Tulasporins A–D,19-Residue Peptaibols from the Mycoparasitic Fungus Sepedonium tulasneanum

Abstract

Four new 19-residue peptaibols, named tulasporins A–D (1–4), were isolated from the semi-solid cultures of Sepedonium tulasneanum. Their structures were elucidated on the basis of extensive ESI-HRMSⁿ fragmentation studies as well as ¹H NMR spectroscopic analyses. Interestingly, the structures of tulasporins A–D (1–4) resemble those of chrysospermins isolated earlier from cultures of S. chrysospermum. Previously, it was hypothesized that the peptaibol production by Sepedonium species correlates with the morphology of the aleurioconidia, as exclusively round-shaped aleurioconidia forming species produced peptaibols. Since the investigated Sepedonium tulasneanum produces oval aleurioconidia, this study can be considered as the first report of peptaibols from a Sepedonium strain with oval-shaped aleurioconidia. Thus, it could be demonstrated that both round as well as oval aleurioconidia forming Sepedonium species are able to produce peptaibols. Tulasporins A-D (1–4), when tested against phytopathogenic fungi, exhibited good growth inhibitory activity against both Botrytis cinerea and Phytophthora infestans, while they were devoid of significant activity against Septoria tritici.