Bisbenzylisoquinoline alkaloids pharmacology

Bisbenzylisoquinoline alkaloids are dimeric benzyltetrahydroisoquinoline alkaloids that are known for their pharmacological activities. A well-described example is the muscle relaxant (+)-tubocurarine, which in crude form serves as an arrow poison for South American Indian tribes. In the biosynthesis of this broad class of dimeric alkaloids, it has been postulated that the mechanism of phenol coupling proceeds by generation of phenolate radicals followed by radical pairing to form either an inter- or intramolecular C - O or C - C bond. Enzyme studies on the formation of bisbenzylisoquinoline alkaloids indicated that a cytochrome P-450-dependent oxidase catalyzes C - O bound formation in the biosynthesis of berbamunine in Berberis cell suspension culture.15 This enzyme, berbamunine synthase (CYP80A1), is one of the few cytochromes P-450 that can be purified to... 

Kuroda, H., Nakazawa, S., Katagiri, K., Shiratori, O., Kozuka, M., Fujitani, K. and Tomita, M. 1976. Antitumor effects of bisbenzylisoquinoline alkaloids. Chemistry and Pharmacology Bulletin, 24 2413-2420. 

The format follows that of the earlier review. The subject of synthesis, however, which formerly constituted a separate chapter, is included in this work, and other coverage has been expanded, particularly in the areas of plant biochemistry and pharmacology. The tabulation of all known bisbenzylisoquinoline alkaloids has been revised and updated. A section listing other major review articles on these alkaloids is also included, and the reader may wish to consult some of these for extensive physical data. In keeping with the original purpose of this treatise, we have tried for a comprehensive overview, with strong emphasis on the specific chemistry of the bisbenzylisoquinoline alkaloids, rather than an exhaustively detailed presentation. 

Bisbenzylisoquinoline alkaloids. Comprehensive tabulation of literature for 1978-1981 (Chemical Abstracts Volumes 88-95), with 164 references. Covers structure revisions, additional (mainly spectral) data on known alkaloids, new sources of known alkaloids, structures, properties, summarized confirmatory reactions of new alkaloids, and biosynthetic evidence. Alkaloids are tabulated by botanical sources and pharmacological activity. A section on methods (CD, luminescence spectra, specific rotation, TLC) is included. 

Pharmacological activities of bisbenzylisoquinoline alkaloids that have appeared between mid-1984 and mid-1986 are given in Table VI. Table VI provides an update of Table II (Section VIII). 

MP Cava, KT Buck, and KL Stuart in The Alkaloids. Vol. 16. pp. 249, The Bisbenzylisoquinoline Alkaloids — Occurrence, Structure and Pharmacology, RHF Manske, Ed., Academic Press, New York (1977). 

Pharmacological Activity Other Biological Activity Protoberberidine Alkaloids Biosynthesis Biological Activity Protopine Alkaloids Benzophenanthridine Alkaloids Phthalideisoquinoline Alkaloids Rhoeadane Alkaloids Dibenzopyrrocoline Alkaloids Pavine and Isopavine (Argemone) Alkaloids Cularine Alkaloids Bisbenzylisoquinoline Alkaloids Biological Activity... 

Previous volumes of this treatise have addressed the occurrence, chemistry, and pharmacology of the major structural types of alkaloids found in Guatteria. Nevertheless, of the 20 bisbenzylisoquinolines described to date as Guatteria constituents, only 2 are discussed in the chapter by Cava et al. (1), and only... 

The bisbenzylisoquinolines have been the subject of many pharmacological studies, motivated originally by the knowledge that quaternary alkaloids of this type are the active constituents of tube curare. Certain nonquaternary bisbenzylisoquinolines, notably belonging to the curine group, are also smooth muscle re-laxants many bisbenzylisoquinolines are hypotensive, and a few possess anti-... 

The known chemistry of the Annonaceae is mainly based on the work of Cave and Leboeuf on the benzyhsoquinoline alkaloids. After this work, several papers were published which evidenced the presence of alkaloids derivatives of isoquinolines. Approximately 800 alkaloids of the types isoquinolines, protoberberine, aporphine, and others were isolated from different genera of the Aimonaceae. Previous chemical and pharmacological investigations have indicated that bisbenzylisoquinolines are important bioactive components existing in plants of the Annonaceae family. Other terpenes, flavonoids, Hgnans, acetogenins, and some aromatic compounds are also found in the family but the alkaloids are the major chemical constituents. 

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