ABSTRACT
The pentacyclic triterpenoids serjanic acid and phytolaccagenic acid as well as a new glycoside, 3- O-beta- D-glucopyranosylphytolaccagenic acid have been isolated from the stem of DIPLOCLISIA GLAUCESCENS (Bl.) Diels (Menispermaceae). New spectroscopic data are furnished for serjanic acid and phytolaccagenic acid.
ABSTRACT
Paracelsin, a hemolytic and membrane active polypeptide antibiotic of the peptaibol class which is excreted by the mold Trichoderma reesei, was obtained by a simplified and rapid isolation procedure utilizing hydrophobic adsorber resins. Investigation by 13C nuclear magnetic resonance spectroscopy and circular dichroism revealed considerable helical portions in solution, and the very recently accomplished sequence determination of paracelsin allows the discussion of the results with regard to the closely related analogues, alamethicin and suzukacillin. A selective cleavage of the peptide was achieved by careful treatment with various acids, and a buffer of pH 8.25 and of high ionic strength made possible the quantitative determination of the C-terminal phenylalaninol released by means of ion-exchange chromatography. The significance of the production of paracelsin and related mycotoxins of the peptaibol class, exhibiting various kinds of biological activity, is discussed with respect to the extensive effort being made towards biotechnological applications of species, strains and cellulolytically highly active mutants of the fungus Trichoderma.
Subject(s)
Anti-Bacterial Agents , Antimicrobial Cationic Peptides , Alamethicin , Chromatography , Chromatography, High Pressure Liquid , Circular Dichroism , Erythrocytes/drug effects , Hemolysis , Humans , Magnetic Resonance Spectroscopy , Molecular Conformation , Peptides/isolation & purification , Peptides/pharmacology , Phenylalanine/analogs & derivatives , Phenylalanine/metabolism , Trichoderma/metabolismABSTRACT
The mutant strain ACN of Pseudomonas aureofaciens ATCC 15926 produces several bromo derivatives of pyrrolnitrin. Five brominated amino- and three brominated nitrophenyl pyrrole compounds could be isolated, and their structures were established by 1H NMR, UV and mass spectroscopy. The isolated amino compounds showed no biological activity; the nitro derivatives inhibited the growth of Neurospora crassa ATCC 9276, though not as effective as pyrrolnitrin itself. 2-Carboxy-4-(2-amino-3-bromophenyl)pyrrole (X) is demonstrated to be an intermediate in the biosynthesis of brominated pyrrolnitrin; the biosynthetic pathway to bromo derivatives of pyrrolnitrin is discussed.
