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