Three New 2,2'-Difurylketone Derivatives and Two New Chromones from the Rehmanniae Radix Praeparata

Chem Biodivers. 2021 Oct;18(10):e2100237. doi: 10.1002/cbdv.202100237. Epub 2021 Sep 7.

Abstract

Rehmanniae Radix Praeparata is the processed products of the root of Rehmannia glutinosa. It has been used as a Traditional Chinese Medicine for thousands of years, and it has been found to possess widely pharmacological activities. In this study, three new 2,2'-difurylketone derivatives (rehmanniaeketone A-C) and two new chromones [3,8-dihydroxy-2-(2-hydroxyethyl)chromone and 3,8-dihydroxy-2-[(2-O-α-D-galactopyranosyloxy)ethyl]chromone] were isolated from the Rehmanniae Radix Praeparata. Furthermore all of the compounds were subjected to cytotoxic testing against the human lung carcinoma A549 cells. The cytotoxic results showed that rehmanniaeketone B and rehmanniaeketone C exhibited more stronger inhibition effects on the cell activity of A549 cells with the IC50 5.23 μM and 2.05 μM than other compounds. And 3,8-dihydroxy-2-(2-hydroxyethyl)chromone exhibited moderately inhibitory activity with the IC50 61 μM. Rehmanniaeketone A and 3,8-dihydroxy-2-[(2-O-α-D-galactopyranosyloxy]chromone showed no inhibitory effects.

Keywords: 2,2′-difurylketone derivatives; Rehmanniae Radix Praeparata; chromones; cytotoxicity; extraction and isolation.

MeSH terms

  • A549 Cells
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Chromones / chemistry
  • Chromones / isolation & purification
  • Chromones / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification
  • Drugs, Chinese Herbal / pharmacology*
  • Humans
  • Ketones / chemistry
  • Ketones / isolation & purification
  • Ketones / pharmacology*
  • Medicine, Chinese Traditional
  • Molecular Structure
  • Rehmannia / chemistry*
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents, Phytogenic
  • Chromones
  • Drugs, Chinese Herbal
  • Ketones