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
Institute for Pharmaceutical Biology, University of Bonn, Bonn, Germany
,
Simon Stephan Martin Stölben
Institute for Pharmaceutical Biology, University of Bonn, Bonn, Germany
,
Stefan Kehraus
Institute for Pharmaceutical Biology, University of Bonn, Bonn, Germany
,
Nicole Merten
Institute for Pharmaceutical Biology, University of Bonn, Bonn, Germany
,
Henrik Harms
Institute for Pharmaceutical Biology, University of Bonn, Bonn, Germany
,
Max Crüsemann
Institute for Pharmaceutical Biology, University of Bonn, Bonn, Germany
,
Idris Arslan
Biomedical Engineering, Pamukkale University, Denizli, Turkey
,
Michael Gütschow
Pharmaceutical Chemistry I, University of Bonn, Bonn, Germany
,
Tanja Schneider
Institute for Medical Microbiology, Immunology and Parasitology (IMMIP), Pharmaceutical Microbiology Unit, University of Bonn, Bonn, Germany
,
Gabriele Maria König
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 (eFirst)

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.

* 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.