Synthesis and antioxidant activity of prenylated resveratrol

Tagor Marsillam Siregar, Emil Budianto, Herry Cahyana, Widajanti Wibowo

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

Resveratrol derivatives have been reported to have important bioactivities. Synthesis of monomeric resveratrol derivatives has been a challenging topic in both organic and medicinal chemistry. A Synthesis of prenylated resveratrol was developed through prenylation between resveratrol (3,5,4'-trihydroxystilbene) and prenyl bromide (3,3-dimethyl allyl bromide) using heterogeneous superbase catalyst γ-Al 2 O 3 /NaOH/Na. The aim of this research is to obtain prenylated resveratrol compound that has important bioactivity and to identify a type of prenylation, O-or C-prenylation. Characterization of the product was carried out using liquid chromatography-mass spectrometry (LC-MS) and nuclear magnetic resonance ( 1 H-NMR). The antioxidant activity of the samples was determined using DPPH radical scavenging assay. The results of LC-MS analysis of the product showed the molecular ion peak at m/z 365.38 [M+H] + that indicated the presence of prenylated resveratrol with two prenyl (C 5 H 9 -) substituent. The 1 H-NMR spectrum of the product indicated that the addition of two prenyl substituent occurs at the hydroxyl group on the structure of resveratrol (O-prenylation). Prenylation caused decreasing free radical scavenging activity of the product (IC 50 = 102,75 ppm) compared to resveratrol (IC 50 = 63,52 ppm) and it means that the addition of prenyl substituents occurs through O-prenylation.

Original languageEnglish
Pages (from-to)1765-1770
Number of pages6
JournalRasayan Journal of Chemistry
Volume11
Issue number4
DOIs
Publication statusPublished - 1 Oct 2018

Keywords

  • Antioxidant activity
  • Prenyl bromide
  • Prenylated resveratrol
  • Prenylation
  • Resveratrol
  • Superbase catalyst γ-Al O /NaOH/Na

Fingerprint Dive into the research topics of 'Synthesis and antioxidant activity of prenylated resveratrol'. Together they form a unique fingerprint.

Cite this