Alkaloids from the stem bark of Micromelum falcatum

Chem Pharm Bull (Tokyo). 2009 Jun;57(6):600-2. doi: 10.1248/cpb.57.600.

Abstract

Two new quinoldione alkaloids, methyl 2-(3-hydroxy-1-methyl-2,4-dioxo-1,2,3,4-tetrahydroquinolin-3-yl)acetate (1) and 3-hydroxy-1-methyl-3-(2-oxopropyl)quinoline-2,4(1H,3H)-dione (2), and two quinolinone alkaloids previously synthesized but first isolated as natural products, N-methylflindersine (3) and 4-hydroxy-3-methoxy-1-methyl-2(1H)-quinolinone (4), were isolated from the stem bark of Micromelum falcatum, together with the known N-methylswietenidine-B (5). Their structures were established mainly on the basis of 1D- and 2D-NMR techniques. All compounds were evaluated for toxicity towards brine shrimp larvae, and 3 showed strong toxicity with an LD(50) value of 1.39 microg/ml.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry*
  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology
  • Animals
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Artemia
  • Drug Screening Assays, Antitumor
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Plant Bark / chemistry
  • Plant Stems / chemistry
  • Quinolines / chemistry*
  • Quinolines / isolation & purification
  • Quinolines / pharmacology
  • Rutaceae / chemistry*
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet

Substances

  • 3-hydroxy-1-methyl-3-(2-oxopropyl)quinoline-2,4(1H,3H)-dione
  • Alkaloids
  • Antineoplastic Agents, Phytogenic
  • Indicators and Reagents
  • Quinolines
  • methyl 2-(3-hydroxy-1-methyl-2,4-dioxo-1,2,3,4-tetrahydroquinolin-3-yl)acetate