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Mycology. 2014 Jul 3;5(3):110-119. Epub 2014 Jun 26.

Sporothriolide derivatives as chemotaxonomic markers for Hypoxylon monticulosum.

Author information

1
Department Microbial Drugs, Helmholtz-Centre for Infection Research , Inhoffenstrasse 7, 38124 Braunschweig , Germany ; German Centre for Infection Research (DZIF) , Inhoffenstraße 7, 38124 Braunschweig , Germany.
2
Institute of Excellence in Fungal Research and School of Science, Mae Fah Luang University , Chiang Rai 57100 , Thailand.
3
Las Muros , F-09420 Rimont , France.

Abstract

During the course of a screening for novel anti-infective agents from cultures of tropical Xylariaceae originating from French Guiana and Thailand, pronounced antifungal activity was noted in extracts of cultures of Hypoxylon monticulosum. A bioassay-guided fractionation led to the known metabolite sporothriolide as active principle. In addition, three new derivatives of sporothriolide were isolated, for which we propose the trivial names sporothric acid, isosporothric acid and dihydroisosporothric acid. Their chemical structures were elucidated by high-resolution electrospray mass spectrometry in conjunction with two-dimensional nuclear magnetic resonance (2D-NMR) spectroscopy. From earlier studies on the biogenesis of the chemically similar canadensolides, we postulate that the new compounds were shunt products, rather than biogenetic precursors of sporothriolide. Interestingly, this compound class, as well as strong antifungal activities, was only observed in multiple cultures of H. monticulosum, but not in several hundreds of Hypoxylon cultures studied previously or concurrently. Therefore, sporothriolide production may constitute a species-specific feature with respect to Hypoxylon and the Xylariaceae, although the compound was previously reported from non-related fungal taxa.

KEYWORDS:

Hypoxylon; antibiotics; chemotaxonomy; furofurandiones; screening; secondary metabolites

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