Lupane triterpenoids, antioxidant potential and antimicrobial activity of Myrciaria floribunda (H. West ex Willd.) O. Berg

Nat Prod Res. 2019 Feb;33(4):506-515. doi: 10.1080/14786419.2017.1402311. Epub 2017 Nov 13.

Abstract

Chemical composition of the methanol extract of Myrciaria floribunda leaves was investigated. The nor-lupane triterpenoids platanic acid and messagenic I acid were identified, along with other known triterpenoids (betulinic aldehyde, ursolic acid acetate and betulinic acid), a new lupane triterpenoid (2α,6α,30-trihydroxybetulinic acid) and the flavonoids catechin, quercetrin and mirycitrin. The structures were determined by spectroscopic methods (NMR, LC-MS, GC-MS). The major isolated compound was betulinic acid. The methanol extract and 2α,6α,30-trihydroxybetulinic acid were evaluated for their DPPH scavenging potential. The tested triterpenoid was one hundred times more active than betulinic acid, but less active than the extract. Screening for antimicrobial activity showed that the methanol extract was active against Staphylococcus aureus and Escherichia coli, but inactive against Candida albicans and Candida krusei, while 2α,6α,30-trihydroxybetulinic acid was inactive to all tested microorganisms.

Keywords: 2α,6α,30-trihydroxybetulinic acid; DPPH; antibacterial activity; betulinic acid.

MeSH terms

  • Anti-Infective Agents / analysis
  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / pharmacology*
  • Antioxidants / analysis
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Betulinic Acid
  • Candida albicans / drug effects
  • Drug Evaluation, Preclinical / methods
  • Flavonoids / chemistry
  • Gas Chromatography-Mass Spectrometry
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Myrtaceae / chemistry*
  • Pentacyclic Triterpenes
  • Plant Extracts / analysis
  • Plant Extracts / chemistry*
  • Plant Extracts / pharmacology
  • Plant Leaves / chemistry
  • Staphylococcus aureus / drug effects
  • Triterpenes / analysis
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification
  • Triterpenes / pharmacology*

Substances

  • Anti-Infective Agents
  • Antioxidants
  • Flavonoids
  • Pentacyclic Triterpenes
  • Plant Extracts
  • Triterpenes
  • lupane
  • Betulinic Acid