Abstract
Fungi have been used by mankind ever since ancient times for a variety of uses, mainly for food (Zadrazil and Karma 1997) or food production (Wolf 1997). The great diversity of substrates and habitats which fungi can successfully colonize reflects the enormous richness of genetic and metabolic resources of these organisms. Until now, fungi have only been surpassed by Actinomycetales as a source for biologically active metabolites. Among the best known are the β-lactams (penicillins and cephalosporins) which are dealt with in Chapter 4 of this Volume. In the following, we wish to review some classes of fungal metabolites which are presently used as medicinal, veterinary or agricultural antibiotics, as well as some newer candidates for development. For pharmacologically active fungal metabolites used as, e.g., immunomodulators or plant growth regulators, the reader is referred to Anke (1997).
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
Avarsson A, Brazhnikov E, Garber M, Zheltonosova J, Chirgadze Y, al-Karadaghi S, LA Svensson LA, Liljas A (1994) Three-dimensional structure of the ribosomal translocase: elongation factor G from Thermus therrnophilus. EMBO J 13: 3669–3677
Anke T (ed) (1997) Fungal biotechnology. Chapman and Hall. London
Anke T, Oberwinkler F, Steglich W, Schramm G (1977) The strobilurins - new antifungal antibiotics from the basidiomycete Strobilurus tenacellus (Pers. ex Fr.) Sing. J Antibiot 30: 806–810
Anke T, Hecht HJ, Schramm G. Steglich W (1979) Antibiotics from basidiomycetes. IX. Oudemansin, an antifungal antibiotic from Oudemansiella mucida (Schrader ex Fr.) Hoehnel ( Agaricales ). J Antibiot 32: 1112–1117
Anke T, Besl H, Mocek U, Steglich W (1983) Antibiotics from basidiomycetes. XVIII. Strobilurin C and oudemansin B, two new antifungal metabolites from Xerula species ( Agaricales ). J Antibiot 36: 661–666
Anke T, Schramm G, Schwalge B, Steffan B, Steglich W (1984) Antibiotika aus Basidiomyceten, XX. Synthese von Strobilurin A und Revision der Stereochemie der natürlichen Strobilurine. Liebigs Ann Chem 1984: 1616–1625
Anke T, Schramm G, Steglich W, von Jagow G (1988) Structure-activity relationships of natural and synhetic Eß-mcthoxyacrylates of the strobilurin and oudemansin series. In: Kleinkauf H, von Döhren H, Jaenicke L (eds) The roots of modern biochemistry. De Gruyter, Berlin, p 657
Anke T, Werle A, Bross M, Steglich W (1990) Antibiotics from basidiomycetes. XXXIII. Oudemansin X, a new antifungal E-ß-methoxyacrylate from Oudemansiella radicata ( Relhan ex Fr.) Sing. J Antibiot 43: 1010–1011
Aoki M, Andoh T, Ueki T, Masuyoshi S, Sugawara K, Oki T (1993) BU-4794F, a new beta-1,3-glucan synthase inhibitor. J Antibiot 46: 952–960
Arigoni D (1962) La struttura di un terpene di nuovo genere. In Gazz Chim Itl 92: 884–901
Arigoni D. von Daehne W, Godfredsen WO, Melera A, Vangedal S (1964) The stereochemistry of fusidic acid. Experentia 20: 344–347
Aviles P, Aliouat EM, Martinez A, Dei-Cas E, Herreros E, Dujardin L, Gargallo-Viola D (2000) In vitro pharmacodynamic parameters of sordarin derivatives in comparison with those of marketed compounds against Pneumocystis carinii isolated from rats. Antimicrob Agents Chemother 44: 1284–1290
Baguley BC, Römmele G, Gruner J, Wehrli W (1979) Papulacandin B: an inhibitor of glucan synthesis in yeast spheroplasts. Eur J Biochem 97: 345–351
Bäuerle J, Anke T (1980) Antibiotics from the genus Mycena and Hydropus scabripes. Planta Med 39: 195–196
Bechter R, Schmid BP (1987) Teratogenicity in vitro–a comparative study of four antimycotic drugs using the whole embryo culture system. Toxicol In Vitro 1: 11–15
Becker WF von Jagow G, Anke T, Steglich W (1981) Oudemansin, strobilurin A, strobilurin B and myxothiazol: new inhibitors of the bci segment of the respiratory chain with an E-ß-methoxyacrylate system as a common structural element. FEBS Lett 132: 329–333
Bendtzen K, Diamant M, Faber V (1990) Fusidic acid, an immunosuppressive drug with similar functions to cyclosporin A. Cytokine 2: 423–429
Benz F, Knüsel F, Nüesch, Trichler, Nyfeler R, KellerSchierlein W (1974) Stoffwechselprodukte von Mikroorganismen. 143. Mitteilung. Echinocandin B, ein neuartiges Polypeptid-Antibiotikum aus Aspergillus nidulans var. echinulatus: Isolierung and Bausteine. Helv Chim Acta 57: 2459–2477
Birch AJ, Cameron DW, Holzapfel CW., Rickards RW (1963) The diterpenoid nature of pleuromutilin. Chem Ind (Lond) 374–375
Birch AJ, Holzapfel CW, Rickards RW (1966) The structure and some aspects of the biosynthesis of pleuromutilin. Tetrahedron (Suppl) 8 Part II: 359–387
Bodley JW, Lin L, Salas M et al (1970) Translocation V. Fusidic acid stabilization of a eukaryotic ribosome-translocation factor-GDP complex. FEBS 11: 153–156
Bossi A, Baumann M, Gerecke M, Kyburz E (1960) Syntheseversuche in der Griseofulvinreihe. I. Mitt. Eine Totalsynthese von Griseofulvin. Hely Chim Acta 43: 2071
Brady A, Lock EA (1992) Inhibition of ferrochelatase and accumulation of porphyrins in mouse hepatocyte cultures exposed to porphyrinogenic chemicals. Arch Toxicol 66: 175–181
Brandt E, Knauseder F, Schmid E, Thym H (1968) Water-soluble antibiotics. Austrian Patent 261,804; Chem Abstr 69,76,054 r
Brian PW, Curtis PJ, Hemming HG (1946) A substance causing abnormal development of fungal hyphae produced by Penicillium janczewskii Zal. I. Biological assay, production and isolation of “curling factor”. Trans Br Mycol Soc 29: 173–187
Brian PW, Curtis Pi, Hemming HG (1949) A substance causing abnormal development of fungal hyphae produced by Penicillium janczewskii Zal. III. Identity of curling factor with griseofulvin. Trans Br Mycol Soc 32: 30–33
Brian PW (1951) Antibiotics produced by fungi. Bot Rev 17: 357–430
Broadbent D (1966) Antibiotics produced by fungi. Bot Rev 32: 219–242
Buchanan MS, Steglich W, Anke T (1999) Strobilurin N and two metabolites of chorismic acid from the fruit-bodies of Mycena crocata ( Agaricales ). Z Naturforsch 54c: 463–468
Burton HS, Abraham EP (1951) Isolation of antibiotics from a species of Cephalosporium. Cephalosporin PI, P2, P3, P4 and P5. Biochem J 50: 168–174
Butters JA, Kendall SJ, Wheeler IE, Hollomon DW (1995) Tubulins: lessons from existing products that can be applied to target new antifungals. In: Dixon GK, Non-ß-Lactam Antibiotics 105
Copping LG, Hollomon DW (eds) Antifungal agents, discovery and mode of action. Bios Scientific Publishers, Oxford, pp 131–142
Capa L. Mendoza A, Lavandera JL, de las Heras GF, Garcia-Bustos JF (1998) Translation elongation factor 2 is part of the target for a new family of antifungals. Antimicrob Agents Chemother 42: 2694–2699
Chain E, Florey HW, Jennings MA, Williams TI (1943) Helvolic acid, an antibiotic produced by Aspergillus fumigatus, mut. helvola Yuill. Br J Exp Pathol 24: 108–119
Chiba H, Kaneto R, Agematu H, Shibamoto N. Yoshioka T, Nishida H, Okamoto R (1993) Mer-WF3010, a new member of the papulacandin family. Il. Structure determination. J Antibiot 46: 356–358
Clemons KV, Stevens DA (2000) Efficacies of sordarin derivatives GM193663, GM211676, and GM237354 in a murine model of systemic eoccidioidomycosis. Antimicrob Agents Chemother 44: 1874–1877
Conolly JD. Hill RA, Ngadjui BT (1994a) Triterpenoids. Nat Product Rep 11: 91–117
Conolly JD, Hill RA, Ngadjui BT (1994b) Triterpenoids. Nat Product Rep 11: 467–492
Cooper A, Hodgin DC (1968) The crystal structure and absolute configuration of fusidic acid methyl ester 3p-brombenzoate. Tetrahedron 24: 909–922
Coval SJ, Puar MS, Phife DW, Teraciano JS, Patel M (1995) SCH57404 an antifungal agent possessing the rare sordaricin skeleton and a tricyclic sugar moiety. J Antibiot 48: 1171–1172
Current WL, Tang J, Boylan C, Watson P, Zeckner D, Turner W, Rodriguez M, Dixon C, Ma D, Radding JA (1995) Glucan biosynthesis as a target for antifungals: the echinocandin class of antifungals. In: Dixon GK, Copping LG, Hollomon DW (eds) Antifungal agents, discovery and mode of action. Bios Scientific Publishers, Oxford, pp 143–160
Curry PT, Reed RN. Martino RM, Kitchin RM (1984) Induction of sister chromatid exchanges in vivo by the mycotoxins sterigmatocystin and griseofulvin. Mutat Res 137: 111–115
Czworkowski J, Wang J. Steitz TA, Moore PB (1994) The crystal structure of elongation factor G complcxed with GDP, at 2.7A resolution. EMBO J 13: 3661–3668
Daferner M, Anke T, Hellwig V, Steglich W. Sterner O (1998) Strobilurin M, tetrachloropyrocatechol and tetrachloropyrocatechol methyl ether: new antibiotics from a Mycena species. J Antibiot 51: 816–822
Daferner M, Mensch S, Anke T, Sterner 0 (1999) Hypoxysordarin, a new sordarin derivative from Hypoxylon croceum. Z Naturforsch 54c: 474–480
Daubcn WG, Kessel CR, Kishi Met al (1982) A formal total synthesis of fusidic acid. J Am Chem Soc 104: 303–305
Debono M, Gordee RS (1994) Antibiotics that inhibit fungal cell wall development. Annu Rev Mocrobiol 48: 471–497
Dominguez JM, Gomez-Lorenzo MG, Martin JJ (1999) Sordarin inhibits fungal protein synthesis by blocking translocation differently to fusidic acid. J Biol Chem 274: 22423–22427
Drews J, Georgopoulos A, Laber G, Schlitze E. Unger J (1975) Antimicrobial activities of 81.723 hfu, a new pleuromutilin derivative. Antimicrob. Agents Chemother 7: 507–516
Egger H, Reinshagen H (1976a) New pleuromutilin derivatives with enhanced antimicrobial activity. I. Synthesis. J Antibiot 29: 915–922
Egger H, Reinshagen H (1976b) New pleuromutilin derivatives with enhanced antimicrobial activity. II. Structure-activity correlations. J Antibiot 29: 923–927
Engler M, Anke T, Klostermeyer D, Steglich W (1995) Hydroxystrobilurin A, a new antifungal E-ß-methoxyacrylate from a Pterula species. J Antibiot 48: 884–885
Engler M. Anke T, Sterner 0 (1998) Production of antibiotics by Collybia nivalis, Omphalotus oleariu,s, a Favolaschia and a Pterula species on natural substrates. Z Naturforsch 53c: 318–324
Florey HW, Chain E, Heattley NG, Jennings MA, Sanders AG, Abraham EP, Florey ME (1949) Antibiotics. Oxford Univ Press, London
Fredenhagen A, Hug P, Peter HH (1990b) Strobilurins F, G and H. three new antifungal metabolites from Bolinea lutea: II. Structure determination - fungicide strobilurin-E -G and -H production. J Antibiot 43: 661–667
Fredenhagen A, Kuhn A, Peter HH, Cuomo V, Giulano U (1990a) Strobilurins F, G and H, three new antifungal metabolites from Bolinea lutea: 1. Fermentation, isolation and biological activity - strobilurin-F, -G and -H, cytostatic antibiotics with fungicide activity. J Antibiot 43: 655–660
Fromtling RA, Abruzzo GK (1989) L-671,329, a new anti-fungal agent. III. In vitro activity, toxicity and efficacy in comparison to aculeacin. J Antibiot 42: 174–178
Fujimura M, Kamakura T, Inoue H, Inoue S. Yamaguchi I (1992) Sensitivity of Neurospora crassa to benzimidazoles and N-phenylcarbamates: effect of amino acid substitutions at position 198 in beta-tubulin. Pestic Biochem Physiol 44: 165–173
Gams W (1971) Cephalosporium-artige Schimmelpilze (Hyphomycetes). Fischer-Verlag, Stuttgart
Gerth K, Irschik H, Reichenbach H, Trowitzsch W (1980) Myxothiazol, an antibiotic from Myxococcus fulvus (Myxobacterales). I. Cultivation, isolation, physicochemical and biological properties. J Antibiot 33: 1474–1479
Godtfredsen WO, Vengedal S (1962) The structure of fusidic acid. Tetrahedron 18: 1029–1048
Godtfredsen WO, Jahnsen S, Lorck H et al. (1962) Fusidic acid. A new antibiotic. Nature 193, 987
Godtfredsen WO, Lorck H. Jahnsen S (1964) Canadian Patent no 930, 786
Godfredsen WO, von Daehne W, Vangedal S, Arigoni D et al (1965) The stereochemistry of fusidic acid. Tetrahedron 21: 3505–3530
Godfredsen WO, Rastrup-Andersen N, Vangedal S, Ollis WD (1979) Metabolites of Fusidium coccineum. Tetrahedron 35: 2419–2431
Gomez-Lorenzo MG, Garcia-Bustos JF (1998) Ribosomal P-protein stalk function is targeted by sordarin. J Biol Chem 273: 25041–25044
Gomez-Lorenzo MG, Spahn CM, Agrawal RK, Grassucci RA, Penczek P, Chakraburtty, K, Ballesta JP, Lavandera JL, Garcia-Bustos JF, Frank J (2000) Three-dimensional cryo-electron microscopy localization of EF2 in the Saccharomyces cerevisiae 80S ribosome at 17.5 A resolution. EMBO J 19: 2710–2718
Graybill JR, Najvar L, Fothergill A, Bocanegra R, de las Heras FG (1999) Activities of sordarins in murine histoplasmosis. Antimicrob Agents Chemother 43: 17162–1718
Grove FK (1964) Griseofulvin and some analogues. In: Zechmeister L (ed) Progress in the chemistry of organic natural products, vol 22. Springer, Vienna New York, pp 201–264
Grove JF’, McGowan JC (1947) Identitiy of griseofulvin and “curling factor”. Nature 160: 574
Grove JF, MacMillian J, Mulholland TPC, Rogers MAT (1952) Griseofulvin, part IV: structure. J Chem Soc (Lond) 3977
Gupta RS (1984) Griseofulvin resistance mutation of Chinese hamster ovary cells that affect the apparent molecular weight of a 200,000-dalton protein. Mol Cell Biol 4: 1761–1768
Haller B, Loeffler W (1969) Stoffwechselprodukte von Mikroorganismen. 71. Mitteilung. Fusidinsäure aus Dermatophyten and anderen Pilzen. Arch Mikrobiol 65: 181–194
Hauser D, Sigg HP (1971) Isolierung and Abbau von Sordarin. Helv Chim Acta 54: 1187–1190
Hawser S, Borgonovi M, Markus A, Isert D (1999) Mulundocandin, an echinocandin-like lipopeptide antifungal agent: biological activities in vitro. J Antibiot 52: 305–310
Hellwig V, Dasenbrock J, Klostermeyer D, Kroiß S, Sindlinger T, Spiteller P, Steffan B, Steglich W, EnglerLohr M, Semar S, Anke T (1999) New benzodioxepin type strobilurins from basidiomycetes. Structural revision and determination of the absolute configuration of strobilurin D and related ß-methoxyacylate antibiotics. Tetrahedron 55: 10101–10118
Herbert RB (1989) The biosynthesis of secondary metabolites. Chapman and Hall, London
Herreros E, Martinez CM, Almela MJ, Marriott MS, De Las Heras FG, Gargallo-Viola D (1998) Sordarins: in vitro activities of new antifungal derivatives against pathogenic yeasts, Pneumocystis carinii, and filamentous fungi. Antimicrob Agents Chemother 42: 2863–2869
Hervey AH (1947) A survey of 500 basidiomycetes for antibacterial activity. Bull Torrey Bot Club 74: 476–503
Hikino H, Asada Y; Arihara S et al (1972) Fungal metabolites.[1. Fusidic acid, a steroidal antibiotic from Isaria kogane. Chem Pharm Bull 20: 1067–1069
Högenauer G (1979) Tiamulin and pleuromutilin. In: Hahn FE (ed) Antibiotics, vol 1. Springer, Berlin Heidelberg New York, pp 340–360
Huber FM (1975) Griseofulvin. In: Corcoran JW, Hahn FE (eds) Antibiotics, vol 3, pp 606–613
Iwamoto T, Fujie A, Sakamoto K, Tsurumi Y, Shigematsu N, Yamashita M, Hashimoto S, Okuhara M, Kohsaka M (1994a) WF11899 A, B and C, novel antifungal lipopeptides. I. Fermentation, isolation and physicochemical properties. J Antibiot 47: 1084–1091
Iwamoto T, Fujie A, Nitta K, Hashimoto S, Okuhara M, Kohsaka M (1994b) WF11899 A, B and C, novel antifungal lipopeptides. II. Biological properties. J Antibiot 47: 1092–1097
Iwasaki S. Sair MI, Igarashi H, Okuda S (1970) Revised structure of helvolic acid. Chem Commun 1119–1120
Johanson U, Hughes D (1994) Fusidic acid-resistant mutations define three regions in elongation factor G of Salmonella typhimurium. Gene 143: 55–59
Justice CJ, Hsu M, Tse B, Ku T, Baljovec J, Schmatz D. Nielsen J (1998) Elongation factor 2 as a novel target for selective inhibition of fungal protein synthesis. J Biol Chem 273: 3148–3151
Kaise H, Munaka K, Sassa T (1972) Structure of viridominic acid C, a new steroidal metabolite of a fungus having chlorosis-inducing activity. Tetrahedron Lett 3: 199–202
Kaneto R, Chiba H, Agematu H, Shibamoto N, Yoshioka T, Nishida H, Okamoto R (1993) Mer-WF3010, a new member of the papulacandin family. 1. Fermentation, isolation and characterization. J Antibiot 46: 247–250
Kavanagh F, Hervey A, Robbins WJ (1951) Antibiotic substances from basidiomycetes. VIII, Pleurotus mutilus (Fr.) Sacc. and Pleurotus passeckerianus Pilat. Proc Natl Acad Sci USA 37: 570–574
Keller-Juslen C, Kuhn M, Loosli HR, Petcher TJ, Weber HP, von Wartburg A (1976) Struktur des CyclopeptidAntibiotikums SL7801 (= Echinocandin B). Tetrahedron Lett 17: 4147–4150
Kennedy TC, Webb G, Cannell RJP, Kinsman OS, Middleton RF, Sidebottom PJ, Taylor NL, Dawson MJ, Buss AD (1998) Novel inhibitors of fungal protein synthesis produced by a strain of Graphium putredinis. Isolation, characterisation and biological properties. J Antibiot 51: 1012–1018
Kerridge D (1986) Mode of action of clinically important antifungal drugs. Adv Microbial Physiol 27: 1–72
Kingston DG, Chen PN, Vercellotti JR (1976) Metabolites of Aspergillus versicolor:6,8-di-O-methylniduruf n, griseofulvin, dechlorogriseofulvin, and 3,8-dihydroxy6-methoxy-l-methylxanthone. Phytochemistry 15: 1037–1039
Kinsman OS, Chalk PA, Jackson HC. Middleton RF, Shuttleworth A, Rudd BAM, Jones CA, Noble HM, Wildman HG, Dawson MJ, Stylli C, Sidebottom PJ, Lamont B, Lynn S, Hayes MV (1998) Isolation and characterisation of an antifungal antibiotic (GR135402) with protein synthesis inhibition. J Antibiot 51: 41–49
Knauseder F, Brandt E (1976) Pleuromutilins: fermentation, structure and biosynthesis. J Antibiot 29: 125–131
Ko B-S, Oritani T, Yamashita K (1990) Synthesis and biological activities of griseofulvin analogs. Agric Biol Chem 54: 2199–2204
Komori T, Itoh Y (1985) Chaetiacandin, a novel papulacandin. II. Structure determination. J Antibiot 38: 544–546
Komori T, Yamashita M, Tsurumi Y, Kohsaka M (1985) Chaetiacandin, a novel papulacandin. I. Fermentation, isolation and characterization. J Antibiot 38: 455459
Kraiczy P, Haase U, Gencic S Flindt S, Anke T, Brandt U, von Jagow G (1996) The molecular basis for the natural resistance of the cytochrome bc, complex from strobilurin-producing basidiomycetes to center Op inhibitors. Eur J Biochem 235: 54–63
Lane MP, Nakashima TT, Vederas JC (1982) Biosynthetic source of oxygens in griseofulvin. Spin-echo resolution of oxygen-18 isotope shifts in carbon-13 NMR spectroscopy. J Am Chem Soc 104: 913–915
Langholz E, Brynskov J, Bendtzen K et al (1992) Treatment of Crohn’s decease with fusidic acid: an antibiotic with immunosuppressive properties similar to cyclosporin. Aliment Pharmacol Ther 6: 495–502
Levin DH, Kyner D, Acs G (1973) Protein initiation in eukaryotes. Formation and function of a ternary complex composed of a partially purified ribosomal factor, methionyl transfer RNAf, and guanosine triphosphate. Proc Natl Acad Sci USA 70: 41–45
MacMillian J (1959) Griseofulvin, part XIV. Some alcoholic reactions and the absolute configuration of griseofulvin. J Chem Soc (Lond) 1823
Mizoguchi J, Saito T, Mizuno K, Hayano K (1977) On the mode of action of a new antifungal antibiotic, aculeacin A: inhibition of cell wall synthesis in Saccharomyces cerevisiae. J Antibiot 30: 308–313
Mizuno K, Yagi A, Satoi S, Takada M, Hayashi M (1977) Studies on aculeacin. I. Isolation and characterization of aculeacin A. J Antibiot 30: 297–302
Mukhopadhyay T, Roy K, Bhat RG, Sawant SN, Blumbach J, Ganguli BN, Fehlhaber HW (1992) Deoxymulundocandin — a new echnocandin type antifungal antibiotic. J Antibiot 45: 618–623
Musilek V, Cerna J, Sasek V, Semerzieva M, Vondracek M (1969) Antifungal antibiotic from the basidiomycete Oudemansiella mucida. I. Isolation and cultivation of a producing strain. Folia Microbiol 14: 377–388
Nicholas GM, Blunt JW, Cole All, Munro MHG (1997) Investigation of the New Zealand basidiomycete Favolaschia calocera: revision of the structures of 9methoxystrobilurins K and L, strobilurin D, and hydroxystrobilurin D. Tetrahedron Lett 38: 7465–7468
Nicot J (1968) Sur L’identité de l’organisme producteur de l’acide fusidique, antibiotique antistaphylococcique. CR Acad Sci 267: 290–292
Nierhaus KH, Wittman HG (1980) Ribosomal function and its inhibition by antibiotics in prokaryotes. Naturwissenschaften 67: 234–250
Ogita T, Hayashi A, Sato S, Furutani W, Sankyo KK (1987) Antibiotic zopfimarin. Japan Patent 62–40292
Oh K, Matsuoka H, Teraoka T, Sumita O. Takatori K, Kurata H (1993) Effects of antimycotics on the biosynthesis of cellular macromolecules in Aspergillus niger protoplasts. Mycopathologia 122: 135–141
Okada H, Kamiya S, Shiina Y, Suwa H, Nagashima M, Nakajima S, Shimokawa H, Sugiyama E. Kondo H, Kojiri K, Suda H (1998) BE-31405, a new antifungal antibiotic produced by Penicillium minioluteum. I. Description of producing organism, fermentation, isolation, physico-chemical and biological properties. J Antibiot 51: 1081–1086
Okada H, Kamiya S, Shiina Y, Suwa H, Nagashima M, Nakajima S. Shimokawa H2Okuda S, Sato T, Hattori T et al (1968) Isolation of 3b-hydroxy-4b-hydroxymethylfusida-17(20)[16,21-cis],24-diene. Tetrahedron Lett 9: 4769–4772
Oxford AE, Raistrick H, Simonart P (1939) Studies on the biochemistry of microorganisms. 60. Griseofulvin, a metabolic product of Penicillium griseofulvura Dierckx. Biochem J 33: 240–248
Oxley P (1966) Cephalosporin Pl and helvolic acid. Chem Commun 729–730
Perez P, Garcia-Atha f, Duran A (1983) Effect of papulacandin B on the cell wall and growth of Geotrichum lattis. J Gen Microbiol 129: 245–250
Perry MJ, Hendricks-Gittins A, Stacey LM et al. (1983) Fusidane antibiotics produced by dermatophytes. J Antibiot 36: 1659–1663
Petraitiene R, Petraitis V, Groll AH, Candelario M, Sein T, Bell A, Lyman CA, McMillian CL, Bacher J, Walsh TJ (1999) Antifungal activity of LY303366, a novel echinocandin B, in experimental disseminated candidiasis in rabbits. Antimicrob Agents Chemother 43: 2148–2155
Pfaller MA, Marco F, Messer SA, Jones RN (1998) In vitro activity of two echinocandin derivatives, I,Y303366 and MK-0991 (L-743,792), against clinical isolates of Aspergillus, Fusarium, Rhizopus, and other filamentous fungi. Diagn Microbiol Infect Dis 30: 25 1255
Pirrung MC, Brown WL, Rege S. Laughton P (1991) Total synthesis of (+)-griseofulvin. J Am Chem Soc 113: 8561–8562
Richter D, Lin L. Bodley JW (1971) Translocation. IX. Pattern of action of antibiotic translocation inhibitors in eukaryotic and prokaryotic systems. Arch Biochem Biophys 147: 186–191
Riedl K (1976) Studies on pleuromutilin and some of its derivatives. J Antibiot 29: 132–139
Roy K, Mukhopadhyay T, Reddy GCS, Desikan KR, Ganguli BN (1987) Mulundocandin — a new lipopeptide antibiotic. I. Taxonomy, fermentation, isolation, and characterization. J Antibiot 40: 275–280
SanMillian MJ, Vazquez D, Modolell J (1975) Interaction of fusidic acid with peptidyl-transfer-ribonucleic-acid ribosome complex. Eur J Biochem 57: 431–440
Satoi S, Yagi A, Asano K, Mizuno K, Watanabe T (1977) Studies on aculeacin. II. Isolation and characterization of aculeacins B, C, D,E, F and G. J Antibiot (Tokyo) 30 (4): 303–307
Sauter H, Steglich W, Anke T (1999) Strobilurine: Evolution einer neuen Wirkstoffklasse. Angew Chem 111:1416–1438, Int Ed 39: 1328–1349
Schmatz DM, Romancheck MA, Pittarelli LA, Schwartz RE, Fromtling RA, Nollstadt KH, Vanmiddlesworth FL,Wilson KE, Turner MJ (1990) Treatment of Pneumocystis carinii pneumonia with 1,3-beta-glucan synthesis inhibitors. Proc Natl Acad Sci USA 87: 5950–5954
Schmatz DM, Powles M, McFadden DC, Pittarelli LA, Liberator PA, Anderson JW (1991) Treatment and prevention of Pneumocystis carinii pneumonia and further elucidation of the P. carinii life cycle with 1,3beta-glucan synthesis inhibitor L-671,329. J Protozool 38: 151S - 153S
Schneider G, Anke H and Sterner 0 (1995), Xylarin, an antifungal Xylaria metabolite with an unusual tricyclic uronic acid moiety. Nat Prod Lett 7: 309–316
Scholer HJ, Polak A (1984) Resistance to systemic anti-fungal agents. In: Bryan LE (ed) Antimicrobial drug resistance, Chap 14, Academic Press, San Diego, pp 393–460
Schramm G (1980) Neue Antibiotika aus Höheren Pilzen (Basidiomyceten). PhD Thesis, Univ Bonn
Schramm G, Steglich W, Anke T, Oberwinkler F (1978) Antibiotika aus Basidiomyceten, III. Strobilurin A and B. antifungische Stoffwechselprodukte aus Strobilurus tenacellus. Chem Ber 111: 2779–2784
Schwalge B (1986) Strobilurin A als Modellverbindung für synthetische Analoga. PhD Thesis, Univ Bonn
Schwartz RE, Giacobbe RA, Bland JA, Monaghan RL (1989) L-671,329, a new antifungal agent. I. Fermentation and isolation. J Antibiot 42: 163–167
Selitrennikoff CP (1995) Antifungal drugs: (l,3)ß-glucan synthase inhibitors. Springer, Berlin Heidelberg New York
Simon B (1994) Antivirale and cytotoxische Wirkstoffe aus Basidiomyceten PhD Thesis, Univ Kaiserslautern
Sloboda RD, Van Blaricom G, Creasy WA, Rosenbaum JL, Malawista SE (1982) Griseofulvin: association with tubulin and inhibition of in vitro microtubule assembly. Biochem Biophys Res Commun 105: 882888
Spahn, CMT, Prescott CD (1996) Throwing a spanner in the works: antibiotics and the translation apparatus. J Mol Med 74: 423–439
Stewart KR (1986) A method for generating protoplasts from Clitopilus pinsitus. J Antibiot 39: 1486–1487
Stringer S, Stringer J, Blase M, Walzer P, Cushion M (1989) Pneumocystis carinii sequence from ribosomal RNA implies a close relationship to fungi. Exp Parasitol 68: 450–461
Taft CS, Zugel M, Selitrennikoff CP (1991) In vitro inhibition of stable 1,3-beta-D-glucan synthase activity from Neurospora crassa. Enzym Inhib 5: 41–49
Taha KF, Chu CK (1991) Isolation of the antibiotic griseofulvin from the fungus Nematospora coryli. J Drug Res 20: 137–141
Tanaka N (1975) Fusidic acid. In: Cocoran JW, Hahn FE (eds) Antibiotics, vol 3. Springer, Berlin Heidelberg New York, pp 436–447
Tomozane H, Takeuchi Y, Chosi T et al (1990) Syntheses and antifungal activities of dl-griseofulvin and its congeners. Chem Pharm Bull 38: 925–929
Traber R, Keller-Juslen C, Loosli HR, Kuhn M, von Wartburg A (1979) Cyclopeptid-Antibiotika aus Aspergillus-Arten. Struktur der Echinocandine C and D. Heiv Chim Acta 62: 1252–1259
Traxler P, Gruner J, Auden JAL (1977a) 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 Antibiot 30: 289–296
Traxler P, Fritz H, Richter WJ (19776) Zur Struktur von Papulacandin B, einem neuen antifungischen Antibiotikum. He1v Chim Acta 60: 578–584
Traxler P, Fritz H, Fuhrer H, Richter WJ (1980) Papulacandins, a new family of antibiotics with antifungal activity. Structures of papulacandins A, B, C and D. J Antibiot 33: 967–978
Trowitzsch W, Reifenstahl G, Wray V, Gerth K (1980) Myxothiazol, an antibiotic from Myxococcus fulvus (Myxobacterales). II. Structure elucidation. J Antibiot 33: 1480–1490
Tubaki K (1954) Studies on Japanese hyphomycetes. I. Coprophilous group. Nagaoa Mycol J Nagao Inst 4: 7–8
Vandcrhaege H, van Dijk P, de Somer P (1965) Identitiy of ramycin with fusidic acid. Nature 205: 710–711
van Dijk PJ, de Somer P (1958) Ramycin. A new antibiotic. J Gen Mirobiol 18: 377–381
VanMiddlesworth F, Omstead MN, Schmatz D, Bartizal K, Fromtling R, Bills G, Nollstadt K, Honeycutt S, Zweerink M, Garrity G, Wilson K (1991) L-687,781, a new member of the papulacandin family of beta1,3-D-glucan synthesis inhibitors. I. Fermentation, isolation, and biological activity. J Antibiot 44: 4551
Verbist L (1990) The antimicrobial activity of fusidic acid. J Antimicrob Chemother 25 (Suppl B): 1–5
Von Jagow G, Gribble GW,Trumpower BL (1986) Mucidin and strobilurin A are identical and inhibit electron transfer in the cytochrome bct complex of the mitochondrial respiratory chain at the same site as myxothiazol. Biochemistry 25: 775–780
von Daehne W, Godfredsen WO, Rasmussen PR (1979) Structure-activity relationship in fusidic acid-type antibiotics. Adv Appl Microbiol 25: 95–146
von Daehne W, Jahnsen S, Kirk I et al (1984) Fusidic acid: properties, biosynthesis, and fermenation. Drugs Pharm Sci 22: 427–449
Vondracek M, Capkova J, Slechta J, Benda A, Musilek V, Cudlin J (1970) Czech Pat 136495 (filed 26.9.1969/ obtained 15.5. 1970 ). Isolierung eines neuen antifungischen Antibiotikums. Bezug: Czech 136492
Vondracek M, Vondrackova J, Sedmera P, Musilek V (1983) Another antibiotic from the basidiomycete Oudemansiella mucida. Coll Czech Chem Commun 48: 1508–1512
Weber W, Anke T, Steffan B, Steglich W (1990a) Antibiotics from basidiomycetes. XXXII. Strobilurin E: a new cytostatic and antifungal E-ß-methoxyacrylate antibiotic from Crepidotusfulvotontentosus Peck. J Antibiot 43: 207–212
Weber W, Anke T, Bross M, Steglich W (1990b) Antibiotics from basidiomycetes, vol XXXIV. In: Strobilurin D, Strobilurin F (eds) Two new cytostatic and antifungal (E)-ß-methoxyacrylate antibiotics from Cyphellopsis anomala ( Pers ex Fr)Sing. Planta Med 56: 446–450
Wichmann CF, Liesch JM, Schwartz RE (1989) L-671,329, a new antifungal agent. II. Structure determination. J Antibiot 42: 168–173
Wilson BJ (1971) Miscellaneous Penicillium toxins. In: Ciegler A, Kadis S, Ajl SJ (eds) Microbial toxins, vol 6. Fungal toxins. Academic Press, San Diego, pp 489–506
Wolf G (1997) Traditional fermented food. In: Anke T (ed) Fungal biotechnology, Chapman and Hall. London, pp 14–25
Wood KA, Kau DA, Wrigley SK, Beneyto R, Renno DV, Ainsworth AM, Penn J, Hill D, Killacky J, Depledge P (1996) Novel ß-methoxyacrylates of the 9-methoxystrobilurin and oudemansin classes produced by the basidiomyccte Favolaschia pustulosa. J Nat Prod 59: 646–649
Xia D, Yu CA, Kim H, Xia JZ, Kachurin AM, Zhang L, Yu L, Deisenhofer J (1997) Crystal structure of the cytochrome bel complex from bovine heart mitochondria. Science 277: 60–66
Zadrazil F, Kamra DN (1997) Edible mushrooms. In: Anke T (ed) Fungal biotechnology. Chapman and Hall, London, pp 14–25
Zambias RA, Hammond ML, Heck J V, Bartizal K, Trainor C, Abruzzo G, Schmatz DM, Nollstadt KM (1992) Preparation and structure-activity relationships of simplified analogues of the antifungal agent cilofungin: a total synthesis approach. J Med Chem 35: 2843–2855
Zapf S, Anke T, Dasenbrock H, Steglich W (1993) Anti-fungal metabolites from Agaricus sp. 89139. Bioengineering 1: 92
Zapf S, Werle A, Anke T, Klostermeyer D. Steffan B and Steglich W (1995) 9-MethoxystrobilurineBindeglieder zwischen Strobilurinen und Oudemansinen. Angew Chem 107: 255–257
Zhanel GG, Karlowsky JA, Harding GA, Balko TV, Zelenitsky SA. Friesen M, Kabani A, Turik M, Hoban DJ (1997) In vitro activity of a new semisynthetic echinocandin, LY-303366, against systemic isolates of Candida species, Cryptococcus neoformans, Blastomyces dermatitidis,and Aspergillus species. Antimicrob Agents Chemother 41:863–865
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2002 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Anke, T., Erkel, G. (2002). Non-β-Lactam Antibiotics. In: Osiewacz, H.D. (eds) Industrial Applications. The Mycota, vol 10. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-10378-4_5
Download citation
DOI: https://doi.org/10.1007/978-3-662-10378-4_5
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-07481-3
Online ISBN: 978-3-662-10378-4
eBook Packages: Springer Book Archive