New sequences and new fungal producers of peptaibol antibiotics antiamoebins

Abstract

Mixtures of the microheterogeneous 16-mer peptaibol antibiotics called antiamoebins (AAM) have been isolated from the culture broths of strains of the filamentous fungi Stilbella erythrocephala ATCC 28144, Stilbella fimetaria CBS 548.84 and Gliocladium catenulatum CBS 511.66. Sequences were determined using on-line HPLC together with positive- and negative-ion electrospray ionization mass spectrometry. Some characteristic features are recognized in the mass spectrometric fragmentation pattern of AAM. From a sample originally used for sequencing AAM (from Hindustan Antibiotics, Ltd., Pimpri, Poona-411018, India), and a sample of AAM commercially available (from Sigma Chemicals, St. Louis, MO, USA) HPLC elution profiles and sequences were assigned. Further, sequences of AAM previously isolated from Emericellopsis synnematicola CBS 176.60 and Emericellopsis salmosynnemata CBS 382.62 were determined. The peptide designated AAM I was the most abundant in all isolates and its structure could be confirmed. AAM II was detectable as a minor component (1.9%) only in the original sample of AAM, but not in the other isolates. The structures of AAM III, IV and V, which had previously been partly assigned, were definitely established, and the new sequences AAM VI-XVI were elucidated. AAM showing Phe1/Leu1 or Phe1/Val1 exchange, respectively, are produced in amounts only by S. erythrocephala. Sequences, HPLC elution profiles ('fingerprints') and relative amounts of peptides of all isolates were correlated. Copyright (C) 2000 European Peptide Society and John Wiley and Sons, Ltd.