Six kanshone C-derived sesquiterpenoid hybrids nardochalaristolones A-D, nardoflavaristolone A and dinardokanshone F from Nardostachys jatamansi DC

Bioorg Chem. 2018 Dec:81:35-43. doi: 10.1016/j.bioorg.2018.07.030. Epub 2018 Aug 2.

Abstract

Four sesquiterpenoid-chalcone hybrids (nardochalaristolones A-D, 1-4), a pair of epimeric sesquiterpenoid-flavonone hybrids ((2'S)- and (2'R)-nardoflavaristolone A, 5 and 6), and a sesquiterpenoid dimer (dinardokanshone F, 7), all sharing a kanshone C-derived sesquiterpenoid unit, were isolated from the underground parts of Nardostachys jatamansi (D.Don) DC. Their structures were elucidated by analysis of the extensive spectroscopic data, and the absolute configurations were established by analysis of 2D NMR spectroscopic data including NOESY data, combined with comparisons of experimental and calculated electronic circular dichroism spectra. Further, the plausible biosynthetic pathways for these compounds were proposed. And the results of SERT activity assay revealed that nardochalaristolones C-D (3 and 4) and nardoflavaristolone A (5 and 6) significantly enhanced SERT activity, while other compounds didn't show any SERT regulatory activities.

Keywords: Caprifoliaceae; Dinardokanshone F; Nardochalaristolones; Nardoflavaristolone A; Nardostachys jatamansi DC..

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chalcone / chemistry
  • Chalcone / isolation & purification*
  • Molecular Structure
  • Nardostachys / chemistry*
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*

Substances

  • Sesquiterpenes
  • Chalcone