Three New Polyphenol Derivatives from the Fruits of Macaranga Monandra and their Antioxidant Potential

Chem Biodivers. 2024 Jul;21(7):e202301816. doi: 10.1002/cbdv.202301816. Epub 2024 Jun 11.

Abstract

Phytochemical investigation of the methanol extract from the fruits of Macaranga monandra (Euphorbiaceae Muell. et Arg.) afforded one new geranylated 1',2'-dihydrophenanthrene and two new flavonoid derivatives, named macamondrin (1), macamondrione A (2) and B (3) respectively. The structures of these compounds were elucidated mainly by NMR, mass spectral data and in comparison with data from the literature. Along with compounds 1-3, nine known compounds among which oleanolic acid (4); daucosterol (5); 3β-acetoxy-11α,12α-epoxytaraxerol (6); 3,3',4-tri-O-methylellagic acid (7); 3,3',4,4'-tetra-O-methylellagic acid (8); 4'-O-methyl-6-isoprenylapigenin (9); 4'-O-methyl-8 isoprenylkaempférol (10); 4'-O-methyl-6-isoprénylkaempférol (11); 6-isoprénylkaempférol (12), were also isolated. Crude extracts as well as isolated compounds were evaluated for their antioxidant activity using the ABTS, DPPH and FRAP methods. It appears that the 50 % radical scavenging concentrations ranging from 6.26 to 11.7 μg/ml on the ABTS radical, from 1.77 to 48.22 μg/ml on the DPPH radical, and from 1.54 to 67.97 μg/ml with the FRAP method. For the compounds tested, very good antioxidant activities were observed, which clearly shows that these molecules can have an anti oxidative stress potentiel.

Keywords: Antioxidant activity; Euphorbiaceae; Flavonoids; Macamondrin; Macamondrione; Macaranga monandra.

MeSH terms

  • Antioxidants* / chemistry
  • Antioxidants* / isolation & purification
  • Antioxidants* / pharmacology
  • Biphenyl Compounds / antagonists & inhibitors
  • Euphorbiaceae* / chemistry
  • Fruit* / chemistry
  • Molecular Structure
  • Picrates / antagonists & inhibitors
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology
  • Polyphenols* / chemistry
  • Polyphenols* / isolation & purification
  • Polyphenols* / pharmacology

Substances

  • Antioxidants
  • Polyphenols
  • Biphenyl Compounds
  • Picrates
  • 1,1-diphenyl-2-picrylhydrazyl
  • Plant Extracts