Mansoins C-F, Oligomeric Flavonoid Glucosides Isolated from Mansoa hirsuta Fruits with Potential Anti-inflammatory Activity

J Nat Prod. 2016 Sep 23;79(9):2279-86. doi: 10.1021/acs.jnatprod.6b00390. Epub 2016 Aug 22.

Abstract

Continued investigation of the polyphenolic pool of the fruits of Mansoa hirsuta afforded four additional members of the new class of glucosylated oligomeric flavonoids comprising a flavanone core linked to 1,3-diarylpropane C6-C3-C6 units. The structures and absolute configurations of mansoins C-F (3-6) were established by analysis of NMR and electronic circular dichroism data. Mansoin C (3) was identified as a diglucosylated heterodimer, whereas mansoins D (4), E (5), and F (6) were identified as triglucosylated heterotrimers, isomeric with mansoin A (1). Mansoin F (6) inhibited TNF-α release by lipopolysaccharide-stimulated THP-1 cells (IC50 of 19.3 ± 1.3 μM) and, as with mansoin A (1), reduced the phosphorylation levels of p-65-NF-κB, when assayed at 50 μM. These results indicate that the potential anti-inflammatory properties of mansoin F (6) are probably due to inhibition of the NF-κB pathway and inhibition of TNF-α release.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification*
  • Anti-Inflammatory Agents / pharmacology*
  • Bignoniaceae / chemistry*
  • Flavonoids / chemistry
  • Flavonoids / isolation & purification*
  • Flavonoids / pharmacology*
  • Fruit / chemistry
  • Glucosides / chemistry
  • Glucosides / isolation & purification*
  • Glucosides / pharmacology*
  • Humans
  • Lipopolysaccharides / pharmacology
  • Molecular Structure
  • NF-kappa B / antagonists & inhibitors
  • Tumor Necrosis Factor-alpha / antagonists & inhibitors

Substances

  • Anti-Inflammatory Agents
  • Flavonoids
  • Glucosides
  • Lipopolysaccharides
  • NF-kappa B
  • Tumor Necrosis Factor-alpha