Oxazinin A, a Pseudodimeric Natural Product of Mixed Biosynthetic Origin from a Filamentous Fungus

A racemic, prenylated polyketide dimer, oxazinin A (1), was isolated from a novel filamentous fungus in the class Eurotiomycetes, and its structure was elucidated spectroscopically. The pentacyclic structure of oxazinin A (1) is a unique combination of benzoxazine, isoquinoline, and a pyran ring. Ox...

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Veröffentlicht in:	Organic letters 2014-09, Vol.16 (18), p.4774-4777
Hauptverfasser:	Lin, Zhenjian, Koch, Michael, Abdel Aziz, May Hamdy, Galindo-Murillo, Rodrigo, Tianero, Ma. Diarey, Cheatham, Thomas E, Barrows, Louis R, Reilly, Chris A, Schmidt, Eric W
Format:	Artikel
Sprache:	eng
Schlagworte:	Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - isolation & purification Anti-Bacterial Agents - pharmacology antibacterial properties Benzoxazines Biological Products chemical reactions chemical structure Eurotiomycetes fungi Fungi - chemistry Heterocyclic Compounds, 4 or More Rings - chemistry Heterocyclic Compounds, 4 or More Rings - isolation & purification Heterocyclic Compounds, 4 or More Rings - pharmacology Letter Molecular Structure Mycobacterium tuberculosis - drug effects polyketides Transient Receptor Potential Channels - antagonists & inhibitors
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Zusammenfassung:	A racemic, prenylated polyketide dimer, oxazinin A (1), was isolated from a novel filamentous fungus in the class Eurotiomycetes, and its structure was elucidated spectroscopically. The pentacyclic structure of oxazinin A (1) is a unique combination of benzoxazine, isoquinoline, and a pyran ring. Oxazinin A (1) exhibited antimycobacterial activity and modestly antagonized transient receptor potential (TRP) channels.
ISSN:	1523-7060 1523-7052 1523-7052
DOI:	10.1021/ol502227x