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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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Article information


Submitted
26 May 2015
Accepted
18 Jun 2015
First published
18 Jun 2015

Org. Biomol. Chem., 2015,13, 7795-7802
Article type
Paper
Author version available

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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