Duboisia hopwoodii

Anabasine Duboisia hopwoodii Duboisia hopwoodii Nicotiana tabacum Nicotiana rustica... 

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

Nicotinoids. Nicotine from tobacco was one of the earliest insecticides and was recommended for use in 1763 as a tea for the destruction of aphids (1,20). Nicotine [54-11 -3], L-l-methyl-2-(3 -pyridyl)pyrrolidine (1) (bp 247°C, d 1.009), is found in the leaves of Nicotiana tobacum and N. rustica (Solanaceae) in amounts ranging from 2 to 14%, and also is found in Duboisia hopwoodii and in Aesclepias syriaca. It occurs as the principal alkaloid along with small amounts of 12 other alkaloids of which nomicotine [494-97-3], 2-(3,-pyridyl)pyrrolidine (2) (bp 270°C, d 1.07 g/mL), and anabasine [494-52-0], l-2-(3 -pyridyl)piperidiae (3) (bp 281°C, d 1.048), are of insecticidal importance (see Alkaloids). Nomicotine occurs as both the D and L forms, the former in D. hopn oodii and the latter commonly predominating in Nicotiana. Anabasine is the chief alkaloid of Anabasis aphylla, where it occurs from 1—2% in the shoots and is found to ca 1% in Nicotianaglauca. 

COtinine [inn] is an alkaloid from leaf tobacco (Nicotiana tabacum) and is also detected in Duboisia hopwoodii (Solanaceae). It is a nicotine metabolite, used as a biomarker for exposure to cigarette smoke. It shows ANTIDEPRESSANT and other behavioural effects in animals, cothromboplastin factorVII. 

In the meantime the presence of alkaloids was observed in many other Australian plants, including a small tree whose leaves are known to the aborigines of central Australia as "pituri". In 1872 the effects of pituri, later identified as foliage of Duboisia hopwoodii (Solanaceae) [5], were studied by Joseph Bancroft [6], a Brisbane medico, who reported as follows ... 

Diplopterys martiusii Bentham—219 Duboisia hopwoodii v. Muel.—256,374,376 Duboisia myoporoides R. Brown—371,376 Duboisia sp.-363.370... 

The main alkaloids of this group have long been considered as characteristic constituents of Nicotiana species. The occurrence of d-nomicotine (246, 247) in Duboisia Hopwoodii F. Muell. (Solanaceae) and of anabasine... 

C,oH,2N20, Mr 176.22, viscous oil, bp. 210-211 C (0.8 kPa), [a] -12.8 (H2O). C. is a tobacco alkaloid occurring in tobacco leaves (Nicotiana tabacum), in Duboisia hopwoodii, and in tobacco smoke. C. is the main metabolite of nicotine. It is probably also formed as an artefact in mammalian organisms by autoxidation of nicotine. 

Nornicotine and anabasine count amongthe minor alkaloids of tobacco. Whereas Nkotiana species contain the (S)-nornicotine, Duboisia hopwoodii produces the (J )-enantiomer. Anabasine is with up to 2.6% the principal alkaloid of Anabasis aphylla. The anabasine content in Nkotiana glauca is comparatively high and reaches 1 %. 

Duboisia hopwoodii (a), Nicotiana glauca (b) and Lobelia inflata (c). 

Nicotine, l-methyl-2 (3-pyridyl) pyrrolidine, is found in tobacco derived from Nicotiana tabacum and other plants of the Solanaceae, including the Australian pituri (Duboisia hopwoodii), whose properties were exploited by the indigenous Australians of the central desert... 

Unlike the pituri, Duboisia hopwoodii, the nicotine-containing species that inhabits the central and western regions of Australia, the two trees/shrubs Duboisia myoporoides and D. leichhardtii, also known as corkwood, are restricted in their distribution to the east coast of Australia and adjacent areas. Corkwood leaves contain the highest levels of atropine and tropane alkaloids in the world, and since World War II have replaced Atropa belladonna and Hyoscyamus niger as the leading source of these alkaloids (Barnard 1952 Roddick 1991). 

Bottomley W, Nottle RA, White DE (1945) The eilkeiloids of Duboisia hopwoodii. Austral J Sd... 

Hibi N, Fujita T, Hatano M, Hashimoto T, Yamada Y (1992) Putrescine A -methyltransferase in cultured roots of Hyoscyamus albus. Plant Physiol 100 826-835 Hicks CS (1936) Observations on the chemistry of rf-nornicotine, an alkaloid of Duboisia hopwoodii. Austral J Exptl Biol Med Sci 14 39-43 Hicks CS, LeMessurier H (1935) Preliminary observations on the chemistry and pharmacology of the alkaloids of Duboisia hopwoodii. Austral J Exptl Biol Med Sci 13 175-188 Hicks CS, Brucke FT, Heuber EF (1935) Pharmacology of Duboisia hopwoodii (rf-nornicotine). 

Peterson N (1979) Aboriginal uses of Australian Solanaceae. In The biology and taxonomy of the Solanaceae. Linnean Society Symposium Series No. 7. Academic Press, London, pp 171-189 Petit (1879) Nicotine from Duboisia hopwoodii. J Pharm Chim 29 338-341 Petrie JM (1917a) The chemical investigation of some poisonous plants in the natural order Solanaceae.III. Occurrence of nor-hyoscyamine in Solandra longiflora. Proc Linnean Soc NSW 41 815-822... 

Rothera ACH (1911) The alkaloid of pituri obtained from Duboisia hopwoodii. Biochem J 5 193-206... 

Self LS, Guthrie FE, Hodgson E (1964) Adaptation of tobacco homworms to the ingestion of nicotine. J Insect Physiol 10 907-914 Senft E (1911) Duboisia hopwoodii F.Muell. (Pituri). Pharmaz Praxis 1... 

Spath E, Hicks CS, Zajic E (1935) liber (/-Nor-nicotin, ein Alkaloid von Duboisia hopwoodii F. v.MueU. Ber 68B 1388-1393... 

Luanratana O, Griffin WJ 1982 Alkaloids of Duboisia hopwoodii. Phytochemistry 21 449 - 451... 

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