Hyoscyamine Hyoscyamus

Hyoscyamus muticus. Leaves, 1-4 leaves and stems, 0-6 seeds, 0-9 to 1-34 stems, 0-6 hyoscyamine. ... 

Hyoscyamus reticulatus. Seeds, 0-08 whole plant, 0-12 to 0-24. A little hyoscyamine. ... 

By extraction of Solanacean drugs, especially Atropa belladonna, Hyoscyamus niger or other species. On careful extraction L-hyoscyamine is obtained first, which can be racemized to atropine by addition of alkali in ethanolic solution. 

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... 

A. Alkaloids 1. Belladonna-type solanaceous tropane alkaloids [Atropine (1), (—)-Hyoscyamine (2), Scopolamine ((—)-Hysoscine)(3)] Atropa belladonna L. (belladonna), Datura metel L., D. stramonium L. (jimson weed), Hyoscyamus niger L. (henbane), Mandragora officinarum L. (European mandrake), and other solanaceous species Anticholinergics (parasympatholytics)... 

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. ... 

Tropane alkaloids Hyoscyamine 6/3-hydroxylase Hyoscyamus niger Atropa belladonna... 

Matsuda, J., Okabe, S., Hashimoto, T. and Yamada, Y. 1991. Molecular cloning of hyoscyamine 6(3-hydroxylase, a 2-oxyglutarate dependent dioxygenase, from cultured roots of Hyoscyamus niger. Journal of Biological Chemistry, 266 9460-9464. 

Hashimoto, T. and Yamada, Y. 1987. Purification and characterization of hyoscyamine 6(3-hydrolase from root cultures of Hyoscyamus niger L. Hydroxylase and epoxidase activities in the preparation. European Journal of Biochemistry, 164 277-285. 

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. 

Hyoscyamus bohemicus F. W. Schmidt H. niger L. Liang Shi (Henbane) (root, leaf) Alkaloid, hyoscyamine, hyoscine, scopolomine, hyoscypierin, choline, mucilage, albumin.60,144,450 This herb is toxic. Antispasmodic activity. 

N.A. Hyoscyamus niger L. Tropane alkaloids, hyoscyamine, hyoscine." A sedative, painkiller, antispamodic. 

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). 

FIGURE 14.3 The henbane (Hyoscyamus niger Linne), a member of the nightshade family, whose leaves, with or without the tops, constitute the official drug Hyoscyamus and are a source of the valuable medicinal alkaloids hyoscyamine and scopolamine. 

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. 

Kartal et al. have discussed the quantitative analysis of hyoscyamine in Hyoscyamus reticulatus L, a plant growing in east Anatolia [71]. 

Both untransformed (Hashimofo and Yamada, 1994) and transformed root cultures of Datura, Hyoscyamus, Atropa and Duboisia species (Robins and Walton, 1993) accumulate high levels of fhe fropane alkaloids, hyoscyamine and scopolamine (Fig. 2.3). These medically imporfanf fropane alkaloids present not only an interesting biochemical problem but also a realistic... 

Some Hyoscyamus and Duboisia root cultures accumulate scopolamine as a major product (Robins and Walton, 1993). In contrast, only traces of scopolamine were found in D. stramonium roots. This implies that the expression of hyoscyamine 6 3-hydroxyIase (H6H) that forms the 6,7-epoxide is variable and, hence, this enz)mie has also been targeted for genetic engineering. 

Tropanone then is reduced via an NADPH-dependent reductase to tropine that has been cloned from Hyoscyamus niger (149, 150). All tropane-producing plants seem to contain two tropinone rednctases, which create a branch point in the pathway. Tropinone reductase I yields the tropane skeleton (Fig. 3b), whereas tropinone rednctase II yields the opposite stereocenter, pseudotropine (151). Tropane is converted to scopolamine or hyoscyamine, whereas the TRII product pseudotropine leads to calystegines (152). These two tropinone reductases have been crystalhzed, and site-directed mutagenesis studies indicate that the stereoselectivity of the enzymes can be switched (153, 154). 

Hyoscyamine is found in Atropa belladonna (night-shade) and in several species of Hyoscyamus from which its name is derived. It is a crystalline compound, m.p. 108.5°, somewhat soluble in water but more readily in chloroform, alcohol or benzene. It is levo rotatory and yields crystalline salts more soluble in water than the base itself. With acids or alkalies hyoscyamine hydrolyzes as previously stated yielding tropine and tropic acid. 

Henbane Hyoscyamus niger 0.04%-0.28% hyoscyamine in leaves Anticholinergic toxicity More sedating than belladonna... 

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. 

The adventitious roots of H. albus and H. niger showed the highest level of 6P- and 7p-hydroxyhyoscyamines. The amount of hyoscyamine in the adventitious roots of H. albus increased remarkably when the roots were cultured in MS or 1/2 MS medium and it became the main alkaloid. In contrast, scopolamine was the main constituent of the adventitious roots of H. albus in Gamborg B5 (B5) [16] and WP media. Thus, in Hyoscyamus species, the ratio of tropane alkaloids produced during the culture pteriod seemed to depend mainly on the culture conditions and not on the species, as described by Hashimoto et al. [17]. In adventitious roots of H. albus the production of 7P-hydroxyhyoscyamine was at its highest level when the roots were cultured in WP medium, whereas the adventitious roots of D. innoxia and S. tangutica did not produce any detectable level of 7P-hydroxyhyoscyamine. In the Duboisia hybrid a trace amount of 7p-hydroxyhyoscyamine was detected. In the adventitious roots of H. aureus, H. muticus and H. pusillus, traces of 7P-hydroxyhyoscyamine were detected (Table 4). 

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