Two pairs of unusual melibiose and raffinose esters from Scrophularia ningpoensis

J Asian Nat Prod Res. 2018 Mar;20(3):255-262. doi: 10.1080/10286020.2017.1329301. Epub 2017 May 24.

Abstract

A pair of unusual melibiose esters (1α/1β) and a pair of unusual raffinose esters (2α/2β), were isolated from Scrophularia ningpoensis. Structures of them were established by detailed spectroscopic analyses to be 6-O-(E)-cinnamoyl-α-d-galactopyranosyl-(1→6)-α(β)-d-glucopyranose (1α/1β) and 6-O-(E)/(Z)-cinnamoyl-α-d-galactopyranosyl-(1→6)-α-d-glucopyranosyl-(1→2)-β-d-fructofuranose (2α/2β), respectively. All these compounds were evaluated for antifouling activity against the settlement of Balanus amphitrite larvae, along with the cytotoxic effect against the proliferation of HeLa cell lines.

Keywords: Scrophularia ningpoensis; Scrophulariaceae; melibiose ester; phenylpropanoid glycoside; raffinose ester.

MeSH terms

  • Animals
  • Biofouling / prevention & control
  • Esters
  • HeLa Cells
  • Humans
  • Larva / drug effects
  • Melibiose / chemistry
  • Melibiose / isolation & purification*
  • Melibiose / pharmacology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Raffinose / chemistry
  • Raffinose / isolation & purification*
  • Raffinose / pharmacology
  • Republic of Belarus
  • Scrophularia / chemistry*

Substances

  • Esters
  • Melibiose
  • Raffinose