Anisodus

Scopolia lurida (Anisodus luridus). Roots, 2 to 2-8, of which about one-fifth is hyoscine (Kreier ). According to Rabinovich and Konovalova, the root contains hyoscyamine and cuscohygrine (p. 103) but no hyoscine. ... 

The absolute configuration of (—)-anisodine [(—)-3a-(2 -hydroxy-tropoyloxy)-6/ ,7/ -epoxytropane, 91], isolated from Anisodus tanguticus by Chinese scientists (24-26), has been shown by chemical means to be (S) at C-2 (27). Similarly, the (—)-3a-(2,3-dihydroxy-2-phenylpropionyloxy)-6,7-epoxytropane [(—)-3a-(2 -hydroxytropoyloxy)-6/ ,7/ -epoxytropane, 91], isolated by Moorhoff (28) from Datura sanguinea, has been shown by X-ray crystallography to possess the (S) configuration at C-2 (29). The results would seem to establish the identity of the two samples. 

Anisodamine is a natural derivative of hyoscyamine mono-hydroxylated at the tropane skeleton (Fig. 1). The compound was extracted from traditional Chinese medicine Anisodus tanguticus evoking typical non-specific effects of cholinergic antagonists (spasmolysis, anaesthesia, mydriasis, analgesia) in combination with... 

Anisodine is a natural TTA that represents a derivative of the scopolamine structure mono-hydroxylated at the tropic acid moiety (Fig. 1). Similar to anisodamine it was extracted from Chinese herb Anisodus tanguticus (Maxim.) Pascher and also exhibits al-AR blocking properties and non-specific anticholinergic effects. Accordingly, in China anisodine is used for the therapy of the same indications as described for anisodamine, most often to treat transmissible shock. Toxicity and side effects of anisodine are smaller than those for atropine, scopolamine and anisodamine [5],... 

A total synthesis of diastereoisomers of anisodamine, an alkaloid from Anisodus tanguticus, has been claimed17 by Chinese authors. ( )-Acetyltropoylation of ( )-/ -acetoxy-3cr-hydroxytropane, followed by partial deacetylation, led to a diastereoisomeric mixture of 6/ -hydroxy-atropines. (—)-(S)-6/l-Hydroxyhyoscy-amine, a natural tropane, had earlier been obtained by total synthesis.18 In view of this and of the non-identity of the i.r. spectra of synthetic mixture and natural anisodamine , it remains uncertain whether the latter is identical with natural (—)-(5 )-6/ff-hydroxyhyoscyamine.18... 

Paullinia cupana (guarana) Selaginella doederleinii (spike moss) Anisodus tanguticus (Zangqie)... 

Ammi visnaga (toothpick weed) Angelica sinensis (dong qua ) Anisodus tanguticus (zangqie), Anthemis species (chamomile) Anthoxanthum odoratum (sweet vernal grass)... 

Mandrake Mandragora species Zang qie Anisodus tanguticus... 

Anisodus tanguticus (Zangqie), a traditional Chinese herbal medicine, contains hyoscyamine and related toxic tropane alkaloids (1). Its active ingredient anisodamine has been used to treat snakebite (2). 

The extracts of roots of Anisodus tanguticus gave apoatropine (3a) and 3a-(4,4,4-trichloro-2-phenylbutyryloxy)tropane (3b). In the reviewers opinion, (3b) is most likely an artefact formed from apoatropine (3a) and chloroform by a radical reaction. 

The tropane alkaloids represent from pharmaceutical point of view one of the most important groups of alkaloids, on the one hand because of the alkaloids atropine (5) and scopolamine (6), both widely used in pharmacotherapy, and on the other hand because of cocaine, most known for is its abuse as a stimulant. The former two alkaloids are extracted from a variety of Solanaceae, and the latter alkaloid is isolated from the leaves of Erythro-xylon coca. For the plant cell and tissue culture of the latter plant we have not been able to find any literature. For the Solanaceae, however, many studies have been published. Several genera of this family have been studied extensively, for example, Anisodus, Atropa, Datura, Duboisia, Hyoscyamus, and Scopolia. Of these Datura has widely been used as a model system for the development of various techniques in plant cell and tissue culture and for basic studies of cultured plant cells, without reference to alkaloid production. 

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). 

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. 

Anisodus tanguticus Shoots Suspension Tropine Atropine Butropine 6-Hydroxyhyoscy amine, 387... 

Root cultures of Datura innoxia were reported to convert atropine, added to the cultures, to scopolamine (386). Non-alkaloid-producing callus cultures of a Duboisia hybrid were shown to be able to convert atropine to scopolamine and 6-hydroxyhyoscyamine (321) (Fig. 8). Root cultures of Hyoscyamus niger are capable of converting atropine to scopolamine, but the opposite reaction was not found (118). Suspension cultures were not capable of either reaction. Yamada and Endo (324) reported that Duboisia leichhardtii root cultures converted added atropine to scopolamine in callus and callus-shoot cultures only very little conversion was observed. A non-alkaloid-producing Anisodus tanguticus cell suspension culture converted added atropine to 6-hydroxyhyoscyamine and scopolamine. The ratio of the two products depended on the time in the growth curve choosen for the feeding of atropine (387). The cell cultures also converted 6-hydroxyhyoscyamine to scopolamine (388). 

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. 

Liu, T., Zhu, P., Cheng, K. D., Meng, C., and He, H. X. (2005) Molecular cloning, expression and characterization of hyoscyamine 6-beta-hydroxylase from hairy roots of Anisodus tanguticus. PlantaMed. 71, 249-253. 

Kai G, Yang S, Zhang Y, Luo X, Fu X, Zhang A, Xiao J (2012) Effects of different elicitors on yield of tropane alkaloids in hairy roots of Anisodus acutangulus. Mol Biol Rep 39(2) 1921-1729. doi 10.1007/sll033-011-0912-l... 

Anisodus, Atropa, Atropanthe, Hyoscyamus, Physochlaina, Przewalskia, Scopolia... 

D. leichhardtii x myoporoides Solanoideae Hyoscyameae clade Anisodus acutangulus C.Y.Wu C.Chen sub nom. Scopolia acutangula A. tanguticus (Maxim.) Pascher sub nom. 

Second, it has to be pointed out that the co-occurrence with scopolamine (hyoscine) is a consistent trait in hyoscyamine-containing species. Furthermore, this fact involves that anisodamine (6P-hydroxyhyoscyamine) must also be synthesized in all these species because it is an intermediate representing the direct precursor in the biosynthesis of scopolamine (Fig. 3.14). Nevertheless, due to a certain accumulation this intermediate could be identified in many species, e.g., in the genera Anthocercis, Cyphanthera, Duboisia, Datura, Hyoscyamus, Physochlaina. The trivial name of this alkaloid has been given due to its occurrence in Anisodus acutangulus. 

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