16892-03-8Relevant academic research and scientific papers
Biosynthesis. Part 28.1,2 Colchicine: Definition of intermediates between O-methylandrocymbine and colchicine and studies on speciosine
Barker, Alan C.,Julian, David R.,Ramage, Robert,Woodhouse, Robert N.,Hardy, Gilbert,McDonald, Edward,Battersby, Alan R.
, p. 2989 - 2994 (1998)
Labelled samples are prepared of demecolcine 3, colchicine 4, N-formyl-N-deacetylcolchlcine 6 and N-deacetylcolchicine 7, the last depending on a new method for its preparation from colchicine. Incorporation experiments with these compounds and with specifically labelled autumnaline 1 support the pathway 2→5→3→6→7→4 as the terminal sequence for the biosynthesis of colchicine. The key intermediate O-methylandrocymbine 2 is isolated from Colchicum autumnale plants together with speciosine 14 and its O-acetyl derivative 15; all three are first isolations from this plant. Speciosine 14 and N-methyldemecolcine 8 are shown to be formed in vivo largely from demecolcine 3 whereas N-formyldemecolcine 5 is the precursor of demecolcine and its N-formyl group is derived from C-3 of autumnaline. This discovery of a tropolone alkaloid which retains both carbons of the ethanamine bridge of 2 is important for future stereochemical work on the ring-expansion process.
ALKALOID SPECIOSEINE FROM Colchicum speciosum
Chommadov, B. Ch.
, p. 218 - 222 (2007/10/02)
The fraction of weak bases from Colchicum speciosum Stev. (family Liliaceae) has yielded a new compound - specioseine.The structure of 10-demethylspeciosine has been established for this base by chemical and spectral methods.
