Tropane alkaloids distribution

Biological Activity of Tropane Alkaloids Distribution of Tropane Alkaloids Piperidine Alkaloids Alkaloids from Piper Species Piperine Alkaloids Involving Condensation with Acetate/Malonate Sedum Alkaloids Lobelia Alkaloids Lycopodium Alkaloids Piperidine Alkaloids in Insects Polyketide-Derived Alkaloids Coniine... 

The tropane alkaloids occur mainly in the plant family Solanaceae but are also found in the families Convolvufaceae, Erythroxylaceae, Proteaceae, and Rhizophoraceae. In addition, the presence of tropane alkaloids has occasionally been indicated in the families Euphorbiaceae and Cruciferae (cf. Tables II and III). For a detailed account of the distribution of tropane alkaloids among species, interested readers should consult Refs. (15-23) and references therein. 

Griffin WJ and Lin GD (2000) Chemotaxonomy and geographical distribution of tropane alkaloids. Phytochemistry 53, 623-637. 

Table 6 Tropane alkaloid analysis by LC-MS and LC-MS/MS for distribution studies in vivo and in vitro... 

N-raethyl group and occur occasionally as minor constituents in plants producing tropane alkaloids [76,77]. A recent survey of the occurrence of calystegines in Solanaceae and Convolvulaceae plants discovered that they are widely distributed in these families [1,2,78-80],... 

TROPANE ALKALOIDS IN ADVENTITIOUS ROOT CULTURES 5.1. Distribution of tropane alkaloids in solanaceous species... 

The tropane alkaloids in Datura and Atropa are largely concentrated in the veins of the leaves (247, 292), but when Cyphormndra is grafted on Datura the greater amount of alkaloids is outside the veins. When Atropa is grafted on tobacco the nicotine is distributed as it is in tobacco leaves (247). 

Hygrine-type alkaloids are very often detected in members of the Solanaceae family which contain tropane alkaloids. In particular, cuscohygrine is present in nearly all cases. In a similar way but in a smaller number of genera, hygrine is distributed in plants which contain tropane alkaloids, as for example in the Erythroxylum species (Erythroxylaceae). 

Tropane alkaloids mainly occur in the Solanaceae family but are also found in other families such as Convolvulaceae, Erythroxylaceae, Proteaceae and Rhizophoraceae. Less frequently, tropane alkaloids have been mentioned in the Euphorbiaceae, Brassicaceae and Olacaceae families which show no taxonomic relationships with Solanaceae. In several species of Erythroxylum, the tropane alkaloids are characterized by a 3 3-hydroxy function and a carboxyl group at C-2 of the tropane nucleus. The most famous representant of this group is cocaine (Fig. 2). In Table 1 the distribution of tropane alkaloids in the plant kingdom is indicated. 

Table 1. Distribution of Tropane Alkaloids in the Plant Kingdom...

As we mentioned above, the isolation of tropane alkaloids is performed from the natural producer plants [1, 6]. Under these conditions, plants in the same stage of development are grown and distributed in a small area facilitating the operations of collection, harvest and even processing of the material [1]. It is worth to point out that the amount of the bioactive compounds is frequently not constant through the different stages of plant development. For this reason it is important to collect medicinal plants in the adequate stage in order to maximize the yield of the desired metabolites. 

Unlike the pituri, Duboisia hopwoodii, the nicotine-containing species that inhabits the central and western regions of Australia, the two trees/shrubs Duboisia myoporoides and D. leichhardtii, also known as corkwood, are restricted in their distribution to the east coast of Australia and adjacent areas. Corkwood leaves contain the highest levels of atropine and tropane alkaloids in the world, and since World War II have replaced Atropa belladonna and Hyoscyamus niger as the leading source of these alkaloids (Barnard 1952 Roddick 1991). 

Our knowledge of the occurrence and distribution of tropane alkaloids in the Convolvulaceae family is based on (i) the isolation and structure elucidation of Convolvulaceae-specific metabolites (T3, T4, T6-A, T6-B, T9) and (ii) extensive GC/MS data. This analytical method is of remarkable advantage due to its high resolution and sensitivity. Thus, even very low concentrations of a metabolite can be identified unequivocally. 

Occurrence in Non-solanaceous/Non-convolvulaceous Taxa. Beside the Erythroxylaceae, tropane bases were detected in further plant families which are again not closely related with the Solanaceae [Brassicaceae, Euphorbiaceae, Proteaceae, Rhizophoraceae (Waterman 1998)]. Eor details on the occurrence and distribution of different types of tropane alkaloids inside the two Solanales family in comparison with the unrelated families mentioned above outside this order see Table 3.7. 

Gorinova Nl, Velcheva MP, Dyulgerov AS, Atanassov A1 (1994) Tropane alkaloids in cell cultures of Physochlaina orientalis. Fitoterapia 65 452-456 Gorrod JW (1993) The mammalian metabolism of nicotine an overwiew. In Gorrod JW, Wahren J (eds) Nicotine and related alkaloids - absorption, distribution, metabolism and excretion. Chapman HaU, London, pp 31 4... 

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