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. 2015 Dec 24;78(12):2917-23.
doi: 10.1021/acs.jnatprod.5b00519. Epub 2015 Dec 7.

Azaphilones from an Acid Mine Extremophile Strain of a Pleurostomophora sp

Andrea A Stierle, Donald B Stierle, Teri Girtsman, T C Mou, Christophe Antczak  1 , Hakim Djaballah  1
Affiliations

Azaphilones from an Acid Mine Extremophile Strain of a Pleurostomophora sp

Andrea A Stierle et al. J Nat Prod. .

Abstract

An extremophilic fungus identified as a Pleurostomophora sp. was isolated from the Berkeley Pit, an acid mine waste lake. When grown in liquid culture, the fungus produced berkchaetoazaphilones A-C (1, 2, and 5), the red pigment berkchaetorubramine (6), and the known compound 4-(hydroxymethyl)quinoline. These compounds were evaluated as inhibitors of matrix metalloproteinase-3, caspase-1, and proinflammatory cytokine production in induced THP-1 cells. Berkchaetoazaphilone B (2) inhibited IL-1β, TNFα, and IL-6 production in the induced inflammasome assay and was cytotoxic toward human retinoblastoma cell line Y79 (IC50 = 1.1 μM), leukemia cell lines CCRF-CEM and SR, and the melanoma cell line LOX IMVI (IC50 = 10 μM).

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Figures

Figure 1
Figure 1
Angular (A) and linear (B) fused azaphilone tricyclic systems isolated from fungi, X = O or N.
Figure 2
Figure 2
Key HMBC correlations for berkchaetoazaphilone A (1).
Figure 3
Figure 3
Selected δΔ values around C-11 of the (R) and (S)-MTPA esters of compound 4. [Δδ=chemical shift of (R)-MTPA ester minus chemical shift of (S)-MTPA ester in ppm].
See this image and copyright information in PMC

References

    1. Montana Bureau of Mines and Geology. [accessed 5/16/11];Berkeley Pit and Butte Mine-Flooding Operable Unit. website: http://www.mbmg.mtech.edu/env-berkeley.htm.

    1. Some of the previous reports of the isolation of secondary metabolites from Berkeley Pit fungi include: Stierle DB, Stierle AA, Patacini B, McIntyre K, Girtsman T, Bolstad E. J Nat Prod. 2011;74:2273–2277.Stierle AA, Stierle DB, Girtsman T. J Nat Prod. 2012;75:344–350.Stierle AA, Stierle DB. In: Studies in Natural Products Chemistry. Atta-Ur-Rahman, editor. Vol. 39. Elsevier Science; Amsterdam: 2013. pp. 1–44.Stierle AA, Stierle DB, Mitman GG, Snyder S, Antczak C, Djaballah H. Nat Prod Commun. 2014;9:87–90.Stierle AA, Stierle DB. Nat Prod Commun. 2014;9:1037–1044.

    1. Vijaykrishna D, Mostert L, Jeewon R, Gams W, Hyde KD, Crous PW. Stud Mycol. 2004;50:387–395.

    1. Microbial ID, Inc. originally identified the organism as Chaetomium funicola (6.58% difference), but alignment of 319 base pairs of the 28S rRNA gene showed a 99% identity with Pleurostomophora richardsiae. It has therefore been designated as Pleurostomophora sp. GenBank Accession # KT728826; NRRL repository # 66319.

    1. Thiery JP, Acioque H, Huang RYJ, Nieto MA. Cell. 2009;139:871–890. - PubMed

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