Alkaloids from Leaves and Flowers of Colchicum autumnale L.¹

Abstract

The alkaloid content in fresh and dry leaves and flowers of Colchicum autumnale ,L. was studied. Results show that 2-and 3-demethylated derivatives of colchicine do not occur in extracts from fresh material but they are present in considerable quantity in material slowly dried before extraction due to enzymatic liberation. Demethylated products are not bound in form of glycosides, but are attached in an unknown manner to cell constituents. In addition to known alkaloi,ds we have found cornigerine, 2and 3-demethyl-N-deacetyl-N-formylcolchicine, 2-and 3-demethyldemecolcine, and a new alkaloid 2-demethylcolchifoline but no alkaloids with,out tropolone ring. Suitably dried Substances from Plants of the Subfamily Wurmbaeoideae and their Derivatives. Part LXXXV. Part LXXXIV: Collection Czechoslov. Chem. Commun. .42,. 1581(1977. leaves and flowers could be used for the commercial isolation of colchicine alkaloidsinstead of seeds and corms which are difficult t o obtain.Downloaded by: University of British Columbia. Copyrighted material.------

Chemical constituents of the different parts ofColchicum baytopiorumand their cytotoxic activities on K562 and HL60 cell lines

“…Alkaloid extraction was carried out for all methanol extracts. The evaporation was done at 35°C, and during the study, direct light protection was provided (Malichova et al, 1979).…”

Transformation of Alkaloids of the Colchicine Type in Leaves and Flowers ofColchicum autumnaleandC. byzantinum

“…In our earlier paper [11], we reported that the fresh material (leaves and flowers) did not contain 2-demethylcoichicine (II) which was found in variable quantities only in the dry material. It was assumed that the O-demethylated derivatives of colchicine (I), N-deacetyl-N-formylcoichicine (XI), and demecolcine (XVII) are intermediary degradation products or that these compounds are enzymatically liberated during drying from the bond with high molecular substances [11]. In dry material (stored over a long period), BucH-Great differences exist in the "coichicine" content (tropolone alkaloids of coichicine type) reported in the literature .…”

“…N1EK found a gradual decrease in the content of tropolone alkaloids [4]. 2-Demethylcolchicine (II) was not found in dry seeds, fresh corms, leaves and flowers [11,15], whereas 3-demethylcoichicine (III) was present in dry seeds and corms; the latter alkaloid might arise in seeds on hydrolysis of colchicoside [16,17]. All the fresh parts of the plant C. autumnale and C. byzantinum contain 2-demethyldemecolcine (XIX) and traces of 3-demethyldemecolcine (Alkaloid CC-7) (XX) [18].…”

“…gravimetric method, the physico-chemical methods determine (according to the method of isolation) the total amount of tropolone alkaloids. The chromatographic methods showed [6][7][8][9][10][11]14] that the leaves and flowers contain, in addition to colchicine, several substances related to coichicine and amorphous residues from which only 3-demethyl-N-deacetylcolchicine (Alkaloid U) (XXII) and 2demethylcoichifoline (IX) could be isolated and identified [9,11]. In our earlier paper [11], we reported that the fresh material (leaves and flowers) did not contain 2-demethylcoichicine (II) which was found in variable quantities only in the dry material.…”

“…The chromatographic methods showed [6][7][8][9][10][11]14] that the leaves and flowers contain, in addition to colchicine, several substances related to coichicine and amorphous residues from which only 3-demethyl-N-deacetylcolchicine (Alkaloid U) (XXII) and 2demethylcoichifoline (IX) could be isolated and identified [9,11]. In our earlier paper [11], we reported that the fresh material (leaves and flowers) did not contain 2-demethylcoichicine (II) which was found in variable quantities only in the dry material. It was assumed that the O-demethylated derivatives of colchicine (I), N-deacetyl-N-formylcoichicine (XI), and demecolcine (XVII) are intermediary degradation products or that these compounds are enzymatically liberated during drying from the bond with high molecular substances [11].…”