Anisodus tanguticus

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. 

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. 

Wang ZB, Wu XQ (1979) Variation of the contents of two alkaloids in Anisodus tanguticus. Zhiwu Xuebao 21 85-87... 

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