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Issue 8, 2006
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Quinolactacins revisited: from lactams to imide and beyond

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Abstract

Chemical analysis of a solid phase fermentation of an Australian Penicillium citrinum strain has returned all known examples of a rare class of N-methyl quinolone lactams, quinolactacins A2 (1), B2 (2), C2 (3) and A1 (4), together with the new quinolactacins B1 (5), C1 (6), D1 (7) and D2 (8), and the novel derivatives quinolonimide (9) and quinolonic acid (10). Complete stereostructures were assigned to all these compounds by detailed spectroscopic analysis and chemical interconversion. Carefully controlled and monitored decomposition studies have confirmed that quinolactacins readily undergo C-3 epimerization and oxidation, and under appropriate conditions convert to quinolonimide and quinolonic acid. Mechanisms for key transformations are proposed. The decomposition studies suggested that only quinolactacins A2 (1) and B2 (2) are genuine natural products, with all other isolated compounds being decomposition artefacts. Quinolactacins C1 (6), C2 (3), and the racemic mixture of quinolactacins D1/D2 (8/7) all displayed notable cytotoxic activity.

Graphical abstract: Quinolactacins revisited: from lactams to imide and beyond

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Article information


Submitted
20 Jan 2006
Accepted
22 Feb 2006
First published
16 Mar 2006

Org. Biomol. Chem., 2006,4, 1512-1519
Article type
Paper

Quinolactacins revisited: from lactams to imide and beyond

B. Clark, R. J. Capon, E. Lacey, S. Tennant and J. H. Gill, Org. Biomol. Chem., 2006, 4, 1512
DOI: 10.1039/B600959J

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