Identification and directed biosynthesis of efrapeptins in the fungusTolypocladium geodes gams (Deuteromycotina: Hyphomycetes).

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.

journal_name

J Chem Ecol

authors

Krasnoff SB,Gupta S

doi

10.1007/BF00992580

subject

Has Abstract

pub_date

1991-10-01 00:00:00

pages

1953-62

issue

10

eissn

0098-0331

issn

1573-1561

journal_volume

17

pub_type

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