[Isolation and chemistry of alkaloids of family Papaver. XL. Contribution to the constitution of oridine-alkaloids].

Biological activity of the alkaloids of Papaver bracteatum Lindl.

Publisher Summary This chapter provides an overview of the chemotaxonomy of two families: Papaveraceae and Fumariaceae Both are very rich in specific alkaloids The family Papaveraceae Juss is subdivided into the subfamilies Hypecoideae Prantl and Kundig and Papaveroideae A Br It embraces 23 genera and ∼430 species The Fumariaceae DC include 7 genera with ∼350 species The alkaloids of the Papaveraceae and Fumariaceae can be subdivided into several constitutional types—that is, simple isoquinolines, benzylisoquinolines, pavines, isopavines, cularines, proaporphines, aporphines, promorphinanes, morphinanes, protoberberines, retroprotoberberines, secoberbines, benzophenanthridines, protopines, phthalideisoquinolines, secophthalideisoquinolines, indenobenzazepines, spirobenzylisoquinolines, and rhoeadines The most widespread alkaloids of the Papaveraceae Juss are protoberberines, benzophenanthridines, and protopines, which, with a few exceptions, are present in all genera The Papaveraceae and Fumariaceae DC are closely related families Their relationship and their independence are well demonstrated by the external structure of the flowers, the various anatomical characteristics of their different organs, and alkaloid content

Chapter 1 Chemotaxonomy of Papaveraceae and Fumariaceae

Total syntheses of the proaporphine alkaloids pronuciferine (6), stepharine (19), amuronine (7), amuroline (24) and of some derivatives thereof, all as racemates, are described.

Über die Synthese des Pronuciferins und einiger weiterer Proaporphin-Alkaloide. 6. Mitteilung über natürliche und synthetische Isochinolinderivate†

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

Publisher Summary In the organization of this chapter, it adds the isoquinoline alkaloids to the group of benzylisoquinoline alkaloids and renames the group of tetrahydroprotoberberine and protoberberine alkaloids into a group of alkaloids of the berbine type because the Papaveraceae plants were also found to contain pseudoprotoberberine bases. The narceineimide alkaloids with two nitrogens were classified with the narceine alkaloids, and the group of spirobenzylisoquinoline alkaloids was subdivided into (a) ochotensimine, (b) hypecorine and canadaline and, (c) peshawarine types of alkaloids. It was deemed necessary to add the group of dimeric alkaloids and the group of those alkaloids which occur in the Papaveraceae plants, but are not derived from isoquinoline or benzylisoquinoline. New information on the alkaloids in the individual Papaveraceae plants contributes to the chemotaxonomic classification of the individual plant species to the correct tribes and genera. For this reason, the section on chemotaxonomy, ecology, and callus tissues has been added.

[Isolation and chemistry of alkaloids of family Papaver. XL. Contribution to the constitution of oridine-alkaloids].

Citations

Biological activity of the alkaloids of Papaver bracteatum Lindl.

Chapter 1 Chemotaxonomy of Papaveraceae and Fumariaceae

Über die Synthese des Pronuciferins und einiger weiterer Proaporphin-Alkaloide. 6. Mitteilung über natürliche und synthetische Isochinolinderivate†

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

Chapter 4 Papaveraceae Alkaloids. II