Strychnobaillonine, an Unsymmetrical Bisindole Alkaloid with an Unprecedented Skeleton fromStrychnos icajaRoots
- 4 March 2014
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Natural Products
- Vol. 77 (4) , 1078-1082
Abstract
A reinvestigation of the roots of Strychnos icaja resulted in the isolation of a new bisindole alkaloid named strychnobaillonine (1) with original C-17–N-1′ and C-23–C-17′ junctions, in addition to sungucine, bisnordihydrotoxiferine, and strychnohexamine (2). Compound 1 showed potent activity against the chloroquine-sensitive 3D7 strain of Plasmodium falciparum in vitro with an IC50 value of 1.1 μM. The structures of the compounds were defined by detailed spectroscopic analyses, especially 1H and 13C NMR, DEPT, HSQC, COSY, NOESY, HMBC, and HRESIMS. The proposed absolute configuration was based on biosynthetic considerations and spectroscopic data (CD, NMR) supported by molecular modeling.Keywords
This publication has 15 references indexed in Scilit:
- Alkaloids from the stem bark of Strychnos icajaPhytochemistry Letters, 2012
- Antiplasmodial Alkaloids from the Stem Bark ofStrychnos malacocladosPlanta Medica, 2011
- About the toxicity of some Strychnos species and their alkaloidsToxicon, 2004
- Indolomonoterpenic alkaloids from Strychnos icaja rootsPhytochemistry, 2003
- Antiplasmodial Activity of Alkaloids from Various Strychnos SpeciesJournal of Natural Products, 2002
- Strychnohexamine from Strychnos icaja, a naturally occurring trimeric indolomonoterpenic alkaloidTetrahedron Letters, 2002
- Strychnogucines A and B, Two New Antiplasmodial Bisindole Alkaloids from Strychnos icajaJournal of Natural Products, 2000
- Stereochemistry of Caracurine VJournal of Natural Products, 2000
- New Antimalarial and Cytotoxic Sungucine Derivatives from Strychnos icaja RootsPlanta Medica, 2000
- New indole aldehydic alkaloids of strychnos variabilisTetrahedron Letters, 1980