Abstract
HPLC analysis of crude dichloromethane extracts of shaken liquid cultures of the hyphomycetous fungusTolypocladium geodes Gams revealed the presence of efrapeptins. These peptides, which have mitochondrial ATPase inhibitory activity as well as antifungal and insecticidal properties, are previously known only from the congeneric species,T. niveum Rostrup. The identity of efrapeptins was confirmed by fast atom bombardment mass spectrometry and by amino acid analysis. HPLC analyses of efrapeptins extracted from single isolates of bothT. geodes andT. niveum indicated that both species produced the same efrapeptins but the profile of relative abundance of the compounds produced was diagnostic for the isolates examined. Efrapeptin F was the major component of the mixture fromT. geodes with the order of abundance of the six efrapeptins detected being F >G>D∼E>H>C. Efrapeptin D was the major component fromT. niveum with the order of abundance of the six efrapeptins detected being D >E>F>C∼G>H. Efrapeptin F diifers from efrapeptin D by a single amino acid residue, efrapeptin F having an alanine where efrapeptin D has a glycine. Addition of alanine to the culture medium increased the relative abundance of efrapeptin F in the profile of both species. Conversely, addition of glycine increased the relative abundance of efrapeptin D in the profile of both species.
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References
Bisset, J. 1983. Notes onTolypocladium and related genera.Can. J. Bot. 61:1311–1329.
Dreyfuss, M., Harri, E., Hofmann, H., Kobel, J., Pache, W., andTscherter, H. 1976. Cyclosporin A and C.Eur. J. Appl. Microbiol. 3:125–133.
Frisvad, J.C. 1986. Taxonomic approaches to mycotoxin identification (taxonomic indication of mycotoxin content in foods), pp. 415–457,in R.J. Cole (ed.). Modern Methods in the Analysis and Structural Elucidation of Mycotoxins. Academic Press, Orlando.
Gupta, S., Krasnoff, S.B., Roberts, D.W., Renwick, J.A.A., Brinen, L., andClardy, J. 1991a. Structures of the efrapeptins-potent inhibitors of mitochondrial ATPase from the fungusTolypocladium niveum.J. Am. Chem. Soc. 113:707–709.
Gupta, S.,Krasnoff, S.B.,Roberts, D.W.,Renwick, J.A.A.,Brinen, L., andClardy, J. 1991b. Structure of efrapeptins from the fungusTolypocladium niveum: Peptide inhibitors of mitochondrial ATPaseJ. Org. Chem. Submitted.
Jackson, C.G., Linnet, P.E., Beechey, R.B., andHenderson, P.J.F. 1979. Purification and preliminary structural analysis of the efrapeptins, a group of antibiotics that inhibit the mito-chondrial adenosine triphosphatase.Biochem. Soc. Trans. 7:224–226.
Katz, E. 1974. Controlled biosynthesis of actinomycins.Cancer Chemother. Rep. 58:83–91.
Katz, E., andDemain, A.L. 1977. The peptide antibiotics ofBacillus: Chemistry, biogenesis, and possible functions.Bacteriol. Rev. 41:449–474.
Kobel, H., andTraber, R. 1982. Directed biosynthesis of cyclosporins.Eur. J. Appl. Microbiol Biotechnol. 14:237–240.
Krasnoff, S.B., Gupta, S., St. Leger, R.J., Renwick, J.A.A., andRoberts, D.W. 1991. Anti-fungal and insecticidal properties of the efrapeptins: Metabolites of the fungusTolypocladium niveum.J. Invert. Pathol. 58:180–188.
Krishna, K., Sukumar, M., andBalaram, P. 1990. Structural chemistry and membrane modifying activity of the fungal polypeptides zervamicins, antiamoebins and efrapeptins.Pure Appl. Chem. 62:1417–1420.
Lundgren, B., Baath, E., andSoderstrom, B.E. 1978. Antagonistic effects ofTolypocladium species.Trans. Br. Mycol. Soc. 70:305–307.
Matha, V., Weiser, J., andRepova, A. 1988. Entomocidal activity of metabolites from strains of fungi of the genusTolypocladium (Deuteromycetes).Microbios Lett. 38:71–73.
Moss, M.O. 1982. The biosynthesis ofFusarium mycotoxins, pp. 195–213,in M.O. Moss and J.E. Smith (eds.). The Applied Mycology ofFusarium. Cambridge University Press, Cambridge.
Stack, M.E., andMislivec, P.B. 1978. Production of xanthomegnin and viomellein by isolates ofAspergillus ochraceus, Penicillium cyclopium, andPenicillium viridicatum.Appl. Environ. Microbiol. 36:552–554.
Weiser, J., andMatha, V. 1988. The insecticidal activity of cyclosporines on mosquito larvae.J. Invert. Pathol. 51:92–93.
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Krasnoff, S.B., Gupta, S. Identification and directed biosynthesis of efrapeptins in the fungusTolypocladium geodes gams (Deuteromycotina: Hyphomycetes). J Chem Ecol 17, 1953–1962 (1991). https://doi.org/10.1007/BF00992580
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DOI: https://doi.org/10.1007/BF00992580