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. 2007 Nov;70(11):1820-3.
doi: 10.1021/np070329z. Epub 2007 Oct 31.

The berkeleyacetals, three meroterpenes from a deep water acid mine waste Penicillium

Donald B Stierle  1 , Andrea A Stierle, Brianna Patacini
Affiliations

The berkeleyacetals, three meroterpenes from a deep water acid mine waste Penicillium

Donald B Stierle et al. J Nat Prod. 2007 Nov.

Abstract

Berkeley Pit Lake is a 1500 ft deep abandoned open-pit copper mine filled with over 1140 billion liters of acidic, metal-sulfate-contaminated water. This harsh environment is proving to be a source of unusual microorganisms that produce novel bioactive compounds. We recently reported the structures of berkeleydione (1) and berkeleytrione (2), two novel hybrid polyketide-terpenoid metabolites isolated from a deep water Penicillium sp. growing in Berkeley Pit Lake. In this paper we report the structures of three new compounds, berkeleyacetals A-C ( 3-5) isolated from extracts of this fungus. The structures of these compounds were deduced by comparison of mass spectral and NMR data to that of berkeleydione (1).

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Figures

Figure 1
Figure 1
Key HMBC correlations for berkeleyacetal A 3.
Figure 2
Figure 2
Proposed correlation of carbon skeletons of berkeleydione and berkeleyacetals.
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References

    1. Montana Bureau of Mines and Geology. Berkeley Pit and Butte Mine-Flooding Operable Unit. [January 10, 2006]. website: http://www.mbmg.mtech.edu/env-berkeley.htm.
    1. Stierle AA, Stierle DB, Parker K, Goldstein E, Bugni T, Baarson C, Gress J, Blake D. J Nat Prod. 2003;66:1097–1100. - PubMed
    1. Stierle DB, Stierle AA, Hobbs JD, Stokken J, Clardy J. Org Lett. 2004;6:1049–1052. - PubMed
    1. Stierle AA, Stierle DB, Kelly K. J Org Chem. 2006;71:5357–5360. - PubMed
    1. Stierle AA, Stierle DB, Kemp K. J Nat Prod. 2004;67:1392–1395. - PubMed

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