Ginkgonitroside, a new nitrophenyl glycoside and bioactive compounds from Ginkgo biloba leaves controlling adipocyte and osteoblast differentiation

Bioorg Med Chem Lett. 2021 Oct 15:50:128322. doi: 10.1016/j.bmcl.2021.128322. Epub 2021 Aug 15.

Abstract

Eight compounds (1-8) including one novel nitrophenyl glycoside, ginkgonitroside (1) were isolated from the leaves of Ginkgo biloba, a popular medicinal plant. The structure of the new compound was characterized using extensive spectroscopic analyses via 1D and 2D NMR data interpretations, HR-ESIMS, and chemical transformation. To the best of our knowledge, the present study is the first to report the presence of nitrophenyl glycosides, which are relatively unique phytochemicals in natural products, in G. biloba. The isolated compounds (1-8) were examined for their effects on the regulation of mesenchymal stem cell (MSC) differentiation. Compounds 1-3 and 8 were able to suppress MSC differentiation toward adipocytes. In contrast, compounds 5 and 8 showed activity promoting osteogenic differentiation of MSCs. These findings demonstrate that the active compounds showed regulatory activity on MSC differentiation between adipocytes and osteocytes.

Keywords: Adipocytes; Ginkgo biloba; Mesenchymal stem cell; Nitrophenyl derivative; Osteocytes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adipocytes / drug effects*
  • Adipocytes / physiology
  • Animals
  • Cell Differentiation / drug effects*
  • Cell Differentiation / physiology
  • Cell Line
  • Ginkgo biloba / chemistry*
  • Glycosides / chemistry
  • Glycosides / pharmacology*
  • Mesenchymal Stem Cells / drug effects*
  • Mice
  • Osteoblasts / drug effects*
  • Osteoblasts / physiology
  • Plant Leaves / chemistry

Substances

  • Glycosides