Bioactive bisbenzylisoquinoline alkaloids from the roots of Stephania tetrandra

Bioorg Chem. 2020 May:98:103697. doi: 10.1016/j.bioorg.2020.103697. Epub 2020 Feb 24.

Abstract

Ten new bisbenzylisoquinoline alkaloids (1-10) and eight known analogues (11-18) were obtained from the roots of Stephania tetrandra. The structures of these compounds were determined by spectroscopic methods, single-crystal X-ray diffraction, electronic circular dichroism analyses, and chemical method. Compounds 1, 15, and 16 showed the better anti-inflammatory activities with IC50 values of 15.26 ± 2.99, 6.12 ± 0.25, and 5.92 ± 1.89 μM, respectively. Compound 18 possessed cytotoxic activities against MCF-7, HCT-116, and HepG2 cell lines with IC50 values of 2.81 ± 0.06, 3.66 ± 0.26, and 2.85 ± 0.15 μM, respectively.

Keywords: Anti-inflammatory activities; Bisbenzylisoquinoline alkaloids; Cytotoxicity; Menispermaceae; Stephania tetrandra.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Benzylisoquinolines / chemistry
  • Benzylisoquinolines / isolation & purification
  • Benzylisoquinolines / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Humans
  • Lipopolysaccharides / antagonists & inhibitors
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects
  • Macrophages / metabolism
  • Mice
  • Molecular Structure
  • Nitric Oxide / antagonists & inhibitors*
  • Nitric Oxide / biosynthesis
  • Plant Roots / chemistry*
  • Stephania tetrandra / chemistry*
  • Structure-Activity Relationship

Substances

  • Anti-Inflammatory Agents
  • Antineoplastic Agents, Phytogenic
  • Benzylisoquinolines
  • Lipopolysaccharides
  • Nitric Oxide