Chemical Constituents from a Mangrove-Derived Actinobacteria Isoptericola chiayiensis BCRC 16888 and Evaluation of Their Anti-NO Activity

Chem Biodivers. 2021 Aug;18(8):e2100211. doi: 10.1002/cbdv.202100211. Epub 2021 Jul 29.

Abstract

Cultivation of the actinobacteria strain Isoptericola chiayiensis, a mangrove-derived actinobacteria that was isolated from a mangrove soil collected in Chiayi County, resulted in the isolation of one new 2-furanone derivative, isopterfuranone (1), one new sesquiterpenoid, isopterchiayione (2), one new benzenoid derivative, isopterinoid (3), five new flavonoids, chiayiflavans A-E (4-8), and 4 metabolites isolated for the first time from nature source, methyl 3-(4-methyl-2,5-dioxopyrrolidin-3-yl)propanoate (9), 3-ethyl-4-methylpyrrolidine-2,5-dione (10), chiayiensol (11) and chiayiensic acid (12). Their structures were determined through in-depth spectroscopic and mass-spectrometric analyses. Most of the isolates showed potent inhibitory effects on NO production in LPS-stimulated RAW 264.7 murine macrophages cells with IC50 values ranging from 9.36 to 40.02 μM. Of these isolates, 4 and 5 showed NO inhibitory activity with IC50 values of 17.14 and 9.36 μM, stronger than the positive control quercetin (IC50 =36.95 μM). This is the first report on flavan metabolites from the genus Isoptericola.

Keywords: Isoptericola chiayiensis; NO inhibition; Promicromonosporaceae; actinobacteria; secondary metabolites.

MeSH terms

  • Actinobacteria / chemistry*
  • Actinobacteria / metabolism
  • Animals
  • Cell Survival / drug effects
  • Flavonoids / chemistry*
  • Flavonoids / isolation & purification
  • Flavonoids / pharmacology
  • Lipopolysaccharides / pharmacology
  • Macrophages / cytology
  • Macrophages / drug effects
  • Macrophages / metabolism
  • Magnetic Resonance Spectroscopy
  • Mice
  • Molecular Conformation
  • Nitric Oxide / metabolism
  • RAW 264.7 Cells
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology
  • Soil Microbiology

Substances

  • Flavonoids
  • Lipopolysaccharides
  • Sesquiterpenes
  • Nitric Oxide

Supplementary concepts

  • Isoptericola chiayiensis