The epipolythiodioxopiperazine (ETP) class of fungal toxins: distribution, mode of action, functions and biosynthesis

Microbiology (United Kingdom) - Tập 151 Số 4 - Trang 1021-1032 - 2005
Donald M. Gardiner1, Violeta Serra2, Barbara J. Howlett1
1School of Botany, The University of Melbourne, Victoria 3010, Australia
2School of Chemistry, Australian National University, ACT 0200, Australia

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Aggarwall, 2004, Role of antibiosis in the biological control of spot blotch (Cochliobolus sativus) of wheat by Chaetomium globosum, Mycopathologia, 157, 369, 10.1023/B:MYCO.0000030446.86370.14

Balzi, 1995, Yeast multidrug resistance: the PDR network, J Bioenerg Biomembr, 27, 71, 10.1007/BF02110333

Beaver, 1994, Lack of correlation between early intracellular calcium ion rises and the onset of apoptosis in thymocytes, Immunol Cell Biol, 72, 489, 10.1038/icb.1994.73

Bell, 1958, The structure of gliotoxin, J Am Chem Soc, 80, 1001, 10.1021/ja01537a065

Bernardo, 2003, A novel redox mechanism for the glutathione-dependent reversible uptake of a fungal toxin in cells, J Biol Chem, 278, 46549, 10.1074/jbc.M304825200

Bissinger, 1994, Molecular cloning and expression of the Saccharomyces cerevisiae STS1 gene product. A yeast ABC transporter conferring mycotoxin resistance, J Biol Chem, 269, 4180, 10.1016/S0021-9258(17)41760-1

Brown, 2003, Characterization of a Fusarium 2-gene cluster involved in trichothecene C-8 modification, J Agric Food Chem, 51, 7936, 10.1021/jf030607+

Buades, 1996, Phylogenetic analysis of the isopenicillin-N-synthetase horizontal gene transfer, J Mol Evol, 42, 537, 10.1007/BF02352283

Bu'Lock, 1992, Sirodesmin biosynthesis, Aust J Chem, 45, 39, 10.1071/CH9920039

Byeng, 1999, New cytotoxic epidithiodioxopiperazines related to verticillin A from a marine isolate of the fungus Penicillium, Nat Prod Lett, 13, 213, 10.1080/10575639908048788

Challis, 2000, Predictive, structure-based model of amino acid recognition by nonribosomal peptide synthetase adenylation domains, Chem Biol, 7, 211, 10.1016/S1074-5521(00)00091-0

Cheeke, 1995, Endogenous toxins and mycotoxins in forage grasses and their effects on livestock, J Anim Sci, 73, 909, 10.2527/1995.733909x

Curtis, 1977, Sirodesmins A, B, C, and G, antiviral epipolythiopiperazine-2,5-diones of fungal origin: X-ray analysis of sirodesmin A diacetate, J Chem Soc Perkin Trans 1, 180, 10.1039/p19770000180

Daly, 2002, Immobilization of Aspergillus fumigatus colonies in a soft agar matrix allows visualization of A549 cell detachment and death, Med Mycol, 40, 27, 10.1080/mmy.40.1.27.33

Debatin, 2002, Chemotherapy: targeting the mitochondrial death pathway, Oncogene, 21, 8786, 10.1038/sj.onc.1206039

De Clercq, 1978, Antireverse transcriptase activity of gliotoxin analogs, Biochem Pharmacol, 27, 635, 10.1016/0006-2952(78)90497-5

Deffieux, 1977, Crystal structure of an original fungal metabolite of 3,6-epidithio-2,5-dioxopiperazines: epicorazine A, Acta Crystallogr, B33, 1474, 10.1107/S0567740877006311

Dekel, 2003, Gliotoxin ameliorates development of fibrosis and cirrhosis in a thioacetamide rat model, Dig Dis Sci, 48, 1642, 10.1023/A:1024792529601

del Sorbo, 2000, Fungal transporters involved in efflux of natural toxic compounds and fungicides, Fungal Genet Biol, 30, 1, 10.1006/fgbi.2000.1206

Ernst-Russell, 1999, Structure revision and cytotoxic activity of the scabrosin esters, epidithiopiperazinediones from the lichen Xanthoparmelia scabrosa, Aust J Chem, 52, 279, 10.1071/C99019

Ferezou, 1977, Structures de deux toxines isolées des cultures de champignon Phoma lingam Tode: la sirodesmine PL et la desacetyl sirodesmine PL, Nouv J Chim, 1, 327

Ferezou, 1980, Sirodesmin PL Biosynthesis in Phoma lingam Tode, J Chem Soc Perkin Trans 1, 1739, 10.1039/p19800001739

Fitzgerald, 1998, Biological control of sporidesmin-producing strains of Pithomyces chartarum by biocompetitive exclusion, Lett Appl Microbiol, 26, 17, 10.1046/j.1472-765X.1998.00260.x

Gardiner, 2004, The sirodesmin biosynthetic gene cluster of the plant pathogenic fungus Leptosphaeria maculans, Mol Microbiol, 53, 1307, 10.1111/j.1365-2958.2004.04215.x

Gardiner, 2005, The ABC transporter gene in the sirodesmin biosynthetic gene cluster of Leptosphaeria maculans is not essential for sirodesmin production but facilitates self-protection, Fungal Genet Biol, 42, 257, 10.1016/j.fgb.2004.12.001

Green, 2000, Skeletal muscle ryanodine receptor channels are activated by the fungal metabolite, gliotoxin, J Membr Biol, 175, 223, 10.1007/s002320001070

Hope, 2004, Invasive aspergillosis: current and future challenges in diganosis and therapy, Clin Microbiol Infect, 10, 2, 10.1111/j.1469-0691.2004.00809.x

Howlett, 2004, Current knowledge of the Brassica napus–Leptosphaeria maculans interaction: a review, Can J Plant Pathol, 26, 1, 10.1080/07060660409507141

Hurne, 2000, Inactivation of rabbit muscle creatine kinase by reversible formation of an internal disulfide bond induced by the fungal toxin gliotoxin, J Biol Chem, 275, 25202, 10.1074/jbc.M002278200

Hurne, 2002, Influx of calcium through a redox sensitive plasma membrane channel in thymocytes causes early necrotic cell death induced by the epipolythiodioxopiperazine toxins, J Biol Chem, 277, 31631, 10.1074/jbc.M201699200

Jordan, 1986, Sporidesmin and gliotoxin induce cell detachment and perturb microfilament structure in cultured liver cells, J Cell Sci, 85, 33, 10.1242/jcs.85.1.33

Joshi, 1999, New verticillin and glisoprenin analogues from Gliocladium catenulatum, a mycoparasite of Aspergillus flavus sclerotia, J Nat Prod, 62, 730, 10.1021/np980530x

Kawahara, 1987, Studies on fungal products. Part 13. Isolation and structures of dithiosilvatin and silvathione, novel dioxopiperazine derivatives from Aspergillus silvaticus, J Chem Soc Perkin Trans 1, 2099, 10.1039/p19870002099

Kawahara, 1989, Structure of a novel epidithiodioxopiperazine, emethallicin A, a potent inhibitor of histamine release from Emericella heterothallica, Chem Pharm Bull, 37, 2592, 10.1248/cpb.37.2592

Kirby, 1980, The biosynthesis of gliotoxin and related epipolythiodioxopiperazines, The Biosynthesis of Mycotoxins, 10.1016/B978-0-12-670650-5.50015-7

Kirby, 1978, cyclo-(l-phenylalanyl-l-seryl) as an intermediate in the biosynthesis of gliotoxin, J Chem Soc Perkin Trans 1, 1336, 10.1039/p19780001336

Kleinwachter, 2001, Epicorazine C, an antimicrobial metabolite from Stereum hirsutum HKI 0195, J Antibiot, 54, 521, 10.7164/antibiotics.54.521

Kroken, 2003, Phylogenomic analysis of type I polyketide synthase genes in pathogenic and saprobic ascomycetes, Proc Natl Acad Sci U S A, 100, 15670, 10.1073/pnas.2532165100

Macdonald, 1975, Biosynthesis of gliotoxin and mycelianamide, Can J Biochem, 53, 475, 10.1139/o75-066

Martin Castro, 2004, Claisen rearrangement over the past nine decades, Chem Rev, 104, 2939, 10.1021/cr020703u

McStay, 2002, Role of critical thiol groups on the matrix surface of the adenine nucleotide translocase in the mechanism of the mitochondrial permeability transition, Biochem J, 367, 541, 10.1042/bj20011672

Moerman, 2003, Evidence that the lichen-derived scabrosin esters target mitochondrial ATP synthase in P388D1 cells, Toxicol Appl Pharmacol, 190, 232, 10.1016/S0041-008X(03)00189-3

Mootz, 1997, Biosynthetic systems for nonribosomal peptide antibiotic assembly, Curr Opin Chem Biol, 1, 543, 10.1016/S1367-5931(97)80051-8

Mullbacher, 1985, Identification of an agent in cultures of Aspergillus fumigatus displaying anti-phagocytic and immunomodulating activity in vitro, J Gen Microbiol, 131, 1251

Mullbacher, 1986, Structural relationship of epipolythiodioxopiperazines and their immunomodulating activity, Mol Immunol, 23, 231, 10.1016/0161-5890(86)90047-7

Mullbacher, 1988, Prevention of graft-versus-host disease by treatment of bone marrow with gliotoxin in fully allogeneic chimeras and their cytotoxic T cell repertoire, Transplantation, 46, 120, 10.1097/00007890-198807000-00022

Munday, 1982, Studies on the mechanism of toxicity of the mycotoxin sporidesmin. I. Generation of superoxide radical by sporidesmin, Chem Biol Interact, 41, 361, 10.1016/0009-2797(82)90112-0

Neuss, 1968, Aranotin and related metabolites from Arachniotus aureus (Eidam) Schroeter. IV. Fermentation, isolation, structure elucidation, biosynthesis, and antiviral properties, Antimicrob Agents Chemother, 8, 213

Nishida, 2005, Fungal metabolite gliotoxin targets flavocytochrome b558 in the activation of the human neutrophil NADPH oxidase, Infect Immun, 73, 235, 10.1128/IAI.73.1.235-244.2005

Orr, 2004, Mechanism of action of the antifibrogenic compound gliotoxin in rat liver cells, Hepatology, 40, 232, 10.1002/hep.20254

Pahl, 1996, The immunosuppressive fungal metabolite gliotoxin specifically inhibits transcription factor NF-κB, J Exp Med, 183, 1829, 10.1084/jem.183.4.1829

Pedras, 1990, Minor phytotoxins from the blackleg fungus Phoma lingam, Phytochemistry, 29, 777, 10.1016/0031-9422(90)80017-B

Reeves, 2004, Correlation between gliotoxin production and virulence of Aspergillus fumigatus in Galleria mellonella, Mycopathologia, 158, 73, 10.1023/B:MYCO.0000038434.55764.16

Rightsel, 1964, Antiviral activity of gliotoxin and gliotoxin acetate, Nature, 204, 1333, 10.1038/2041333b0

Rodriguez, 1992, Gliotoxin: inhibitor of poliovirus RNA synthesis that blocks the viral RNA polymerase 3Dpol, J Virol, 66, 1971, 10.1128/JVI.66.4.1971-1976.1992

Rouxel, 1988, Biological effects of sirodesmin PL, a phytotoxin produced by Leptosphaeria maculans, Plant Sci, 57, 45, 10.1016/0168-9452(88)90140-9

Salvi, 2004, Gliotoxin induces Mg2+ efflux from intact brain mitochondria, Neurochem Int, 45, 759, 10.1016/j.neuint.2004.01.001

Schweizer, 1994, Gliotoxin stimulates Ca2+ release from intact rat liver mitochondria, Biochemistry, 33, 13401, 10.1021/bi00249a028

Sekita, 1981, Mycotoxin production by Chaetomium spp. and related fungi, Can J Microbiol, 27, 766, 10.1139/m81-119

Serena, 2003, In vitro activities of new antifungal agents against Chaetomium spp. and inoculum standardization, Antimicrob Agents Chemother, 47, 3161, 10.1128/AAC.47.10.3161-3164.2003

Seya, 1986, Studies on fungal products. IX. Dethiosecoemestrin, a new metabolite related to emestrin, from Emericella striata, Chem Pharm Bull, 34, 2411, 10.1248/cpb.34.2411

Shah, 1991, Clinical isolates of yeast produce a gliotoxin-like substance, Mycopathologia, 116, 203, 10.1007/BF00436836

Smith, 1990, Cloning and heterologous expression of the penicillin biosynthetic gene cluster from Penicillum chrysogenum, Biotechnology, 8, 39

Sock, 1999, Pathogenicity of sirodesmin-deficient mutants of Phoma lingam, J Phytopathol, 147, 169

Stillwell, 1974, Production, isolation, and antimicrobial activity of hyalodendrin, a new antibiotic produced by a species of Hyalodendron, Can J Microbiol, 20, 759, 10.1139/m74-116

Suhadolnik, 1958, Biosynthesis of gliotoxin. I. Incorporation of phenylalanine-1- and -2-C14, J Am Chem Soc, 80, 4391, 10.1021/ja01549a071

Sutton, 1994, In vivo immunosuppressive activity of gliotoxin, a metabolite produced by human pathogenic fungi, Infect Immun, 62, 1192, 10.1128/IAI.62.4.1192-1198.1994

Takahashi, 1994, Leptosins I and J, cytotoxic substances produced by a Leptosphaeria sp. Physico-chemical properties and structures, J Antibiot, 47, 1242, 10.7164/antibiotics.47.1242

Trown, 1972, Mechanism of action of gliotoxin: elimination of activity by sulfhydryl compounds, Antimicrob Agents Chemother, 2, 261, 10.1128/AAC.2.4.261

Tsunawaki, 2004, Fungal toxin gliotoxin inhibits assembly of the human respiratory burst NADPH oxidase, Infect Immun, 72, 3373, 10.1128/IAI.72.6.3373-3382.2004

Tudzynski, 1999, Evidence for an ergot alkaloid gene cluster in Claviceps purpurea, Mol Gen Genet, 261, 133, 10.1007/s004380050950

Van der Pyl, 1992, Inhibition of farnesyl-protein transferase by gliotoxin and acetylgliotoxin, J Antibiot, 45, 1802, 10.7164/antibiotics.45.1802

Vigushi, 2004, Gliotoxin is a dual inhibitor of farnesyltransferase and geranylgeranyltransferase I with antitumor activity against breast cancer in vivo, Med Oncol, 21, 21, 10.1385/MO:21:1:21

Walton, 2000, Horizontal gene transfer and the evolution of secondary metabolite gene clusters in fungi: an hypothesis, Fungal Genet Biol, 30, 167, 10.1006/fgbi.2000.1224

Ward, 2002, Ancestral polymorphism and adaptive evolution in the trichothecene mycotoxin gene cluster of phytopathogenic Fusarium, Proc Natl Acad Sci U S A, 99, 9278, 10.1073/pnas.142307199

Waring, 1995a, DNA synthesis precedes gliotoxin induced apoptosis, Cell Death Differ, 2, 201

Waring, 1995b, Gliotoxin inactivates alcohol dehydrogenase by either covalent modification or free radical damage mediated by redox cycling, Biochem Pharmacol, 49, 1195, 10.1016/0006-2952(95)00039-3

Weindling, 1941, Experimental consideration of the mold toxins of Gliocladium and Trichoderma, Phytopathology, 31, 991

Weindling, 1936, The isolation of a toxic substance from the culture filtrate of Trichoderma, Phytopathology, 26, 1068

Winstead, 1960, Biosynthesis of gliotoxin. II. Further studies on the incorporation of carbon-14 and tritium-labeled precursors, J Am Chem Soc, 82, 1644, 10.1021/ja01492a031

Wright, 2001, Gliotoxin stimulates the apoptosis of human and rat hepatic stellate cells and enhances the resolution of liver fibrosis, Gastroenterology, 121, 685, 10.1053/gast.2001.27188

Young, 2001, Molecular cloning and genetic analysis of an indole-diterpene gene cluster from Penicillium paxilli, Mol Microbiol, 39, 754, 10.1046/j.1365-2958.2001.02265.x

Yu, 2004, Clustered pathway genes in aflatoxin biosynthesis, Appl Environ Microbiol, 70, 1253, 10.1128/AEM.70.3.1253-1262.2004