Datura stramonium, alkaloid

At this writing anticholinergic agents are not widely used for the symptomatic treatment of asthma, although compounds such as atropine [51 -55-8] C17H23NO3, (18) have been used for centuries (111). Inhalation of the smoke produced by burning herbal mixtures, such as Datura Stramonium provided bronchodilation and rehef from some of the symptoms of asthma. The major active component in these preparations was atropine or other closely related alkaloids (qv). 

Biosynthesis of tropan alkaloids hyosciamine and scopolamine by isomerization of alkaloid littorine in Datura. stramonium and related species 98CSR207. 

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... 

The cholinergic hallucinogens all have common chemical constituents that are responsible for their pharmacological effects (Robbers et al. 1996). These are the tropane alkaloids hyoscyamine, scopolamine (or hyoscine), and atropine (figure 9.16). It is scopolamine, and not atropine or hyoscyamine, which primarily produces the central and hallucinogenic effects because it is the only one that passes the blood-brain barrier sufficiently. However, all three have peripheral effects. Datura stramonium contains 0.1-0.65% tropane alkaloids, which is principally... 

Other plants of the nightshade family, including Atropa belladonna (deadly nightshade), Hyoscyamus niger (black henbane), and Datura stramonium (Jimson weed), contain atropine-like toxins that are anticholinergic, blocking the muscarinic receptors. An incidence in southern Utah of cattle poisoned on black henbane, with many death losses, was recently reported (Pfister, 2003). Atropine and atropine-like alkaloids are discussed Section 2.2.1.7. 

The tropane alkaloids (—)-hyoscyamine and (—)-hyoscine are found in the toxic plants deadly nightshade (Atropa belladonna) and thornapple (Datura stramonium) and are widely used in medicine. Hyoscyamine, usually in the form of its racemate atropine, is used to dilate the pupil of the eye, and hyoscine is employed to control motion sickness. Both alkaloids are esters of (—)-tropic acid. 

The base-catalysed racemization of the alkaloid (-)-hy oscy amine to ( )-hyoscyamine (atropine) is an example of enolate anion participation. Alkaloids are normally extracted from plants by using base, thus liberating the free alkaloid bases from salt combinations. (—)-Hyoscyamine is found in belladonna Atropa belladonna) and stramonium Datura stramonium) and is used medicinally as an anticholinergic. It competes with acetylcholine for the muscarinic site of the parasympathetic nervous system, thus preventing the passage of nerve impulses. However, with careless extraction using too much base the product isolated is atropine, which has only half the biological activity of (—)-hyoscyamine, since the enantiomer (+)-hyoscyamine is essentially inactive. 

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. ... 

Robins, R. J., Parr, A. J. and Walton, N. J. 1991. Studies on the biosynthesis of tropane alkaloids in Datura stramonium L. transformed root cultures. 2. on the relative contributions of L-arginine and L-ornithine to the formation of the tropane ring. Planta, 183 196-201. 

Atropine and scopolamine, the main toxic alkaloids of Datura stramonium and Datura ferox, were detected and quantified using HPLC-ESl-MS both in Datura seeds and in the gastric content of a man whose death was ascribed to a fatal heart attack [100]. 

Scopalamine Alkaloid Motion sickness Datura stramonium (Jimson weed)... 

Atropine and its naturally occurring congeners are tertiary amine alkaloid esters of tropic acid (Figure 8-1). Atropine (hyoscyamine) is found in the plant Atropa belladonna, or deadly nightshade, and in Datura stramonium, also known as jimsonweed (Jamestown weed), sacred Datura, or thorn apple. Scopolamine (hyoscine) occurs in Hyoscyamus niger, or henbane, as the /(-) stereoisomer. Naturally occurring atropine is /(-)-hyoscyamine, but the compound readily racemizes, so the commercial material is racemic d,/-hyoscyamine. The /(-) isomers of both alkaloids are at least 100 times more potent than the d(+) isomers. 

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... 

The atropine series contains a number of very closely allied alkaloids of which the chief are atropine, hyoscyamine, and hyoscine (also called scopolamine). They are found in the roots and leaves of many plants of the Solanaceae, notably belladonna (Atropa belladonna), henbane (Hyoscyamus niger), the thorn apple or jimson weed (Datura stramonium), and some members of the Duboisia and Scopolia genera. These plants were used during the Middle Ages as sorcerer s drugs and have been smoked, chewed, or imbibed in the form of decoctions by primitive people for the hallucinations and frenzy they produce (Figure 14.1). 

Note The best-known antimuscarinic or anticholinergic drugs are the belladonna alkaloids. The major drugs in this class are atropine, hyoscyamine, and scopolamine. A number of plants belonging to the potato family (Solanaceae) contain similar alkaloids. Atropa belladonna (deadly nightshade), Hyoscyamus niger (henbane), Datura stramonium (jimsonweed or thorn apple), and several species of Scopolia also contain belladonna alkaloids. 

Elicitation is effective in enhancing metabolite synthesis in some cases, such as in production of paclitaxel by Taxus cell suspension cultures [2] and tropane alkaloid production by suspension cultures of Datura stramonium [3]. Increasing the activity of metabolic pathways by elicitation, in conjunction with end-product removal and accumulation in an extractive phase, has proven to be a very successful strategy for increasing metabolite productivity [4]. For example, two-phase operation with elicitation-enhanced alkaloid production in cell suspension cultures of Escherichia californica [5,6]. 

Furoquinoline Alkaloids.—Well-known furoquinoline alkaloids have been identified for the first time in twelve species of the Rutaceae (see the Table 2.5.8,9,11—13,15,16 on p an(j rare trimethoxydictamnine halfordinine (1 R1 = R2 = R3 = OMe) has been obtained from Araliopsis tabouensis2 and from Teclea verdoorniana.12 The isolation of y-fagarine and skimmianine from Tylophora asthmatica (Asclepiadaceae)14 and skimmianine from Datura stramonium (Solanaceae)4 is of considerable taxonomic interest. 

The usefulness of GC-MS analysis for biosynthetic studies was demonstrated by Patterson and O Hagan [74] in their investigation of the conversion of littorine to hyoscyamine after feeding transformed root cultures of Datura stramonium with deuterium-labeled phenyllactic adds. This study complements previous investigations on the biosynthesis of the tropate ester moiety of hyoscyamine and scopolamine [75], where GC-MS played a key role. It also has general relevance in the biosynthetic pathway of tropane alkaloids in the entire plant kingdom [76]. 

Two enz)mies of pyrrolidine alkaloid formation responsible for the conversion of putrescine to the N-methylpyrrolinium ion have been investigated in some detail. PMT, partially purified from cultures of Hyoscyamus niger and fully characterized from Datura stramonium, has been cloned by differential screening of complementary deoxyribonucleic acid (cDNA) libraries from high- and low-nicotine-yielding N. tabacum plants (Hibi et ah, 1994). The enzyme shows considerable sequence homology to spermidine synthase but is distinct from this enz)mie as it only shows PMT activity when expressed in Escherichia coli. MPO has been isolated in pure form from N. tabacum transformed root cultures (McLauchlan et ah, 1993). It is quite widely spread in... 

Robins, R.J., Abraham, T., Parr, A.J., Eagles, J. and Walton, N.J. (1997) The biosynthesis of tropane alkaloids Datura stramonium the identity of the intermediate between N-methylpyrrolinium salt and tropinone.. Am. Chem. Soc., 119,10929-34. 

Patterson S, O Hagan D. Biosynthetic studies on the tropane alkaloid hyoscyamine in Datura stramonium hyoscyamine is stable to in vivooxidtion and is not derived from Uttorine via a vicinal interchange process. Phytochemistry 2002 61 323-329. 

O Hagan D, Robins RJ, Wilson M, Wong CW, Berry M. Hu-orinated tropane alkaloids generated by directed biosynthesis in transformed root cultures of Datura stramonium. J. Chem Soc. Perkins Trans. 1. 1999 2117-2120. 

Tropane alkaloids, such as hyoscyamine and/or scopolamine, occur in the solanaceous plants Atropa belladonna, Datura stramonium, Hyoscyamus niger, and Mandragora officinarum. These alkaloids are powerful anticholinergic agents and can elicit peripheral symptoms (for example blurred vision, dry mouth) as well as central effects (for example drowsiness, delirium). They can potentiate the effects of anticholinergic medicaments. 

Datura stramonium (Jimson weed) is a naturally occurring plant that is ingested to induce hallucinogenic effects. Toxicity after ingestion is due to an atropine-containing alkaloid that is present in all parts of the plant but is particularly concentrated in the seeds. 

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