Two new iridoid glycosides from Gardeniae Fructus

Carbohydr Res. 2021 Mar:501:108259. doi: 10.1016/j.carres.2021.108259. Epub 2021 Feb 15.

Abstract

Two new iridoid glycosides, genipin 1,10-di-O-α-l-rhamnoside (1) and genipin 1,10-di-O-β-d-xylopyranoside (2), along with thirteen known compounds (3-15) were isolated from Gardeniae Fructus. Their structures were elucidated by physical data analyses such as NMR, UV, IR, HR-ESI-MS, as well as chemical hydrolysis. All compounds were tested for their tyrosinase inhibitory and antioxidant activities. At a concentration of 25 μM, compound 13 showed obvious mushroom tyrosinase inhibition activity with % inhibition value of 36.52 ± 1.98%, with kojic acid used as the positive control (46.09 ± 1.29%). At a concentration of 1 mM, compounds 8 and 9 exhibited considerable DPPH radical scavenging activities, with radical scavenging rates of 48.54 ± 0.47%, 58.59 ± 0.39%, respectively, with l-ascorbic acid used as the positive control (59.02 ± 0.77%).

Keywords: Antioxidant; Gardeniae fructus; Iridoid glycoside; Tyrosinase.

MeSH terms

  • Agaricales / enzymology
  • Carbohydrate Conformation
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification
  • Enzyme Inhibitors / pharmacology*
  • Gardenia / chemistry*
  • Iridoid Glycosides / chemistry
  • Iridoid Glycosides / isolation & purification
  • Iridoid Glycosides / pharmacology*
  • Monophenol Monooxygenase / antagonists & inhibitors*
  • Monophenol Monooxygenase / metabolism

Substances

  • Enzyme Inhibitors
  • Iridoid Glycosides
  • Monophenol Monooxygenase