Protoberberine alkaloids, biological

The protoberberine alkaloids and their derivatives show at least three types of biological activity antimicrobial, uterine, and antileukemic and antineo-plastic. ... 

Plants that contain protoberberine alkaloids are reported to be used as analgesics, antiseptics, sedatives, and stomatics in Chinese folk medicine. In Indian and Islamic folk medicine, such plants are used for bleeding disorders and eye diseases, and as antiseptics, sedatives, stomatics, and uterine muscle depressants. Both quaternary alkaloids and their tetrahydro derivatives possess many substantiated biological and therapeutic effects, e.g., pahnatine, jatrorrhizine, and tetrahydropahnatine have been reported to show in vitro antimalarial activity. In China, tetrahydropalmatine is used as an analgesic, and has been reported to exhibit bradycardial, hypotensive, and sedative activities 4). 

Biological Activities Related for Protoberberine Alkaloids in the Literature between... 

The pharmacological investigations being carried out with the protoberberine alkaloids have been showing, as the years advance, a growing and relevant number of very important biological activities. 

Based on the data compiled between 1986 and 2001, one can effectively observe that very simple living systems, such as bacteria and fungi, and more complex organic systems, have shown susceptibility to the diverse biological activities exercised by the protoberberine alkaloids. This fact denotes the number of possibilities that can arise in the near future for the utilization of this class of alkaloids as tools to benefit health care, in the area of experimental pharmacology, or even as preventive or curative therapeutic agents. 

As the study of the protoberberine alkaloids is continuously expanding, other biological activities will undoubtedly be either reported or evaluated in more detail in the near future, foreseeing an optimization and growth of the knowledge already consolidated. A complete list of all of the biological activities reported for the protoberberine alkaloids is presented in Table III. 

Following the previous reviews published by Manske (1954), Jeffs (1967), and Bhakuni (1986), it is easy to see that the research on these alkaloids has grown substantially. This review covers the period from 1986 to 2001, and it shows that there were 589 citations describing studies on the phytochemistry and/or biological activities of 138 protoberberine alkaloids isolated from 310 plants from 13 families. Among the families cited as producers of protoberberine alkaloids, a simple analysis of Fig. 1, calls attention to the vast majority of citations from plants of the family Papaveraceae with 332 citations (45% of the total), followed by the family Berberidaceae with 144 citations (19%), and the family Ranunculaceae with 90 citations (12%). In terms of the number of different protoberberine alkaloids isolated from the families, again the family Papaveraceae comes in first place with 54 different alkaloids (39%), followed by the family Menispermaceae with 42 (30%), and the family Annonaceae with 36 (26%) different alkaloids. Chart 1 also shows that the families Apocynaceae, Fabaceae, Polygalaceae, and Rubiaceae each had only one alkaloid of this type described in the period. 

This volume of The Alkaloids Chemistry and Biology might be called The Brazilian Volume since each of the three chapters is compiled and written exclusively by Brazilian authors. This is definitely a reflection of the tremendous current Brazilian interest in the investigation and potentiation of their vast array of natural resources, and particularly of alkaloid-bearing plants. In this volume, the recent progress relating to three groups of alkaloids, the protoberberine alkaloids, the Stemona alkaloids, and the alkaloids of the plant family Hernandiaceae is reviewed. 

The first chapter, by da-Cunha, Fechine, Guedes, Barbosa-Filho, and da Silva is an overview of the protoberberine alkaloids from the aspects of their distribution, very diverse biological activities, and NMR data. This is the first review of this important group of alkaloids in twenty years. 

The most important aspect of coralyne is its ability to inhibit DNA relaxation in a fashion significantly similar to the most potent antitumour alkaloid camptothecin, which is known to exert this property [242], Presumably, the most notable biological action of these alkaloids appears to be topoisomerase inhibition [238-242], which has direct relevance to their DNA intercalating property. In this context. Pilch et al. [167] described a mixed binding mode model (Fig. 16) in which the protoberberine structure constitutes portions that can intercalate or bind to the minor groove of DNA. Wang et al. [240] demonstrated that coralyne (Ci) and several of its derivatives (Ce to Ch) (Scheme 5), including the partial saturated... 

A number of reviews on various aspects of QBA have been published. The principal information can be found in the two books on isoquinoline alkaloids by Shamma [1,2] and the reviews by Santavy [3,4] and Simanek [5] in The Alkaloids series. A highly valuable review of the physical and spectral data and the occurence of the 88 benzophenanthridine alkaloids has been compiled by the Shamma group [6], Preininger has summarized the distribution of QBA in plant species of the Papaveraceae and Fumariace-ae families [7]. A review by Dostal and Potacek specifically devoted to the in vitro nucleophilic conversions of QBA appeared in 1990 [8], Surveys on the biological activities [9-11] and biosynthetic formation [12,13] of these alkaloids have been published. Well-designed reviews of the syntheses of the QBA are also available [14-16]. Hanaoka and Mukai presented a treatise on the biomimetic syntheses of the benzophenanthridines from the protoberberines in volume 14 of the Studies in Natural Products Chemistry series [17]. Quite recently, a book by Bentley treating isoquinoline alkaloids also involved benzophenathridines [18]. 

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