Cytotoxic and antimalarial beta-carboline alkaloids from the roots of Eurycoma longifolia

J Nat Prod. 2003 Oct;66(10):1324-7. doi: 10.1021/np030277n.

Abstract

Three new [n-pentyl beta-carboline-1-propionate (1), 5-hydroxymethyl-9-methoxycanthin-6-one (2), and 1-hydroxy-9-methoxycanthin-6-one (3)] and 19 known beta-carboline alkaloids were isolated from the roots of Eurycoma longifolia. The new structures were determined by comprehensive analyses of their 1D and 2D NMR and mass spectral data and by chemical transformation. These compounds were screened for in vitro cytotoxic and antimalarial activities, and 9-methoxycanthin-6-one (4) and canthin-6-one (5) demonstrated significant cytotoxicity against human lung cancer (A-549) and human breast cancer (MCF-7) cell lines.

Publication types

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

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology
  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / isolation & purification*
  • Anti-HIV Agents / pharmacology
  • Antimalarials / chemistry
  • Antimalarials / isolation & purification*
  • Antimalarials / pharmacology
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Breast Neoplasms
  • Carbolines / chemistry
  • Carbolines / isolation & purification*
  • Carbolines / pharmacology
  • Drug Screening Assays, Antitumor
  • Eurycoma / chemistry*
  • Female
  • Humans
  • Lung Neoplasms
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Roots / chemistry
  • Plants, Medicinal / chemistry*
  • Tumor Cells, Cultured / drug effects

Substances

  • 1-hydroxy-9-methoxycanthin-6-one
  • 5-hydroxymethyl-9-methoxycanthin-6-one
  • Alkaloids
  • Anti-HIV Agents
  • Antimalarials
  • Antineoplastic Agents, Phytogenic
  • Carbolines
  • n-pentyl beta-carboline-1-propionate