Duboisia leichhardtii

The hyoscyamine system is found alone in some adult Duboisia Leichhardtii and possibly in some southern D. myoporoides. It produces tropine and nortropine only, which are esterified with tropic acid, or as in ajooatropine found in belladonna, with atropic acid, and to a small extent with the isoprene acids referred to above. Some tropine or nortropine may occur as such. Scopine, -tropine and dihydroxytropane are absent. 

Endo, T., Hamaguchi, H., Eriksson, T. and Yamada, Y. 1991. Alkaloid biosynthesis in somatic hybrids of Duboisia leichhardtii F. Muell., and Nicotiana tabacum L. Planta, 183 505-510. 

Genus Duboisia (Family Solanaceae) comprises four species, Duboisia leichhardtii F. Muell, D. myoporoides R. Br., D. hapwoodii F. Muell and recently discovered D. arenitensis L. A. Craven, B. J. Lepschi L. A. R. Haegi, and the leaves of D. leichhardtii and D. myoporoides, as well as... 

Even if the alkaloid content is quite high, an important step in the establishment of root cultures is the selection of the best clones which combine good growth and high alkaloid production. The occurrence of clonal variations allows the selection of high-producing lines. Mano et al. [78] were able to select a clone of hairy roots of Duboisia leichhardtii, producing 2.1 % DW scopolamine, more than twice the amount found in the leaves of the non-transformed plants. 

Y. Mano, Y. Yamada, and H. Okawa. Sumitomo Chemical Co., Ltd. Jpn. Kokai Tokkyo Koho. JP 63226280 A2, 20-9-1988. JP 87-63092, 17-3-1987. Tropane alkaloids and their manufacture with plant tissue culture of Duboisia (hairy roots, Duboisia leichhardtii). Chem. Abstr. 110, 171822p. 

Scopolamine production in a line selected from 750 hairy root cultures of Duboisia leichhardtii could reach 78 mg/liter (329). The maximum percentage of scopolamine detected in one of the cell lines was 2.1% (DW). In some cell lines some scopolamine was also found in the medium however, atropine levels in roots and media were low (0.07-0.82%). The growth index of the roots was found to depend on the inoculum size the larger the inoculum, the lower the growth index. 

Duboisia leichhardtii Roots Pseudotropine Scopine Scopoline Atropine Acetylpseudotropine Acetylscopine Acetylscopoline Scopolamine 324... 

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). 

Mano Y, Nabeshima S, Matsui C, Ohkawa H (1986) Production of tropane alkaloids by hairy root cultures of Scopolia japonica. Agric Biol Chem 50 2715-2722 Mano Y, Ohkawa H, Yamada Y (1989) Production of tropane alkaloids by hairy root cultures of Duboisia leichhardtii transformed by Agrobacterium rhizogenes. Plant Sci 59 191-201... 

Although the production of tropane alkaloids in tissue culture of solanaceous plants usually is low, hairy root cultures of Duboisia leichhardtii produced 1.1% (dry weight) of scopolamine (Ellis, 1988). Cultures of this genus have been studied widely because they synthesize both nicotine-... 

Searching for other producing systems, differentiated shoot cultures of H. albus L., Duboisia leichhardtii F.MueU., D. myoporoides R.Br., Datura metel L., and Scopolia parviflora (Dunn.) Nakai. were initiated on different media (B5 or MS, supplied with 10 pM BAP alone, or in combination with 0.1 or 1.0 pM NAA) [45,48,49, 52, 53]. Analyses showed that hyoscyamine 1 and scopolamine 6 were not presented or were detected at extremely low concentrations in these plant... 

Duboisia leichhardtii F. Muell. Callus B5 10 NAA+1 BAP Continuous light tr" tr [48]... 

Duboisia leichhardtii Scopolamine Hairy root culture... 

If any Tl-type alkaloids occur in a specific taxon, there may be present between only one metabolite (e.g., Anthocercis littorea) and up to six congeners of this type [e.g., Cyphanthera albicans, Hyoscyamus pusillus (4) Datura inoxia (5) Duboisia myoporoides (6)]. Such alkaloids are normally accompanied by one or more different types of tropane alkaloids (T3 - T6 Schizanthoideae T7-D), e.g., alkaloid extracts obtained from the leaves of Duboisia leichhardtii contained hyoscyamine as the principal component accompanied by minor congeners like scopolamine (hyoscine) as well as different Tl-type esters (e.g., butropine, valtropine). Both latter... 

Cyphanthera clade Duboisia leichhardtii isol. isol. isol. isol. isol. (3,4)... 

De Garcia LA, Rodriguez PH, Martinez M (1985) Alkaloid contents in some Colombian Brugmansia species. Rev Mex Cienc Farmac 16 11-13 De la Fuente G, Reina M, Munoz O, San Martin A, Girault JP (1988) Tropane alkaloids from Schizanthus pinnatus. Heterocycles 27 1887-1897 Deckers W, Maier J (1953) Two new alkaloids from Duboisia leichhardtii. Chem Ber 86 1423-1428... 

Griflin WJ (1965) The alkaloids of Duboisia leichhardtii. Australasian J Pharm 46 128-131 Griffin WJ, Lin GD (2000) Chemotaxonomy and geographical distribution of tropane alkaloids. Phytochemistry 53 623-637... 

V. Alkaloids in cultured cells of Duboisia leichhardtii. Yakugaku ZassM 100 574—575 Karrer P, Widmer R (1925) Konfiguration des Nikotins. Optisch akdve Hygrmsaure. Helv Chim Acta 8 364-368... 

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