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Review
. 2008 Aug 27;13(8):1875-96.
doi: 10.3390/molecules13081875.

Rigorous biogenetic network for a group of indole alkaloids derived from strictosidine

László F Szabó  1
Affiliations
Review

Rigorous biogenetic network for a group of indole alkaloids derived from strictosidine

László F Szabó. Molecules. .

Abstract

Strictosidine, the precursor of more than 2,500 indole alkaloids, was isolated from four species of three plant families. By searching the Dictionary of Natural Products on DVD it was found that about 150 indole alkaloids were obtained from the same species (coalkaloids), which is a direct proof of their common origin. On the base of their three-dimensional structure, taxonomic properties and standard reaction mechanisms an extended network was established which involved the four fundamental skeletons, the three types of carbon framework in the secologanin subunit and all major groups of indole alkaloids derived from secologanin and tryptamine (except a few minor groups, in which only less then 10 alkaloids were known). The system was extended to the heterodimer indole alkaloids and the quinoindole alkaloids as well.

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Figures

Scheme 1
Scheme 1
The Coupling Reaction.
Scheme 2
Scheme 2
System of Indole Alkaloids Derived from Secologanin.
Scheme 3
Scheme 3
Primary Cyclizations of Vincosan.
Scheme 4
Scheme 4
Further Representatives of the Malindan and Vallesiachotaman Skeletons.
Scheme 5
Scheme 5
Further Cyclic Systems Derived from the Corynanthean Skeleton.
Scheme 6
Scheme 6
Chemotaxonomic Interrelations between Strychnan and Aspidospermatan Alkaloids.
Scheme 7
Scheme 7
Central Role of Stemmadenine and Secodine Derivatives.
Scheme 8
Scheme 8
Formation of Type II and Type III Alkaloids.
Scheme 9
Scheme 9
Some Coalkaloids with Rearranged Secologanin Subunits.
Scheme 10
Scheme 10
Types of Heterodimer Indole Alkaloids.
Scheme 11
Scheme 11
Selected Examples of Heterodimer Indole Alkaloids.
Scheme 12
Scheme 12
Some Special Structures.
Scheme 13
Scheme 13
A Special Case.
See this image and copyright information in PMC

References

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