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However, as stated above a plant under the name of Kreysigia multiflora has been shown to contain appreciable amount of homoaporphine, homoproaporphine and colchicine-type alkaloids [ 50 , , ], and this plant is either Tripladenia or a species of Schelhammera. The collection data for the material used by Badger and Bradbury [ ] indicate that their original isolation is done on Tripladenia cunninghamii.

Our nanospray mass spectrometry screening has confirmed the presence of colchicine in both Schelhammera and Tripladenia [ 49 ]. The three remaining tribes constitute the classical subfamily Wurmbaeoideae [ 45 ] or Colchicaceae in its strict sense [ 46 ] and several reviews of their alkaloid contents have been published [ 41 , 44 , 52 , , ]. Besides colchicine- and lumicolchicine-type alkaloids Iphigenieae also contain homoaporphine and homomorphine alkaloids [ , , , ], while only colchicine- and lumicolchicine-type alkaloids have been reported from the few species investigated from the tribe Anguillarieae [ 44 , ].

The most species-rich tribe is Colchiceae, which also contains Colchicum and Gloriosa the two most studied genera, and it is reported to contain all structural types present in Colchicaceae except for homoerythrinan alkaloids [ 97 , , , , , , , , , , , , , , , , , , , , , , ]. Combining this distribution data with the hypothetical biosynthetic network in Fig. Since this pathway contains the androcymbine-type alkaloids as an intermediate, these are also expected to have a family-wide distribution.

The homoaporphine and homoproaporphine alkaloids are both present in the tribe Colchiceae, while only homoaporphines are present in the tribe Iphigenieae. This could indicate that the two types are biosynthesized by independent pathways, and that homoproaporphines are not precursors for homoaporphines as would be suggested by analogy with benzylisoquinoline alkaloids.

There is some experimental evidence that this is the case [ 57 ]. The homoerythrinan alkaloids are often discussed together with their erythrinan counterparts [ , , ], and their biosynthesis is considered to be analogous to these. The two possible pathways to homoerythrinan alkaloids in Fig. A pathway analogous to that proposed for erythrinan alkaloids [ , ] would include androcymbine-type intermediates, while a pathway from diarylazahexenoid-type precursors would by-pass these and directly produce dibenzo[ d,f ]azecines.

Regardless of the validity of any of these hypotheses, the large structural variation and the high proportion and wide range of biological activities associated with alkaloids make them a highly interesting compound-type for medicinal chemists. However, the research focus is often limited to a very small number of compounds with extraordinary activity, such as colchicine in the present example.

This might be due to presence of low concentrations of minor components, bias in selection of screening assays for biological activity, or skewed sampling of plant material. We argue that by accepting the notion that natural products are prevalidated for biological activity and taking evolutionary aspects into account, these potential problems can be attenuated and open new avenues of interesting research.

Of the phenethylisoquinoline alkaloids of Colchicaceae only colchicine-type alkaloids have been, and is still, extensively investigated and the activity under scrutiny has almost exclusively been that of cytotoxicity. This leaves seven structural groups of alkaloids within the family for which we today have very little information on possible biological activities and roles. Especially interesting from this perspective are the homoerythrinan alkaloids, seemingly absent in most of the family and replacing colchicine-type alkaloids in Tripladenieae.

With the presence of these alkaloids in several distantly related plant groups it is imperative to predict that they have biological activities of potential for human use, and the reported molluscicidal and insecticidal activities can be considered as a starting point and need further investigations.


From an evolutionary standpoint it is also obvious that the sampling of Colchicaceae has been very skewed. This is notable for the early lineages as well as the second most species rich genus Wurmbea. Compared to the structural diversity of known benzylisoquinoline and Amaryllidaceae alkaloid types, which have at least analogous biosynthesis patterns, the phenethylisoquinoline alkaloids of Colchicaceae is a small group.

This could be the result of undersampling of different phylogenetic lineages within the family. It has been argued that we only take advantage of a very small fraction of the plant biodiversity around us. As an example De Luca and co-workers propose in depth collaborative investigations of plant metabolomes, using new technologies to elucidate and modify biosynthetic pathways to create larger yields or new chemically diverse biological active compounds [ ].

Another option for finding new compounds or activities, as argued here, is taking advantage of evolutionary evidence in selection of the plants or compounds to be studied. The phylogenetic distribution of specific compounds predicts at least one of either presence of biosynthetic pathways or advantageous biological activity, thus identifying less known or unstudied chemistry. Based on the known phylogenetic hypothesis in Fig.

The structure of osmium tetraoxide-cinchona alkaloid complexes

In conclusion we have shown how thinking about evolution can influence selection of plant material in drug lead discovery, and how knowledge about phylogenetic relationships may be used to evaluate predicted biosynthetic pathways and identify priority species for further study. The author s confirm that this article content has no conflicts of interest. Europe PMC requires Javascript to function effectively.

3B 6.11 Alkaloids

Recent Activity. The snippet could not be located in the article text. This may be because the snippet appears in a figure legend, contains special characters or spans different sections of the article. Bentham Science Publishers. Curr Top Med Chem. Published online Jan. PMID: S, Copenhagen DK, Denmark. This article has been cited by other articles in PMC.

Abstract The subject of chemosystematics has provided insight to both botanical classification and drug development. Keywords: Alkaloids, biosynthetic pathways, colchicaceae, colchicine, evolution, phylogenetic prediction. Table 1. Uvularieae Disporum Salisb. Uvularia L. Tripladenia D. Don Iphigenieae Camptorrhiza E. Phillips Iphigeniopsis Buxb. Iphigenia Kunth Anguillarieae Baeometra Salisb. Wurmbea Thunb. Anguillaria R. Dipidax Lawson ex Salisb.

Neodregea C. Wright Onixotis Raf. Colchiceae Colchicum L. Androcymbium Willd. Bulbocodium L. Merendera Ramond Gloriosa L. Littonia Hook. Hexacyrtis Dinter Ornithoglossum Salisb. Sandersonia Hook. Open in a separate window. Phenethylisoquinolines Type A Six phenethylisoquinoline alkaloids have been described from Colchicaceae, see Fig. Structural diversity of the phenethylisoquinoline alkaloids in Colchicaceae.

Homoproaporphines Type B These minor alkaloids, see Fig. Structural diversity of the homoproaporphine alkaloids in Colchicaceae. Homoaporphines Type C These alkaloids were last reviewed in , see Fig. Structural diversity of the homoaporphine alkaloids in Colchicaceae. Androcymbines Type D This group, see Fig. Structural diversity of the colchicine-type alkaloids in Colchicaceae. Allocolchicines Type F These alkaloids are also called dibenzocycloheptylamines, see Fig. Lumicolchicines Type G There is a debate whether these alkaloids, see Fig. Structural diversity of the lumicolchicine alkaloids in Colchicaceae.

Homoerythrinans Type I This group of alkaloids has a very narrow distribution within Colchicaceae and has only been found in the Australian genera Schelhammera and Kuntheria [ , , , , ], of which the latter is a relatively recent taxonomic split from the former [ ]. Structural diversity of the homoerythrinan alkaloids in Colchicaceae. Miscellaneous Alkaloids Five alkaloids, see Fig. Phylogeny of Colchicaceae and Alkaloid Distribution A phylogenetic hypothesis of plant relationships is dependent on sampling size, which is a function of the number of investigated plant species and the number of characters in the matrix.

Presence of Pathways Combining this distribution data with the hypothetical biosynthetic network in Fig. Bate-Smith EC. The phenolic constituents of plants and their taxonomic significance I. The phenolic constituents of plants and their taxonomic significance II.

Swain T, editor. Chemical plant taxonomy. Harborne J. Chemosystematics and coevolution. Pure App. Dahlgren RMT. A revised system of classification of the angiosperms. The distribution of characters within an angiosperm system I. Some embryological characters. Complex pigment evolution in the Caryophyllales. New Phytol. Evidence for the monophyletic evolution of benzylisoquinoline alkaloid biosynthesis in angiosperms. Corrected version Phytochemistry.

Parallel evolution of glucosinolate biosynthesis inferred from congruent nuclear and plastid gene phylogenies. Patterns of embryological and biochemical evolution in the asterids. Abbott HCDS, editor. Cambridge MA. The Riverside Press; The chemical basis of plant forms.

Franklin Institute Lecture Natural products as sources of new drugs over the 30 years from to Expanding the ChemGPS chemical space with natural products. Novel chemical space exploration via natural products. Journal of Medicinal Chemistry. Do biologically relevant compounds have more chance to be drugs. QSAR Comb. Cheminformatic analysis of natural products and their chemical space. Newman DJ. Natural products as leads to potential drugs an old process or the new hope for drug discovery.

Bon RS, Waldmann H. Bioactivity-guided navigation of chemical space. Charting navigating and populating natural product chemical space for drug discovery. Larsson S. Can phylogeny predict chemical diversity and potential medicinal activity of plants. A case study of Amaryllidaceae.

BMC Evo. In The Alkaloids Chemistry and Biology. Chapter 5 The pharmacology and therapeutic aspects of colchicine. Colchicine in clinical medicine. A guide for internists. The tubulin colchicine domain a molecular modelling per-spective. Hartung EF.

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History of the use of Colchicum and related medicaments in gout. Annals of the Rheumatic Diseases. Evans WC. Trease and Evans Pharmacognosy. Saunders Elsevier Edinburgh. New York. Analgesic-antipyretics and anti-inflammatory agents drugs employed in the treatment of gout. Yang LPH. Methods of inducing doubling of chromosomes in plants by treatment with colchicine. Tjio JH, Levan A. The chromosome number of man. Schmidts M, Bastians H. Mitotic drug targets and the development of novel anti-mitotic anticancer drugs. Drug Resi. Microtubule-binding natural products for cancer therapy. Planta Med.

Desacetylmethylcolchicine in treatment of myeloid leukaemia. They have shown that when the major groups of plant secondary natural products are examined, alkaloids rank the lowest in feeding preference 7.

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In this paper we will examine potential relationships between the chemistry of alkaloids in the host plants and effects that these compounds may have on insect herbivores. In many cases the specific alkaloid that is produced by a particular plant has different effects on different insects. When the data are available, specific associations between the plant alkaloids and the feeding behavior of the insect herbivore will be made.

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