Of sanguinarine

Oxysanguinarine, C2oH430gN, was isolated by Spath, Schlemmer, Schenck and Gempp by chromatographic analysis of blood root alkaloids, and was also prepared by oxidation of sanguinarine nitrate by potassium ferricyanide in alkaline solution. It was purified by crystallisation from... 

Tyler, R. T., Eilert, U., Rijnders, C. O., Roewer, I. A. and Kurz, W. G. W. 1988. Semicontinuous production of sanguinarine and dihydrosanguinarine by Papaver somniferum L. cell suspension cultures treated with fungal homogenate. Plant Cell Reports, 1 410 13. 

The cytotoxic effects of sanguinarine,385 chelidonine,385 and chelidonine methiodide386 and the effect of sanguinarine on cardiac ATPase387 have been studied. 

The possible relationship of sanguinarine to glaucoma in epidemic tropical hydropsy which is frequent in India has been referred to (666, 677, 687). The oil from Argemona mexicana L., whose seeds... 

The recent synthesis [Eq. (2)] of sanguinarine chloride, involving the irradiation of anhydroprotopine, provides an interesting variant of the more usual coupling procedure.166b... 

Nandi, R. and Maiti, M. 1985. Binding of sanguinarine to desoxyribonucleic acid of differing base composition. Biochem. Pharmacol. 34, 321-324... 

Fig. 2. pH effect on the partition coefficient (K) of sanguinarine, one of the benzophenan-thridine alkaloids produced in cell cultures of E. californica, of in situ extraction with silicone fluid... 

EILERT, U., KURZ, W.G.W., CONSTABEL, F Stimulation of sanguinarine accumulation in Papaver somniferum cell cultures by fungal elicitors. J. Plant Physiol., 1985,119, 65-76. 

P450 enzyme, protopine 6-hydroxylase, to yield an intermediate that rearranges to dihydrosanguinarine (40). This intermediate also serves as the precursor to the benzo(c)phenanthridine alkaloid macarpine (Fig. la). The copper-dependent oxidase dihy-drobenzophenanthridine oxidase, which has been purified (41, 42), then catalyzes the formation of sanguinarine from dihydrosanguinarine. 

Short-term studies of sanguinarine have shown some plaque and gingivitis reduction. " " In the long-term studies of the product in a dentifrice form, no significant reduction in plaque or gingivitis occurred, with the exception of one study in which the product was used as a dentifrice and as a mouthrinse. " ... 

Hanna, J.J. Johnson, J.D. Kuftinec, M.M. Six month evaluation of sanguinarine products in orthodontic patients. In Program and Abstracts, American Association of Dental Research Montreal, Canada, March 1988, (abstract). 

It has been well known since the discovery of sanguinarine and chelerythrine [19,20,24,25] that, in contrast to their bright coloured salts, their free bases are colourless and pass into non-polar solvents even from slightly alkaline media along with other tertiary alkaloids. All QBA of the sanguinarine type have the same behaviour. Generally, the procedure for the isolation of QBA is the same as for most non-quaternary alkaloids with typical properties, i.e. a clasrical acid-base process followed by the extraction of the liberated free bases into non-polar solvents. 

Methoxydihydrofagaiidine has been reportedly obtained from Zcmthoxylum nitidum DC. [110]. The 6-ethoxydihydroderivatrves of sanguinarine and chelerythrine have similar origins [5,6]. 

The structure of 33 has been supported by using elemental analysis, mass spectrometry and NMR spectroscopy [119]. However, the NMR spectra provided a more complex depiction. They indicated the presence of five species in a CDCI3 solution of sanguinarine fi ee base (I) a major bimole-cular stereoisomer, the racemate 6R,6"R + 6S,6 S, vsdiich is thermodynamically voured according to AMI calculations [120] (II) a minor isomer, a... 

Babich H, Zuckerbraun HL, Barber IB, Babich SB Borenfreund E (1996b) Cytotoxicity of sanguinarine chloride to cultured human cells from oral tissue. Pharmacology and Toxicology 78 397-A03. 

Since both UC and DT proliferated well and contained a considerable amount of sanguinarine when grown in WP liquid medium at 22 °C, the effect of WP macro salts concentration on the growth and alkaloid production was studied by using either UC or DT as an inoculum (Table 23). 

Many secondary metabolites are produced in the roots of plants. Treatment of roots separated from the plants with Agrobacterium rhizogenes can cause them to grow rapidly as hairy roots .455 This can cause increased production of the desired compounds. Hairy root cultures of Catharan thus roseus made more vindoline than cell cultures.456 Such cultures of Papaver somniferum produced up to 2-10% dry weight of sanguinarine.457 Cultures of Sesa mum indicum made 50 times as much of the antimicrobial compound 9.50 as the intact plant.458... 

J. Benzophenanthridine Alkaloids.—The lysosomal character of sanguinarine (237 R1 = H, R2 + R3 = 0CH20), added to the latex of Chelidonium majus, has been described.230... 

Table 6 summarizes the results of alkaloid isolation studies. The structure of the new alkaloid bocconine (239) from Bocconia cordata was deduced mainly on the basis of n.m.r. studies.231 The c/D-ring substitution pattern was indicated by comparison of its n.m.r. spectrum with those of sanguinarine and chelery-thrine. The downfield shift of the C(11)-H by 0.67 p.p.m. in 5,6-dihydrobocconine... 

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