Datura species

Main alkaloid of Atropa belladonna Hyoscyamus niger several Datura species like suaveolens, sanguinea, Candida, metel, stramonium. 

The tropane alkaloids (—)-hyoscyamine and (—)-hyoscine are among the most important of the natural alkaloids used in medicine. They are found in a variety of solanaceous plants, including Atropa belladonna (deadly nightshade), Datura stramonium (thornapple) and other Datura species, Hyoscyamus niger (henbane), and Duboisia species. These alkaloids... 

Tropine derivatives are typically found in certain highly poisonous Solanaceae species, most notably Atropa belladonna (deadly nightshade), Datura stramonium (thornapple), other Datura species, Duboisia myoporoides (corkwood elm), Hyoscyamus niger (henbane) and other Hyoscyamus species. Other sources include Convolvulus species (Convolvulaceae), Erythroxylum coca (coca), other Erythroxylum species (Erythroxylaceae) and Bruguiera species (Rhizophoraceae). 

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. 

The 6-hydroxyhyoscyamine which occurs in low concentration (0.005%) in Datura species is an intermediate in the in vivo conversion of hyoscyamine into hyoscine. This has now been isolated in a relatively high yield (0.5%) from a Duboisia hybrid. 

Synonyms Datura species Datura arborea-. Datura cornigera Datura folium Datura suaveo-lens Datura stramonium Angel s trumpet Downy thorn apple Horn-of-plenty Stinkweed Thornapple Black henbane Chemical/Pharmaceutical/Other Class Anticholinergic... 

Datura species are abused for psychedelic properties. Historically, D. Stramonium had been used by the American Indians as a folk medicine and in religious activities. Stramonium has been used in homeopathic asthma preparations. Datura does not have a therapeutic use. 

Atropine is the optically inactive mixture of dextro- and laevo-hyoscyamine. Laevo-hyoscyamine alone occurs in nature. The hest source of hyoscyamine is a variety of henbane indigenous in Egypt, Soudan and India, known as Hyoscyamus muticus, in the various parts of which it has been shown to be present in the following proportions leaves 1.4% stems 0.6 % seeds 0.87-1.34%. Atropine is also manufactured from the root of Scopolia carniolica, in which hyoscyamine is present to the extent of 0.43-0.51% and from A ropa belladonna, the leaves of which contain, on the average, 0.4%, and the roots 0.5%, of hyoscyamine. Many other solanaceous plants of the Datura species contain these alkaloids, in varying, and smaller, amounts, often associated with hyoscine or scopolamine. 

Atropine was isolated by Mein in 1831 (58), and since then the synthesis of both atropine and scopolamine has been achieved (59,60). A biogenetic scheme for the synthesis of atro-pine-like alkaloids in datura species starting from ornithine has been described (61). 

Serious symptoms are seldom seen. The most common symptoms are stomach troubles, stomach pains, vomiting, diarrhoea, that can lead to loss of fluid. More specific problems might occur with certain plant poisonings for instance dilation of the pupil, redness of the skin, heart palpitations in poisoning with atropine, a component of Belladonna and Datura-species, disturbances in cardiac rhythm (Digitalis, Nerium, Aconite), convulsions (Aconite, Cowbane) these are among the most poisonous species of plants. 

This section summarises recent work on alkaloids containing the pyrrolidine nucleus. A short review concerning the synthesis of this group has appeared. A variety of Labiatae plants have been screened and some of them have been shown to contain pyrrolidine alkaloids. Cuskhygrine has been found in the roots of three Datura species and stachydrine has been obtained from Capparis spinosa3 The structure of trichostachine (1) Piper trichostachyon) has been elucidated by spectral means and confirmed by synthesis. Ficine (5), an interesting flavonoid alkaloid, has been synthesised. Friedel-Crafts reaction between... 

The growth and alkaloid production of callus tissues of four Datura species, cultured in various media, have also been studied 13 the species investigated include D. stramonium, D. stramonium var. tatula (L) Torrey, D. stramonium L. var. godronii Danert, and D. innoxia Mill. Generally, the alkaloids formed were similar regardless of species, or of substances added to the culture medium atropine, scopolamine, tropine, apoatropine, and five unidentified alkaloids were detected by t.l.c. 

Tropane Alkaloids.—Previous research had shown that the tiglic acid (55) moieties of the ester alkaloids of Datura species, e.g. (56), (57), and meteloidine (58), arise specifically from L-isoleucine (52). " This amino-acid is also a source for angelic acid (the geometric isomer of tiglic acid) in Cynoglossum officinale and it is degraded in animal tissues to tiglic acid, probably by way of 2-keto-3-... 

Table 1 Constituent alkaloids of three Datura species, two Anthocercis species and a Physalis species...

Atropine Atropa belladonna. Datura species, Hyoscyamus species 5.20 Atropa HR Datura HR 0.1-0.2 g/liter 0.1-0.2 g/liter... 

The cell and tissue culture of the major tropane alkaloid-producing species does not apparently offer any special problems. The regeneration of plantlets from callus and tissue cultures seems to be routine (286,307,309,323,325,332,350-352). Plants have also been regenerated from protoplasts of Atropa belladonna (353), Duboisia myoporoides (354), and Hyoscyamus muticus (355,356). Cryopreservation has been reported for Anisodus and Datura species (349,357). 

H. Kamata and S. Marumo. Nippon Kayaku Co., Ltd. Jpn. Kokai Tokkyo Koho. JP 63216491 A2, 8-9-1988. JP 87-49949, 6-3-1987. Manufacture of atropine and scopolamine from indoleacetic acid derivatives by plant tissue culture (Duboisia, Hyoscyamus, Scopolia, and Datura species). Chem. Abstr. 110, 210979s. 

For the isolation of atropine, Atropa belladonna. Datura species (e.g., D. stramonium and D. innoxia), and Hyoscyamus species are presently being used, which have atropine as the major compound. Hyoscyamus muticus is of interest for industrial-scale isolation, having an average alkaloid content of about 0.035-2.15% (365) in the leaves, with only small amounts of other alkaloids. Duboisia species, small trees whose leaves contain scopolamine as the major alkaloid during a certain period of seasonal development, are the main source for the industrial isolation of scopolamine. The leaves of Hyoscyamus niger and Datura stramonium were widely used in pharmacy, they contain, besides atropine as the main alkaloid, considerable amounts of scopolamine, the ratio of atropine to scopolamine being, respectively, about 2 1 and 1.2 1. They contain, respectively, 0.1-0.16% (365) and 0.02-0.08% total alkaloid. In Atropa belladonna, atropine is the m or alkaloid, with only small amounts of scopolamine the alkaloid content of the roots is about 0.3-0.7%, that of the leaves 0.2-0.6%. 

Generally the Solanaceae cell and tissue cultures follow the alkaloid production pattern as found in the plant. For the production of atropine, Atropa belladonna. Datura stramonium, and Datura innoxia (see Tables XIV and XV, e.g., 291,292,296) cultures are particularly suited. For the production of scopolamine, Hyoscyamus species (see Table XVII, e.g., 291,292,296,339,365), Duboisia species (see Table XVI, e.g., 291,292, 296), Scopolia species (e.g., 52,296,348), Anisodus acutangulus (349), and some Datura species (see Table XV, e.g., 291,292,296,316) are of interest. 

Romeike 382) reported that several cultures of Datura species grown on 2,4-D were unable to esterify tropine with tropic acid. Only a D. innoxia culture grown on NAA was capable of this bioconversion. Scopolia lurida, Hyoscyamus niger, and Atropa belladonna were incapable of any esterification of tropine. Hiraoka et al. 383) could not confirm these results with their Datura cell lines, but they found that D. innoxia is capable of acetylation of other compounds, such as pseudotropine, scopine, and scopoline, as well. A series of other plants tested, for example, Atropa belladonna and Scopolia japonica, were unable to carry out such an... 

S. occurs as the (-)-form (hyoscine) in several Solan-aceae genera [e. g. Atropa belladonna (deadly nightshade), Datura species (thorn apple), Duboisia species, Hyoscyamus species (henbane), Mandragora officinalis (mandrake), and Scopolia species (banewort)]. Racemic S. (atroscine) is a natural product of the Solanaceae Datura innoxia, Hyoscyamus niger, and Scopolia camiolica. S. is easily hydrolyzed in acidic and alkaline solution to tropic acid and scopine. 

Increasing the concentration of the alkaloid scopolamine in medicinal plants has been the target of much research. First results were obtained in the late 1980s when somatic hybridization was used to increase the content in Datura species, and the transformation of Atropa belladonna with the enzyme hyoscyamine-6-beta-hydroxylase lead to a shift from hyoscyamine to a nearly exclusive production of scopolamine (Figure 2.7) [60]. 

Since chemical synthesis of tropane alkaloids is difficult and expensive, these compounds are still extracted from plants belonging to several species of Solanaceae family including, Hyoscyamuns niger L., Anisodus tanguticus, Scopolia tangutica Maxim, Atropa belladonna, and several Datura species. 

Ornithine is incorporated into pyrrolidine rings unsym-metrically in several Datura species, but a symmetrical intermediate is involved in Nicotiana species, Erythroxylum coca, Duboisia leichardtii, Hyoscyamus albus, and Nicandra physaloides (Leete, 1990). 

Nash, R. J., M. Rothschild, E. A. Porter, A. A. Watson, R. D. Waigh, and P. G. Waterman, Calystegines in Solanum and Datura species and the death s head hawk-moth (Acherontia atropus), Phytochemistry, 34, 1281-1283 (1993). 

As the preceding discussion shows, the Hterature which invokes the existence of an intermediate with C2v symmetry between ornithine/arginine and the tro-panes in Datura species commonly assumes that this intermediate is located on the pathway between the amino acids and M-methylpyrrolinium salt (10). From studies of the incorporation of more advanced precursors into tropine (1) to be discussed in detail below, it is becoming apparent that this assumption may not necessarily be warranted. 

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