Flavan derivative enantiomers and drimane sesquiterpene lactones from the Inonotus obliquus with neuroprotective effects

Bioorg Chem. 2020 Mar:96:103588. doi: 10.1016/j.bioorg.2020.103588. Epub 2020 Feb 5.

Abstract

A pair of new flavan derivative enantiomers (1a and 1b), four new drimane sesquiterpene lactones (2-5) and a known compound (6) were isolated from Inonotus obliquus. Their structures were determined by comprehensive spectroscopic analyses. Compounds 1a/1b were separated by chiral chromatographic column successfully. The absolute configurations of compounds 1-5 were determined by comparison of their experimental and calculated ECD spectra. Notably, compounds 1a/1b represented the first pair of enantiomers in nature with tetrahydrofuran-flavan skeleton. A plausible biosynthetic pathway for (±)-1 was also proposed. All isolates were evaluated for their neuroprotective activities against H2O2-induced cell injury in SH-SY5Y cells. The results showed that compound 2 exhibited moderate neuroprotective activity at the concentration of 25.0 µM.

Keywords: Drimane sesquiterpene; Flavan derivative; Inonotus obliquus; Neuroprotective activity; SH-SY5Y cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line
  • Flavonoids / chemistry
  • Flavonoids / pharmacology
  • Humans
  • Inonotus / chemistry*
  • Lactones / chemistry
  • Lactones / pharmacology
  • Neurons / drug effects
  • Neuroprotective Agents / chemistry*
  • Neuroprotective Agents / pharmacology*
  • Oxidative Stress / drug effects
  • Polycyclic Sesquiterpenes / chemistry*
  • Polycyclic Sesquiterpenes / pharmacology*
  • Stereoisomerism

Substances

  • Flavonoids
  • Lactones
  • Neuroprotective Agents
  • Polycyclic Sesquiterpenes
  • drimane