Kinetic study of the rearrangement of deuterium-labeled 4'-O-methylnorbelladine in Leucojum aestivum shoot cultures by mass spectrometry. Influence of precursor feeding on amaryllidaceae alkaloid accumulation.
Alkaloids from plants of the family Amaryllidaceae have important pharmacological properties and can be regarded as derivatives of the common precursor 4'-O-methylnorbelladine (6) via intramolecular oxidative phenol coupling. Their biosynthetic pathway, particularly in Leucojum aestivum, has not yet been totally elucidated. Therefore, shoot cultures of this plant were subcultured in medium containing the labeled precursor 4'-O-methyl-d(3)-norbelladine (3) at various concentrations (0.05, 0.10, and 0.20 g/L) and were incubated for various periods of time (15, 30, and 40 days). The aim of this work was to study the influence of this precursor on both labeled and native alkaloid accumulation. Biotransformation into galanthamine (1) and lycorine (2) in shoot cultures was demonstrated using HPLC coupled to mass spectrometry. A maximal amount of 0.16% of 1 referred to the dry weight was obtained at day 15 in shoots fed with 0.10 g/L of precursor. In addition, a 20.5% dry weight of 2 was reached after 40 days of feeding with 0.20 g/L of precursor.
Groupe S.U.C.R.E.S.,  UMR 7565 CNRS-Nancy-Université , BP 70239, 54506 Nancy-Vandœuvre, France.
Anna
A
El Tahchy
Agata
A
Ptak
Michel
M
Boisbrun
Elvina
E
Barre
Catherine
C
Guillou
François
F
Dupire
Françoise
F
Chrétien
Max
M
Henry
Yves
Y
Chapleur
Dominique
D
Laurain-Mattar
D047151:Amaryllidaceae Alkaloids / Q000032:analysis / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D003903:Deuterium; D005602:France; D005702:Galantamine / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D007700:Kinetics; D013058:Mass Spectrometry; D015394:Molecular Structure; D010617:Phenanthridines / Q000737:chemistry* / Q000378:metabolism
D047151:Amaryllidaceae Alkaloids; D010617:Phenanthridines; D005702:Galantamine; D003903:Deuterium; C015330:lycorine