New potently bioactive alkaloids from Crinum erubescens

Bioorg Med Chem. 2016 Nov 1;24(21):5418-5422. doi: 10.1016/j.bmc.2016.08.058. Epub 2016 Aug 30.

Abstract

Antimalarial bioassay-guided fractionation of the swamp lily Crinum erubescens led to the isolation of four compounds with potent antiplasmodial activity. Compounds 1 and 2 were determined from their spectroscopic data to be the known pesticidal compound cripowellin A and the known pesticidal and antiproliferative compound cripowellin B. 1D and 2D-NMR techniques were used to determine the identities of 3 and 4 as the new compounds cripowellin C and D. A fifth compound was identified as the known alkaloid hippadine, which was inactive against Plasmodium falciparum. The antiplasmodial IC50 values of compounds 1-4 were determined to be 30±2, 180±20, 26±2, and 260±20nM, respectively, and their antiproliferative IC50 values against the A2780 human ovarian cancer cell line were 11.1±0.4, 16.4±0.1, 25±2, and 28±1nM.

Keywords: Amaryllidaceae; Antimalarial; Crinum; Cripowellin; Hippadine.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, N.I.H., Extramural

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology*
  • Antimalarials / chemistry
  • Antimalarials / isolation & purification
  • Antimalarials / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Crinum / chemistry*
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Humans
  • Molecular Structure
  • Parasitic Sensitivity Tests
  • Plasmodium falciparum / drug effects*
  • Structure-Activity Relationship

Substances

  • Alkaloids
  • Antimalarials