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Discovery of new mitorubrin derivatives from Hypoxylon fulvo-sulphureum sp. nov. (Ascomycota, Xylariales)

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Abstract

A specimen of the Hypoxylon rubiginosum complex featuring unusual bicoloured stromata was collected in northern Thailand and examined by means of classical morphological methodology, complemented by studies of its secondary metabolites using high performance liquid chromatography coupled with diode array and electrospray mass spectrometric detection (HPLC-DAD/MS), and molecular phylogenetic analysis of its ITS and partial beta-tubulin DNA sequences. In addition, the ultrastructure of its ascospores was examined by SEM. The chemotaxonomic studies revealed the presence of two putatively unknown, apparently specific azaphilone pigments in the stromata. These metabolites were consequently isolated to purity by preparative HPLC and identified by means of nuclear magnetic resonance spectroscopy and high resolution mass spectrometry as the novel natural products, (+)-6″-hydroxymitorubrinol acetate (1) and (+)-6″-hydroxymitorubrinol (3).

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Acknowledgments

We gratefully acknowledge support from the curators of various international culture collections and herbaria, above all, BCC and MFLUCC, who provided important specimens for the present study.

The field sampling in Thailand benefited from a joint TRF-DAAD PPP academic exchange grant by the German Academic Exchange Service (DAAD) and the Thai Royal Golden Ph.D. Jubilee-Industry program (RGJ) to Kevin D. Hyde, Eric Kuhnert, and Marc Stadler. The DAAD and the Argentina Ministerio de Ciencia, Tecnología e Innovación Productiva are also gratefully acknowledged for an academic exchange grant involving Eric Kuhnert, Esteban Benjamin Sir and Marc Stadler.

We thank Simone Heitkämper for her excellent assistance in the molecular work and Benjarong Thongbai for help with the fieldwork. Furthermore, we are grateful to various colleagues at the HZI: Kathrin I. Mohr and Wera Collisi for conducting the bioassays and Christel Kakoschke for recording NMR spectra. Manfred Rohde is thanked for SEM recordings. For measurements of the HPLC–HRMS data we are grateful to Aileen Teichmann. We also thank Philine Wotsch for technical assistance in culture maintenance.

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Authors and Affiliations

  1. Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET), Av. 13 Rivadavia 1917, Buenos Aires, C1033AAJ, Argentina

    Esteban Benjamin Sir

  2. Fundación Miguel Lillo, Laboratory Mycology, Miguel Lillo 251, San Miguel de Tucumán, CP 4000, Tucumán, Argentina

    Esteban Benjamin Sir

  3. Department of Microbial Drugs, Helmholtz-Zentrum für Infektionsforschung GmbH, Inhoffenstrasse 7, 38124, Braunschweig, Germany

    Eric Kuhnert, Frank Surup & Marc Stadler

  4. German Centre for Infection Research (DZIF), Partner Site Hannover-Braunschweig, 38124, Braunschweig, Germany

    Eric Kuhnert, Frank Surup & Marc Stadler

  5. Institute of Excellence in Fungal Research and School of Science, Mae Fah Luang University, Chiang Rai, 57100, Thailand

    Kevin D. Hyde

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  1. Esteban Benjamin Sir
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  2. Eric Kuhnert
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Correspondence to Marc Stadler.

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Sir, E.B., Kuhnert, E., Surup, F. et al. Discovery of new mitorubrin derivatives from Hypoxylon fulvo-sulphureum sp. nov. (Ascomycota, Xylariales). Mycol Progress 14, 28 (2015). https://doi.org/10.1007/s11557-015-1043-1

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