Microbial natural products as a source of antifungals

Demain, 1983, New applications of microbial products, Science, 219, 709, 10.1126/science.6337397 Omura, 1986, Philosophy of new drug discovery, Microbiol Rev, 50, 259, 10.1128/mr.50.3.259-279.1986 Beck-Sague, 1993, Secular trends in the epidemiology of nosocomial fungal infections in the United States. 1980–90. National Nosocomial Infections Surveillance System, J Infect Dis, 167, 1247 Diamond, 1991, The growing problem of mycoses in patients infected with the human immunodeficiency virus, Rev Infect Dis, 13, 480, 10.1093/clinids/13.3.480 Georgopapadakou, 1994, Human mycoses: drugs and targets for emerging pathogens, Science, 264, 371, 10.1126/science.8153622 Carledge, 1997, Clinically significant azole cross-resistance in Candida isolates from HIV-positive patients with oral candidiasis, AIDS, 11, 1839, 10.1097/00002030-199715000-00008 Granier, 2000, Invasive fungal infections. Epidemiology and new therapies, Presse Med, 29, 2051 Fleet, 1991, Cell walls, 199 Turner, 1997, Echinocandin antifungal agents, 315 Nyfeler, 1974, Metabolites of microorganisms. 143. Echinocandin B, a novel polypeptideantibiotic from Aspergillus nidulans var. echinulatus: isolation and structural components, Helv Chim Acta, 57, 2459 Bouffard, 1996, L-743,872, a novel antifungal lipopeptide: synthesis and structure-activity relationships of new aza-substituted pneumocandins. [abstract F27], 104 Schwartz, 1992, Pneumocandins from Zalerion arboricola. I Discovery and isolation, J Antibiotics, 45, 1853, 10.7164/antibiotics.45.1853 Bills, 1999, Reclassification of a pneumocandin-producing anamorph, Glarea lozoyensis gen. et sp. nov., previously identified as Zalerion arboricola, Mycol Res, 103, 179, 10.1017/S095375629800687X Bouffard, 1994, Synthesis and antifungal activity of novel cationic pneumocandin Bo derivatives, J Med Chem, 37, 222, 10.1021/jm00028a003 Abruzzo, 1997, Evaluation of the echinocandin antifungal MK-0991 (L-743,872): efficacies in mouse models of disseminated aspergillosis, candidiasis and cryptococcosis, Antimicrob Agents Chemother, 41, 2333, 10.1128/AAC.41.11.2333 Smith, 1996, Evaluation of pneumocandin L-743,872 in neutropenic mouse models of disseminated candidiasis and aspergillosis [abstract F41], 107 Powles, 1998, Efficacy of MK-991 (L-743,872), a semisynthetic, pneumocandin, in murine models of Pneumocystis carinii, Antimicrob Agents Chemother, 42, 1985, 10.1128/AAC.42.8.1985 González, 2001, Correlation between antifungal susceptibilities of Coccidioides immitis in vitro and antifungal treatment with caspofungin in a mouse model, Antimicrob Agents Chemother, 45, 1854, 10.1128/AAC.45.6.1854-1859.2001 Arathoon, 1998, A randomized, double-blind, multicenter trial of MK-0991, an echinocandin antifungal agent, vs. amphotericin B for the treatment (Tx) of oropharyngeal (OPC) and esophageal (EC) candidiasis in adults, Clin Infect Dis, 27, 939 Maertens, 2000, Multicenter, noncomparative study to evaluate safety and efficacy of caspofungin (CAS) in adults with invasive aspergillosis (IA) refractory R or Intolerant (I) to amphotericin B (AMB), AMB lipid formulations (lipid AMB), or azoles. [abstract J-1103], 371 Ikeda, 2000, Efficacy of FK463, a new lipopeptide antifungal agent, in mouse models of disseminated candidiasis and aspergillosis, Antimicrob Agents Chemother, 44, 614, 10.1128/AAC.44.3.614-618.2000 Petraitis, 2001, Dosagedependent antifungal efficacy of V-echinocandin (LY303366) against experimental fluconazol-resistant oropharyngeal and esophageal candidiasis, Antimicrob Agents Chemother, 45, 471, 10.1128/AAC.45.2.471-479.2001 Takashi T, Higashiimazato et al. Cyclic hexapeptides having antibiotic activity. International patent, WO 0064927, 2000. Aoki M, Kowada C et al. Aerothicin analogs, their preparation and use. International patent, WO 0005251, 2000. Roy, 1987, Mulundocandin, a new lipopentide antibiotic. I Taxonomy, fermentation, isolation and characterization, J Antibiotics, 40, 275, 10.7164/antibiotics.40.275 Ohyama, 2000, Arborcandins A, B, C, D, E and F, novel 1, 3-φ-glucan synthase inhibitors: production and biological activity, J Antibiotics, 53, 1108, 10.7164/antibiotics.53.1108 Fujie, 2000, FR901469, a novel antifungal antibiotic from an unidentified fungus no. 11243 I. Taxonomy, fermentation, isolation, physicochemical prpoerties and biological properties, J Antibiotics, 53, 912, 10.7164/antibiotics.53.912 Kaida, 2001, New cyclic depsipeptide antibiotics, clavariopsins A and B, produced by an aquatic hyphomycete, Clavariopsis aquatica. I. Taxonomy, fermentation, isolation and biological properties, J Antibiotics, 54, 17, 10.7164/antibiotics.54.17 Traxler, 1977, Papulacandins, a new family of antibiotics with antifungal activity. I. Fermentation, isolation, chemical and biological characterization of papulacandins A, B, C, D and E, J Antibiotics, 30, 289, 10.7164/antibiotics.30.289 Georgopapadakou, 1995, The fungal cell wall as a drug target, Trends Microbiol, 3, 98, 10.1016/S0966-842X(00)88890-3 Yeung, 1996, Preparation and antifungal activity of fusacandin analogs: C-6' sidechain esters, Bioorg Med Chem Lett, 6, 819, 10.1016/0960-894X(96)00113-8 Onishi, 2000, Discovery of novel antifungal beta (1, 3)-glucan synthase inhibitors, Antimicrob Agents Chemother, 44, 368, 10.1128/AAC.44.2.368-377.2000 Cabello, 2001, The discovery of arundifungin, a novel antifungal compound produced by fungi. Biological activity and taxonomy of the producing organisms, Int Microbiol, 4, 93, 10.1007/s101230100020 Peláez, 2000, The discovery of enfumafungin, a novel antifungal compound produced by an endophytic Hormonema species. Biological activity and taxonomy of the producing organism, Syst Appl Microbiol, 23, 333, 10.1016/S0723-2020(00)80062-4 Vicente, 2001, Antimicrobial activity of ergokonin A from Trichoderma longibrachiatum, J Appl Microbiol, 91, 806, 10.1046/j.1365-2672.2001.01447.x Feldmesser, 2000, The effect of the echinocandin analogue caspofungin on cell wall glucan synthesis by Cryptococcus neoformans, J Infect Dis, 182, 1791, 10.1086/317614 Ruiz-Herrera, 1992, Chitin biosynthesis in fungi, vol. 4, 281 Shaw, 1991, The function of chitin synthases 2 and 3 in the Saccharomyces cerevisiae cell cycle, J Cell Biol, 114, 111, 10.1083/jcb.114.1.111 Gabib, 1991, Differential inhibition of chitin synthetases 1 and 2 from Saccharomyces cerevisiae by polyoxin D and nikkomycins, Antimicrob Agents Chemother, 35, 170, 10.1128/AAC.35.1.170 Hector, 1986, Synergistic action of nikkomycins X and Z with papulacandin B on whole cells and regenerating protoplasts of Candida albicans, Antimicrob Agents Chemother, 29, 389, 10.1128/AAC.29.3.389 Li, 1999, In vitro antifungal activity of nikkomycin Z in combination with fluconazole or itraconazole, Antimicrob Agents Chemother, 43, 1401, 10.1128/AAC.43.6.1401 Cohen, 1993, Chitin synthesis and degradation as targets for pesticide action, Arch Insect Biochem Physiol, 22, 245, 10.1002/arch.940220118 Hwang, 2000, Phellinsin A, a novel chitin synthesis inhibitor produced by Phellinus sp. Pl3, J Antibiotics, 53, 903, 10.7164/antibiotics.53.903 Vijayakumar, 1996, Arthrichitin. A new cell wall active metabolite from Arthrinium phaeospermum, J Org Chem, 61, 6591, 10.1021/jo960769n Schlingmann, 1998, Cell wall active antifungal compounds produced by the marine fungus Hypoxylon oceanium LL-15G256 II. Isolation and structure determination, J Antibiotics, 51, 303, 10.7164/antibiotics.51.303 Van Der Vaart, 1996, The retention mechanism of cell wall proteins in Sccharomyces cerevisiae. Wall bound Cwp2p is b1, 6-glucosylated, Biochim Biophys Acta, 1291, 206, 10.1016/S0304-4165(96)00067-0 Oki, 1988, Pradimicin, a novel class of potent antifungal anbiotics, J Antibiotics, 41, 1701, 10.7164/antibiotics.41.1701 Takeuchi, 1988, New antifungal antibiotics benanomicins A and B from an Actinomycete, J Antibiotics, 41, 807, 10.7164/antibiotics.41.807 Fromtling, 1998, Human mycoses and current antifungal therapy, Drug News Perspect, 11, 185 Wells, 1983, The isolation and characterization of a mutant strain of Saccharomyces cerevisiae that requires a long chain base for growth and for synthesis of phosphosphingolipids, J Biol Chem, 258, 10200, 10.1016/S0021-9258(17)44439-5 Zweerink, 1992, Characterization of a novel, potent, and specific inhibitor of serine palmitoyltransferase, J Biol Chem, 267, 25032, 10.1016/S0021-9258(19)74001-0 Mandala, 1995, The discovery of australifungin, a novel inhibitor of sphinganine N-acyltransferase from Sporormiella australis. Producing organism, fermentation, isolation and biological activity, J Antibiotics, 48, 349, 10.7164/antibiotics.48.349 Nickels, 1996, A ceramide-activated protein phosphatase mediates ceramide-induced G1 arrest of Saccharomyces cerevisae, Genes Dev, 10, 382, 10.1101/gad.10.4.382 Wu, 1995, Regulation of lipid biosynthesis in Saccharomyces cerevisiae by fumonisin B1, J Biol Chem, 270, 13171, 10.1074/jbc.270.22.13171 Oh, 1997, Suppresor gene analysis reveals an essential role for sphingolipids in transport of glycosylphosphatidylinositol-anchored proteins in Saccharomyces cerevisiae, J Biol Chem, 272, 17376, 10.1074/jbc.272.28.17376 Horn, 1992, Sphingofungins E and F. Novel serine palmitoyltransferase inhibitors from Paecilomyces variotii, J Antibiotics, 47, 376 Mandala, 1994, Inhibition of serine palmitoyltransferase activity by lipoxamycin, J Antibiotics, 47, 376, 10.7164/antibiotics.47.376 Mandala, 1997, Viridiofungins, novel inhibitors of sphingolipid synthesis, J Antibiotics, 50, 339, 10.7164/antibiotics.50.339 Wang, 1991, Inhibition of sphingolipid biosynthesis by fumonisins. Implications for diseases associated with Fusarium moniliforme, J Biol Chem, 266, 14486, 10.1016/S0021-9258(18)98712-0 Nagiec, 1997, Sphingolipid synthesis as a target for antifungal drugs. Complementation of the inositol phosphorylceramide synthase defect in a mutant strain of Saccharomyces cerevisiae by the AUR1 gene, J Biol Chem, 272, 9809, 10.1074/jbc.272.15.9809 Mandala, 1997, Khafrefungin, a novel inhibitor of sphingolipid synthesis, J Biol Chem, 272, 32709, 10.1074/jbc.272.51.32709 Mandala, 1998, Rustmicin, a potent antifungal agent, inhibits sphingolipid synthesis at inositol phosphoceramide synthase, J Biol Chem, 273, 14942, 10.1074/jbc.273.24.14942 Mandala, 2001, Isolation and characterization of novel inhibitors of sphingolipid synthesis: australifungin, viridiofungins, rustmicin, and khafrefungin, Meth Enzymol, 311, 335, 10.1016/S0076-6879(00)11094-8 VanMiddlesworth, 1992, Sphingofungins A, B, C, and D; a new family of antifungal agents. I. Fermentation, isolation and biological activity, J Antibiotics, 45, 861, 10.7164/antibiotics.45.861 Whaley, 1970, Production, isolation, characterization, and evaluation of lipoxamycin, a new antifungal agent, Antimicrob Agents Chemother, 10, 455 Onishi, 1997, Antimicrobial activity of viridiofungins, J Antibiotics, 50, 334, 10.7164/antibiotics.50.334 Miyake, 1995, Serine palmitoyltransferase is the primary target of a sphingosine.like immunosuppressant, ISP.1/Myriocin, Biochem Biophys Res Commun, 211, 396, 10.1006/bbrc.1995.1827 Takesako, 1991, Aureobasidins, new antifungal antibiotics. Taxonomy, fermentation, isolation, and properties, J Antibiotics, 44, 919, 10.7164/antibiotics.44.919 Takatsu, 1985, Rustmicin, a new macrolide antibiotic active against wheat stem rust fungus, J Antibiotics, 38, 1806, 10.7164/antibiotics.38.1806 Fauth, 1986, Galbonolides A and B- two non glycosidic antifungal macrolides, J Antibiotics, 39, 1760, 10.7164/antibiotics.39.1760 Harris, 1998, Inhibition of fungal sphingolipid biosynthesis by rustmicin, galbonolide B and their new 21-hydroxy analogs, J Antibiotics, 51, 837, 10.7164/antibiotics.51.837 Takesako, 1993, Biological properties of aureobasidin A, a cyclic depsipeptide antifungal antibiotic, J Antibiotics, 46, 1414, 10.7164/antibiotics.46.1414 Hall, 1992, Screening assays for protein synthesis inhibitors, J Antibiotics, 45, 1697, 10.7164/antibiotics.45.1697 Kamath, 1989, Role of yeast Elongation Factor 3 in the Elongation Cycle, J Biol Chem, 264, 15423, 10.1016/S0021-9258(19)84845-7 Skogerson, 1977, Dissimilarity in chain elongation factor requirements between yeasts and rat liver ribosomes, J Biol Chem, 252, 1471, 10.1016/S0021-9258(17)40680-6 Dominguez, 1998, Sordarins: a new class of antifungal with selective inhibition of the protein synthesis elongation cycle in yeasts, Antimicrob Agents Chemother, 42, 2274, 10.1128/AAC.42.9.2274 Justice, 1998, Elongation factor 2 as a novel target for selective inhibition of fungal protein synthesis, J Biol Chem, 273, 3148, 10.1074/jbc.273.6.3148 Belfield, 1995, Translation elongation factor-3 (EF-3): an evolving eukaryotic ribosomal protein?, J Mol Evol, 41, 367, 10.1007/BF01215185 Sigg HP, Binningen Stoll C. Antibiotic SL, 2266. United States patent, US 3432598, 1969. Hauser, 1971, Isolierung und abbau von sordarin, Helv Chim Acta, 54, 1178, 10.1002/hlca.19710540427 Vasella A. Uber ein neuartiges diterpen aus Sordaria Araneosa Cain. PhD Thesis. Eidgenö ssischen Technischen Hochschule, Zürich., 1972. Dominguez, 1998, Identification of elongation Factor 2 as the essential protein targeted by sordarins in Candida albicans, Antimicrob Agents Chemother, 42, 2279, 10.1128/AAC.42.9.2279 Ogita T, Hayashi A, Sato S, Furaya K. Antibiotic zofimarin. Jpn Kokai Tokkyo Koho JP 6240292, 1987. Okada H, Kamiya S, Shiina Y et al. Antifungal substance BE-31405. Japanese patent JP 6157582, 1994. Okada, 1998, BE-31405, a new Antifungal Antibiotic produced by Penicillium minioluteum, J Antibiotics, 51, 1081, 10.7164/antibiotics.51.1081 Coval, 1995, SCH 57404 an antifungal agent possessing the rare sordaricin skeleton and a tricyclic sugar moiety, J Antibiotics, 48, 1171, 10.7164/antibiotics.48.1171 Schneider, 1995, Xylarin, an antifungal Xylaria metabolite with an unusual tricyclic uronic acid moiety, Natural products letters, 7, 309, 10.1080/10575639508043227 Daferner, 1999, Hypoxysordarin, a new sordarin derivative from, Hypoxylon croceum Z Naturforsch, 54c, 474, 10.1515/znc-1999-7-803 Martin JJ, Chicharro-Gonzalo J, Gómez JRR et al. Antifungal sordaridin derivatives. United States patent, US 6054478, 2000. Balkovec JM, Tse B et al. Sordarin derivatives. United States patent, US 6040463, 2000. Hirano A, Torigoe K, Ogawa H et al. Derivatives of antifungal substance BE-31405 and process for producing the same. United States patent, US 6087390, 2000. Kinsman, 1998, Isolation and characterisation of an antifungal antibiotic (GR 135402) with protein synthesis inhibition, J Antibiotics, 51, 41, 10.7164/antibiotics.51.41 Gargallo-Viola, 1999, Sordarins as antifungal compounds, Current Opinion Anti-Infective Investigational Drugs, 1, 297 Aviles, 2000, In vitro pharmacodynamic parameters of sordarin derivatives in comparison with those of marked compounds against Pneumocystic carinii isolated from rats, Antimicrobial Agents Chemother, 44, 1284, 10.1128/AAC.44.5.1284-1290.2000 Herreros, 1998, Sordarins: in vitro activities of new antifungal derivatives against pathogenic yeast, Pneumocystis carinii, and filamentous fungi, Antimicrob Agents Chemother, 42, 2863, 10.1128/AAC.42.11.2863 Graybill, 1999, Activities of sordarins in murine histoplasmosis, Antimicrob Agents Chemother, 43, 1716, 10.1128/AAC.43.7.1716 Clemons, 2000, Efficacies of sordarin derivatives GM193663, GM211676, and GM237354 in a murine model of systemic coccidioidomycosis, Antimicrob Agents Chemother, 44, 1874, 10.1128/AAC.44.7.1874-1877.2000 Oakley, 1997, In vivo activity of GM237354 in a neutropenic murine model of aspergillosis. [abstract F61], 156 Herreros, 2000, Preliminary toxicology of azasordarins. [abstract 1691], 389 Herreros, 2001, Antifungal activities and cytotoxicity studies of six new azasordarins, Antimicrob Agents Chemother, 45, 3132, 10.1128/AAC.45.11.3132-3139.2001 Peacock, 1993, therapy. past, present, and future, Infect Dis Clin Pract, 2, 81, 10.1097/00019048-199303000-00001 Ueki, 1996, UK-2A, B and C, novel antifungal antibiotics from Streptomyces sp. 517–02. Fermantation, isolation, and biological properties, J Antibiotics, 49, 639, 10.7164/antibiotics.49.639 Ueki, 1997, UK-3A, a novel antifungal antibiotics from Streptomyces sp. 517–02. Fermantation, isolation, structural elucidation and biological properties, J Antibiotics, 50, 551, 10.7164/antibiotics.50.551 Suay, 2000, Screening of Basidiomycetes for antimicrobial activities, Antonie Van Leeuwenhoek J Microbiology, 78, 129, 10.1023/A:1026552024021 Peláez, 1998, Endophytic fungi from plants living on gypsum soils as a source of secondary metabolites with antimicrobial activity, Mycol Res, 102, 755, 10.1017/S0953756297005662 Collado J, González del Val A, Platas G et al. Endophytic mycoflora from halophytes of the Ebro Delta (NE Spain). Screening of antimicrobial activities. In: International Symposium: Bioactive Fungal Metabolites—Impact and Exploitation, Swansea. British Mycological Society, 2001; 4. Mizuno, 1977, Studies on aculeacin. I Isolation and characterization of aculeacin A, J Antibiotics, 30, 297, 10.7164/antibiotics.30.297 Tscherter H, Dreyfuss MM. Antibiotics from a Cryptosporiopsis species and their therapeutic use. Sandoz S. A, Assignee Belg Patent, 889, 955, 1982. Noble, 1991, An echinocandin from an endophytic Cryptosporiopsis sp. and Pezicula sp. in Pinus sylvestris and Fagus sylvatica, Mycol Res, 95, 1439, 10.1016/S0953-7562(09)80401-2 Strobel, 1999, Cryptocandin, a potent antimycotic from the endophytic fungus Cryptosporiopsis cf. Quercina, Microbiol UK, 145, 1919, 10.1099/13500872-145-8-1919 Hori Y. A novel series of antifungal lipopeptide antibiotics. In: The 14th Symposium of Kanto Branch of the Mycological Society of Japan Diversity of Fungal Metabolites, the Recent Topics and Future, Tokyo. Kanto Branch of the Mycological Society of Japan, 1999; 4. Gunawardana, 1997, Corynecandin: a novel antifungal glycolipid from Coryneum modonium, J Antibiotics, 50, 884, 10.7164/antibiotics.50.884 Kaneto, 1993, Mer-WF3010. A new member of the papulacandin family. I Fermentation, isolation and characterization, J Antibiotics, 46, 247, 10.7164/antibiotics.46.247 Aoki, 1993, BU-4794F, a new Φ-1,3-glucan synthase inhibitor, J Antibiotics, 46, 952, 10.7164/antibiotics.46.952 VanMiddlesworth, 1991, L-687,781, a new member of the papulacandin family of 1,3-d-glucan synthesis inhibitors. I. Fermentation, isolation and biological activity, J Antibiotics, 44, 45, 10.7164/antibiotics.44.45