Turbinatine, a Potential Key Intermediate in the Biosynthesis of Corynanthean-Type Indole Alkaloids
Authors:
- Carmen Lucia CardosoCarmen Lucia Cardoso
- Dulce Helena Siqueira SilvaDulce Helena Siqueira Silva
- Daniela Maria TomazelaDTDaniela Maria Tomazela
- Hugo VerliHVHugo Verli
- Maria Claudia Marx YoungMaria Claudia Marx Young
- Maysa FurlanMFMaysa Furlan
- Marcos Nogueira EberlinMEMarcos Nogueira Eberlin
- Vanderlan da Silva BolzaniVanderlan da Silva Bolzani
- 17 June 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Natural Products
- Vol. 66 (7) , 1017-1021
Abstract
Extraction of the leaves of Chimarrhis turbinata has led to the isolation of turbinatine (1), a new corynanthean-type indole alkaloid, besides four known indole alkaloids, strictosidine, 5α-carboxystrictosidine, vallesiachotamine, and isovallesiachotamine. The structural determination of 1 was based on 1D and 2D spectroscopic data. An evaluation of the DNA-damaging activities of the isolates was performed by means of a bioassay using mutant strains of Saccharomyces cerevisiae, which indicated these compounds were weakly active.Keywords
This publication has 6 references indexed in Scilit:
- Highly diastereoselective mercury-mediated synthesis of functionalized 2-azabicyclo[3.3.0]octane derivativesTetrahedron Letters, 2002
- Recent progress in the chemistry of monoterpenoid indole alkaloids derived from secologaninNatural Product Reports, 1999
- First Direct and Detailed Stereochemical Analysis of StrictosidineJournal of Natural Products, 1997
- Vallesiachotamine and Isovallesiachotamine from the Seeds of Strychnos tricalysioidesPlanta Medica, 1982
- Carbon-13 NMR Shift Assignments of Amines and Alkaloids1979
- General methods of synthesis of indole alkaloids. 14. Short routes of construction of yohimboid and ajmalicinoid alkaloid systems and their carbon-13 nuclear magnetic resonance spectral analysisJournal of the American Chemical Society, 1976