Melotenuines A-E, cytotoxic monoterpenoid indole alkaloids from Melodinus tenuicaudatus

Fitoterapia. 2019 Oct:138:104347. doi: 10.1016/j.fitote.2019.104347. Epub 2019 Aug 27.

Abstract

Five new monoterpenoid indole alkaloids, melotenuines A-E (1-5), along with 18 known indole alkaloids, were isolated from the twigs and leaves of Melodinus tenuicaudatus. The structures of the new alkaloids were determined by a combination of MS, NMR and ECD analysis. Melotenuine A (1) represents the first example of aspidosperma-meloscandonine type bisindole alkaloids characterized by a methylene bridge between the two monomers, while melotenuine B (2) possessed a rare eburnamine-melsocandonine skeleton. All of the new indole alkaloids were evaluated for in vitro cytotoxicities against five human cancer cell lines. Among them, alkaloid 4 showed specific cytotoxicity against HL-60 cell line with IC50 value (5.15 ± 0.16 μM) comparable with that of positive control.

Keywords: Aspidosperma-meloscandonine type; Melodinus tenuicaudatus; Melotenuines A-E; Monoterpenoid indole alkaloids.

MeSH terms

  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Apocynaceae / chemistry*
  • Cell Line, Tumor
  • China
  • Drug Screening Assays, Antitumor
  • HL-60 Cells
  • Humans
  • Molecular Structure
  • Phytochemicals / isolation & purification
  • Phytochemicals / pharmacology
  • Plant Leaves / chemistry*
  • Secologanin Tryptamine Alkaloids / isolation & purification
  • Secologanin Tryptamine Alkaloids / pharmacology*

Substances

  • Antineoplastic Agents, Phytogenic
  • Phytochemicals
  • Secologanin Tryptamine Alkaloids