menna ME (1992) Trichothecene Production by Fusarium Species Isolated from Grain and Pasture Throughout New Zealand. Mycopathologia 120: 167
Seifert KA, Louis-Seize G, Savard ME (1997) The Phylogenetic Relationships of Two Trichothecene-Producing Hyphomycetes, Spicellum roseum and Trichothecium roseum. Mycologia 89: 250
Harri E, Loeffler W, Sigg HP, Stahelin H, Stoll Ch, Tamm Ch, Wiesinger D (1962) Über die Verrucarine und Roridine, eine Gruppe von cytostatisch hochwirksamen Antibiotica aus Myrothecium-Arten. Helv Chim Acta 45: 839
Adams PM, Hanson JR (1972) Sesquiterpenoid Metabolites of Trichoderma polysporum and T. sporulosum. Phytochemistry 11: 423
Ayer WA, Miao S (1993) Secondary Metabolites of the Aspen Fungus Stachybotrys cylindrospora. Canad J Chem 71: 487
Jarvis BB, Zhou Y, Jiang J, Wang S, Sorenson WG, Hintikka E-L, Nikulin M, Parikka P, Etzel RA, Dearborn DG (1996) Toxigenic Molds in Water-Damaged Buildings: Dechlorogriseofulvins from Memnoniella echinata. J Nat Prod 59: 553
Choi SU, Choi EJ, Kim KH, Kim NY, Kwon B-M, Kim SU, Bok SH, Lee SY, Lee CO (1996) Cytotoxicity of Trichothecenes to Human Solid Tumor Cells in Vitro. Arch Pharm Res 19: 6
Lauren DR, Ashley A, Blackwell BA, Greenhalgh R, Miller JD, Neish GA (1987) Trichothecenes Produced by Fusarium crookwellense DAOM 193611. J Agric Food Chem 35: 884
Miller JD, MacKenzie S (2000) Secondary Metabolites of Fusarium venenatum Strains with Deletions in the Tri5 Gene Encoding Trichodiene Synthase. Mycologia 92: 764
Corley DG, Rottinghaus GE, Tracy JK, Tempesta MS (1986) New Trichothecene Mycotoxins of Fusarium sporotrichioides (MC-72083). Tetrahedron Lett 27: 4133
Pineiro MS, Scott PM, Kanhere SR (1996) Mycotoxin Producing Potential of Fusarium graminearum Isolates from Uruguayan Barley. Mycopathologia 132: 167
McCormick SP, Hohn TM (1997) Accumulation of Trichothecenes in Liquid Cultures of a Fusarium sporotrichioides Mutant Lacking a Functional Trichothecene C-15 Hydroxylase. Appl Environ Microbiol 63: 1685
Jarvis BB, Lee Y-W, Yatawara CS, Mazzocchi DB, Flippen-Anderson JL, Gilardi R, George C (1985) 7α-Hydroxytrichodermol, a New Trichothecene from Myrothecium roridum. Appl Environ Microbiol 50: 1225
El-Kady IA, Moubasher MH (1982) Toxigenicity and Toxins of Stachybotrys Isolates from Wheat Straw Samples in Egypt. Exptl Mycol 6: 25
Ueno Y, Aikawa Y, Okumura H, Sugura Y, Nakamura K, Masuma R, Tanaka T, Young CJ, Savard ME (1997) Trichothecenes Produced by Fusarium Species Fn 2B. Maikotokishin 45: 25; (1998) Chem Abstr 128: 44831
Greenhalgh R, Levandier D, Adams W, Miller JD, Blackwell BA, McAlees AJ, Taylor A (1986) Production and Characterization of Deoxynivalenol and Other Secondary Metabolites of Fusarium culmorum (CMI 14764, HLX 1503). J Agric Food Chem 34: 98
Plattner RD, Tjarks LW, Beremand MN (1989) Trichothecenes Accumulated in Liquid Culture of a Mutant of Fusarium sporotrichioides NRRL 3299. Appl Environ Microbiol 55: 2190
Kim K-H, Lee Y-W, Mirocha CJ, Pawlosky RJ (1990) Isoverrucarol Production by Fusarium oxysporum CJS-12 Isolated from Corn. Appl Environ Microbiol 56: 260
Pathre SV, Mirocha CJ, Christensen CM, Behrens J (1976) Monoacetoxyscirpenol. A New Mycotoxin Produced by Fusarium roseum Gibbosum. Appl Environ Microbiol 24: 97
Sobolev VS, Eller KI, Boltyenskaya EV, Dmitrieva IV, Tutelyan VA (1984) Study of Toxin Production by Fusarium sporotrichiella. Isv Akad Nauk SSSR, Ser Biol 137; Chem Abstr 100: 171231
Sanson DR, Corley DG, Barnes CL, Searles S, Schlemper EO, Tempesta MS, Rottinghaus GE (1989) New Mycotoxins from Fusarium sambucinum. J Org Chem 54: 4313
Luo Y, Lin F, Yang J, Zhang J, Ye Y, Li Y, Jiang Y, Zhang N, Wang Z (1993) Analysis and Identification of Fusarium Mycotoxins in Corn Culture of Fusarium camptoceras. Zhenjun Xuebao 12: 77; Chem Abstr 119: 153704
McLachlan A, Shaw KJ, Hocking AD, Pitt JI, Nguyen THL (1992) Production of Trichothecene Mycotoxins by Australian Fusarium Species. Food Addit Contam 9: 631
Liu W, Sundheim L, Langseth W (1998) Trichothecene Production and the Relationship to Vegetative Compatibility Groups in Fusarium poae. Mycopathologia 140: 105
O’Donnell K, Cigelnik E, Casper HH (1998) Molecular Phylogenetic, Morphological, and Mycotoxin Data Support Reidentification of the Quorn Mycoprotein Fungus as Fusarium venenatum. Fungal Genet Biol 23: 57
Szathmary CI, Mirocha CJ, Palyusik M, Pathre SV (1976) Identification of Mycotoxins Produced by Species of Fusarium and Stachybotrys Obtained from Eastern Europe. Appl Environ Microbiol 32: 579
Cole RJ, Dorner JW, Cox RH, Cunfer BM, Cutler HG, Stuart BP (1981) The Isolation and Identification of Several Trichothecene Mycotoxins from Fusarium heterosporum. J Nat Prod 44: 324
Kononenko GP, Soboleva NA, Leonov AN (1990) 3,7,8,15-Tetrahydroxy-12,13-epoxytrichothec-9-ene in a Culture of Fusarium graminearum. Khim Prir Soedin 267; Chem Nat Compd (Engl Transl) 26: 219
Godtfredson WO, Vangedal S (1965) Trichodermin, a New Sesquiterpene Antibiotic. Acta Chem Scand 19: 1088
Cutler HG, Cole PD, Arrendale RF, Bassfield RL, Cox RH, Roberts RG, Hanlin RT (1986) Dendrostilbella sp. (85–25), a New Source of Trichodermin. Agric Biol Chem 50: 2667
Greenhalgh R, Meier R-M, Blackwell BA, Miller JD, Taylor A, ApSimon JW (1984) Minor Metabolites of Fusarium roseum (ATCC 28114). J Agric Food Chem 32: 1261
Greenhalgh R, Meier R-M, Blackwell BA, Miller JD, Taylor A, ApSimon JW (1986) Minor Metabolites of Fusarium roseum (ATCC 28114), Part 2. J Agric Food Chem 34: 115
Zamir LO, Devor KA, Sauriol F (1991) Biosynthesis of the Trichothecene 3-Acetyldeoxynivalenol. Identification of the Oxygenation Steps After Isotrichodermin. J Biol Chem 266: 14992
Gardner D, Glen AT, Turner WB (1972) Calonectrin and 15-Deacetylcalonectrin, New Trichothecanes from Calonectria nivalis. J Chem Soc, Perkin Trans 1: 2576
Loeffler W, Mauli R, Ruesch ME, Stahelin H (1967) Monodeacetylanguidin. German Patent 1233098, Jan 26, 1967; Chem Abstr 66: 84744
Steyn PS, Vleggaar R, Rabie CJ, Kriek NPJ, Harington JS (1978) Trichothecene Mycotoxins from Fusarium sulphureum. Phytochemistry 17: 949
Bergers WWA, van der Stap JGMM, Kientz CE (1985) Trichothecene Production in Liquid Stationary Cultures of Fusarium tricinctum NRRL 3299 (Synonym: F. sporotrichioides): Comparison of Quantitative Brine Shrimp Assay with Physicochemical Analysis. Appl Environ Microbiol 50: 656
Evidente A, Randazzo G, Visconti A, Bottalico A (1989) Isolation of 15-Acetoxyscirpendiol from a Culture of Fusarium poae on Corn. Mycotoxin Res 5: 30
Ichihara A, Katayama K, Teshima H, Oikawa H, Sakamura S (1996) Chaetoglobosin O and Other Phytotoxic Metabolites from Cylindrocladium floridanum, a Causal Fungus of Alfalfa Black Rot Disease. Biosci Biotech Biochem 60: 360
Ishii K, Pathre SV, Mirocha CJ (1978) Two New Trichothecenes Produced by Fusarium roseum. J Agric Food Chem 26: 649
Richardson KE, Toney GE, Haney CA, Hamilton PB (1989) Occurrence of Scirpentriol and Its Seven Acetylated Derivatives in Culture Extracts of Fusarium sambucinum NRRL 13495. J Food Prot 52: 871
Visconti A, Mirocha CJ, Logrieco A, Bottalico A, Solfrizzo M (1989) Mycotoxins Produced by Fusarium acuminatum. Isolation and Characterization of Acuminatin: A New Trichothecene. J Agric Food Chem 37: 1348
Corley DG, Rottinghaus GE, Tempesta MS (1986) Novel Trichothecenes from Fusarium sporotrichioides. Tetrahedron Lett 27: 427
Hesketh AR (1992) Metabolic Studies on the Transformation of Trichodiene to Trichothecene Mycotoxins. Mycotoxin Res 8: 52
Ishii K, Ueno Y (1981) Isolation and Characterization of Two New Trichothecenes from Fusarium sporotrichioides Strain M-1-1. Appl Environ Microbiol 42: 541
Glaz ET, Csanyi E, Gyimesi J (1966) Supplementary Data on Crotocin — An Antifungal Antibiotic. Nature (London) 212: 617
Achilladelis B, Hanson JR (1969) Minor Terpenoids of Trichothecium roseum. Phytochemistry 8: 765
Plattner RD, Al-Hetti MB, Weisleder D, Sinclair JB (1988) A New Trichothecene from Trichothecium roseum. J Chem Res (S): 311
Langley P, Shuttleworth A, Sidebottom PJ, Wrigley SK, Fisher PJ (1990) A Trichothecene from Spicellum roseum. Mycol Res 94: 705
Loukaci A, Kayser O, Bindseil K-U, Siems K, Frevert J, Abreu PM (2000) New Trichothecenes Isolated from Holarrhena floribunda. J Nat Prod 63: 52
Iida A, Konishi K, Kubo H, Tomioka K, Tokuda H, Nishino H (1996) Trichothecinols A, B and C, Potent Anti-Tumor Promoting Sesquiterpenoids from the Fungus Trichothecium roseum. Tetrahedron Lett 37: 9219
Okuchi M, Itoh M, Kaneko Y, Doi S (1968) A New Antifungal Substance Produced by Myrothecium. Agric Biol Chem 32: 394; idem (1973) Sesquiterpene Antibiotic, Compound A-2, Minor Component from Myrothecium, I. Fermentation, Isolation, Physicochemical Properties, and the Structure. J Antibiot 26: 562
Habermehl G (1989) Isolation and Structure of New Toxins from Plants. Pure Appl Chem 61: 377
Greenhalgh R, Blackwell BA, Savard M, Miller JD, Taylor A (1988) Secondary Metabolites Produced by Fusarium sporotrichioides DAOM 165006 in Liquid Culture. J Agric Food Chem 36: 216
Ueno Y, Sato N, Ishii K, Sakai K, Tsunoda H, Enomoto M (1973) Biological and Chemical Detection of Trichothecene Mycotoxins of Fusarium Species. Appl Microbiol 25: 699
Sigg HP, Mauli R, Flury F, Hauser D (1965) Die Konstitution von Diacetoxyscirpenol. Helv Chim Acta 48: 962
Gilgan MW, Smalley EB, Strong FM (1966) Isolation and Partial Characterization of a Toxin from Fusarium tricinctum on Moldy Corn. Arch Biochem Biophys 114: 1
Hussein HM, Baxter M, Andrew IG, Franich RA (1991) Mycotoxin Production by Fusarium Species Isolated from New Zealand Maize Fields. Mycopathologia 113: 35
Cole M, Rolinson GN (1972) Microbial Metabolites with Insecticidal Properties. Appl Microbiol 24: 660
Mirocha CJ, Abbas HK, Kommedahl T, Jarvis BB (1989) Mycotoxin Production by Fusarium oxysporum and Fusarium sporotrichioides Isolated from Baccharis spp. from Brazil. Appl Environ Microbiol 55: 254
Ishii K (1975) Two New Trichothecenes Produced by Fusarium sp. Phytochemistry 14: 2469
Ripperger H, Seifert K, Romer A, Rullkotter J (1975) Isolierung von Diacetoxyscirpenol aus Fusarium solani var. coeruleum. Phytochemistry 14: 2298
Greenhalgh R, Miller JD, Visconti A (1991) Toxigenic Potential of Fusarium compactum R8287 and R8293. J Agric Food Chem 39: 809
Ghosal S, Biswas K, Srivastava RS, Chakrabarti DK, Chaudhary KCB (1978) Toxic Substances Produced by Fusarium, V: Occurrence of Zearalenone, Diacetoxyscirpenol, and T-2 Toxin in Moldy Corn Infected with Fusarium moniliforme Sheld. J Pharm Sci 67: 1768
Scott PM, Harwig J, Blanchfield BJ (1980) Screening Fusarium Strains Isolated from Overwintered Canadian Grains for Trichothecenes. Mycopathologia 72: 175
Vesonder RF, Golinsky P, Plattner R, Zeitkiewicz DL (1991) Mycotoxin Formation by Different Geographic Isolates of Fusarium crookwellense. Mycopathologia 113: 11
Suzuki T, Kurisa M, Hoshino Y, Ichinoe M, Nose N, Tokumaru Y, Watanabe A (1980) Production of Trichothecene Mycotoxins of Fusarium sp. in Wheat and Barley Harvested in Saitama Prefecture. J Food Hyg Soc Jpn 21: 43
Altomare C, Logrieco A, Bottalico A, Mule G, Moretti A, Evidente A (1995) Production of Type A Trichothecenes and Enniatin B by Fusarium sambucinum Fuckel sensu lato. Mycopathologia 129: 177
Ishii K, Sakai K, Ueno Y, Tsunoda H, Enomoto M (1971) Solaniol, a Toxic Metabolite of Fusarium solani. Appl Microbiol 22: 718
Ueno Y, Ishii K, Sakai K, Kanaeda S, Tsunoda H, Tanaka T, Enomoto M (1972) Toxological Approaches to the Metabolites of Fusaria, IV. Microbial Survey on “Bean-Hulls Poisoning of Horses” with the Isolation of Toxic Trichothecenes, Neosolaniol and T-2 Toxin of Fusarium solani M-1-1. Jpn J Exp Med 42: 187
Ueno Y, Sato N, Ishii K, Sakai K, Enomoto M (1972) Toxological Approaches to the Metabolites of Fusaria, V. Neosolaniol, T-2 Toxin and Butenolide, Toxic Metabolites of Fusarium sporotrichioides NRRL 3510 and Fusarium poae 3287. Jpn J Exp Med 42: 461
Harwig J, Scott PM, Stoltz DR, Blanchfield BJ (1979) Toxins of Molds from Decaying Tomato Fruit. Appl Environ Microbiol 38: 267
Ueno Y, Ishii K, Sawano M, Ohtsubo K, Matsuda Y, Tanaka T, Kurata H, Ichinoe M (1977) Toxological Approaches to the Metabolites of Fusaria, XI. Trichothecenes and Zearalenone from Fusarium Species Isolated from River Sediments. Jpn J Exp Med 47: 177
Desjardins AE, Plattner RD (1989) Trichothecene Toxin Production by Strains of Gibberella pulicaris (Fusarium sambucinum) in Liquid Culture and in Potato Tubers. J Agric Food Chem 37: 388
Bosch U, Mirocha CJ (1992) Toxin Production by Fusarium Species from Sugar Beets and Natural Occurrence of Zearalenone in Beets and Beet Fibers. Appl Environ Microbiol 58: 3233
Abramson D, Clear RM, Smith DM (1993) Trichothecene Production by Fusarium spp. Isolated from Manitoba Grain. Canad J Plant Pathol 15: 147
Altomare C, Ritieni A, Perrone G, Fogliano V, Mannina L, Logrieco A (1995) Production of Neosolaniol by Fusarium tumidum. Mycopathologia 130: 179
Ilus T, Ward PJ, Nummi M, Adlercreutz H, Gripenberg J (1977) A New Mycotoxin from Fusarium. Phytochemistry 16: 1839
Greenhalgh R, Fielder DA, Blackwell BA, Miller JD, Charland J-P, ApSimon JW (1990) Some Minor Secondary Metabolites of Fusarium sporotrichioides DAOM 165006. J Agric Food Chem 38: 1978
Baldwin NCP, Bycroft BW, Dewick PM, Gilbert J, Holden I (1985) Biosynthesis of Trichothecene Mycotoxins in Fusarium culmorum Cultures. Z Naturforsch C40: 514
Lee Y-W, Mirocha CJ, Schroeder DJ, Walser MM (1985) TPD-1, a Toxic Component Causing Tibial Dyschondroplasia in Broiler Chickens, and Trichothecenes from Fusarium roseum “graminearum”. Appl Environ Microbiol 50: 102
Tutel’yan VA, Eller KI, Sobolev VS, Avren’eva LI, Rozynov BV, Bogdanova IA (1984) T-2 Triol — A New Mycotoxin Produced by Fusarium sporotrichiella. Dokl Akad Nauk SSSR 274: 727; Chem Abstr 101: 3609
Lansden JA, Cole RJ, Dorner JW, Cox RH, Cutler HG, Clark JD (1978) A New Trichothecene Mycotoxin from Fusarium tricinctum. J Agric Food Chem 26: 246
Bilai VI, Tutel’yan VA, Ellanskaya IA, Eller KI, Sobolev VS (1983) Component Composition of Trichothecenes Produced by Fusarium sporotrichiella Bilai. Mikrobiol Zh (Kiev) 45: 45; (1984) Chem Abstr 100: 46671
Lamprecht SC, Marasas WFO, Sydenham EW, Theil PG, Knox-Davies PS, van Wyk PS (1989) Toxicity to Plants and Animals of an Undescribed, Neosolaniol Acetate-Producing, Fusarium sp. from Soil. Plant Soil 114: 75
Jarvis BB, Vrudhula VM, Midiwo JO, Mazzola EP (1983) New Trichoverroids from Myrothecium verrucaria: Verrol and 12,13-Deoxytrichodermadiene. J Org Chem 48: 2576
Jarvis BB, Sorenson WG, Hintikka E-L, Nikulin M, Zhou Y, Jiang J, Wang S, Hinkley S, Etzel RA, Dearborn D (1998) Study of Toxin Production by Isolates of Stachybotrys chartarum and Memnoniella echinata Isolated During a Study of Pulmonary Hemisiderosis in Infants. Appl Environ Microbiol 64: 3620
Bamburg JR, Strong FM (1969) Mycotoxins of the Trichothecene Family Produced by Fusarium tricinctum and Trichoderma lignorum. Phytochemistry 8: 2405
Kotsonis FN, Ellison RA (1975) Assay and Relationship of HT-2 Toxin and T-2 Toxin Formation in Liquid Culture. Appl Microbiol 30: 33
El-Maghraby OMO, El-Kady IA, Soliman S (1995) Mycoflora and Fusarium Toxins of Three Types of Corn Grains in Egypt with Special Reference to Production of Trichothecene Toxins. Microbiol Res 150: 225
Visconti A, Mirocha CJ, Bottalico A, Chelkowski J (1985) Trichothecene Mycotoxins Produced by Fusarium sporotrichioides Strain P-11. Mycotoxin Res 1: 3
Corley DG, Miller-Wideman M, Durley RC (1994) Isolation and Structure of Harzianum A: A New Trichothecene from Trichoderma harzianum. J Nat Prod 57: 422
Jarvis BB, Midiwo JO, Stahly GP, Pavanasasivam G, Mazzola EP (1980) Trichodermadiene: A New Novel Trichothecene. Tetrahedron Lett 21: 787
Jarvis BB, Pavanasasivam G, Holmlund CE, DeSilva T, Stahly GP (1981) Biosynthetic Intermediates to the Macrocyclic Trichothecenes. J Amer Chem Soc 103: 472
Bean GA, Fernando T, Jarvis BB, Bruton B (1984) The Isolation and Identification of Trichothecene Mycotoxins from a Plant Pathogenic Strain of Myrothecium roridum. J Nat Prod 47: 727
Jarvis BB, Salemme J, Morais A (1995) Stachybotrys Toxins, 1. Nat Toxins 3: 10
Laurent D, Guella G, Roquebert M-F, Farinole F, Mancini I, Pietra F (2000) Cytotoxins, Mycotoxins and Drugs from a New Deuteromycete, Acremonium neo-caledoniae, from the Southwestern Lagoon of New Caledonia. Planta Med 66: 63
Jarvis BB, Vrudhula VM (1983) New Trichoverroids from Myrothecium verrucaria: 16-Hydroxytrichodermadienediols. J Antibiot 36: 459
Jarvis BB, Lee Y-W, Comezoglu SN, Yatawara CS (1986) Trichothecenes Produced by Stachybotrys atra from Eastern Europe. Appl Environ Microbiol 51: 915
El-Maghraby OMO, Bean GA, Jarvis BB, Aboul-Nasr MB (1991) Macrocyclic Trichothecenes Produced by Stachybotrys Isolated from Egypt and Eastern Europe. Mycopathologia 113: 109
Jarvis BB, DeSilva T, McAlpine JB, Swanson SJ, Whittern DN (1992) New Trichoverroids from Myrothecium verrucaria Isolated by High Speed Countercurrent Chromatography. J Nat Prod 55: 1441
Jarvis BB, Wang S, Ammon HL (1996) Trichoverroid Stereoisomers. J Nat Prod 59: 254
Gorst-Allman CP, Steyn PS, Vleggaar R, Rabie CJ (1985) Structure Elucidation of a Novel Trichothecene Glycoside Using 1H and 13C Nuclear Magnetic Resonance Spectroscopy. J Chem Soc, Perkin Trans 1: 1553
Bekele E, Rottinghaus AA, Rottinghaus GE, Casper HH, Fort DM, Barnes CL, Tempesta MS (1991) Two New Trichothecenes from Fusarium sporotrichioides. J Nat Prod 54: 1303
Bamburg JR, Riggs NV, Strong FM (1968) The Structures of Toxins from Two Strains of Fusarium tricinctum. Tetrahedron 24: 3329
Vesonder RF, Ellis JJ, Rohwedder WK (1981) Swine Refusal Factors Elaborated by Fusarium Strains and Identified as Trichothecenes. Appl Environ Microbiol 41: 323
Burmeister HR, Ellis JJ, Yates SG (1971) Correlation of Biological to Chromatographic Data for Two Mycotoxins Elaborated by Fusarium. Appl Microbiol 21: 673
Burmeister HR, Ellis JJ, Vesonder RF (1981) Survey for Fusaria That Produce an Antibiotic That Causes Conidia of Penicillium digitatum to Swell. Mycopathologia 74: 29
Yagen B, Joffe AZ (1976) Screening of Toxic Isolates of Fusarium poae and Fusarium sporotrichioides Involved in Causing Alimentary Toxic Aleukia. Appl Environ Microbiol 32: 423
Ghosal G, Chakrabarti DK, Chaudhary KCB (1976) Toxic Substances Produced by Fusarium I: Trichothecene Derivatives from Two Strains of Fusarium oxysporum f. sp. carthami. J Pharm Sci 65: 160
Soares da Silva N, Kemmelmeir C (1994) Identification of Mycotoxins Produced by Fusarium graminearum Isolates Grown on Maize (Zea mays L). Arg Biol Tecnol 37: 551; (1995) Chem Abstr 122: 284356
Eller KI, Sobolev VS, Rozynov BV, Tutel’yan BV (1985) 3′-Hydroxy-T-2 Toxin — A New Mycotoxin from Fusarium sporotrichiella. Dokl Akad Nauk SSSR 283: 1481; Chem Abstr 103: 210548
Kotsonis FN, Ellison RA, Smalley EB (1975) Isolation of Acetyl-T-2 Toxin from Fusarium poae. Appl Microbiol 30: 493
Bloem RJ, Smitka TA, Bunge RH, French JC, Mazzola EP (1983) Roridin L-2, a New Trichothecene. Tetrahedron Lett 24: 249
Jarvis BB, Vrudhula VM, Pavanasasivam G (1983) Trichoverritone and 16-Hydroxyroridin L-2, New Trichothecenes from Myrothecium roridum. Tetrahedron Lett 24: 3539
Jarvis BB, Wang S, Cox C, Rao MM, Philip V, Varashin MS, Barros CS (1996) Brazilian Baccharis Toxins: Livestock Poisoning and the Isolation of Macrocyclic Trichothecene Glucosides. Nat Toxins 4: 58
Chakrabarti DK, Ghosal S (1986) Occurrence of Free and Conjugated 12,13-Epoxytrichothec-9-enes and Zearalenone in Banana Fruits Infected with Fusarium moniliforme. Appl Environ Microbiol 51: 217
Bennett GA, Peterson RE, Plattner RD, Shotwell OL (1981) Isolation and Purification of Deoxynivalenol and a New Trichothecene by High Pressure Liquid Chromatography. J Amer Oil Chem Soc 58: 1002A
Yoshizawa T, Morooka N (1973) Deoxynivalenol and Its Monoacetate: New Mycotoxins from Fusarium roseum and Moldy Barley. Agric Biol Chem 37: 2933
Vesonder RF, Ciegler A, Jenson AH (1973) Isolation of the Emetic Principle from Fusarium-Infected Corn. Appl Microbiol 26: 1008
Vesonder RF, Ciegler A, Jenson AH (1977) Production of Refusal Factors by Fusarium Strains on Grains. Appl Environ Microbiol 34: 105
El-Banna AA, Scott PM, Lau P-Y, Sakuma T, Platt HW, Campbell V (1984) Formation of Trichothecenes by Fusarium solani var. coeruleum and Fusarium sambucinum in Potatoes. Appl Environ Microbiol 47: 1169
Bosch U, Mirocha CJ, Abbas HK, di Menna M (1989) Toxicity and Toxin Production by Fusarium Isolates from New Zealand. Mycopathologia 108: 73
Abbas HK, Bosch U (1990) Evaluation of Trichothecene and Nontrichothecene Mycotoxins Produced by Fusarium in Soybeans. Mycotoxin Res 6: 13
Ramakrishna Y, Bhat RV, Ravindranath V (1989) Production of Deoxynivalenol by Fusarium Isolates from Samples of Wheat Associated with a Human Mycotoxicosis Outbreak and from Sorghum Cultivars. Appl Environ Microbiol 55: 2619
Styriak I, Conkova E, Bohm J (1994) Occurrence of Fusarium sacchari var. subglutinans and Its Mycotoxin Production Ability in Broiler Feed. Folia Microbiol 39: 579
Vesonder RF, Ciegler A, Jenson AH, Rohwedder WK, Weisleder D (1976) Co-Identity of the Refusal and Emetic Principle from Fusarium-Infected Corn. Appl Environ Microbiol 31: 280
Tatsuno T (1968) Toxicologic Research on Substances from Fusarium nivale. Cancer Res 28: 2393
Golinski P, Vesonder RF, Latus-Zietkiewicz D, Perkowski J (1988) Formation of Fusarenone X, Nivalenol, Zearalenone, α-trans-Zearalenol, β-trans-Zearalenol, and Fusarin C by Fusarium crookwellense. Appl Environ Microbiol 54: 2147
Sugiura Y, Fukasaku K, Tanaka T, Matsui Y, Ueno Y (1993) Fusarium poae and Fusarium crookwellense, Fungi Responsible for the Natural Occurrence of Nivalenol in Hokkaido. Appl Environ Microbiol 59: 3334
Raza SK, Mallet AI, Howell SA, Thomas PA (1994) An In-Vitro Study of the Sterol Content and Toxin Production of Fusarium Isolates from Mycotic Keratitis. J Med Microbiol 41: 204
Sundheim L, Nagayama S, Kawamura O, Tanaka T, Brodal G, Ueno O (1988) Trichothecenes and Zearalenone in Norwegian Barley and Wheat. Norwegian J Agric Sci 2: 49
Ghosal S, Chakrabarti DK, Srivastava AK, Srivastava RS (1982) Toxic 12,13-Epoxytrichothecenes from Anise Fruits Infected with Trichothecium roseum. J Agric Food Chem 30: 106
Blight MM, Grove JF (1974) New Metabolic Products of Fusarium culmorum. Toxic Trichothec-9-en-8-ones and 2-Acetyl-quinazolin-4(3H)-one. J Chem Soc, Perkin Trans 1: 1691
Greenhalgh R, Neish GA, Miller JD (1983) Deoxynivalenol, Acetyldeoxynivalenol, and Zearalenone Formation by Canadian Isolates of Fusarium graminearum on Solid Substrates. Appl Environ Microbiol 46: 625
Miller JD, Taylor A, Greenhalgh R (1983) Production of Deoxynivalenol and Related Compounds in Liquid Culture by Fusarium graminearum. Canad J Microbiol 29: 1171
Ueno Y, Ueno I, Tatsuno T, Ohokubo K, Tsunoda H (1969) Fusarenone-X, a Toxic Principle of Fusarium nivale Culture Filtrate. Experientia 25: 1062
Xu Y-C, Huang X, Cai Y-S (1982) Isolation and Structure of CBD2 — A New Trichothecene Toxin. Weishengwu Xuebao 22: 35; Chem Abstr 96: 196245
Freeman GG, Morrison RI (1948) Trichothecin: An Antifungal Metabolic Product of Trichothecium roseum Link. Nature (Lond) 162: 30
Combrinck S, Gelderblom WCA, Spies HSC, Burger BV, Theil PG, Marasas WFO (1988) Isolation and Characterization of Trichothecin from Corn Cultures of Fusarium graminearum MRC 1125. Appl Environ Microbiol 54: 1700
Corley DG, Rottinghaus GE, Tempesta MS (1987) Toxic Trichothecenes from Fusarium sporotrichioides (MC-72083). J Org Chem 52: 4405
Yoshizawa T, Shirota T, Morooka NJ (1978) Toxic Substances in Infected Cereals, VI. Deoxynivalenol and Its Acetate as Feed Refusal Principles in Rice Cultured with Fusarium roseum No. 117 (ATCC 28114). J Food Hyg Soc Jpn 19: 178
Tatsuno T, Morita Y, Tsunoda H, Umeda M (1970) Recherches Toxicologiques des Substances Metaboliques du Fusarium nivale, VII. La Troisieme Substance Metabolique de F. nivale, le Diacetate de Nivalenol. Chem Pharm Bull 18: 1485
Otsuka T, Okamoto Y, Hosoya T (1997) Herbicidal F-11073 Manufacture with Acremonium. Japanese Patent 09 118682 1997; Chem Abstr 127: 49311
Chatterjee K, Pawlosky RJ, Mirocha CJ, Zhu T-X (1986) Production of Deepoxy-Diacetoxyscirpenol in a Culture of Fusarium graminearum. Appl Environ Microbiol 52: 311
Jarvis BB, Midiwo JO, Guo M (1989) 12,13-Deoxytrichoverrins from Myrothecium verrucaria. J Nat Prod 52: 663
Bohner B, Fetz E, Harri E, Sigg HP, Stoll Ch, Tamm Ch (1965) Verrucarine und Roridine, 8. Mitteilung. Über die Isolierung von Verrucarin H, Verrucarin J, Roridin D und Roridin E aus Myrothecium-Arten. Helv Chim Acta 48: 1079
Smitka TA, Bunge RH, Bloem RJ, French JC (1984) Two New Trichothecenes, PD 113325 and PD 113326. J Antibiot 37: 823
Harrach B, Mirocha CJ, Pathre SV, Palyusik M (1981) Macrocyclic Trichothecene Toxins Produced by a Strain of Stachybotrys atra from Hungary. Appl Environ Microbiol 41: 1428
Vittimberga JS, Vittimberga BM (1965) The Muconomycins, II. Muconomycin B, a New Biologically Active Compound. J Org Chem 30: 746
Jarvis BB, Midiwo JO, Bean GA, Aboul-Nasr MB, Barros CS (1988) The Mystery of Trichothecene Antibiotics in Baccharis Species. J Nat Prod 51: 736
Eppley RM, Mazzola EP, Highet RJ, Bailey WJ (1977) Structure of Satratoxin H, a Metabolite of Stachybotrys atra. Application of Proton and Carbon-13 Nuclear Magnetic Resonance. J Org Chem 42: 240
Rizzo I, Varsavky E, Haidukowski M, Frade H (1997) Macrocyclic Trichothecenes in Baccharis coridifolia Plants and Endophytes and Baccharis artemisioides Plants. Toxicon 35: 753
Namikoshi M, Kobayashi H, Yoshimoto T, Meguro S, Akano K (2000) Isolation and Characterization of Bioactive Metabolites from Marine-Derived Filamentous Fungi Collected from Tropical and Sub-Tropical Coral Reefs. Chem Pharm Bull 48: 1452
Zurcher W, Tamm Ch (1966) Verrucarine und Roridine, 13. Mitteilung. Isolierung von 2′-Dehydroverrucarin A als Metabolit von Myrothecium roridum Tode ex Fr., Gattungstyp bei Fries. Helv Chim Acta 49: 2594
Smitka TA, Bunge RW, French JC, Bloem RJ (1984) 12′-Hydroxyverrucarin J and Isosatratoxin H. U.S. Patent 4436750, 13 Mar. 1984; Chem Abstr 101: 5555
Jarvis BB, Lee Y-W, Comezoglu FT, Comezoglu SN, Bean GA (1985) Myrotoxins: A New Class of Macrocyclic Trichothecenes. Tetrahedron Lett 26: 4859
Jarvis BB, Comezoglu FT, Lee Y-W, Flippen-Anderson JL, Gilardi RD, George CF (1986) Novel Trichothecenes from Myrothecium roridum. Bull Soc Chim Belg 95: 681
Croft WA, Jarvis BB, Yatawara CS (1986) Airborne Outbreak of Trichothecene Toxicosis. Atmos Environ 20: 549
Zhang L, Gong B, Hao W (2000) Immunosuppressants Isolated from a Phoma sp. 299. Studies on Compounds SIPI 299-B and 299-O. Zhongguo Kangshengsu Zazhi 25: 9; Chem Abstr 133: 309033
Jarvis BB, Midiwo JO, DeSilva T, Mazzola EP (1981) Verrucarin L, a New Macrocyclic Trichothecene. J Antibiot 34: 120
Tamm Ch, Sigg HP, Harri E (1965) Verrucarine H, J, and K. Belgian Patent 638972, April 21, 1964; Chem Abstr 62: 8947; idem (1968) Verrucarin K Antibiotic. Swiss Patent 436570, Nov. 15, 1967; Chem Abstr 68: 67750
Tamm Ch: Personal communication
Breitenstein W, Tamm Ch (1977) Verrucarins and Roridins, Part 34. Verrucarin K, the First Natural Trichothecene Derivative Lacking the 12,13-Epoxy Group. Helv Chim Acta 60: 1522
White EP, Mortimer PH, di Menna ME (1977) Chemistry of the Myrothecium Toxins. In: Wyllie TD, Morehouse LG (eds.) Mycotoxic Fungi, Mycotoxins, Mycotoxicoses, Vol. 1, p. 465. Dekker, New York
Kishaba AN, Shankland DL, Curtis RW, Wilson MC (1962) Substances Inhibitory to Insect Feeding with Insecticidal Properties from Fungi. J Econ Entomol 55: 211
Vittimberga BM (1963) The Muconomycins, I. Studies on the Structure of Muconomycin A, a New Biologically Active Compound. J Org Chem 28: 1786
Jarvis BB, Yatawara CS (1986) Roritoxins, New Macrocyclic Trichothecenes from Myrothecium roridum. J Org Chem 51: 2906
Matsumoto M, Minato H, Uotani N, Matsumoto K, Kondo E (1977) New Antibiotics from Cylindrocarpon sp. J Antibiot 30: 681
Eppley RM, Mazzola EP, Stack ME, Dreifuss PA (1980) Structures of Satratoxin F and Satratoxin G, Metabolites of Stachybotrys atra: Application of Proton and Carbon-13 Nuclear Magnetic Resonance Spectroscopy. J Org Chem 45: 2522
Jarvis BB, Stahly GP, Pavanasasivam G, Mazzola EP (1980) Structure of Roridin J, a New Macrocyclic Trichothecene from Myrothecium verrucaria. J Antibiot 33: 256
Bata A, Harrach B, Ujszaszi K, Kis-Tamas A, Lasztity R (1985) Macrocyclic Trichothecene Toxins Produced by Stachybotrys atra Strains Isolated in Middle Europe. Appl Environ Microbiol 49: 678
Minato H, Katayama T, Tori K (1975) Vertisporin, a New Antibiotic from Verticinimonosporium diffractum. Tetrahedron Lett 16: 2579
Namikoshi M, Akano K, Meguro S, Kasuga I, Mine Y, Takahashi T, Kobayashi H (2001) A New Macrocyclic Trichothecene, 12,13-Deoxyroridin E, Produced by the Marine-Derived Fungus Myrothecium roridum Collected in Palau. J Nat Prod 64: 396
Eppley RM, Bailey WJ (1973) 12,13-Epoxy-Δ9-Trichothecenes as the Probable Mycotoxins Responsible for Stachybotryotoxicosis. Science 181: 758
Busam L, Habermehl GG (1982) Accumulation of Mycotoxins by Baccharis coridifolia: A Reason for Livestock Poisoning. Naturwiss 69: 392
Jarvis BB, Midiwo JO, Tuthill D, Bean GA (1981) Interaction Between the Antibiotic Trichothecenes and the Higher Plant Baccharis megapotamica. Science 214: 460
Whyte AC, Gloer JB, Scott JA, Malloch J (1996) Cercophorins A-C: Novel Antifungal and Cytotoxic Metabolites from the Coprophilous Fungus Cercophora areolata. J Nat Prod 59: 765
Jarvis BB, Wang S (1999) Stereochemistry of the Roridins. Diastereoisomers of Roridin E. J Nat Prod 62: 1284
Freckman WG, Jakubowski ZL, Bunge RH, French JC, Balta LE (1984) Antibiotic Roridin E-2. Canadian Patent 1157405, 22 Nov., 1983; Chem Abstr 100: 137375
Kobayashi A, Nakai Y, Kawasaki T, Kawazu K (1989) Fungal Trichothecenes Which Promote Callus Initiation from the Alfalfa Cotyledon. Agric Biol Chem 53: 585
Jarvis BB, Wells KM, Lee Y-W, Bean GA, Kommedahl T, Barros CS, Barros SS (1987) Macrocyclic Trichothecene Mycotoxins in Brazilian Species of Baccharis. Phytopathol 77: 980
Jarvis BB, Pena NB, Rao MM, Comezoglu SN, Comezoglu TF, Mandava NB (1985) Allelopathic Agents from Parthenium hysterophorus and Baccharis megapotamica. In: Thompson AC (ed.) The Chemistry of Allelopathy. Biochemical Interactions. ACS Symposium Series 268, p. 149
Samples D, Hill DW, Bridges CH, Camp BJ (1984) Isolation of a Mycotoxin (Roridin A) from Phomopsis sp. Vet Hum Toxicol 26: 21
Jarvis BB, Midiwo JO, Flippen-Anderson JL, Mazzola EP (1982) Stereochemistry of the Roridins. J Nat Prod 45: 440
Isaka M, Punya J, Lertwerawat Y, Tanticharoen M, Thebtaranonth Y (1999) Antimalarial Activity of Macrocyclic Trichothecenes Isolated from the Fungus Myrothecium verrucaria. J Nat Prod 62: 329
Sugawara T, Tanaka A, Nagai K, Suzuki K, Okada G (1997) New Members of the Trichothecene Family. J Antibiot 50: 778
Jarvis BB, Comezoglu SN, Rao MM, Pena NB, Boettner FE, Williams TM, Forsyth G, Epling B (1987) Isolation of Macrocyclic Trichothecenes from a Large-Scale Extract of Baccharis megapotamica. J Org Chem 52: 45
Habermehl GG, Busam L, Heydel P, Mebs D, Tokarnia CH, Dobereiner J, Spraul M (1985) Macrocyclic Trichothecenes: Cause of Livestock Poisoning by the Brazilian Plant Baccharis coridifolia. Toxicon 23: 731
Habermehl GG, Busam L, Stegemann J (1984) Miotoxin A: A Novel Macrocyclic Trichothecene from the Brazilian Plant Baccharis coridifolia. Z Naturforsch C39: 212
Habermehl GG, Busam L (1984) Miotoxin B and C, zwei neue macrocyclische Trichothecene aus Baccharis coridifolia DC. Liebigs Ann Chem: 1746
Kupchan SM, Streelman DR, Jarvis BB, Dailey RG, Sneden AT (1977) Isolation of Potent New Antileukemic Trichothecenes from Baccharis megapotamica. J Org Chem 42: 4221
Kupchan SM, Jarvis BB, Dailey RG, Bright W, Bryan RF, Shizuri Y (1976) Baccharin, a Novel Potent Antileukemic Trichothecene Triepoxide from Baccharis megapotamica. J Amer Chem Soc 98: 7092
Habermehl GG, Busam L, Spraul M (1985) Macrocyclische Trichothecene aus Baccharis coridifolia, II. Miotoxin D und Isomiotoxin D, zwei neue macrocyclische Trichothecene aus Baccharis coridifolia DC. Liebigs Ann Chem: 633
Jarvis BB, Comezoglu SN, Ammon HL, Breedlove CK, Miller RW, Woode MK, Streelman DR, Sneden AT, Dailey RG, Kupchan SM (1987) New Macrocyclic Trichothecenes from Baccharis megapotamica. J Nat Prod 50: 815
Zamir LO, Devor KA, Nikolakakis A, Nadeau Y, Sauriol F (1992) Structures of New Metabolites from Fusarium Species: An Apotrichothecene and Oxygenated Trichodienes. Tetrahedron Lett 33: 5181
Greenhalgh R, Blackwell BA, Pare JRJ, Miller JD, Levandier D, Meier R-M, Taylor A, ApSimon JW (1986) Isolation and Characterization by Mass Spectrometry and NMR Spectroscopy of Secondary Metabolites of Some Fusarium Species. In: Steyn PS, Vleggaar R (eds.) Mycotoxins and Phycotoxins, p. 137. Elsevier, Amsterdam
Roesslein L, Tamm Ch, Zurcher W, Reisen A, Zehnder M (1988) Sambucinic Acid, a New Metabolite of Fusarium sambucinum. Helv Chim Acta 71: 588
Mohr P, Tamm Ch, Zurcher W, Zehnder M (1984) Sambucinol and Sambucoin, Two New Metabolites of Fusarium sambucinum Possessing Modified Trichothecene Structures. Helv Chim Acta 67: 406
Greenhalgh R, Fielder DA, Morrison LA, Charland J-P, Blackwell BA, Savard ME, ApSimon JW (1989) Secondary Metabolites of Fusarium Species: Apotrichothecene Derivatives. J Agric Food Chem 37: 699
Corley DG, Rottinghaus GE, Tempesta MS (1987) Secondary Metabolites from Fusarium. Two Modified Trichothecenes from Fusarium sporotrichioides MC-72083. J Nat Prod 50: 897
Schmidt R, Zajkowski P, Wink J (1995) Toxicity of Fusarium sambucinum Fuckel sensu lato to Brine Shrimp. Mycopathologia 129: 173
Ziegler FE, Nangia A, Tempesta MS (1988) Sporol: A Structure Revision. Tetrahedron Lett 29: 1665
Kononenko GP, Bekker AR, Leonov AL, Soboleva NA (1991) Gramilaurone, a Novel Natural Sesquiterpenoid from Fusarium graminearum Schw. Tetrahedron Lett 32: 1893
Nozoe S, Machida Y (1970) Structure of Trichodiene. Tetrahedron Lett 2671
VanMiddlesworth F, Desjardins AE, Taylor SL, Plattner RD (1986) Trichodiene Accumulation by Ancymidol Treatment of Gibberella pulicaris. Chem Commun 1156
Desjardins AE, Plattner RD, Beremand MN (1987) Ancymidol Blocks Trichothecene Biosynthesis and Leads to Accumulation of Trichodiene in Fusarium sporotrichioides and Gibberella pulicaris. Appl Environ Microbiol 53: 1860
Hesketh AR, Gledhill L, Marsh DC, Bycroft BW, Dewick PM, Gilbert J (1990) Isotrichodiol: A Post-Trichodiene Intermediate in the Biosynthesis of Trichothecene Mycotoxins. Chem Commun 1184
Patakova-Juzlova P, Rezanka T, Viden I (1998) Identification of Volatile Metabolites from Rice Fermented by the Fungus Monascus purpureus. Folia Microbiol 43: 407
Wilkins K (2000) Volatile Sesquiterpenes from Stachybotrys chartarum. Environ Sci Pollut Res 7: 77
Zamir LO, Nikolakakis A, Huang L, St-Pierre P, Sauriol F, Sparace S, Mamer O (1999) Biosynthesis of 3-Acetyldeoxynivalenol and Sambucinol. Identification of the Two Oxygenation Steps After Trichodiene. J Biol Chem 274: 12269
McCormick SP, Taylor SL, Plattner RD, Beremand MN (1989) New Modified Trichothecenes Accumulated in Solid Culture by Mutant Strains of Fusarium sporotrichioides. Appl Environ Microbiol 55: 2195
Zook M, Johnson K, Hohn T, Hammerschmidt R (1996) Structural Characterization of 15-Hydroxytrichodiene, a Sesquiterpenoid Produced by Transformed Tobacco Cell Suspension Cultures Expressing a Trichodiene Synthase Gene from Fusarium sporotrichioides. Phytochemistry 43: 1235
Zamir LO, Devor KA, Morin N, Sauriol F (1991) Biosynthesis of Trichothecenes: Oxygenation Steps Post-trichodiene. Chem Commun 1033
Zamir LO (1989) Biosynthesis of 3-Acetyldeoxynivalenol and Sambucinol. Tetrahedron 45: 2277
Zamir LO, Devor KA, Nadeau Y, Sauriol F (1987) Structure Determination and Biosynthesis of a Novel Metabolite of Fusarium culmorum, Apotrichodiol. J Biol Chem 262: 15354
Zamir LO, Nikolakakis A, Sauriol F, Mamer O (1999) Biosynthesis of Trichothecenes and Apotrichothecenes. J Agric Food Chem 47: 1823
Fort DM, Barnes CL, Tempesta MS, Casper HH, Bekele E, Rottinghaus AA, Rottinghaus GE (1993) Two New Modified Trichothecenes from Fusarium sporotrichioides. J Nat Prod 56: 1890
Nozoe S, Machida Y (1972) The Structures of Trichodiol and Trichodiene. Tetrahedron 28: 5105
Hesketh AR, Bycroft BW, Dewick PM, Gilbert J (1993) Revision of the Stereochemistry in Trichodiol, Trichotriol and Related Compounds, and Concerning Their Role in the Biosynthesis of Trichothecene Mycotoxins. Phytochemistry 32: 105
McCormick SP, Taylor SL, Plattner RD, Beremand MN (1990) Bioconversion of Possible T-2 Toxin Precursors by a Mutant Strain of Fusarium sporotrichioides NRRL 3299. Appl Environ Microbiol 56: 702
Flesch P, Voigt-Scheuermann I (1993) Isolation and Identification of Iso-Trichothecin from Cultures of the Fungus Trichothecium roseum. Wein Wiss 48: 15
Burgess LW, Forbes GA, Windels C, Nelson PE, Marasas WFO (1993) Characterization and Distribution of Fusarium acuminatum subsp. armeniacum subsp. nov. Mycologia 85: 119
Nirenberg H (1995) Morphological Differentiation of Fusarium sambucinum Fuckel s. st., F. torulosum (Berk. et Curt.) Nirenberg comb. nov. and F. venenatum Nirenberg sp. nov. Mycopathologia 129: 131
Thrane U, Hansen U (1995) Chemical and Physiological Characterization of Taxa in the Fusarium sambucinum Complex. Mycopathologia 129: 183
Gams W (1989) Taxonomy and Nomenclature of Microdochium nivale (Fusarium nivale). In: Chelkowski J (ed.) Fusarium Mycotoxins, Taxonomy and Pathogenicity, p. 195. Elsevier, Amsterdam
Hintikka E-L (1977) Stachybotrys. In: Wyllie TD, Morehouse LG (eds.) Mycotoxic Fungi, Mycotoxins, Mycotoxicoses, Vol. 1, p. 91. Dekker, New York
Jong S-C, Birmingham JM, Ma G (1993) In: Stedmans ATCC Fungus Names, p. 242. Williams and Wilkins, Baltimore
Panozishvili K, Zolnikova NY, Vorovkov AV (1972) Verrucarin A from Dendrodochium toxicum. Chem Nat Compd (Eng Transl) 8: 244
Panozishvili K, Borovkov AV (1974) Roridin A from Dendrodochium toxicum. Chem Nat Compd (Eng Transl) 10: 408
Tulloch M (1972) The Genus Myrothecium Tode ex Fr. Commonwealth Mycological Institute, Mycological Papers 130: 1
Miller JD, Greenhalgh R, Wang Y, Lu M (1991) Trichothecene Chemotypes of Three Fusarium Species. Mycologia 83: 121
Ichinoe M, Kurata H, Sugiura Y, Ueno Y (1983) Chemotaxonomy of Gibberella zeae with Special Reference to the Production of Trichothecenes and Zearalenone. Appl Environ Microbiol 46: 1364
Logrieco A, Bottalico A, Altomare C (1988) Chemotaxonomic Observations on Zearalenone and Trichothecene Production by Gibberella zeae from Cereals in Southern Italy. Mycologia 80: 892
Szecsi A, Bartok T (1995) Trichothecene Chemotypes of Fusarium graminearum Isolated from Corn in Hungary. Mycotoxin Res 11: 85
Mule G, Logrieco A, Stea G, Bottalico A (1997) Clustering of Trichothecene-Producing Fusarium Strains Determined from 28S Ribosomal DNA Sequences. Appl Environ Microbiol 63: 1843
Tamm Ch, Breitenstein W (1980) The Biosynthesis of Trichothecene Mycotoxins. In: Steyn PS (ed.) The Biosynthesis of Mycotoxins. A Study in Secondary Metabolism, p. 69. Academic Press, New York
Hanson JR, Marten T, Siverns M (1974) Studies in Terpenoid Biosynthesis, Part XII. Carbon-13 Nuclear Magnetic Resonance Spectra of the Trichothecanes and the Biosynthesis of Trichothecolone from [2-13C]-Mevalonic Acid. J Chem Soc, Perkin Trans 1: 1033
Achilladelis B, Hanson JR (1968) Studies in Terpenoid Biosynthesis, 1. The Biosynthesis of Metabolites of Trichothecium roseum. Phytochemistry 7: 589
Cane DE, Swanson S, Murthy PPN (1981) Trichodiene Biosynthesis and the Enzymatic Cyclization of Farnesyl Pyrophosphate. J Amer Chem Soc 103: 2136
Cane DE, Ha H-J, Pargellis C, Waldmeier F, Swanson S, Murthy PPN (1985) Trichodiene Biosynthesis and the Stereochemistry of the Enzymatic Cyclization of Farnesyl Pyrophosphate. Bioorg Chem 13: 246
Cane DE, Ha H-J (1988) Trichodiene Biosynthesis and the Role of Nerolidyl Pyrophosphate in the Enzymatic Cyclization of Farnesyl Pyrophosphate. J Amer Chem Soc 110: 6865
Cane DE (1989) Stereochemical Studies of Natural Products Biosynthesis. Pure Appl Chem 61: 493
Cane DE (1990) Enzymatic Formation of Sesquiterpenes. Chem Rev 90: 1089
Arigoni D, Cane DE, Muller B, Tamm Ch (1973) The Mode of Incorporation of Farnesyl Pyrophosphate into Verrucarol. Helv Chim Acta 56: 2946
Blackwell BA, Miller JD, Greenhalgh R (1985) 13C NMR Study of the Biosynthesis of Toxins by Fusarium graminearum. J Biol Chem 260: 4243
Zamir LO, Nadeau Y, Nguyen C-D, Devor K, Sauriol F (1987) Mechanism of 3-Acetyldeoxynivalenol Biosynthesis. Chem Commun 127
Evans R, Hanson JR (1976) Studies in Terpenoid Biosynthesis, Part XIV. Formation of the Sesquiterpene Trichodiene. J Chem Soc, Perkin Trans 1: 326
Hohn TM, VanMiddlesworth F (1986) Purification and Characterization of the Cyclase Trichodiene Synthetase from Fusarium sporotrichioides. Arch Biochem Biophys 251: 756
Hohn TM, Beremand MN (1989) Regulation of Trichodiene Synthase in Fusarium sporotrichioides and Gibberella pulicaris (Fusarium sambucinum). Appl Environ Microbiol 55: 1500
Cane DE, Chiu H-T, Liang P-H, Anderson KS (1997) Pre-Steady-State Kinetic Analysis of the Trichodiene Reaction Pathway. Biochemistry 36: 8332
Cane DE, Yang G, Xue Q, Shim JH (1995) Trichodiene Synthase. Substrate Specificity and Inhibition. Biochemistry 34: 2471
Cane DE, Shim JH, Xue Q, Fitzsimons BC, Hohn TM (1995) Trichodiene Synthase. Identification of Active Site Residues by Site-Directed Mutagenesis. Biochemistry 34: 2480; (1997) 36: 9636
Cane DE, Xue Q, Fitzsimons BC (1996) Trichodiene Synthase. Probing the Role of the Highly Conserved Aspartate-Rich Region by Site-Directed Mutagenesis. Biochemistry 35: 12369
Hohn TM, Beremand PD (1989) Isolation and Nucleotide Sequence of a Sesquiterpene Cyclase Gene from the Trichothecene-Producing Fungus Fusarium sporotrichioides. Gene 79: 131
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
Proctor RH, Hohn TM, McCormick SP (1995) Reduced Virulence of Gibberella zeae Caused by Disruption of a Trichothecene Toxin Biosynthetic Gene. Mol Plant-Microbe Interact 8: 593
Fekete C, Logrieco A, Giczey G, Hornok L (1997) Screening of Fungi for the Presence of the Trichodiene Synthase Encoding Sequence by Hybridization to the Tri5 Gene Cloned from Fusarium poae. Mycopathologia 138: 91
Hohn TM, Plattner RD (1989) Expression of the Trichodiene Synthase Gene of Fusarium sporotrichioides in Escherichia coli Results in Sesquiterpene Production. Arch Biochem Biophys 275: 92
Cane DE, Wu Z, Oliver JS, Hohn TM (1993) Overproduction of Soluble Trichodiene Synthase from Fusarium sporotrichioides in Escherichia coli. Arch Biochem Biophys 300: 416
Hohn TM, Ohlrogge JB (1991) Expression of a Fungal Sesquiterpene Cyclase Gene in Transgenic Tobacco. Plant Physiol 97: 460
Desjardins AE, Hohn TM, McCormick SP (1992) Effect of Gene Disruption of Trichodiene Synthase on the Virulence of Gibberella pulicaris. Mol Plant-Microbe Interact 5: 214
Proctor RH, Hohn TM, McCormick SP (1997) Restoration of Wild-Type Virulence to Tri5 Disruption Mutants of Gibberella zeae via Gene Reversion and Mutant Complementation. Microbiology UK 143: 2583
Niessen ML, Vogel RF (1998) Group Specific PCR-Detection of Potential Trichothecene-Producing Fusarium Species in Pure Cultures and Cereal Samples. System Appl Microbiol 21: 618
Doohan FM, Weston G, Rezanoor HN, Parry DW, Nicholson P (1999) Development and Use of a Reverse Transcription-PCR Assay to Study Expression of Tri5 by Fusarium Species In Vitro and In Planta. Appl Environ Microbiol 65: 3850
Machida Y, Nozoe S (1972) Biosynthesis of Trichothecin and Related Compounds. Tetrahedron Lett 1969
Zamir LO, Gauthier MJ, Devor KA, Nadeau Y, Sauriol F (1989) Trichodiene Is a Precursor to Trichothecenes. Chem Commun: 598
Zamir LO, Devor KA (1987) Kinetic Pulse-Labeling Study of Fusarium culmorum. J Biol Chem 262: 15348
Gledhill L, Hesketh AR, Bycroft BW, Dewick PM, Gilbert J (1991) Biosynthesis of Trichothecene Mycotoxins: Cell-Free Epoxidation of a Trichodiene Derivative. FEMS Microbiol Lett 81: 241
Hohn TM, Desjardins AE, McCormick SP (1995) The Tri4 Gene of Fusarium sporotrichioides Encodes a Cytochrome P450 Monooxygenase Involved in Trichothecene Biosynthesis. Mol Gen Genet 248: 95
Hesketh AR, Gledhill L, Marsh DC, Bycroft BW, Dewick PM, Gilbert J (1991) Biosynthesis of Trichothecene Mycotoxins: Identification of Isotrichodiol as a Post-Trichodiene Intermediate. Phytochemistry 30: 2237
Kimura M, Kaneko I, Komiyama M, Takatsuki A, Koshino H, Yoneyama K, Yamaguchi I (1998) Trichothecene 3-O-Acetyl-transferase Protects both the Producing Organism and Transformed Yeast from Related Mycotoxins. J Biol Chem 273: 1654
Evans R, Hanson JR, Marten T (1976) Studies in Terpenoid Biosynthesis, Part XVI. Formation of the Sesquiterpenoid Trichothecin. J Chem Soc, Perkin Trans 1: 1212
Zamir LO, Devor KA, Nikolakakis A, Sauriol F (1990) Biosynthesis of Fusarium culmorum Trichothecenes. The Roles of Isotrichodermin and 12,13-Epoxytrichothec-9-ene. J Biol Chem 265: 6713
Zamir LO, Devor KA, Nikolakakis A, Sauriol F (1996) Biosynthesis of the Trichothecene 3-Acetyldeoxynivalenol: Cell-Free Hydroxylations of Isotrichodermin. Canad J Microbiol 42: 828
Hesketh AR, Gledhill L, Bycroft BW, Dewick PM, Gilbert J (1993) Potential Inhibitors of Trichothecene Biosynthesis in Fusarium culmorum: Epoxidation of a Trichodiene Derivative. Phytochemistry 32: 93
Zamir LO, Nikolakakis A, Devor KA, Sauriol F (1996) Biosynthesis of the Trichothecene 3-Acetyldeoxynivalenol. Is Isotrichodermin a Biosynthetic Precursor? J Biol Chem 271: 27353
Udell MN, Dewick PM (1989) Metabolic Conversions of Trichothecene Mycotoxins: De-Esterification Reactions Using Cell-Free Extracts of Fusarium. Z Naturforsch 44C: 660
Alexander NJ, Hohn TM, McCormick SP (1998) The TRI11 Gene of Fusarium sporotrichioides Encodes a Cytochrome P-450 Monooxygenase Required for C-15 Hydroxylation in Trichothecene Biosynthesis. Appl Environ Microbiol 64: 221
Zamir LO, Farah CA (2000) Is Fusarium culmorum Isotrichodermin-15-hydroxylase Different from Other Fungal Species? Canad J Microbiol 46: 143
McCormick SP, Hohn TM, Desjardins AE (1996) Isolation and Characterization of Tri3, a Gene Encoding 15-O-Acetyl-transferase from Fusarium sporotrichioides. Appl Environ Microbiol 62: 353
Brown DW, McCormick SP, Alexander NJ, Proctor RH, Desjardins AE (2001) A Genetic and Biochemical Approach to Study Trichothecene Diversity in Fusarium sporotrichioides and Fusarium graminearum. Fungal Genet Biol 32: 121
Beremand MN, Desjardins AE (1988) Trichothecene Biosynthesis in Gibberella pulicaris: Inheritance of C-8 Hydroxylation. J Industrial Microbiol 3: 167
Alexander NJ, Proctor RH, McCormick SP, Plattner RD (1997) Genetic and Molecular Aspects of the Biosynthesis of Trichothecenes by Fusarium. Cereal Res Commun 25: 315
Park JJ, Chu FS (1996) Partial Purification and Characterization of an Esterase from Fusarium sporotrichioides. Nat Toxins 4: 108
Beremand MN, VanMiddlesworth F, Taylor S, Plattner RD, Weisleder D (1988) Leucine Auxotrophy Specifically Alters the Pattern of Trichothecene Production in a T-2 Toxin-Producing Strain of Fusarium sporotrichioides. Appl Environ Microbiol 54: 2759
VanMiddlesworth F, Beremand MN, Isbell TA, Weisleder D (1990) T-2 Toxin Biosynthesis: Origin of the Isovalerate Side Chain. J Org Chem 55: 1237
Baldwin NCP, Bycroft BW, Dewick PM, Gilbert J (1986) Metabolic Conversions of Trichothecene Mycotoxins: Biotransformation of 3-Acetyldeoxynivalenol into Fusarenone X. Z Naturforsch 41C: 845
Hohn TM, McCormick SP, Desjardins AE (1993) Evidence for a Gene Cluster Involving Trichothecene-Pathway Biosynthetic Genes in Fusarium sporotrichioides. Curr Genet 24: 291
Hohn TM, Desjardins AE, McCormick SP (1993) Analysis of Tox5 Gene Expression in Gibberella pulicaris Strains with Different Trichothecene Production Phenotypes. Appl Environ Microbiol 59: 2359
Wuchiyama J, Kimura M, Yamaguchi I (2000) A Trichothecene Efflux Pump Encoded by Tri102 in the Biosynthetic Gene Cluster of Fusarium graminearum. J Antibiot 53: 196
Proctor RH, Hohn TM, McCormick SP, Desjardins AE (1995) Tri6 Encodes an Unusual Zinc Finger Protein Involved in Regulation of Trichothecene Biosynthesis in Fusarium sporotrichioides. Appl Environ Microbiol 61: 1923
Hohn TM, Krishna R, Proctor RH (1999) Characterization of a Transcriptional Activator Controlling Trichothecene Toxin Biosynthesis. Fungal Genet Biol 26: 224
Matsumoto G, Wuchiyama J, Shingu Y, Kimura M, Yoneyama K, Yamaguchi I (1999) The Trichothecene Biosynthesis Regulatory Gene from the Type B Producer Fusarium Strains: Sequence of Tri6 and Its Expression in Escherichia coli. Biosci Biotechnol Biochem 63: 2001
Alexander NJ, McCormick SP, Hohn TM (1999) Tri12, a Trichothecene Efflux Pump from Fusarium sporotrichioides: Gene Isolation and Expression in Yeast. Mol Gen Genet 261: 977
Muhitch MJ, McCormick SP, Alexander NJ, Hohn TM (2000) Transgenic Expression of the Tri101 or PDR5 Gene Increases Resistance of Tobacco to the Phytotoxic Effects of the Trichothecene 4,15-Diacetoxyscirpenol. Plant Sci 157: 201
Kimura M, Shingu Y, Yoneyama K, Yamaguchi I (1998) Features of Tri101, the Trichothecene 3-O-Acetyltransferase Gene, Related to the Self-Defense Mechanism in Fusarium graminearum. Biosci Biotechnol Biochem 62: 1033
Kimura M, Matsumoto G, Shingu Y, Yoneyama K, Yamaguchi I (1998) The Mystery of the Trichothecene 3-O-Acetyltransferase Gene. Analysis of the Region Around Tri101 and Characterization of Its Homologue from Fusarium sporotrichioides. FEBS Lett 435: 163
McCormick SP, Alexander NJ, Trapp SE, Hohn TM (1999) Disruption of Tri101, the Gene Encoding Trichothecene 3-O-Acetyltransferase, from Fusarium sporotrichioides. Appl Environ Microbiol 65: 5252
Trapp SC, Hohn TM, McCormick S, Jarvis BB (1998) Characterization of the Gene Cluster for Biosynthesis of Macrocyclic Trichothecenes in Myrothecium roridum. Mol Gen Genet 257: 421
Jarvis BB, Mokhtari-Rejali N, Schenkel EP, Barros CS, Matzenbacher NI (1991) Trichothecene Mycotoxins from Brazilian Baccharis Species. Phytochemistry 30: 789
Bertoni MD, Cabral D (1991) Ceratopycnidium baccharidicola sp. nov. from Baccharis coridifolia in Argentina. Mycol Res 95: 1014
Rosso ML, Maier MS, Bertoni MD (2000) Macrocyclic Trichothecene Production by the Fungus Epibiont of Baccharis coridifolia. Molecules 5: 345
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Grovey, J.F. (2007). The Trichothecenes and Their Biosynthesis. In: Herz, W., Falk, H., Kirby, G.W. (eds) Progress in the Chemistry of Organic Natural Products. Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, vol 88. Springer, Vienna. https://doi.org/10.1007/978-3-211-49389-2_2
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