New PKS-NRPS tetramic acids and pyridinone from an Australian marine-derived fungus, Chaunopycnis sp.
Org Biomol Chem
; 13(28): 7795-802, 2015 Jul 28.
Article
em En
| MEDLINE
| ID: mdl-26107107
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).
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Base de dados:
MEDLINE
Assunto principal:
Ascomicetos
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Piridonas
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Pirrolidinonas
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Bactérias
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Antibacterianos
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Antineoplásicos
Limite:
Animals
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Humans
País como assunto:
Oceania
Idioma:
En
Ano de publicação:
2015
Tipo de documento:
Article