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Planta Med 2017; 83(12/13): 1044-1052
DOI: 10.1055/s-0042-124493
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Biosynthetic Studies on Acetosellin and Structure Elucidation of a New Acetosellin Derivative[*]

Peter Hufendiek
1   Institute for Pharmaceutical Biology, University of Bonn, Bonn, Germany
,
Simon Stephan Martin Stölben
1   Institute for Pharmaceutical Biology, University of Bonn, Bonn, Germany
,
Stefan Kehraus
1   Institute for Pharmaceutical Biology, University of Bonn, Bonn, Germany
,
Nicole Merten
1   Institute for Pharmaceutical Biology, University of Bonn, Bonn, Germany
,
Henrik Harms
1   Institute for Pharmaceutical Biology, University of Bonn, Bonn, Germany
,
Max Crüsemann
1   Institute for Pharmaceutical Biology, University of Bonn, Bonn, Germany
,
Idris Arslan
4   Biomedical Engineering, Pamukkale University, Denizli, Turkey
,
Michael Gütschow
2   Pharmaceutical Chemistry I, University of Bonn, Bonn, Germany
,
Tanja Schneider
3   Institute for Medical Microbiology, Immunology and Parasitology (IMMIP), Pharmaceutical Microbiology Unit, University of Bonn, Bonn, Germany
,
Gabriele Maria König
1   Institute for Pharmaceutical Biology, University of Bonn, Bonn, Germany
› Author Affiliations
Further Information

Publication History

received 07 October 2016
revised 13 December 2016

accepted 16 December 2016

Publication Date:
12 January 2017 (online)

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Abstract

Natural products from fungi, especially Ascomycota, play a major role in therapy and drug discovery. Fungal strains originating from marine habitats offer a new avenue for finding unusual molecular skeletons. Here, the marine-derived fungus Epicoccum nigrum (strain 749) was found to produce the azaphilonoid compounds acetosellin and 5′,6′-dihydroxyacetosellin. The latter is a new natural product. The biosynthesis of these polyketide-type compounds is intriguing, since two polyketide chains are assembled to the final product. Here we performed 13C labeling studies on solid cultures to prove this hypothesis for acetosellin biosynthesis.

Key words

Acetosellin - Epicoccum nigrum - Didymellaceae - azaphilones - polyketides - isotope labeling

* Dedicated to Prof. Max Wichtl in recognition of his outstanding contribution to pharmacognosy research.


Supporting Information

Spectroscopic data including UV, CD, IR, 1H NMR, 13C NMR, 2D-NMR, and LCESIMS, and data of bioassays of compounds 1 and 2 as well as labeling experiments are available as Supporting Information.

 

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