Characterization and Nonenzymatic Transformation of Three Types of Alkaloids from Streptomyces albogriseolus MGR072 and Discovery of Inhibitors of Indoleamine 2,3-Dioxygenase

Org Lett. 2019 Nov 1;21(21):8577-8581. doi: 10.1021/acs.orglett.9b03149. Epub 2019 Oct 15.

Abstract

The known benzonaphthyridine alkaloid, albogrisin A (1), and six new compounds, including two pyrazinone stereoisomers, albogrisin B (2)/B' (2'), together with four 4H-pyrroloquinolinones, two diastereoisomers, albogrisin C (3)/C' (3'), and their methyl esters, albogrisin D (4)/D' (4'), were isolated from mangrove-derived Streptomyces albogriseolus MGR072. 2 and 2' are converted into 1 in acidic aqueous solution but into 3/3' and 4/4' in 0.05% trifluoroacetic acid acetonitrile. 4 and 4' are new indoleamine 2,3-dioxygenase 1 inhibitors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Indoleamine-Pyrrole 2,3,-Dioxygenase / antagonists & inhibitors*
  • Naphthyridines / chemistry
  • Naphthyridines / pharmacology*
  • Stereoisomerism
  • Streptomyces / chemistry*

Substances

  • Alkaloids
  • Enzyme Inhibitors
  • Indoleamine-Pyrrole 2,3,-Dioxygenase
  • Naphthyridines

Supplementary concepts

  • Streptomyces albogriseolus