Linaburiosides A-D, acylated iridoid glucosides from Linaria buriatica

Phytochemistry. 2020 Mar:171:112247. doi: 10.1016/j.phytochem.2019.112247. Epub 2020 Jan 8.

Abstract

Four previously undescribed acylated iridoid glucosides, linaburiosides A‒D, one undescribed iridoid, 7-deoxyiridolactonic acid, and one known acylated iridoid glucoside, iridolinarin C, were isolated from the aerial parts of a Mongolian traditional herbal medicine, Linaria buriatica. Linaburiosides A‒D had an acyl moiety corresponding to 7-deoxyiridolactonic acid. Detailed spectroscopic analyses of linaburiosides A‒D and 7-deoxyiridolactonic acid led to the assignment of their structures. The absolute configuration of 7-deoxyiridolactonic acid was elucidated by application of the PGME method; those of linaburiosides A‒D were assigned on the basis of chemical conversions, as well as application of the modified Mosher's method. The absolute configuration of iridolinarin C was also elucidated in this study. Anti-inflammatory and antiproliferative activities of isolated compounds and their derivatives were evaluated.

Keywords: Anti-inflammatory activity; Iridoid glucoside; Linaria buriatica; Mongolian traditional herbal medicine; Plantaginaceae.

MeSH terms

  • A549 Cells
  • Acylation
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology*
  • Glucosides / chemistry
  • Glucosides / isolation & purification
  • Glucosides / pharmacology*
  • Humans
  • Interleukin-1beta / antagonists & inhibitors
  • Interleukin-1beta / biosynthesis
  • Iridoids / chemistry
  • Iridoids / isolation & purification
  • Iridoids / pharmacology*
  • Linaria / chemistry*
  • Lipopolysaccharides / antagonists & inhibitors
  • Lipopolysaccharides / pharmacology
  • MCF-7 Cells
  • Microglia / drug effects
  • Microglia / metabolism
  • Molecular Conformation
  • Phytochemicals / chemistry
  • Phytochemicals / isolation & purification
  • Phytochemicals / pharmacology*
  • Tumor Cells, Cultured

Substances

  • Anti-Inflammatory Agents
  • Glucosides
  • Interleukin-1beta
  • Iridoids
  • Lipopolysaccharides
  • Phytochemicals