CT2108A and B: New Fatty Acid Synthase Inhibitors as Antifungal Agents

A systematic screen for new natural products that displayed antifungal activity by inhibition of fungal fatty acid synthase (FAS) led to the discovery of two new fungal metabolites, designated CT2108A (1) and CT2108B (2). The metabolites were produced by Penicillium solitum (Westling) strain CT2108...

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Veröffentlicht in:	Journal of natural products (Washington, D.C.) D.C.), 2003-08, Vol.66 (8), p.1041-1046
Hauptverfasser:	Laakso, Jodi A, Raulli, Robert, McElhaney-Feser, Gail E, Actor, Paul, Underiner, Ted L, Hotovec, Brian J, Mocek, Ursula, Cihlar, Ronald L, Broedel, Sheldon E
Format:	Artikel
Sprache:	eng
Schlagworte:	Antibiotics (antibacterial agents, antifungal agents) Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents antifungal agents Antifungal Agents - chemistry Antifungal Agents - isolation & purification Antifungal Agents - pharmacology antifungal properties Applied microbiology azaphilones Benzopyrans - chemistry Benzopyrans - isolation & purification Benzopyrans - pharmacology Biological and medical sciences Candida Candida albicans - drug effects carbon cell lines chemical structure Cryptococcus laurintic Cryptococcus neoformans enzyme inhibitors Enzyme Inhibitors - chemistry Enzyme Inhibitors - isolation & purification Enzyme Inhibitors - pharmacology epoxides Epoxy Compounds - chemistry Epoxy Compounds - isolation & purification Epoxy Compounds - pharmacology Fatty Acid Synthases - antagonists & inhibitors fatty-acid synthase Fermentation Fundamental and applied biological sciences. Psychology Humans Inhibitory Concentration 50 ligases metabolites Microbiology Molecular Structure Nuclear Magnetic Resonance, Biomolecular patulodin Penicillium - chemistry Penicillium - metabolism Penicillium solitum protons Pyrans quinones Saccharomyces cerevisiae Saccharomyces cerevisiae - drug effects Saccharomyces cerevisiae - enzymology spectral analysis stereochemistry Wyoming
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Zusammenfassung:	A systematic screen for new natural products that displayed antifungal activity by inhibition of fungal fatty acid synthase (FAS) led to the discovery of two new fungal metabolites, designated CT2108A (1) and CT2108B (2). The metabolites were produced by Penicillium solitum (Westling) strain CT2108 and were classified as azaphilones. The structures of these new metabolites were determined using a variety of 1D and 2D NMR experiments, including COSY, HMQC, and HMBC. The chemical conversion of CT2108A to CT2108B was effected using WCl6. The related metabolite, patulodin (3), was also isolated from the fermentation culture of this P. solitum isolate. Both new compounds inhibited fungal FAS, and neither was found to significantly inhibit human FAS activity.
ISSN:	0163-3864 1520-6025
DOI:	10.1021/np030046g