4,21-Secovincanol, a Novel Immunosuppressive Monoterpenoid Indole Alkaloid from Kopsia Hainanensis

Chem Biodivers. 2021 May;18(5):e2100084. doi: 10.1002/cbdv.202100084. Epub 2021 Mar 30.

Abstract

4,21-Secovincanol (1), a novel C-21/N-4 cleavage monoterpenoid indole alkaloid, along with four analogs (2-5), were obtained from the aerial parts of Kopsia hainanensis. Structurally, compound 1 might be a derivative of epivincanol (2) via C-21/N-4 cleavage. Their structures were confirmed by means of comprehensive spectroscopic data analysis and comparison with the reported data. All isolates significantly inhibited Con A-stimulated mice splenocytes proliferation at 10-40 μM in a dose-dependent manner in vitro. Especially, compound 3 exhibited potent activities comparable to positive control (Dexamethasone, DXM).

Keywords: 4,21-secovincanol; Kopsia hainanensis; immunosuppressive activity; monoterpenoid indole alkaloid.

MeSH terms

  • Animals
  • Apocynaceae / chemistry*
  • Cell Proliferation / drug effects
  • Concanavalin A / antagonists & inhibitors
  • Concanavalin A / pharmacology
  • Dose-Response Relationship, Drug
  • Immunosuppressive Agents / chemistry
  • Immunosuppressive Agents / isolation & purification
  • Immunosuppressive Agents / pharmacology*
  • Mice
  • Molecular Structure
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology*
  • Spleen / drug effects*

Substances

  • Immunosuppressive Agents
  • Plant Extracts
  • Concanavalin A