Solanaceae, tropane alkaloids

Outside the Solanaceae, tropane alkaloids occur in two other plant families. Within the Erythroxylaceae, the genus Erythroxylum comprises about 200 widely distributed, tropical species found mainly in South America and Madagascar. Peruvian coca Erythroxylum coca) is the only plant currently cultivated for cocaine production, which occurs at concentrations between 0.2% and 1% (w/w) in the leaves (Griffin and Lin 2000) (Figure 4.5). A few other Erythroxylum species also produce cocaine, including Trujillo coca E. novogranatense... 

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. 

The family Solanaceae consists of about 85 genera and 2800 species of plants, of which, 80 are of medicinal value in the Asia-Pacific region. Solanaceaeare well known for their parasympatholytic tropane alkaloids, such as hyoscyamine. Classic examples are Atropa belladonna L. (belladona herb, British Pharmacopoeia 1963), Datura stramonium L. (stramonium, British Pharmacopoeia, 1963), and the dried leaves and flowering tops of Hyoscyamus... 

Certain plants of the family Solanaceae, such as Atropa belladonna L., Hyoscyamus niger L., and Datura stramonium L., have been used medicinally for centuries in Europe because they contain tropane-type alkaloids.For example, atropine (1) [a racemic mixture of (+)- and (—)-hyoscyamine (2)] and (-)-hyoscyamine are competitive antagonists at the muscarinic acetylcholine receptor site, leading to antispasmodic and antiallergic effects. Scopolamine [(—)-hyoscine)] (3) is used in a transdermal patch for the prevention of motion sickness. Since these tropane alkaloids penetrate the blood-brain barrier, they also have psychoactive effects. ... 

The tropane alkaloids, especially hyoscine (scopolamine) (18), have been used to treat PD since they increase DA activity by antagonizing cholinergic activity at the muscarinic receptors in the striatum. The naturally occurring alkaloids, foimd in various genera of the Solanaceae, are not... 

Plants containing indoleamines include Psilocybe mushrooms, morning glory and Virola. Plants containing tropane alkaloids such as the muscarinic antagonists scopolamine and atropine are found in some members of the Solanaceae plant family—including datura, mandrake, henbane and... 

These are the group of alkaloids that possess a 8-methyl-8-aza-hicyclo [l,2,3]octane or tropane skeleton, e.g. atropine, cocaine and scopolamine. Tropane alkaloids occur mainly in plants from the families Solanaceae and Erythroxylaceae. 8-Aza-hicyclo[l,2,3]octane, i.e. tropane without the 8-methyl group, is known as nortropane. 

Tropane alkaloids, principally hyoscyamine and hyoscine, are also found in two other medicinal plants, scopolia and mandrake, but these plants find little current use. Scopolia (Scopolia carniolica Solanaceae) resembles belladonna in appearance, though it is considerably smaller. Both root and leaf materials have been employed medicinally. The European mandrake (Mandragora officinarum Solanaceae) has a complex history as a hypnotic, a general panacea, and an aphrodisiac. Its collection has been surrounded by much folklore and superstition, in that pulling it from the ground was said to drive its collector mad due to the unearthly shrieks emitted. The roots are frequently forked and are loosely likened to a man or woman. Despite the Doctrine of Signatures, which teaches that the appearance of an object indicates its special properties, from a pharmacological point of view, this plant would be much more efficient as a pain-reliever than as an aphrodisiac. 

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 are an important class of natural products possessing different and interesting pharmacological activities. Hyoscyamine (atropine in the racemate form), scopolamine, and cocaine are the major representatives of this class. They are commonly found in plant materials, mainly in genera belonging to three families Solanaceae, Erythroxylaceae, and Convolvulaceae. The importance of these compounds requires that there are accurate analytical methods for their determination in plants and in biological matrices. This chapter describes the state-of-the-art of analytical procedures (extraction and analysis) for analyzing tropane alkaloids. 

Drager, B., Funck, C., Hohler, A., Mrachatz, G., Portsteffen, A., Schaal, A. and Schmidt, R. (1994) Calystegines as a new group of tropane alkaloids in Solanaceae. Plant Cell Tiss. Org. Cult., 38, 235 0. 

The family Solanaceae is one of the important and interesting plant families. It may be classified into four groups based on their usefulness and chemical composition of alkaloids contained (1) Nicotiana spp. such as N. tabacum and N. rustica, which provide tobacco and contain nicotiana alkaloids such as nicotine and nomicotine (2) Hyoscyamus, Scopolia, Atropa, and Datura species, which are pharmacologically important and contain tropane alkaloids such as hyocyamine, scopolamine, and tropine (3) Solanum spp., which are sometimes the starting material for production of synthetic steroids for medical uses and which contain solanum alkaloids and (4) Capsicum, Solanum, and Lycoper-sicum species, which serve as foods and are alkaloid-free. 

Atropa belladonna L. (Solanaceae) is a perennial herb native to Europe and West Asia. The plant contains tropane alkaloids such as scopolamine and hyoscyamine, which are used as spasmolytics and anesthetics. 

These alkaloids are from a structural point of view, esters between the alcohols such as tropine in e.g. hyoscyamine and scopine in e.g. scopolamine and different ahphatic and aromatic acids, mainly tropic acid. The tropane alkaloids within the family Solanaceae belong mainly to the tropine series, whereas the Coca-alkaloids from the family Erythroxylaceae mainly belong to the pseudo-tropine series. 

Tropane Alkaloids found in plants of the family Solanaceae, especially Datura suaveokns, Brupismansia and Brunsfdsia species. The alkaloid Hyoscine (scopolamine) in high doses can cause hallucinations giving the sensation of flying through the air, hence... 

A few new alkaloids have been isolated during investigations on Australasian plants. The major alkaloid of two Australian shrubs, Anthocercis viscosa R. Br. and A. fasciculata F. Muell. (fam. Solanaceae), has been identified as (—)-hyo-scyamine. The same base (partly racemic) is one of the seven alkaloidal constituents of A. littorea Labill. another is meteloidine. The major alkaloid, however, is littorine, which has been identified as R-(—)-3a-(2-hydroxy-3-phenylpro-pionyloxy)tropane (1). The isolation of tropane alkaloids from the Anthocercis species justifies the inclusion of this genus in the Solanaceae previously it had been included in the Scrophulariaceae but had recently been transferred to the Solanaceae on botanical grounds. Recently, littorine has also been isolated from Datura sanguinea R. and P. ... 

Plants in the Solanaceae family produce a variety of alkaloids, some of them having a considerable therapeutic importance. One such group of alkaloids possesses a tropane nucleus. Tropane alkaloids are structurally related natural products having in common the azabicyclo[3.2.1]octane structure and therefore the systematic name for tropane is 8-methyl-8 azabicyclo[3.2.1]octane (Fig. 1). The majority of these alkaloids are esters between organic acids and hydroxytropanes. 3a-Hydroxytropane, called tropine, is the amino alcohol most frequently encountered. In addition, its 3 (3-isomer (pseudotropine), the di- (3,6- 3,7- or 6,7-) and trihydroxylated... 

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. 

Tropane alkaloids are particularly numerous in the species of Atropa, Datura (inch Brugmansia), Duboisia and Hyoscyamus. It is noteworthy that classical alkaloids such as hyoscyamine, scopolamine, i.e. esters with tropic acid or related acids of alkamines derived from tropane, are restricted to the Solanaceae [7],... 

Evans, VKC. 1979. Tropane alkaloids in the Solanaceae In Hawkes, J.G. etaL (Eds.) The Biolop and Taxonomy of the Solanaceae. (Linnean Society Symposium Series, Number 7) Academic Press, London, England, pp. 241-254. 

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