Hyoscyamus albus

Sauerwein, M. and Shimomura, K. 1991. Alkaloid production in hairy roots of Hyoscyamus albus transformed with Agrobacterium rhizogenes. Phytochemistry, 30 3277-3280. 

HIBI, N FUJITA, T., HATANO, M., HASHIMOTO, T YAMADA, Y., Putrescine V-methyltransferase in cultured roots of Hyoscyamus albus. Plant Physiol., 1992,100, 826-835. 

Hyoscyamus albus H. aureus H. muticus H. niger H. pusillus... 

NEW ALKALOIDS FROM SOLANACEOUS PLANTS 4.1. jp-Hydroxyhyoscyamine from Hyoscyamus albus hairy roots... 

Hyalbidone from Hyoscyamus albus hairy roots... 

Fig 1. Alkaloids isolated from hairy root cultures of Hyoscyamus albus. 

Hyoscyamus plants, namely henbane, have been known to man from ancient times as a remedy for various diseases. One of the allied species of Hyoscyamus niger (described as Hyoscyamus leaf in the European Pharmacopoeia), Hyoscyamus albus is grown on the European Continent, particularly in France, and in the Indian subcontinent [1]. Quantitatively and qualitatively its alkaloids appear similar to those of H. niger [1]. 

The influence of phytohormones and light on the production of tropane alkaloids in transformed roots of Hyoscyamus albus was investigated [25]. In adventitious roots cultured in the dark, the addition of lAA (up to 4 mg/1) to the culture medium only slightly affected alkaloid production (Fig. 8a). On the other hand, when the adventitious roots were cultured under light, the alkaloid content decreased with the addition of lAA. Any combination of lAA with kinetin rapidly... 

Fig. 14. Hyoscyamus albus hairy roots transformed with Agrobacterium rhizogenes MAFF 03-01724. The roots were cultured in a 21 air-lift type fermenter with phytohormone-free WP liquid medium for 28 days.

ODC has been isolated from Hyoscyamus albus root cultures [111]. It is known that tropane alkaloids can be synthesized from both ornithine and arginine, although the arginine route is favoured. The activity of ADC in root cultures of H. albus is twice that of ODC... 

Recently, it has been shown that the biosynthetic pathway between ornithine and hyoscyamine must be different in Datura and Hyoscyamus albus (48), i.e. the conversion of ornithine to the 1-methyl-A1-pyrrolinium salt (a precursor of hyoscyamine) can proceed by two pathways, one of which (in Datura) cannot involve free putrescine (48). 

Hyalbidone (182) was isolated from hairy root cultures of Hyoscyamus albus which were transformed with Agrobacterium rhizogenes. Its structure was established using MS and one-and two-dimensional H and 13C NMR [463]. Feeding [1-13C, 2-2h]-acetate to the above cultures of Hyoscyamus albus gave little incorporation of label into 182, suggesting that 182 was either not derived from tropine, or was located near the end of the biosynthetic pathway [464],... 

Doerk-Schmitz, K., Witte, L., and Alfermann, A. W. (1994) Tropane alkaloid patterns in plants and hairy roots of Hyoscyamus albus Phytochemistry 35,107—110. 

Hygrocybe psittacina var. psittacina Hesler et Smith-313 Hyoscyamus albus L.-3S7 Hyoscyamus aureus L.-367 Hyoscyamus boveanus (Dunal ex DC.)... 

El Bazoui A, Bellimam MA, Lancar 1, Soulaymani A. Gas-liquid chromatography-mass spectrometry investigation of tropane alkaloids in Hyoscyamus albus L. from Morocco. Z Naturforsch C 2012 67(9 - 10) 461-5. 

Ornithine is incorporated into pyrrolidine rings unsym-metrically in several Datura species, but a symmetrical intermediate is involved in Nicotiana species, Erythroxylum coca, Duboisia leichardtii, Hyoscyamus albus, and Nicandra physaloides (Leete, 1990). 

Four reports describe investigations of the incorporation of various isotopo-mers of acetic acid labeled with stable isotopes into the tropane alkaloids. The first of these, by Sankawa and Noguchi [42], reported the regiochemistry of [ 1,2- C2] acetate incorporation into hyoscyamine (3) in Hyoscyamus albus. Surprisingly at the time, it was found that the resonances due C-2 and C-4 both showed coupling to the resonance assigned to C-3. The authors concluded that two labeled species were present in the sample, one in which an intact bond from acetate was introduced in such a fashion that C-2 and C-3 were bond-labeled and another one in which C-4 and C-3 were bond-labeled. The analysis of the C NMR spectra of other alkaloids, the 6)3- hydroxy derivatives of (3), isolated from this experiment indicated an identical pattern of incorporation of acetate into these substances as well. 

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