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From these early reviews a much wider distribution for colchicine was inferred [ 43 ]. However, refined chemical detection methods have discarded many reports as false positives [ 41 , 44 ]. The more restricted distribution originally proposed coincided largely with the, at that time, recently introduced lilioid subfamily Wurmbaeoideae [ 45 ], today more familiar as the family Colchicaceae [ 46 ]. With the advent of molecular systematics based on comparison of DNA sequences it was shown that a few genera such as Disporum Salisb. Investigation of crude alkaloid extracts with mass spectrometry has also confirmed that colchicine is present in, and restricted to, the genera of Colchicaceae in this wider circumscription [ 49 ].
An Australian species described under the name Kreysigia multiflora Rchb. However the exact identity of this species is confounded by the application of this name to plants belonging to Schelhammera as well as Tripladenia.
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Just as genera have been included in the family based on phylogenetic analysis of nucleotide data, analysis of such data has also resulted in a notable exclusion. The genus Disporum was considered to be present in both Asia and North America, but results from genetic studies have shown that the North American representatives should be treated as a distinct genus, Prosartes D.
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Don, and be moved to the family Liliaceae [ 51 ]. The family Colchicaceae as currently circumscribed thus constitutes 15 genera and about species, of which more than half belong to Colchicum [ 48 ]. A number of reviews on phenethylisoquinoline alkaloids can be found in the literature [eg. However, they usually only treat a particular group of a specific structural type and will be exemplified under the respective alkaloid type below.
The present contribution provides a review of Colchicaceae alkaloids of all types as well as perspectives of their origin, evolution and hypothetical biosynthetic pathways. In the Combined Chemical Dictionary [ 53 ] there are about entries with structurally elucidated alkaloids reported from Colchicaceae genera. They are biosynthetically derived from condensation of phenylalanine and tyrosine to a phenethylisoquinoline precursor, which has been shown by several feeding experiments in elucidation of colchicine biosynthesis [ 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 , 63 , 64 , 65 ].
Based on proposed biosynthesis, feeding experiments and analogies of pathways elucidated for benzylisoquinoline alkaloids, as presented in Fig. Phenethylisoquinolines and homoerythrinans have also been isolated from Dysoxylum in the mahogany family Meliaceae, which also contain a dibenzo[ d,f ]azecine alkaloid [ 53 , 66 , 67 , 68 , 69 ].
The homoerythrinan alkaloids also have additional disjunct occurrences in the monogeneric New Caledonian family Phellinaceae [ 53 , 70 ] and the gymnosperm families Taxodiaceae, Podocarpaceae and Cephalotaxaceae [ 53 , 71 , 72 ]. Another group of alkaloids derived from phenethylisoquinoline precursors are the cephalotaxines unique for the family Cephalotaxaceae, which has recently been reviewed [ 73 ]. Thus, in total there are ten structural types of alkaloids with a possible common precursor.
The hypothetical network of their interrelations as presented in Fig. The included diarylazahexanoid precursors could constitute alternative biosynthetic pathways to homoerythrinan alkaloids explaining their disjunct distribution. Hypothetical network of phenethylisoquinoline derived alkaloids based on proposed biosynthesis, feeding experiments and analogies of pathways elucidated for benzylisoquinoline alkaloids.
A: phenethylisoquinolines; B: homoproaporphines; C: homoaporphines; D: androcymbines; E: colchicines; F: allocolchicines; G: lumicolchicines; H: dibenzo[ d,f ]azecines; I: homoerythrinans; and J: cephalotaxines. Six phenethylisoquinoline alkaloids have been described from Colchicaceae, see Fig. There are only few reports of isolation of these alkaloids [ 74 , 75 , 76 , 77 , 78 ], perhaps due to their proposed functions as precursors and thus efficient transformation into other structural types.
They do not seem to have been tested for biological activity, but phenethylisoquinolines from Dysoxylum have shown effects on isolated rat cardiac muscle [ 79 ]. These minor alkaloids, see Fig. Several homoproaporphines have been investigated for cholinergic activity [ 99 , ], showing moderate anticholinesterase activities. These alkaloids were last reviewed in , see Fig.
This group, see Fig. Structural diversity of the androcymbine homomorphinan alkaloids in Colchicaceae. This is the largest group of alkaloids within Colchicaceae as of today, see Fig. A statement that is true even if, as done here, the allo- and lumicolchicine derivatives are excluded. They commonly interact with tubulin and are considered to be a main toxic principle of Colchicaceae plants.
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They have also been evaluated for anticholinesterase activity [ ]. This is the first isolated group of alkaloids containing a tropolone ring in their structure, a fact that has been used to distinguish them from other alkaloids in simple TLC screenings due to a positive Oberlin-Zeisel reaction when sprayed with FeCl 3 after treatment with HCl vapor [ 41 ], and are thus sometimes known as tropolonic alkaloids.
This name would however also include the unrelated tropoloisoquinoline alkaloids described from Abuta in the moonseed family Menispermaceae [ , , ]. A further ten colchicine-type alkaloids have been described as minor components from Colchicum and Gloriosa species since that review [ 78 , , , , ]. Even though colchicine itself is deemed to be too toxic as an anti-cancer drug, investigation of compounds binding to the same site and interacting with tubulin is an active field of research [ ]. There is also a continued interest in modification of the colchicine-type core to modify toxicity and activity of these compounds [ , , , ].
These alkaloids are also called dibenzocycloheptylamines, see Fig. They usually retain the colchicine-type alkaloids ability to bind to tubulin but are less toxic, which has yielded some interest as potential antitumor drugs [ 34 , ]. Structural diversity of the allocolchicine alkaloids in Colchicaceae. There is a debate whether these alkaloids, see Fig. In contrast to allocolchicines the lumicolchicine-derivatives lack specific binding to tubulin.
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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 [ ]. However, among the phenethylisoquinoline alkaloids this is a very widespread group present in Dysoxylum of Meliaceae [ 66 ], Phelline of Phellinaceae [ 70 ], Athrotaxis of Taxodiaceae [ 71 ], Manoao of Podocarpaceae [ 72 ], and Cephalotaxus of Cephalotaxaceae [ 73 ]. Some homoerythrinan alkaloids can even be found in several of these families, eg.
The ten homoerythrinan-type alkaloids found in Colchicaceae, see Fig. The alkaloid 3-epischelhammericine as well as other alkaloids from Dysoxylum have shown molluscicidal activity and cardiac effects [ 67 , 79 ], and dyshomoerythrine from Manoao is reported to have insecticidal activity [ ]. Five alkaloids, see Fig. They are all isolated from different species of Colchicum [ , , , ]. Structural diversity of miscellaneous phenethylisoquinoline alkaloids in Colchicaceae.
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. In molecular systematic studies based on nuclear sequences the characters will equal the number of nucleotides in the sequence used for analysis. For Colchicaceae a family wide investigation based on chloroplast gene sequences, representing fourteen out of fifteen genera the single species of Kuntheria was not sampled has been published [ 47 ].
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A genus-level tree based on those results, with Kuntheria placed together with Schelhammera and Tripladenia , is shown in Fig. The phylogenetic hypothesis and classification for Colchicaceae modified from Vinnersten and co-workers [46, 47]. The dendrogram clearly shows that the groups not traditionally associated with phenethylisoquinoline alkaloids constitute the basal clades of the family. As further discussed in the text this highlights them as potential new sources of Colchicaceae alkaloids, or even new structural types of phenethylisoquinoline alkaloids.
Chemosystematic prediction is likewise dependent on sampling size, here as a function of the number of investigated plant species and the limits of detection for the compounds of interest using a specific method. As the Colchicaceae alkaloids span from alkaline compounds, over aprotic or quaternary nitrogen compounds insensitive to pH-changes, to phenolic alkaloids even within the different structural types the isolation method may bias the detection of compounds [ ].
Another bias in reviewing Colchicaceae alkaloids may be the strong focus on detection of colchicine itself in the literature. This alkaloid is by far the most commonly reported compound, and it has been shown to be present in all investigated genera of the family by nanospray-MS again with the single species of Kuntheria unsampled [ 49 ].
However, the similarities between the systematic and chemical sampling on genus level makes Colchicaceae a good case study in evolution of chemical characters. The genera Uvularia and Disporum have been treated as part of the now defunct family Uvulariaceae, which by some authors also have included Schelhammera including the later segregated Kuntheria and Tripladenia , though these latter genera have also been placed in the former Convallariaceae [ 46 , ].
Burchardia has been reported to be devoid of tropolonic alkaloids [ ], and its relationship to the rest of Colchicaceae have been questioned and sometimes it is instead treated in a monogeneric family Burchardiaceae [ ]. The alkaloid chemistry of the early diverging lineages, Burchardieae and Uvularieae, has not been investigated in any detail according to standard literature searches, but the three genera are confirmed to contain colchicine [ 49 ].
The chemistry of the tribe Tripladenieae, which is restricted to eastern Australia extending to New Guinea, have in comparison been fairly extensively investigated. The genera Schelhammera and Kuntheria are unique in Colchicaceae by producing homoerythrinan instead of colchicine-type alkaloids as major components [ , , , , ]. Further investigations are needed to see if this is the case for Tripladenia as well. 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.
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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. 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.
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.
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Each volume provides, through its distinguished authors, up-to-date and detailed coverage of particular classes or sources of alkaloids. Over the years, this series has become the standard in natural product chemistry to which all other book series aspire. The Alkaloids, Chemistry and Pharmacology endures as an essential reference for all natural product chemists and biologists who have an interest in alkaloids, their diversity, and their unique biological profile. Business seller information. Contact details. Return policy. You must return items in their original packaging and in the same condition as when you received them.
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