NMR-Guided Isolation of Anti-inflammatory Carabranolides from the Fruits of Carpesium abrotanoides L

J Nat Prod. 2024 Jul 26;87(7):1786-1797. doi: 10.1021/acs.jnatprod.4c00338. Epub 2024 Jul 10.

Abstract

Carabranolides present characteristic NMR resonances for the cyclopropane moiety, which distinctly differ from those of other compounds and were used for an NMR-guided isolation in this study. As a result, 11 undescribed carabranolides (1-11), along with five known ones (12-16), were isolated from the fruits of Carpesium abrotanoides L. Compounds 1-11 are new esters of carabrol at C-4 with different carboxylic acids. Their structures were elucidated by HRESIMS and NMR spectroscopic data analysis. The biological evaluation showed that compounds 2-4, 15, and 16 exhibited significant inhibitory activity against LPS-induced NO release with an IC50 value of 5.6-9.1 μM and dose-dependently decreased iNOS protein expression in RAW264.7 cells.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents* / chemistry
  • Anti-Inflammatory Agents* / isolation & purification
  • Anti-Inflammatory Agents* / pharmacology
  • Asteraceae* / chemistry
  • Fruit* / chemistry
  • Lipopolysaccharides / pharmacology
  • Magnetic Resonance Spectroscopy
  • Mice
  • Molecular Structure
  • Nitric Oxide Synthase Type II / antagonists & inhibitors
  • Nitric Oxide* / antagonists & inhibitors
  • Nitric Oxide* / biosynthesis
  • RAW 264.7 Cells
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology

Substances

  • Anti-Inflammatory Agents
  • Lipopolysaccharides
  • Nitric Oxide
  • Nitric Oxide Synthase Type II
  • Sesquiterpenes