New aurone epoxide and auronolignan from the heartwood of Cotinus coggygria Scop

Nat Prod Res. 2019 Oct;33(19):2837-2844. doi: 10.1080/14786419.2018.1508141. Epub 2018 Dec 4.

Abstract

New aurone epoxide, 2,10-oxy-10-methoxysulfuretin (14), and new auronolignan (15), named cotinignan A, were isolated by silica gel column and semipreparative HPLC chromatography from the methylene chloride/methanol extract of Cotinus coggygria Scop. heartwood. In addition, thirteen known secondary metabolites namely sulfuretin, 2,3-trans-fustin, fisetin, butin, butein, taxifolin, eriodictyol, 3',5,5',7-tetrahydroxyflavanone, 3',4',7-trihydroxyflavone, 3-O-methyl-2,3-trans-fustin, 3-O-galloyl-2,3-trans-fustin, β-resorcylic acid and 3-O-β-sitosterol glucoside were isolated as well. Their structures were elucidated by 1D and 2D NMR, HR-ESI-MS, IR and UV. Ten out of eleven isolated flavonoids possess 7, 3' and 4' hydroxy groups. These structural features could be considered as chemotaxonomic characteristic of flavonoids from C. coggygria. Cotinignan A (15) represents new subclass of secondary metabolites - auronolignans.

Keywords: Scop; NMR; cotinignan A; flavonoids; semipreparative HPLC.

Publication types

  • Video-Audio Media

MeSH terms

  • Anacardiaceae / chemistry*
  • Anacardiaceae / metabolism
  • Benzofurans / chemistry*
  • Benzofurans / metabolism
  • Chalcones / chemistry
  • Chalcones / metabolism
  • Chromatography, High Pressure Liquid
  • Epoxy Compounds / chemistry*
  • Epoxy Compounds / metabolism
  • Flavanones / chemistry
  • Flavanones / metabolism
  • Flavonoids / analysis
  • Flavonoids / chemistry
  • Flavonoids / metabolism
  • Flavonols
  • Hydroxybenzoates / chemistry
  • Hydroxybenzoates / metabolism
  • Molecular Structure
  • Plant Extracts / chemistry
  • Secondary Metabolism
  • Wood / chemistry*
  • Wood / metabolism

Substances

  • Benzofurans
  • Chalcones
  • Epoxy Compounds
  • Flavanones
  • Flavonoids
  • Flavonols
  • Hydroxybenzoates
  • Plant Extracts
  • aurone
  • fustin
  • butein
  • beta-resorcylic acid
  • sulfuretin
  • fisetin
  • eriodictyol