Saliniquinones A–F, New Members of the Highly Cytotoxic Anthraquinone-γ-Pyrones from the Marine Actinomycete Salinispora arenicola

Brian T. Murphy; Tadigoppula Narender; Christopher A. Kauffman; Matthew Woolery; Paul R. Jensen; William Fenical

doi:10.1071/CH10068

RESEARCH FRONT

Saliniquinones A–F, New Members of the Highly Cytotoxic Anthraquinone-γ-Pyrones from the Marine Actinomycete Salinispora arenicola

Brian T. Murphy ^A , Tadigoppula Narender ^A , Christopher A. Kauffman ^A , Matthew Woolery ^A , Paul R. Jensen ^A and William Fenical ^A ^B

+ Author Affiliations

- Author Affiliations

^A Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California–San Diego, La Jolla, CA 92093-0204, USA.

^B Corresponding author. Email: wfenical@ucsd.edu

Australian Journal of Chemistry 63(6) 929-934 https://doi.org/10.1071/CH10068
Submitted: 5 February 2010 Accepted: 12 May 2010 Published: 11 June 2010

Abstract

Six new anthraquinone-γ-pyrones, saliniquinones A–F (1–6), which are related to metabolites of the pluramycin/altromycin class, were isolated from a fermentation broth of the marine actinomycete Salinispora arenicola (strain CNS-325). Their structures were determined by analysis of one- and two-dimensional NMR spectroscopic and high-resolution mass spectrometric data. The relative and absolute configurations of compounds 1–6 were determined by analysis of NOESY NMR spectroscopic data and by comparison of circular dichroism and optical rotation data with model compounds found in the literature. Saliniquinone A (1) exhibited potent inhibition of the human colon adenocarcinoma cell line (HCT-116) with an IC₅₀ of 9.9 × 10^–9 M. In the context of the biosynthetic diversity of S. arenicola, compounds 1–6 represent secondary metabolites that appear to be strain specific and thus occur outside of the core group of compounds commonly observed from this species.

Acknowledgements

This research was funded by the National Institutes of Health (NIH), National Cancer Institute (NCI) under grant R37 CA 044848 (to W.F.). The authors gratefully acknowledge Alexandra Besser (SIO) for performing the HCT-116 bioassay and Ariane Jansma (UCSD) for assistance obtaining NMR spectra. T. Narender acknowledges the Department of Science and Technology (DST), New Delhi, India for the award of BOYSCAST fellowship to visit the University of California San Diego.

References

Saliniquinones A–F, New Members of the Highly Cytotoxic Anthraquinone-γ-Pyrones from the Marine Actinomycete Salinispora arenicola

Abstract

Acknowledgements

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