Salinazinones A and B: Pyrrolidinyl-Oxazinones from Solar Saltern-Derived Streptomyces sp. KMF-004

Org Lett. 2015 Oct 16;17(20):5024-7. doi: 10.1021/acs.orglett.5b02495. Epub 2015 Oct 8.

Abstract

Salinazinones A (1) and B (2), two unprecedented pyrrolidinyl-oxazinones, were isolated from the culture broth of Streptomyces sp. KMF-004 from a solar saltern at Aphae Island, Korea. The structures of these salinazinones, which are unusual and consist of 2-methylpropenyl-1,3-oxazin-6-one bearing 1-oxopyrrolidinyl substituents, were assigned by spectral and chemical analyses using Mosher's method, circular dichroism (CD), and calculated ECD. Salinazinones are the first examples of a natural alkaloid class composed of an oxazinone-pyrrolidone conjugate.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Circular Dichroism
  • Lipopolysaccharides / pharmacology
  • Mice
  • Molecular Structure
  • Nitric Oxide / biosynthesis
  • Oxazines / chemistry
  • Oxazines / isolation & purification*
  • Oxazines / pharmacology
  • Pyrrolidines / chemical synthesis*
  • Pyrrolidines / chemistry
  • Pyrrolidines / pharmacology
  • Republic of Korea
  • Streptomyces / chemistry*

Substances

  • Lipopolysaccharides
  • Oxazines
  • Pyrrolidines
  • salinazinone A
  • salinazinone B
  • Nitric Oxide