Benzylisoquinoline alkaloids distribution

The benzylisoquinoline alkaloids are widely distributed in nature and are intermediates in the biosynthesis of alkaloids of this family (2, 3). It is not surprising therefore that several groups (6, 7, 15, 23) have examined their spectra. Among the alkaloids that have been studied are reticuline (26) (7), norlaudanosine (27) (7), laudanosine (28) (6, 15), and the cis- and trans-N-oxides of laudanosine, 29 and 30, respectively (7). The chemical shifts of laudanosine are recorded in Table IV and the structures of the alkaloids may be found in Fig. 4. 

Protoberberines The protoberberine alkaloids are the most widely distributed benzylisoquinoline alkaloids. Hundreds of alkaloids of this series are discovered that they were yielded from the tetrahydroisoquinoline catalyzed by BBE [16], the berberine bridge... 

Distribution of Benzylisoquinoline Alkaloids Ipecacuanha Alkaloids Biosynthesis... 

Other families known to possess isoquinoline alkaloids include the Alangiaceae, Chenopodiaceae (a family related to the Cactaceae), Fabaceae, Musaceae, Nymphaeaceae, and Sterculiaceae (Lundstrom, 1983). At least four species of the Chenopodiaceae contain isoquinoline alkaloids, whereas other species contain P-phenylethylamines. Many of the plants that contain benzylisoquinoline alkaloids also contain smaller amounts of isoquinoline alkaloids. Among these are plants belonging to the Annonaceae, Euphorbiaceae, Fuma-riaceae, Hemandiaceae, Menispermaceae, Monimiaceae, Papaveraceae, Ranunculaceae, and Rhamnaceae (Lundstrom, 1983). The distribution of benzylisoquinoline alkaloids is discussed in more detail below. 

The protoberberine alkaloids are one of the most widely distributed groups of the benzylisoquinoline alkaloids (a subgroup of these is called berberine alkaloids ). Approxi-... 

Fig. 3.12. Correlation of the evolutionary advancement parameters relative to the oxidation levels (EAq) of benzylisoquinoline alkaloids (Barreiros, Kaplan, Gottlieb unpublished data) and Sporne s (76) evolutionary advancement indices of families belonging to the superorders Magnoliiflorae (circles) and Ranunculiflorae (squares) [sensu Dahlgren (18)]. The EA, values represent the weighted means of the oxidation levels of all benzylisoquinoline alkaloids known to occur in the family. The genus is taken as the fundamental taxonomic unit - i.e., the oxidation level of one compound present in n genera enters the list of oxidation levels n times in order to heighten the significance of the breadth of the compound s distribution...

The first chapter, by Barbosa-Filho, da-Cunha, and Gray, describes in great detail the tremendous volume of research that has been conducted in recent years on the alkaloids of the Menispermaceae, a family which produces a wide structural range of benzylisoquinoline alkaloids. The second chapter is a very special collaborative effort by three Japanese chemistry groups led by Somei, Murakami, and Ninomiya discussing the recent developments on the synthesis of the ergot alkaloids. Finally, Skaltsounis, Mitaku, and Tillequin discuss the diverse acridone alkaloids from the perspectives of their isolation, distribution, synthesis, and biological properties. 

Some twenty-seven populations of Bulgarian T. minus have been studied for their chromosome number, and dimeric alkaloids have been detected in thirteen of them. It was noted that the hexaploid cytotype is more commonly found in the lowlands, while the decaploids are more typical to the mountains above 1500 meters. In addition, bisbenzylisoquinolines are found only in the hexaploids, while aporphine-benzylisoquinolines occur only in the decaploids. It may be assumed from this research that up to two cytotypes and two chemotypes have been detected in Bulgaria that show an attitudinal pattern of distribution. 

These more complex phenylalanine-derived alkaloids, benzylisoquinolines and others, are also found in ca. 40 families the exact number depends on how the various families are delimited. In about 12 of them the occurrence of the alkaloids is rare. The main distribution in the subclass Magnoliidae, Dictoyledons (Dahlgren 1980), is as follows ... 

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