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Andrastin A and barceloneic acid metabolites, protein farnesyl transferase inhibitors from Penicillium albocoremium: chemotaxonomic significance and pathological implications

Published online by Cambridge University Press:  30 September 2005

David P. OVERY ,
Thomas O. LARSEN ,
Petur W. DALSGAARD ,
Karla FRYDENVANG ,
Richard PHIPPS ,
Murray H. G. MUNRO  and
Carsten CHRISTOPHERSEN
David P. OVERY
Affiliation:
Centre for Microbial Biotechnology, Biocentrum-DTU, Building 221, Technical University of Denmark, DK-2800 Kgs. Lyngby, Denmark. E-mail: do@biocentrum.dtu.dk Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch, New Zealand.
Thomas O. LARSEN
Affiliation:
Centre for Microbial Biotechnology, Biocentrum-DTU, Building 221, Technical University of Denmark, DK-2800 Kgs. Lyngby, Denmark. E-mail: do@biocentrum.dtu.dk
Petur W. DALSGAARD
Affiliation:
Marine Chemistry Section, Department of Chemistry, University of Copenhagen, DK-2100 Copenhagen, Denmark.
Karla FRYDENVANG
Affiliation:
Department of Medicinal Chemistry, The Danish University of Pharmaceutical Sciences, DK-2100 Copenhagen, Denmark.
Richard PHIPPS
Affiliation:
Centre for Microbial Biotechnology, Biocentrum-DTU, Building 221, Technical University of Denmark, DK-2800 Kgs. Lyngby, Denmark. E-mail: do@biocentrum.dtu.dk
Murray H. G. MUNRO
Affiliation:
Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch, New Zealand.
Carsten CHRISTOPHERSEN
Affiliation:
Marine Chemistry Section, Department of Chemistry, University of Copenhagen, DK-2100 Copenhagen, Denmark.
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Abstract

A survey of Penicillium albocoremium was undertaken to identify potential taxonomic metabolite markers. One major and four minor metabolites were consistently produced by the 19 strains surveyed on three different media. Following purification and spectral studies, the metabolites were identified as the known protein farnesyl transferase inhibitors andrastin A (1) and barceloneic acid A (2) along with barceloneic acid B (3), barceloneic lactone (4), and methyl barceloneate (5). These compounds are significant taxonomic markers for P. albocoremium; moreover this is the first report of a methyl ester of a barceloneic acid being produced as a secondary metabolite. Tissue extracts created following pathogenicity trials involving P. albocoremium and Allium cepa confirmed the production of these five metabolites in planta. Barceloneic acid B was found to be biologically active against a P388 murine leukemia cell line.

Type
Research Article
Information
Mycological Research , Volume 109 , Issue 11 , November 2005 , pp. 1243 - 1249
Copyright
The British Mycological Society 2005

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