Parisvaniosides A-E, five new steroidal saponins from Paris vaniotii

Steroids. 2022 Jan:177:108949. doi: 10.1016/j.steroids.2021.108949. Epub 2021 Dec 8.

Abstract

The species of Paris genus is a prolific source of structurally diverse steroidal saponins responsible for multivarious biological properties. The first phytochemical investigation on the steroidal saponin constituents from the rhizomes of Paris vaniotii Lévl. led to the discovery and structural characterization of four new spirostanol saponins, named parisvaniosides A-D (1-4), and one new furostanol glycoside, named parisvanioside E (5), along with eleven known analogues (6-16). Their structures were unambiguously established on the basis of extensive spectroscopic analysis and comparison with the reported spectroscopic data. Compound 1 is a rare spirostanol saponin sharing with a C-9/C-11 double bond and a peroxy group located between C-5 and C-8 of the aglycone, whereas 3 and 4 are unusual C-27 steroidal sapoins with hydroxyl/methoxyl at both C-5 and C-6. Furthermore, 5 is the first furostanol saponin with a unique aglycone featuring two trisubstituted double bonds in ring B. All isolated saponins were evaluated for their anti-inflammatory effects on a lipopolysaccharide (LPS)-stimulated nitric oxide (NO) production model in RAW 264.7 macrophages.

Keywords: Furostanol saponins; Melanthiaceae; Paris vaniotii Lévl.; Parisvaniosides A–E; Spirostanol saponins.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology*
  • Dose-Response Relationship, Drug
  • Liliaceae / chemistry*
  • Lipopolysaccharides / antagonists & inhibitors
  • Lipopolysaccharides / pharmacology
  • Mice
  • Molecular Conformation
  • Nitric Oxide / antagonists & inhibitors
  • Nitric Oxide / biosynthesis
  • RAW 264.7 Cells
  • Saponins / chemistry
  • Saponins / isolation & purification
  • Saponins / pharmacology*
  • Steroids / chemistry
  • Steroids / isolation & purification
  • Steroids / pharmacology*
  • Structure-Activity Relationship

Substances

  • Anti-Inflammatory Agents
  • Lipopolysaccharides
  • Saponins
  • Steroids
  • Nitric Oxide