Phytochemical and biological studies of Atriplex inflata f. Muell.: isolation of secondary bioactive metabolites

J Pharm Pharmacol. 2017 Aug;69(8):1064-1074. doi: 10.1111/jphp.12735. Epub 2017 May 2.

Abstract

Objectives: This work describes the phytochemical and biological investigation of the Tunisian Atriplex inflata F. Muell (Chenopodiaceae).

Methods: Their chemical structures were elucidated on the basis of extensive spectroscopic methods, including 1D NMR and 2D NMR, ESI-HRMS and comparison with available literature data. The isolates were evaluated for their antioxidant activity by the DPPH , ABTS+• , Fe3+ and catalase assays and also for their antibacterial and anticholinesterase activity.

Key findings: The chemical study of Atriplex inflata F. Muell led to the isolation of two fatty acids (9E)-methyl-8,11,12-trihydroxyoctadec-9-enoate 1 and (9E)-8,11,12-trihydroxyoctadecenoic acid 2 together with (Z)-litchiol B 3 and 20-hydroxyecdysone 4. Three of which are reported here for the first time in Atriplex genus. Based on the biosynthesis of hydroxylated arachidonic acid and derivatives, a plausible biogenesis pathway of the two fatty acids (1 and 2) was proposed. (Z)-litchiol B (3) was found to be the most active against Staphylococcus aureus. According to the literature, this is the first time that compounds 1, 2 and 3 were tested for their eventual biological activity.

Conclusions: In the results of the present work, we have proposed the biogenesis pathway of unsaturated fatty acid and described the structure-activity relationship.

Keywords: Atriplex inflata; antibacterial; anticholinesterase; antioxidant; secondary metabolites.

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / metabolism
  • Antioxidants / chemistry
  • Antioxidants / isolation & purification
  • Antioxidants / metabolism
  • Atriplex*
  • Biological Products / chemistry
  • Biological Products / isolation & purification
  • Biological Products / metabolism
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / isolation & purification
  • Cholinesterase Inhibitors / metabolism
  • Free Radical Scavengers / chemistry
  • Free Radical Scavengers / isolation & purification
  • Free Radical Scavengers / metabolism
  • Microbial Sensitivity Tests / methods
  • Phytochemicals / chemistry
  • Phytochemicals / isolation & purification*
  • Phytochemicals / metabolism*
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification*
  • Plant Extracts / metabolism*
  • Plant Roots
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Antioxidants
  • Biological Products
  • Cholinesterase Inhibitors
  • Free Radical Scavengers
  • Phytochemicals
  • Plant Extracts