Ophiorrhines A and B, Two Immunosuppressive Monoterpenoid Indole Alkaloids from Ophiorrhiza japonica

Org Lett. 2018 Dec 21;20(24):7926-7928. doi: 10.1021/acs.orglett.8b03489. Epub 2018 Dec 10.

Abstract

Two monoterpenoid indole alkaloids, ophiorrhines A (1) and B (2), were obtained from plant Ophiorrhiza japonica BI. Their structures were elucidated by extensive spectroscopic methods and single crystal X-ray diffraction. Compounds 1 and 2 possess a novel spirocyclic ring system. Its biosynthesis pathway is proposed. Compound 2 exhibits potent inhibitory activity against concanavalin A (Con A) induced T cell proliferation and lipopolysaccharide (LPS) induced B lymphocyte cell proliferation with IC50 values 13.3 and 7.5 μM, respectively. Compound 1 exhibits significant inhibition specifically against the LPS-induced proliferation of B lymphocyte cells with IC50 value 18.6 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Humans
  • Leukemia, B-Cell / chemically induced
  • Leukemia, B-Cell / drug therapy*
  • Leukemia, B-Cell / pathology
  • Lipopolysaccharides / antagonists & inhibitors
  • Lipopolysaccharides / pharmacology
  • Molecular Structure
  • Rubiaceae / chemistry*
  • Secologanin Tryptamine Alkaloids / chemistry
  • Secologanin Tryptamine Alkaloids / isolation & purification
  • Secologanin Tryptamine Alkaloids / pharmacology*
  • Structure-Activity Relationship

Substances

  • Lipopolysaccharides
  • Secologanin Tryptamine Alkaloids