Isolation of Flavonoids and Flavonoid Glycosides from Myrsine africana and Their Inhibitory Activities against Mushroom Tyrosinase

J Nat Prod. 2018 Jan 26;81(1):49-56. doi: 10.1021/acs.jnatprod.7b00564. Epub 2018 Jan 4.

Abstract

Bioassay-guided fractionation of the methanol extract of the shoots of Myrsine africana led to the isolation of the new compound myricetin 3-O-(2″,4″-di-O-acetyl)-α-l-rhamnopyranoside (9) and 11 known compounds. The known compounds quercetin 3-O-(3″,4″-di-O-acetyl)-α-l-rhamnopyranoside (8), rutin (10), quercetin 3-O-α-l-rhamnopyranoside (11), and myricetin 3-O-α-l-rhamnopyranoside (12) are reported for the first time from the methanol extract of the shoots of M. africana. Compounds 10 and 12 showed significant inhibition of tyrosinase with 50% inhibition (IC50 values) of the enzyme at 0.13 ± 0.003 and 0.12 ± 0.002 mM, respectively, which was supported by the docking fitness scores obtained through molecular docking analysis. In addition, compounds 1-12 displayed significant antioxidant activity with IC50 values ranging 1.90 to 3.90 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Agaricales / drug effects*
  • Antioxidants / chemistry
  • Antioxidants / pharmacology
  • Flavonoids / chemistry*
  • Flavonoids / pharmacology*
  • Glycosides / chemistry*
  • Glycosides / pharmacology*
  • Molecular Docking Simulation / methods
  • Myrsine / chemistry*
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology
  • Quercetin / analogs & derivatives
  • Quercetin / chemistry
  • Quercetin / pharmacology

Substances

  • Antioxidants
  • Flavonoids
  • Glycosides
  • Plant Extracts
  • quercetin-3-O-alpha-L-rhamnopyranoside
  • myricetin
  • Quercetin