Literature DB >> 16808526

Berkelic acid, a novel spiroketal with selective anticancer activity from an acid mine waste fungal extremophile.

Andrea A Stierle1, Donald B Stierle, Kal Kelly.   

Abstract

Berkeley Pit Lake is an abandoned open-pit copper mine filled with 30 billion gallons of acidic, metal-contaminated water. This harsh environment is proving to be a source of unusual microorganisms that produce novel bioactive metabolites. Bioassay-guided fractionation using signal transduction enzyme assays led to the isolation of the novel spiroketal, berkelic acid 1, and of the known gamma-pyrone, spiciferone A 4. Berkelic acid has shown selective, nanomolar activity against OVCAR-3, an ovarian cancer cell line in the National Cancer Institute cell line screen. The isolation and characterization of these compounds are reported here.

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Year:  2006        PMID: 16808526     DOI: 10.1021/jo060018d

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  33 in total

1.  Lessons and revelations from biomimetic syntheses.

Authors:  Mina Razzak; Jef K De Brabander
Journal:  Nat Chem Biol       Date:  2011-11-15       Impact factor: 15.040

2.  Caspase-1 inhibitors from an extremophilic fungus that target specific leukemia cell lines.

Authors:  Andrea A Stierle; Donald B Stierle; Teri Girtsman
Journal:  J Nat Prod       Date:  2012-02-01       Impact factor: 4.050

Review 3.  Leveraging ecological theory to guide natural product discovery.

Authors:  Michael J Smanski; Daniel C Schlatter; Linda L Kinkel
Journal:  J Ind Microbiol Biotechnol       Date:  2015-10-05       Impact factor: 3.346

4.  Caspase-1 and -3 inhibiting drimane sesquiterpenoids from the extremophilic fungus Penicillium solitum.

Authors:  Donald B Stierle; Andrea A Stierle; Teri Girtsman; Kyle McIntyre; Jesse Nichols
Journal:  J Nat Prod       Date:  2012-01-25       Impact factor: 4.050

5.  Generation of Dithianyl and Dioxolanyl Radicals Using Photoredox Catalysis: Application in the Total Synthesis of the Danshenspiroketallactones via Radical Relay Chemistry.

Authors:  Yifan Deng; Minh D Nguyen; Yike Zou; K N Houk; Amos B Smith
Journal:  Org Lett       Date:  2019-02-26       Impact factor: 6.005

6.  Gold(I)-Mediated Cycloisomerization/Cycloaddition Enables Bioinspired Syntheses of Neonectrolides B-E and Analogues.

Authors:  Thomas J Purgett; Matthew W Dyer; Bryce Bickel; James McNeely; John A Porco
Journal:  J Am Chem Soc       Date:  2019-09-12       Impact factor: 15.419

Review 7.  Culturability and secondary metabolite diversity of extreme microbes: expanding contribution of deep sea and deep-sea vent microbes to natural product discovery.

Authors:  Robin K Pettit
Journal:  Mar Biotechnol (NY)       Date:  2010-05-01       Impact factor: 3.619

8.  Antineoplastic agents 582. Part 1: Isolation and structure of a cyclobutane-type sesquiterpene cancer cell growth inhibitor from Coprinus cinereus (Coprinaceae).

Authors:  George R Pettit; Yanhui Meng; Robin K Pettit; Delbert L Herald; Fiona Hogan; Zbigniew A Cichacz
Journal:  Bioorg Med Chem       Date:  2010-06-12       Impact factor: 3.641

9.  Synthesis of (-)-berkelic acid.

Authors:  Xiaoxing Wu; Jingye Zhou; Barry B Snider
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  A Cycloaddition Strategy for Use toward Berkelic Acid, an MMP Inhibitor and Potent Anticancer Agent Displaying a Unique Chroman Spiroketal Motif.

Authors:  Yaodong Huang; Thomas R R Pettus
Journal:  Synlett       Date:  2008-05-11       Impact factor: 2.454

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