Phytochemical, antimicrobial and antiquorum-sensing studies of pulicaria undulata L.: a revision on the structure of 1β,2α,3β,19α,23-pentahydroxy-urs-12-en-28-oic acid

Nat Prod Res. 2020 Mar;34(6):804-809. doi: 10.1080/14786419.2018.1503658. Epub 2018 Nov 13.

Abstract

Phytochemical study of the aerial part of Pulicaria undulata L. led to the isolation of nine compounds. The structure of 1β,2α,3β,19α,23-pentahydroxy-urs-12-en-28-oic acid (4) was revised and confirmation of the stereochemical configuration of the hydroxyl groups was established using NOESY and selective decoupling experiments. The other compounds were identified as 1,2-dehydro-1,10α-dihydropseudoivalin (1), axillarin (2), grandifloric acid-15-β-glucoside (3), myrianthic acid (5), caffeic acid (6), quercetin (7), paniculoside IV (8) and caffeic anhydride (9). The structures were characterized by 1 D, 2 D NMR spectroscopy and confirmed with HRMS. Antimicrobial and antiquorum-sensing activities of the different extracts and isolated compounds of the plant were investigated. Generally, the phenolic rather than the terpenoidal compounds exhibited remarkable antimicrobial and antiquorum-sensing activity.[Formula: see text].

Keywords: 1β,2α,3β,19α-pentahydroxy-urs-12-en-28-oic acid; Antimicrobial; Antiquorum-sensing; Asteraceae; Pentahydroxy triterpenoid; Pentahydroxy ursolic acid; Pulicaria undulata.

MeSH terms

  • Anti-Infective Agents / isolation & purification*
  • Anti-Infective Agents / pharmacology
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Phenols / isolation & purification
  • Phenols / pharmacology
  • Phytochemicals / isolation & purification*
  • Phytochemicals / pharmacology
  • Plant Extracts / chemistry
  • Pulicaria / chemistry*
  • Quorum Sensing / drug effects*
  • Triterpenes / chemistry*
  • Triterpenes / isolation & purification
  • Triterpenes / pharmacology

Substances

  • Anti-Infective Agents
  • Phenols
  • Phytochemicals
  • Plant Extracts
  • Triterpenes