[en] A strain of Acremonium luzulae (Fuckel) W. Gams was selected in screening new microorganisms for biological control of fruit postharvest diseases, especially gray and blue mold diseases on apples and strawberries. This strain manifests a very strong activity against a large number of phytopathogenic fungi. In this work, the product responsible for this antifungal activity was isolated from modified Sabouraud dextrose broth cultures of A. luzulae. It was purified to homogeneity by reverse-phase column chromatography. On the basis of UV, infrared, and 1H and 13C nuclear magnetic resonance spectra, mass spectral analysis, and the amino acid composition of the acid hydrolysates, the antibiotic was determined to be cyclosporin C. Cyclosporin C showed a broad-spectrum activity against filamentous phytopathogenic fungi but no activity against bacteria or yeasts. Its antifungal activity is only fungistatic. In contrast to Tolypocladium inflatum, another cyclosporin-producing strain, A. luzulae, did not produce additional cyclosporins. This was confirmed by in vivo-directed biosynthesis.
Disciplines :
Microbiology
Author, co-author :
Moussaif, M.
Jacques, Philippe ; Université de Liège > Agronomie, Bio-ingénierie et Chimie (AgroBioChem) > Bio-industries
Schaarwachter, P.
Budzikiewicz, H.
Thonart, Philippe ; Université de Liège - ULiège > Gembloux Agro-Bio Tech - Biochimie et microbiologie industrielles
Language :
English
Title :
Cyclosporin C Is the Main Antifungal Compound Produced by Acremonium Luzulae
Publication date :
May 1997
Journal title :
Applied and Environmental Microbiology
ISSN :
0099-2240
eISSN :
1098-5336
Publisher :
American Society for Microbiology, Washington, United States - District of Columbia
scite shows how a scientific paper has been cited by providing the context of the citation, a classification describing whether it supports, mentions, or contrasts the cited claim, and a label indicating in which section the citation was made.
Bibliography
Aarnio, T. H., and S. N. Agathos. 1989. Production of extracellular enzymes and cyclosporin by Tolypocladium inflatum and morphologically related fungi. Biotechnol. Lett. 11:759-764.
Bach, J. F. 1989. Cyclosporine in autoimmune diseases. Transplant. Proc. 21(Suppl. 1):97-101.
Bellavita, N. C., P. Ceccherelli, and M. Raffaele. 1970. Structure du virescenoside C, nouveau métabolite de Oospora virescens (Link) Wallr. Eur. J. Biochem. 15:356-359.
Bellavita, N. C., P. Ceccherelli, R. Fringuelli, and M. Ribaldi. 1975. Ascochlorin: a terpenoid metabolite from Acremonium luzulae. Phytochemistry 14:807.
Berdy, J., A. Aszalos, M. Bostian, and K. L. McNitt. 1981. Small (microbial) terpenes, p. 93-134. In J. Berdy, A. Aszalos, M. Bostian, and K. L. McNitt (ed.), Handbook of antibiotic compounds, vol. VI. CRC Press, Inc. Boca Raton, Fla.
Billich, A., and R. Zocher. 1987. Enzymatic synthesis of cyclosporin A. J. Biol. Chem. 262:17258-17259.
Borel, J. F. 1989. Pharmacology of cyclosporine (Sandimmun). IV. Pharmacological properties in vivo. Pharmacol. Rev. 41:259-371.
Borel, J. F. 1986. Cyclosporin and its future. Prog. Allergy 38:9-18.
Borel, J. F., C. Feurer, H. U. Gubler, and H. Stähelin. 1976. Biological effects of cyclosporin A: a new antilymphocytic agent. Agents Actions 6:468-475.
Bram, R. J., D. T. Hung, P. K. Martin, S. L. Schreiber, and G. R. Crabtree. 1993. Identification of the immunophilins capable of mediating inhibition of signal transduction by cyclosporin A and FK506: roles of calcineurin binding and cellular location. Mol. Cell. Biol. 13:4760-4769.
Dickinson, C. H. 1968. Gliomastix Guéguen. Mycol. Pap. 115:1-27.
Dreyfuss, M. M. 1986. Neue Erkenntnisse aus einem pharmakologischen Pilz-screening. Sydowia 39:22-36.
Dreyfuss, M., E. Härri, H. Hofmann, H. Kobel, W. Pache, and H. Tscherter. 1976. Cyclosporin A and C. New metabolites from Trichoderma polysporum (Link ex Pers.) Rifai. Eur. J. Appl. Microbiol. 3:125-133.
Fischer, G., B. Wittmann-Liebold, K. Lang, T. Kiethaber, and F. X. Schmid. 1989. Cyclophilin and peptidyl-prolyl cis-trans isomerase are probably identical proteins. Nature 337:476-478.
Gams, W. 1971. Tolypocladium. Eine Hyphomycetengattung mit geschwollenen Phialiden. Persoonia 6:185-191.
Gurusiddaiah, S., L. D. Winward, D. Burger, and S. O. Graham. 1979. Pantomycin: a new antimicrobial antibiotic. Mycologia 71:103-118.
Heitman, J., N. R. Mowa, and M. N. Hall. 1992. Proline isomerases at the crossroads of protein folding, signal transduction, and immunosuppression. New Biol. 4:448-460.
Jacques, P., M. Ongena, I. Gwose, D. Seinsche, H. Schröder, P. Delfosse, P. Thonart, K. Taraz, and H. Budzikiewicz. 1995. Structure and characterization of isopyoverdin from Pseudomonas putida BTP1 and its relation to the biogenetic pathway leading to pyoverdins. Z. Naturforsch. Teil C 50:622-629.
Kessler, H., H. R. Loosli, and H. Oschkinat. 1985. Peptides conformations. Assignement of the 1H, 13C, and 15N-NMR spectra of cyclosporin A in CDCl3 and C6D6 by a combination of homo- and heteronuclear two dimensional techniques. Helv. Chim. Ada 68:661-681.
Kleinkauf, H., and H. Von Döhren. 1990. Nonribosomal biosynthesis of peptide antibiotics. Eur. J. Biochem. 192:1-15.
Kobel, H., and R. Traber. 1982. Directed biosynthesis of cyclosporins. Eur. J. Appl. Microbiol. Biotechnol. 14:237-240.
Lawen, A., and R. Zocher. 1990. Cyclosporin synthetase. The most complex peptide synthesizing multienzyme polypeptide so far described. J. Biol. Chem. 265:11355-11360.
Lawen, A., R. Traber, D. Geyl, R. Zocher, and H. Kleinkauf. 1989. Cell-free biosynthesis of new cyclosporins. J. Antibiot. 40:1283-1289.
Maiorca, R., F. Scolari, F, Savoldi, S. Sandrini, P. Scaini, and L. Cristinelli. 1989. Cyclosporin and renal injury. Adv. Exp. Med. Biol. 252:273-284.
Myers, B. D. 1986. Cyclosporine nephrotoxicity. Kidney Int. 30:964-974.
Nakajima, H., T. Hamasaki, K. Tanaka, Y. Kimura, S.-I. Udagawa, and Y. Horie. 1988. Production of cyclosporin by fungi belonging to the genus Neocosmospora. Agric. Biol. Chem. 53:2291-2292.
Onions, A. H. S., and B. L. Brady. 1987. Taxonomy of Penicillium and Acremonium. Biotechnol. Handb. 1:1-36.
Polonsky, J., Z. Baskevitch, N. C. Bellavita, P. Ceccherelli, B. L. Buckwalter, and E. Wenkert. 1972. Carbon-13-nuclear magnetic resonance spectroscopy of naturally occurring substances. Biosynthesis of virescenosides. J. Am. Chem. Soc. 94:4369-4370.
Razafindralambo, H., M. Paquot, C. Hbid, P. Jacques, J. Destain, and P. Thonart. 1993. Purification of antifungal lipopeptides by reversed-phase high-performance liquid chromatography. J. Chromatogr. 639:81-85.
Sadeg, N., C. Pham-huy, P. Rucay, S. Righenzi, O. Halle-Pannenko, J. R. Claude, H. Bismuth, and H-T. Duc. 1993. In vitro and in vivo comparative studies on immunosuppressive properties of cyclosporines A, C, D and metabolites M1, M17 and M21. Immunopharmacol. Immunotoxicol. 15:163-177.
Sadeg, N., C. Pham-huy, C. Martin, J. M. Warnet, and J. R. Claude. 1994. In vitro comparative study on nephrotoxicity of cyclosporine A, its metabolites M1, M17, M21, and its analogues cyclosporines C and D in suspensions of Rabbit renal cortical cells. Drug Chem. Toxicol. 17:93-111.
Sawai, K., T. Okuno, Y. Terada, Y. Harada, K. Sawamura, H. Sasaki, and S. Takau. 1981. Isolation and properties of two antifungal substances from Fusarium solani. Agric. Biol. Chem. 45:1223-1228.
Schmidt, B., D. Riesner, A. Lawen, and H. Kleinkauf. 1992. Cyclosporin synthetase is a 1.4 MDa multienzyme polypeptide. Re-evaluation of the molecular mass of various peptide synthetases. FEBS Lett. 307:355-360.
Takahashi, N., T. Hayano, and M. Suzuki. 1989. Peptidyl-prolyl cis trans isomerase is the cyclosporin A binding protein cyclophilin. Nature 337:473-475.
Traber, R., H. Hofmann, and H. Kobel. 1989. Cyclosporins. New analogues by precursor directed biosynthesis. J. Antibiot. 40:591-597.
Traber, R., H. Hofmann, H. R. Loosli, M. Ponelle, and A. Von Wartburg. 1987. Neue Cyclosporinc aus Tolypocladium inflatum. Die Cyclosporine K-Z. Helv. Chim. Acta 70:13-36.
Traber, R., M. Kuhn, A. Ruegger, H. Lichti, H. R. Loosli, and A. Von Wartburg. 1977. Die Struktur von Cyclosporin C. Helv. Chim. Acta 60:1247-1255.
Von Arx, E., M. Faupel, and M. Brugger. 1976. Das 4-4′-tetremethyl diamino-diphenylmethan Reagenz (TDM): eine Modifikation der Chloro-o-tolidin-Farbereaktion für die dünnschicht-Chromatographie. J. Chromatogr. 120:224-228.
Von Arx, J. A. 1986. Tolypocladium, a synonym of Beauveria. Mycotaxon 25:153-158.
Von Wartburg, A., and R. Traber. 1986. Chemistry of the natural cyclosporin metabolites. Prog. Allergy 38:28-45.
Weber, G., K. Schörgendorfer, E. Schneider-Scherzer, and E. Leitner. 1994. The peptide synthetase catalyzing cyclosporine produection in Tolypocladium niveum is encoded by a giant 45,8-kilobase open reading frame. Curr. Genet. 26:120-125.
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