Original Article

The Journal of Antibiotics (2005) 58, 390–396; doi:10.1038/ja.2005.49

Heptemerones AapproxG, Seven Novel Diterpenoids from Coprinus heptemerus: Producing Organism, Fermentation, Isolation and Biological Activities

Melanie Kettering1, Carola Valdivia3, Olov Sterner3, Heidrun Anke1 and Eckhard Thines2

  1. 1Institute for Biotechnology and Drug Research (IBWF), Erwin-Schrödinger-Strasse 56, D-67663 Kaiserslautern, Germany
  2. 2Department of Biotechnology, University of Kaiserslautern, D-67663 Kaiserslautern, Germany
  3. 3Division of Organic and Bioorganic Chemistry, University of Lund, P.O.Box 124, S-22100 Lund, Sweden

Correspondence: H. Anke, Institute for Biotechnology and Drug Research (IBWF), Erwin-Schrödinger-Strasse 56, D-67663 Kaiserslautern, Germany. E-mail: anke@ibwf.de; E. Thines, Department of Biotechnology, University of Kaiserslautern, D-67663 Kaiserslautern, Germany. E-mail: thines@ibwf.de

Received 18 March 2005; Accepted 6 June 2005.

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Abstract

Seven novel diterpenoids, named heptemerones AapproxG, were isolated from the broth of submerged cultures of Coprinus heptemerus, a basidiomycete which previously had not been known to produce secondary metabolites. The compounds were purified by solid phase extraction and silica gel chromatography followed by preparative HPLC. Among the biological activities the inhibition of fungal germination was the most potent, and depended highly on the composition of the assay medium. In water, inhibition occurred at 5approx10 fold lower concentrations as compared to complex media. Heptemerone G was the most active compound with MICs starting at 1 microg/ml. Four of the antifungal compounds exhibited plant protective activity in a leaf segment assay using Magnaporthe grisea as the pathogen. Growth of yeasts and bacteria was hardly affected. Cytotoxic activities were moderate and only heptemerone D was phytotoxic.

Keywords:

Coprinus heptemerus, heptemerones, diterpenes, inhibition of conidial germination, Magnaporthe grisea

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References

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