Termisoflavones A-C, Isoflavonoid Glycosides from Termite-Associated Streptomyces sp. RB1

J Nat Prod. 2016 Dec 23;79(12):3072-3078. doi: 10.1021/acs.jnatprod.6b00738. Epub 2016 Dec 2.

Abstract

Three new isoflavonoid glycosides, termisoflavones A-C (1-3), and eight isoflavonoids (4-11) were isolated from termite-associated Streptomyces sp. RB1 recovered from the cuticle of the South African termite, Macrotermes natalensis. The structures of new compounds were determined by spectroscopic methods including 1D and 2D NMR and HR-MS analysis, as well as comparison of their NMR data with those of related isoflavonoid glycoside derivatives. The absolute configurations of the sugar moieties were clarified by chemical reactions. None of the isolates (1-11) displayed antifungal or antimicrobial activities (MICs > 100 μg/mL), whereas compounds 6 and 11 ameliorated cisplatin-induced kidney cell damage to 80% of the control value at a cisplatin dose of 25 μM.

MeSH terms

  • Acetylcysteine / pharmacology
  • Animals
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Candida albicans / drug effects
  • Cisplatin / pharmacology
  • Cryptococcus / drug effects
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Isoflavones / chemistry
  • Isoflavones / isolation & purification*
  • Isoptera / microbiology*
  • Kidney / cytology
  • Kidney / drug effects
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • South Africa
  • Streptomyces / chemistry*

Substances

  • Anti-Bacterial Agents
  • Glycosides
  • Isoflavones
  • termisoflavone A
  • termisoflavone B
  • termisoflavone C
  • Cisplatin
  • Acetylcysteine