CGC-MS of alkaloids inLeucojum aestivum plants and theirin vitro cultures

Abstract

Underivatised alkaloid mixtures extracted from intact plants and in vitro cultures of Leucojum aestivum (Amaryllidaceae) were investigated by capillary GC-MS. Excellent peak resolution for the alkaloids was exhibited and isomers of galanthamine and N-formylnorgalanthamine were well separated. Fourteen alkaloids of galanthamine, lycorine and crinane types were identified, 11 in the intact plants and eight in the in vitro cultures.

Plant Sources of Galanthamine: Phytochemical and Biotechnological Aspects

“…Apart from galanthamine, three other alkaloids with a higher Ache inhibitory activity than galanthamine, namely sanguinine, N-allylnorgalanthamine and N-(14-methylallyl) norgalanthamine, have been isolated from snowflake (10,13,22). the percentage of galanthamine in the alkaloid mixture of leaves was reported for one population (12%) (9). Galanthamine was found to vary from 4 to 99 % of all compounds in the alkaloid mixtures of dormant bulbs from eighteen Bulgarian populations (22).…”

“…The galanthamine proportion in alkaloid mixtures of L. aestivum shoot-clumps varies greatly among different lines, sometimes consisting almost 100 %. Another major alkaloid in L. aestivum shootclumps, lycorine, can reach up to 77% of total alkaloids (9,22 alkaloid patterns, which may be used to control the plant source of galanthamine substances. the introduction of crops with a higher proportion of galanthamine in the alkaloid mixtures is also of interest because it will facilitate the isolation and purification of this compound and could reduce the extraction costs.…”

“…Phytochemical studies have revealed the occurrence of about 36 alkaloids in the alkaloid mixtures of L. aestivum (5, 9, 10, 13, 22, 29, 30, 41, 42, 46; table 1), which also show geographical variations in their distribution. As an example, leucotamine and methylleucotamine (29), two galanthamine type alkaloids, were isolated from plants grown in Japan, but they were not detected in plants collected in Bulgaria (9,22,46). Apart from galanthamine, three other alkaloids with a higher Ache inhibitory activity than galanthamine, namely sanguinine, N-allylnorgalanthamine and N-(14-methylallyl) norgalanthamine, have been isolated from snowflake (10,13,22).…”

“…however, the degree of cell and tissue differentiation, strongly influences the galanthamine content in these two species (38,44), and the lowest levels of galanthamine have been found in calli: 12 ug/g for L aestivum and 0.03 ug/g for N. confusus both referred to dry weight. As shoot-clump cultures have a higher ability to synthesise this compound, they have been used as a model system for studies on in vitro galanthamine production (8,9,38,44,45). the galanthamine content in shoot-clumps was found to vary when the cultures were cultivated on nutrient media with different combinations of phytohormones (20).…”

Influence of auxins on somatic embryogenesis and alkaloid accumulation in Leucojum aestivum callus

“…Galanthamine is produced on a large scale from Bulgarian Leucojum aestivum [4] and also by chemical synthesis [5][6][7]. However, the synthesis is complicated and time consuming because galanthamine has three asymmetric carbons requiring stereochemically controlled synthesis.…”