Bioactive lipids from the fruits of Solanum xanthocarpum and their anti-inflammatory activities

Fitoterapia. 2022 Mar:157:105134. doi: 10.1016/j.fitote.2022.105134. Epub 2022 Jan 24.

Abstract

Bioactive lipids widely found in daily consumed plants and animals are essential or beneficial to health and some of them are important physiological regulators in the human body. In our current investigation, 18 bioactive lipids (1-18), including 8 sphingolipids (1-8), 7 oxylipins (9-15), 3 phenolic lipids (16-18) were isolated from the fruits of Solanum xanthocarpum. And compounds 1, 9, 15, 16, and 18 were new lipids. In this study, homologues (4-8, 16, and 17) and configuration isomers (2 and 3) of bioactive lipids were separated, and NMR combined with MS/MS2 was an effective method to identify these compounds. These findings provided the reference for the separation and structural identification of bioactive lipids. The anti-inflammatory activities of all isolated lipids were evaluated by their inhibition of the NO release of LPS-induced RAW 264.7 cells. Aglycone components of sphingolipids, oxylipids with free carboxylic acid groups, phenylpropionic acid-fatty acid glyceride polymer exhibited significant anti-inflammatory activities. Further analysis by molecular docking revealed the interactions of bioactive compounds with the iNOS protein.

Keywords: Anti-inflammatory; Lipids; Oxylipins; Phenolic lipids; Sphingolipids.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / pharmacology*
  • Fruit / chemistry*
  • Gas Chromatography-Mass Spectrometry
  • Hydrolysis
  • Inhibitory Concentration 50
  • Lipids / chemistry
  • Lipids / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Mice
  • Molecular Docking Simulation
  • Molecular Structure
  • Oxylipins / chemistry
  • Oxylipins / pharmacology
  • Phenols / chemistry
  • Phenols / pharmacology
  • Phytochemicals / chemistry
  • Phytochemicals / pharmacology*
  • RAW 264.7 Cells
  • Solanum / chemistry*
  • Sphingolipids / chemistry
  • Sphingolipids / pharmacology
  • Tandem Mass Spectrometry

Substances

  • Anti-Inflammatory Agents
  • Lipids
  • Oxylipins
  • Phenols
  • Phytochemicals
  • Sphingolipids