Cichorins D-F: Three New Compounds from Cichorium intybus and Their Biological Effects

Molecules. 2020 Sep 11;25(18):4160. doi: 10.3390/molecules25184160.

Abstract

Cichorium intybus L., (chicory) is employed in various traditional medicines to treat a wide range of diseases and disorders. In the current investigation, two new naphthalane derivatives viz., cichorins D (1) and E (2), along with one new anthraquinone cichorin F (3), were isolated from Cichorium intybus. In addition, three previously reported compounds viz., β-sitosterol (4), β-sitosterol β-glucopyranoside (5), and stigmasterol (6) were also isolated from Cichorium intybus. Their structures were established via extensive spectroscopic data, including 1D (1H and 13C) and 2D NMR (COSY, HSQC and HMBC), and ESIMS. Cichorin E (2) has a weak cytotoxic effect on breast cancer cells (MDA-MB-468: IC50: 85.9 µM) and Ewing's sarcoma cells (SK-N-MC: IC50: 71.1 µM); cichorin F (3) also illustrated weak cytotoxic effects on breast cancer cells (MDA-MB-468: IC50: 41.0 µM and MDA-MB-231: IC50: 45.6 µM), and SK-N-MC cells (IC50: 71.9 µM). Moreover compounds 1-3 did not show any promising anthelmintic effects.

Keywords: Asteraceae; Cichorium intybus; anthraquinone; cytotoxic effects; naphthalene; natural product.

MeSH terms

  • Anthelmintics
  • Anthraquinones / isolation & purification
  • Anthraquinones / pharmacology*
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Cichorium intybus / chemistry*
  • Humans
  • Inhibitory Concentration 50
  • Magnetic Resonance Spectroscopy
  • Medicine, Traditional
  • Molecular Structure
  • Naphthalenes / chemistry
  • Plant Extracts / chemistry*
  • Sterols / isolation & purification
  • Sterols / pharmacology*

Substances

  • Anthelmintics
  • Anthraquinones
  • Naphthalenes
  • Plant Extracts
  • Sterols
  • naphthalene