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Issue 28, 2015
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New PKS-NRPS tetramic acids and pyridinone from an Australian marine-derived fungus, Chaunopycnis sp.

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Abstract

Chemical analysis of a marine-derived fungus, Chaunopycnis sp. (CMB-MF028), isolated from the inner tissue of a pulmonate false limpet Siphonaria sp., collected from rock surfaces in the intertidal zone of Moora Park, Shorncliffe, Queensland, yielded the tetramic acid F-14329 (1) and new analogues, chaunolidines A–C (2–4), together with the new pyridinone chaunolidone A (5), and pyridoxatin (6). Structures inclusive of absolute configurations were assigned to 1–6 on the basis of detailed spectroscopic analysis, X-ray crystallography, electronic circular dichroism (ECD), biosynthetic considerations and chemical interconversion. Chaunolidine C (4) exhibits modest Gram-positive antibacterial activity (IC50 5–10 μM), while chaunolidone A (5) is a selective and potent inhibitor (IC50 0.09 μM) of human non-small cell lung carcinoma cells (NCI-H460). Tetramic acids 1–4 form metal chelates with Fe(III), Al(III), Cu(II), Mg(II) and Zn(II).

Graphical abstract: New PKS-NRPS tetramic acids and pyridinone from an Australian marine-derived fungus, Chaunopycnis sp.

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Publication details

The article was received on 26 May 2015, accepted on 18 Jun 2015 and first published on 18 Jun 2015


Article type: Paper
DOI: 10.1039/C5OB01058F
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2015,13, 7795-7802
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    New PKS-NRPS tetramic acids and pyridinone from an Australian marine-derived fungus, Chaunopycnis sp.

    Z. Shang, L. Li, B. P. Espósito, A. A. Salim, Z. G. Khalil, M. Quezada, P. V. Bernhardt and R. J. Capon, Org. Biomol. Chem., 2015, 13, 7795
    DOI: 10.1039/C5OB01058F

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