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

Org Lett. 2014 Sep 19;16(18):4774-7. doi: 10.1021/ol502227x. Epub 2014 Sep 4.

Abstract

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.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Benzoxazines
  • Biological Products
  • Fungi / chemistry*
  • Heterocyclic Compounds, 4 or More Rings / chemistry
  • Heterocyclic Compounds, 4 or More Rings / isolation & purification*
  • Heterocyclic Compounds, 4 or More Rings / pharmacology
  • Molecular Structure
  • Mycobacterium tuberculosis / drug effects
  • Transient Receptor Potential Channels / antagonists & inhibitors

Substances

  • Anti-Bacterial Agents
  • Benzoxazines
  • Biological Products
  • Heterocyclic Compounds, 4 or More Rings
  • Transient Receptor Potential Channels
  • oxazinin A