Hyoscyamus species

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 adventitious roots were established from leaf segments (ca. 5x5 mm) of axenic shoot culture or intact plants (in the case of Duboisia) (surface-sterilized with 75 % EtOH for 10 sec and 2 % NaClO containing 1 drop/40 ml Tween 20 for 10 minutes) on Murashige-Skoog (MS) [7] solid medium containing 1 mg/1 lAA or 0.1 mg/1 NAA in the dark at 25 C, except for Hyoscyamus species. The roots were subcultured every 4-8 weeks in liquid medium (50 ml/100 ml flask) containing the same phytohormone as used for their induction (0.5 mg/1 lAA or 0.1 mg/1 NAA). Root cultures of Hyoscyamus species were established from the roots of axenic plants in vitro and subcultured in phytohormone-free MS liquid medium (50 ml/KX) ml flask). 

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). 

Hairy roots of Datura innoxia, Duboisia hybrid M-II-8-6, Scopolia tangutica and the Hyoscyamus species were established by the co-culture method using their leaf discs with A. rhizogenes 15834. In addition, H. albus was transformed with A. rhizogenes strain MAFF 03-01724 [15]. 

The hairy root cultures of Hyoscyamus species have been studied for alkaloid production by several researchers [3, 23, 24]. However, the influence of phytohormones and light on the production of tropane alkaloids in transformed roots of this genus has not been reported in detail. In this section, we describe the alkaloid production by H. albus hairy roots cultured under different conditions. 

Naturally occurring hyoscine is a combination of laevo-tropic acid with inactive hyoscine. It is found, mostly in conjunction with hyoscyamine, in many species of Datura. In D. arborea, D. fastuosa, and D. metel, the alkaloid consists chiefly of hyoscine whilst D. stramonium contains principally hyoscyamine, with some hyoscine. It is present also in Scopolia and Hyoscyamus species, for instance in Scopolia japonica and Hyoscyamus niger. 

Hyoscine N-oxide has been shown to be a constituent of the roots, leaves, and stems of Datura stramonium and Hyoscyamus niger, and the iV-oxides of hyoscyamine have been isolated from the seeds, roots, leaves, and stems of Atropa belladonna. Control experiments established that the iV-oxides were not formed during the isolation procedure. Four Hyoscyamus species have also... 

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... 

Scopolamine Duboisia species, Hyoscyamus species 26.00 Duboisia HR Hyoscyamus HR 0.08 g/liter 0.4% DW... 

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. 

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. 

Hyoscyamine (18) is produced in the roots of Datura (Solanaceae), but not in the leaves. This is the most common alkaloid in solanaceous plants (Cordell, 1978). This alkaloid inhibits germination of certain seeds, inhibits radicle growth in Linum, and is toxic to Lemna (Wink, 1993). Hyoscyamine, usually obtained from Hyoscyamus species) is a powerful anticholinergic drug. Hyoscyamine is a feeding deterrent for several insects (Wink, 1993). 

Bahmanzadegan A, Sefidkon F, Sonboli A (2009) Determination of Hyoscyamine and Scopolamine in Four Hyoscyamus Species fiom Iran. Iran J Pharm Res 8(l) 65-70... 

Gerrard AW (1880) Tropane alkaloids of Duboisia myoporoides. Pharm J 11 383 Ghani A (1985) Cuscohygrine from some solanaceous plants. Ind J Pharm Sci 47 127-129 Ghani A, Evans WC, Woolley VA (1972) Alkaloids of Hyoscyamus species. Bangladesh Pharmac J 1 12-14... 

A. belladonna and Hyoscyamus species are known for their content of the tropane alkaloids hyoscyamine (35) and scopolamine. Leaves of A. belladonna... 

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... 

Species of Datura, Hyoscyamus and other tropane-containing genera are of more risk to humans than animals. These plants and their seeds have been used for religious or social functions with ritualistic emphasis. Numerous cases of bizarre and often aggressive behavior have been reported in people using seeds or teas from these plants (Burrows and Tyrl, 2002). As recently as October of 2003, a report appeared at CNN.com of four teenagers who ate Jimson weed seeds. All hallucinated and had to be hospitalized. Two were sedated and placed on life-support to prevent danger to themselves and others. The same press release reported that Centers for Disease Control and Prevention... 

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)... 

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... 

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. 

In fhe early 1980s, root cultures of Nicotiana, Hyoscyamus, Datura and Duboisia species were found fo give high yields of nicotine and tropane alkaloids and have proved useful fools for recent studies of the biosynthetic pathways to these alkaloids. Genetically transformed and untransformed root cultures have been generated and used as models for biosynthetic studies (Rhodes et al, 1990 Robins et al, 1994a,b Wildi and Wink, 2002). 

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... 

Recent investigations of the regulation of the tropane alkaloid pathway in Datura, Hyoscyamus and Atropa species have focused on understanding the enzymes involved at the branch points and in investigating the role these play in regulating the flux into the different groups of products. 

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. 

Esters of tropic acid occur in nature and have a comparatively long history of use as drugs. Atropine (DL hyoscyamlne) and Its optical Isomers, the D and L-hyoscyamlnes, and scopolamine (L-hyoselne) and its optical Isomer, D -hyosclne, have been obtained from such plants as deadly nightshade (Atropa belladonna), jimsonweed (Datura stramonium), henbane (Hyoscyamus nlger), horsenettle (Solanum carollnense). and various species of Scopolla. nie L Isomers of both esters are more potent than the D Isomers. 

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. 

---