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

Shang, Zhuo, Li, Li, Esposito, Breno P., Salim, Angela A., Khalil, Zeinab G., Quezada, Michelle, Bernhardt, Paul V. and Capon, Robert J. (2015) New PKS-NRPS tetramic acids and pyridinone from an Australian marine-derived fungus, Chaunopycnis sp.. Organic and Biomolecular Chemistry, 13 28: 7795-7802. doi:10.1039/c5ob01058f


Author Shang, Zhuo
Li, Li
Esposito, Breno P.
Salim, Angela A.
Khalil, Zeinab G.
Quezada, Michelle
Bernhardt, Paul V.
Capon, Robert J.
Title New PKS-NRPS tetramic acids and pyridinone from an Australian marine-derived fungus, Chaunopycnis sp.
Formatted title
New PKS-NRPS tetramic acids and pyridinone from an Australian marine-derived fungus, Chaunopycnis sp.
Journal name Organic and Biomolecular Chemistry   Check publisher's open access policy
ISSN 1477-0520
1477-0539
Publication date 2015-07-28
Year available 2015
Sub-type Article (original research)
DOI 10.1039/c5ob01058f
Open Access Status Not Open Access
Volume 13
Issue 28
Start page 7795
End page 7802
Total pages 8
Place of publication Cambridge, United Kingdom
Publisher Royal Society of Chemistry
Collection year 2016
Language eng
Formatted 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).
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2016 Collection
School of Chemistry and Molecular Biosciences
Institute for Molecular Bioscience - Publications
 
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Created: Thu, 16 Jul 2015, 16:30:45 EST by Susan Allen on behalf of Institute for Molecular Bioscience