Duboisia myoporoides

HjO), a picrate, m.p. 253° (dec.) and furnishes a dibenzoate, whose sulphate has [a] ° + 52-1° (EtOH) and hydrochloride, B. HCl. 2H2O, m.p. 115° or 205° (dry), + 41-8° (dilute alcohol) and nitrate, B. HNO3, m.p. 197°. On reduction with hydriodic acid and red phosphorus the dihydroxytropane is converted into tropane and on treatment with phosphorus oxychloride it yields a base, CgHjgON, b.p. 188°/752 mm., picrate, m.p. 177° (dec.). This dihydroxytropane is probably represented by formula (XIII).The dibenzoyl-derivative has local ansesthetic properties. The wovaleryl ester is the alkaloid valeroidine found in Duboisia myoporoides (p. 90). 

Fig. 2.6 Map of Eastern Australia and Tasmania showing places referred to in the discussion of Duboisia myoporoides...

Gritsanapan, W. and Griffin, W. J. 1991. Alkaloid variation within Duboisia myoporoides. Phytochemistry 30 2667-2669. 

Loftus Hills, K., Bottomley, W. and Mortimer, P. 1. 1953. Occurrence of nicotine together with hyoscine in Duboisia myoporoides. Nature 171 435. 

Mortimer, P. I. and Wilkinson, S. 1957. Occurrence of nicotine, anabasine, and isopeUetietine in Duboisia myoporoides. J. Chem. Soc. 3967-3970. 

Nicotine Nicotiana tabacum Nicotiana rustica Duboisia hopwoodii Duboisia myoporoides... 

The simple piperidine pelletierine from Punica granatum (pomegranate) (Punicaceae) and Duboisia myoporoides (Solanaceae) is an anthelmintic. The simple piperidine derivatives deoxy-mannojirimycin (DMJ) and deoxynojirimycin (DNJ) from Lonchocarpus species (Fabaceae) are glycosidase inhibitors because they are structurally similar to the pyranose (six-membered ring) sugar moieties of the glycosidase disaccharide substrates. 

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). 

D. innoxia [Datura potion for S. Am. Indian sacrificial victim pre-sacrifice stupor], Duboisia myoporoides, Hyoscyamus niger (henbane), Metfysticodendron amesianum, Scopolia carniolica (Solanaceae)... 

Nicotine Duboisia myoporoides, Mcotiana T D-REL (nACh-R agonist)... 

An alkaloid obtained from various solanaceous plants, Hyoscyamus muticus and Duboisia myoporoides being the best sources. It is the laevo-isomer of atropine. 

Tigloidine was first isolated from Duboisia myoporoides (Solana-ceae) but is now synthesised. 

Duboisia myoporoides-D. leichhardlii hybrid (M-II-8-6) D. myoporoides-D. leichhardlii hybrid (M-II-8-14)... 

The leaves of Duboisia myoporoides from New Caledonia contain nicotine and nornicotine the alkaloid content of this plant is very different from the same species... 

Duboisia myoporoides from New Caledonia proved to have the same topane constituents as the Austt alian Duboisia but in an entirely different proportion here scopolamine is the major alkaloid, not hyoscyamine. 

In this chapter, production of isoquinoline alkaloids by callus and root organ cultures of ipecac and production of tropane alkaloids by root organ cultures of Duboisia myoporoides-D. leichhardtii hybrid are described. 

Tropane alkaloid production in root cultures of a Duboisia myoporoides — D. leichhardtii hybrid... 

Callus and root organ cultures of Duboisia have been studied with a view to develop a new method to obtain tropane alkaloids more efficiently [64-66]. In solanaceous plants, which produce tropane alkaloids, cultured roots produce them but calli do not [65] or only in very small amounts [66]. Root organ culture might be a useful method to produce tropane alkaloids and suitable culture conditions for growth and alkaloid production must be established. In this section, the effects of auxins including lAA chloro-derivatives on the growth and alkaloid yields in root organ cultures of Duboisia myoporoides - D. leichhardtii hybrid are described [67, 68]. 

The Duboisia myoporoides - D. leichhardtii hybrid (M-II-8-6), which was used for explants, is cultivated at the Research Center for Medicinal Plant Resources, Tsukuba, Japan. Leaves were dipped in 75% ethanol for 10 seconds, rinsed in sterilized water, surface-sterilized for 10 minutes in 2% sodium hypochlorite containing Tween 20 (1 drop per 40 ml) and then washed three times with sterilized water. Leaf segments (ca. 5x5 mm) were incubated on MS solid medium containing 1 mg/1 lAA and 3% sucrose in the dark at 25 "C. Within 3 weeks, adventitious roots developed. 

To elucidate the factors for the growth differences, Deno et al. measured the amount of lAA present in the hairy and adventitious roots of Duboisia myoporoides by HPLC, and detected fairly high contents in the hairy roots during the culture (185, 159 and 103 pmoEg fresh weight lAA at day 7, 17 and 35, respectively) in contrast to the lower contents in the adventitious roots (81 and 93 pmoEg fresh weight lAA at day 13 and 30,... 

Quantitative analysis of hyoscyamine in Duboisia myoporoides and in D. leichhardtii. Peak areas are measured. 

The Australian species Duboisia myoporoides R.Br., family Solanaceae, is a bush-tree, which grows on the east coast of Australia, New Caledonia and adjacent islands. Its leaves contain about 2% alkaloids. Leaves harvested in October contain hyo-scyamine as the main alkaloid, whereas leaves harvested in April have scopolamine as the main alkaloid. (Fig. 3)... 

Scopolamine is extracted from the leaves of Duboisia myoporoides., R.Br. and also from aerial parts of Datura san uinea Ruiz et Pav., cultivated in Equador. (Fig. 4)... 

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