Methods of isolating alkaloids of the colchicine series

A Grand Challenge. 3. Unbiased Phenotypic Function of Metabolites from Australia Plants Gloriosa superba and Alangium villosum against Parkinson’s Disease

“…Subsequent chromatographic separation of the fractions of G. superba resulted in the isolation and characterization of 14 secondary metabolites, including four new lumicolchicine glucosides, β-lumicolchicosides A–C ( 1 – 3 ) and γ-lumicolchicoside A ( 4 ), together with the known 2- O -demethyl-β-lumicolchicine ( 5 ), 2- O -demethyl- N -deacetyl- N -formyl-β-lumicolchicine ( 6 ), N -deacetyl- N -formyl-β-lumicolchicine ( 7 ), β-lumicolchicine ( 8 ), colchicine ( 9 ), 3- O -demethylcolchicine ( 10 ), 2- O -demethylcolchicine ( 11 ), N -deacetyl- N -formylcolchicine ( 12 ), 2- O -demethyl- N -deacetyl­formylcolchicine ( 13 ), and cornigerine ( 14 ) …”

“…Tubulosine and its congeners displayed a phenotypic profile with major effects on tubulin-and EEA-1-related cytological markers. Subsequent chromatographic separation of the fractions of G. superba resulted in the isolation and characterization of 14 secondary metabolites, including four new lumicolchicine glucosides, β-lumicolchicosides A−C (1−3) and γ-lumicolchicoside A (4), together with the known 2-O-demethyl-βlumicolchicine (5), 56 2-O-demethyl-N-deacetyl-N-formyl-βlumicolchicine (6), 57 N-deacetyl-N-formyl-β-lumicolchicine (7), 58 β-lumicolchicine (8), 59 colchicine (9), 59 3-O-demethylcolchicine (10), 60 2-O-demethylcolchicine (11), 61 N-deacetyl-N-formylcolchicine (12), 62 2-O-demethyl-N-deacetylformylcolchicine (13), 61 and cornigerine (14). 63 Subsequent chromatographic separation of A. villusom fractions resulted in the isolation and characterization of nine secondary metabolites, including four new benzoquinolizidine N-oxides, tubulosine N β 5 -oxide (15), isotubulosine N α 5 -oxide (16), 9-demethyltubulosine N β 5 -oxide (17), and 9-demethylisotubulosine N α 5 -oxide (18), along with the known tubulosine (19) 64,65 and its analogues isotubulosine (20), 66,67 9demethyltubulosine (21), 68 9-demethylisotubulosine (22), 67,69 and deoxytubulosine (23).…”

Reviewing Colchicaceae Alkaloids – Perspectives of Evolution on Medicinal Chemistry

“…As the Colchicaceae alkaloids span from alkaline compounds, over aprotic or quaternary nitrogen compounds insensitive to pH-changes, to phenolic alkaloids even within the different structural types the isolation method may bias the detection of compounds [130]. Another bias in reviewing Colchicaceae alkaloids may be the strong focus on detection of colchicine itself in the literature.…”

“…Chemosystematic prediction is likewise dependent on sampling size, here as a function of the number of investigated plant species and the limits of detection for the compounds of interest using a specific method. As the Colchicaceae alkaloids span from alkaline compounds, over aprotic or quaternary nitrogen compounds insensitive to pH-changes, to phenolic alkaloids even within the different structural types the isolation method may bias the detection of compounds [ 130 ]. Another bias in reviewing Colchicaceae alkaloids may be the strong focus on detection of colchicine itself in the literature.…”