Biotransformation of (RS)-reticuline and morphinan alkaloids by cell cultures of Papaver somniferum

Minor alkaloids of Fumaria indica seeds

Two new isoquinoline alkaloids, named fumaranine (2) and fumarostrejdine (10), along with 18 known alkaloids were isolated from aerial parts of Fumaria officinalis. The structures of the isolated compounds were elucidated on the basis of spectroscopic analyses and by comparison with literature data. The absolute configuration of the new compound 2 was determined by comparing its circular dichroism spectra with those of known analogs. Compounds isolated in sufficient amounts were evaluated for their acetylcholinesterase, butyrylcholinesterase, prolyl oligopeptidase (POP), and glycogen synthase kinase-3β inhibitory activities. Parfumidine (8) and sinactine (15) exhibited potent POP inhibition activities (IC50 99±5 and 53±2 μM, resp.).

Isoquinoline Alkaloids from Fumaria officinalis L. and Their Biological Activities Related to Alzheimer's Disease.

Publisher Summary This chapter describes characteristic features of the nuclear magnetic resonance (NMR) spectra of alkaloids, illustrated by examples taken predominantly from papers published during the period January 1969–June 1972. In many of these papers, alkaloid structures have been assigned using NMR structure correlations established prior to the period under review and in some cases this work has been included. The classification of the alkaloids into groups follows that adopted in the Chemical Society specialist report on alkaloids. The classification occasionally differs from that in alkaloid texts on the basis of the volume of NMR data available, a relatively small alkaloid group may be allotted a full sub-section and an important family incorporated into a related group. In addition, if NMR spectral similarities between certain alkaloids are great enough then these alkaloids are discussed together even though this necessitates removal of the alkaloid from its “natural” section. S0066410308603282

Nuclear Magnetic Resonance of Alkaloids

From whole plants of Bulbocodium vernum L. the flavone luteoline (I) and the alkaloids colchicine (II), N-formyl-N-deacetylcolchicine (III), 3-demethylcolchicine (V), (+)-bulbocodine (IX) and (−)-kreysigine (XI) were isolated in crystals. The presence of 2-demethylcolchicine (IV), s- (VII) and γ-lumicolchicine (VIII), demecolcine (VI) and five not identified alkaloids was demonstrated by thin-layer chromatography. On the basis of ultraviolet, infrared and mass spectra, PMR.-analysis (Overhauser effect), and circular dichroism, the (6a-R, 8a-S)homo-proaporphine structure IX, with one methoxy group at C-2, has been assigned to (+)-bulbocodine. The (6a-R)-structure (XI) was deduced for (−)-kreysigine by comparing its optical rotation and circular dichroism which the values of (−)-multifloramine (X), the structure of which is known.

Alkaloide Von Bulbocodium vernum L Inhaltstoffe der Liliaceae‐Wurmbaeoideae. 75. Mitteilung

The nuclear Overhauser effect has been used to confirm the structures proposed for two alkaloids isolated from Fumaria officinalis L.

Nuclear overhauser effect studies on fumaria alkaloids

Structures are proposed for three alkaloids isolated from Fumaria officinalisL. The three alkaloids, with a common ring system, are structurally related to the known ochotensimine.

C.-Y. Chen

Papers

Nuclear overhauser effect studies on fumaria alkaloids

The structures of three alkaloids from Fumaria officinalis L.

The structure and configuration of caseamine and caseadine two novel tetrahydroprotoberberines from Corydalis caseana A. Gray.