Ovine ill-thrift in Nova Scotia. 9. Production of experimental quantities of isocyanide metabolites of Trichoderma hamatum

Abstract

Laboratory cultures of Trichoderma hamatum produce metabolites that are characterized by an isocyanide functionality. Three such metabolites predominate. One is the known compound trichoviridin (I). The other two, described here for the first time, are 3-(3-isocyano-6-oxabicyclo[3,1,0]hex-2-en-5-yl)acrylic acid (II) and a very unstable compound 3-(3-isocyanocyclopent-2-enylidene-)propionic acid (III). Production of these three metabolites by a random sample of wild isolates of the fungus has been examined. At least one of these isocyanides was isolated from all cultures in which the culture broth inhibited the growth of Micrococcus luteus. The relative amounts of the three isocyanides produced by individual isolates were not the same and cultures were found in which I, II, or III was the main product. The isocyanide III was produced by all wild isolates which had antibiotic activity in their culture broth, and it was present in the concentration range 2–40 mg∙L⁻¹.