Anti-inflammatory and cytotoxic carbazole alkaloids from Murraya kwangsiensis

Phytochemistry. 2020 Feb:170:112186. doi: 10.1016/j.phytochem.2019.112186. Epub 2019 Nov 12.

Abstract

Chemical investigation of the traditional Chinese medicine, Murraya kwangsiensis, led to the isolation of 16 undescribed biscarbazole alkaloids, kwangsines A-M, two undescribed natural products, (+/-)-bispyrayafoline C, and 19 known monomeric analogues. (±)-Bispyrayafoline C and (±)-kwangsines A-C are four pairs of biscarbazole atropisomers, and they were separated by chiral HPLC to obtain the optically pure compounds. The structures of the undescribed compounds were elucidated on the basis of HRESIMS and NMR data analysis. Their absolute configurations were assigned via comparison of the specific rotation, ECD exciton coupling method, as well as comparison of experimental and calculated ECD data. A compound showed significant inhibition on NO production in lipopolysaccharide-stimulated BV-2 microglial cells, and four compounds exhibited moderate cytotoxicities against HepG2 cells, with IC50 values less than 20 μM.

Keywords: Anti-inflammation; Atropisomers; Biscarbazole alkaloids; Cytotoxicity; Murraya kwangsiensis (C.C. Huang) C.C. Huang; Rutaceae.

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology*
  • 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*
  • Carbazoles / chemistry
  • Carbazoles / isolation & purification
  • Carbazoles / pharmacology*
  • Cell Line
  • Cell Proliferation / drug effects
  • Density Functional Theory
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Hep G2 Cells
  • Humans
  • Mice
  • Molecular Structure
  • Murraya / chemistry*
  • Nitric Oxide / antagonists & inhibitors
  • Nitric Oxide / biosynthesis
  • Phytochemicals / chemistry
  • Phytochemicals / isolation & purification
  • Phytochemicals / pharmacology*
  • Structure-Activity Relationship

Substances

  • Alkaloids
  • Anti-Inflammatory Agents
  • Antineoplastic Agents, Phytogenic
  • Carbazoles
  • Phytochemicals
  • carbazole
  • Nitric Oxide