New polyacetylenes from Echinophora cinerea (Boiss.) Hedge et Lamond

Nat Prod Res. 2017 Oct;31(19):2256-2263. doi: 10.1080/14786419.2017.1300797. Epub 2017 Mar 10.

Abstract

Echinophora cinerea aerial parts are used in folk medicine to cure gastric diseases and as a food seasoning in cheese and yogurt. Besides several pharmacological effects have been assigned to Echinophora spp., there is no phytochemical investigation on this genus other than our previous publication on flavonoids. An acetone extract of E. cinerea afforded three new (1-3) polyacetylenes, one rare monoterpenoid glycoside as verbenone-5-O-β-D-glycopyranoside (4) and one prenylated coumarin as osthol (5). The structures of all new compounds were elucidated using modern spectroscopic methods, including 2D NMR and mass analyses. The potency of the compounds to induce cell death was determined on SKNMC, PC3 and MCF-7 cell lines using MTT method in which compounds 1 and 2 showed moderate cytotoxic effects, especially against PC3 cells.

Keywords: Echinophora cinerea; Polyacetylene; monoterpenoid glycoside, echinophorin, PC3; verbenone.

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology
  • Apiaceae / chemistry*
  • Cell Death / drug effects*
  • Cell Line, Tumor
  • Coumarins / chemistry
  • Coumarins / isolation & purification
  • Coumarins / pharmacology
  • Flavonoids / chemistry
  • Glycosides / chemistry
  • Glycosides / isolation & purification
  • Glycosides / pharmacology
  • Humans
  • MCF-7 Cells
  • Medicine, Traditional
  • Molecular Structure
  • Plant Components, Aerial / chemistry
  • Polyynes / chemistry
  • Polyynes / isolation & purification*
  • Polyynes / pharmacology
  • Prenylation

Substances

  • Antineoplastic Agents
  • Coumarins
  • Flavonoids
  • Glycosides
  • Polyynes
  • coumarin