Beijinchromes A-D, Novel Aromatic Compounds Isolated from Nocardia beijingensis NBRC 16342

Chem Pharm Bull (Tokyo). 2019;67(8):775-777. doi: 10.1248/cpb.c19-00364.

Abstract

Nocardia is a potent bacterial producer of bioactive compounds. From a culture of Nocardia beijingensis NBRC 16342, we isolated four aromatic compounds, named beijinchromes A-D (1-4). We purified them by silica gel chromatography and reverse phase HPLC, and identified their structures by NMR and high resolution (HR)-MS analyses. 1, 2, and 4 are novel 1,2,3,8-tetrasubstituted naphthalenes, and 3 is a novel 3,8-disubstituted ortho-naphthoquinone. 1 and 2 exert antioxidant activities, and 3 exhibits antibiotic activity. Remarkably, the putative biosynthetic gene clusters for 1-4 are widely distributed in 37 Nocardia species, implying their potential to produce this family of compounds and important biological functions of beijinchromes.

Keywords: Nocardia; aromatic compound; secondary metabolite.

MeSH terms

  • Molecular Structure
  • Naphthalenes / chemistry*
  • Naphthalenes / isolation & purification
  • Naphthalenes / pharmacology
  • Naphthoquinones / chemistry*
  • Naphthoquinones / isolation & purification
  • Naphthoquinones / pharmacology
  • Nocardia / chemistry*
  • Stereoisomerism

Substances

  • Naphthalenes
  • Naphthoquinones
  • 1,2-naphthoquinone