Rubia tinctorum roots

Rubia tinctorum roots Alizarin, alizarin glucoside, purpurin, pseudopurpurin, lucidin glucoside, lucidin primeveroside, munjistin, ruberythric acid EtOH/H20, H2S04 A ACN B ammonium formate/FA with EDTA 250, 254 nm/ESI (+) Post column modification of eluent (5% NH3 in H20) for NI mode... 

Rubia tinctorum roots Alizarin, munjistin, purpurin, pseudopurpurin, lucidin, nordamnacanthal (as glycosides or aglycones) MeOH/H20, TFA, HCI, H20 (enzymatic hydrolysis) ACN/AcONH4 254 nm/ESI (+) Hydrolysis optimization, characterization of root components... 

Fig. 2.147. UV (254) trace of a crude extract of Rubia tinctorum roots and mass spectra (single MS) of the chromatographic peaks for individual anthraquinones lucidin primeveroside (1), ruberythic acid (2), pseudopurpurin (5) and munjistin (6). Mass spectra (a-b) were obtained with NI-ESI with post-column addition of ammonia. Reprinted with permission from G. C. H. Derksen et al. [320].

For the extraction of colourants from Rubia tinctorum (Figure 13.2) roots, mostly methanol, [42] water-methanol (with the addition of n-amyl alcohol in the case of lake extraction)[19,20] or water-ethanol solutions[38] are used. Additional hydrolysis can be performed with hydrochloric acid[8,19,20,34] and trifluoroacetic acid,[42] but also with madder root enzymes,[42] responsible for cleavage of anthraquinone glycosides into the corresponding aglycones and sugars. 

G.C.H. Derksen, T.A. van Beek, JE. Groot and A. Capelle, High performance liquid chromato graphic method for the analysis of anthraquinone glycosides and aglycones in madder root (Rubia tinctorum L.), J. Chromatogr. A, 816, 277 281 (1998). 

The British are coming, the British are coming cried Paul Revere. Well, he could hardly have missed them, decked out in their bright red coats. The attire of the British soldier tended to undermine military strategy, but the color had nothing to do with battle tactics. It had to do with economics. The British uniforms were required, by royal decree, to be dyed red in order to support British agricultural interests, specifically the cultivation of the madder plant (Rubia tinctorum). It was from the roots of this plant that the brilliant red dye known as alizarin was extracted. Alizarin was not produced in the colonies, and... 

In recent decades, numerous dyer s plants of the type of madder (Rubia tinctorum L.) have again been investigated for their constituents. With the aid of modern methods of instrumental analysis, no less than 23 different components belonging to the class of hydroxyanthraquinones have been identified in madder roots (32-3A), for instance, besides five hydroxyanthraquinone glycosides, of which rubia-nin (Constitution VIII in table I) (35) is of particular interest,... 

In contrast to Rubia tinctorum, the roots of this plant contain no lucidin (V). 

Rubia tinctorum alizarin and purpurin can be clearly identified by the marked spots. Pseudopurpurin has been converted into purpurin by decarboxylation, because the old extraction method (boiling with 10% sulfuric acid, followed by shaking with ethyl acetate) has been used to isolate the dyes from the madder roots. 

Galium spp., Aspemla odorata, Relbunium hypocarpum (Rubiaceae) glycoside in Rubia tinctorum (Rubiaceae) [root]... 

The blue dye indigo, derived from the plant Indigofera tinctoria, has been used in India for thousands of years. Traders introduced it to the Mediterranean area and then to Europe. Tyrian purple, a natural dark purple dye obtained from the mucous gland of a Mediterranean snail of the genus Murex, was a symbol of royalty before the collapse of the Roman empire. Alizarin, a bright red dye obtained from madder root Rubia tinctorum), a plant native to India and northeastern Asia, has been found in cloth entombed with Egyptian mummies. 

Turkey Red.—Alizarin is the chief constituent of the coloring matter Turkey red, which has been known since ancient times and which was obtained from the root of the madder plant, Rubia tinctorum L. The substance is of special interest because the determination of its constitution was one of the early triumphs of organic chemistry and because it was the first natural dye to be synthetically prepared. The name is derived from the oriental name for the madder, viz., alizari. In the madder root it is present as a glucoside known as ruberythric acid, which, on hydrolysis by fermentation or by boiling with acids, yields glucose and alizarin. Alizarin is a solid which sublimes as orange red needles, m.p. 289°, insoluble in water but slightly soluble in alcohol. 

The use of herbal medicines prepared from the root of Rubia tinctorum (madder) is no longer permitted in Germany. Root extracts have shown genotoxic effects in several test systems, which are attributed to the presence of the anthraquinone derivative lucidin. One of the other main components, alizarin primeveroside, is transformed into 1-hydroxyanthraquinone when given orally to the rat, in which this metabolite has carcinogenic activity (6). 

Rubia. Madder. Rubia tinctorum. W. I. 603. Radix. The root. 

Additionally, 1-hydroxyanthraquinones present in certain medicinal plants such as Rubia tinctorum L. (madder root) are genotoxic agents and mice... 

ABSTRACT The roots of Rubia tinctorum L. (madder) are the source of a natural dye. In this review for the first time all the different information on Rubia tinctorum available in the literature is summarised. The dye components are anthraquinones which probably contribute to the resistance of the plant against fungi in the soil. Madder roots have been used to dye textiles in many parts of the world since ancient times and an overview of the historical development, cultivation, harvesting and dyeing techniques of madder is given. The anthraquinone alizarin, the hydrolysis product of ruberythric acid, is supposed to be the main dye component of Rubia tinctorum. The chemical synthesis of alizarin and the biosynthesis of the anthraquinones in Rubia tinctorum are described. As far as the purification, structure elucidation and structures of isolated compounds are concerned, the review confines itself to the anthraquinones of madder. Finally the pharmacology and medicinal uses of madder and pure anthraquinones are discussed. This review supplements and updates earlier partial reviews on madder or anthraquinones by Schweppe, Thomson and Wijnsma. 

The roots of Rubia tinctorum L. (madder) are the source of a natural dye and they have been used to dye textiles in many parts of the world since ancient times [1], The dye components are anthraquinones [1] with alizarin, the hydrolysis product of ruberythric acid, being the main dye component of Rubia tinctorum. The anthraquinones probably contribute to the resistance of the plant against fungi in the soil [2]. 

Rubia tinctorum is native in Southern and Southeast Europe, in the Mediterranean area, Asia Minor and in the Caucasus. Nowadays the plant also grows in China and Japan, up to the Malaysian Archipelago, in the Western part of North America, in Mexico and South America. In earlier days madder was cultivated in Central and Western Europe. Nowadays most of the plants are found in the wild [3], In The Netherlands madder is again cultivated for its roots in the province of Groningen since about ten years. 

Some anthraquinones isolated from Rubia tinctorum are believed to be artefacts for example the anthraquinones which show the presence of a 2-methoxymethyl or 2-ethoxymethyl group. These anthraquinones have been formed during the extraction of lucidin with boiling methanol or ethanol [4,68,97]. According to Schweppe the anthraquinones purpurin (1,2,4-trihydroxy anthraquinone) and purpuroxanthin (1,3-dihydroxy-anthaquinone) are formed from respectively pseudopurpurin (3-carboxy-1,2,4-trihydroxyanthraquinone) and munjistin (2-carboxy-l,3-dihydroxy-anthraquinone) during drying of the roots [3]. Some anthraquinones were only isolated once from Rubia tinctorum. It is thus doubtful whether these... 

The roots of Rubia tinctorum have been used for dyeing textiles in many parts of the world since ancient times. Madder was widely cultivated in Western Europe for the dye industry until the beginning of the twentieth century. Rubia tinctorum contains useful anthraquinone mordant dyes. Dried roots of madder contain the hydroxy anthraquinones alizarin, pseudopurpurin, rubiadin, purpurin, purpuroxanthin and some minor anthraquinones. Anthraquinone derivatives are good mordant dyes if they satisfy the following conditions ... 

Common madder (Rubia tinctorum) [46] is a plant already known in the Middle East back in ancient times. From its roots a red extract, called lake, could be isolated (Fig. 2.17). It was already described by Phny the Elder. The Arabic name for the red root is alizari . 

Roots of the Rubia tinctorum plant. Roots were known as alizari, hence alizarin... 

Anthragallol, 1,2,3-trihydroxyanthraquinone, is fotmd as a major dye component in roots Rubia tinctorum L. and is therefore a principal constiment of madder dyes. It is designated by the Colour Index (1971) as Cl 58200. S3mthesis is from galhc acid and benzoic acid with sulfuric acid at 125°C or from phthalic anhydride and pyrogaUol with sulfuric acid at 160 C (Seuberlich, 1877 cf. Merck Index, 1996). It is found in the following forms ... 

Anthragallol-2,3-dimethyl ether is extracted from the seed of Morinda citrifolia L. and the roots of Rubia tinctorum L. Anthragalloltrimethyl ether extracted from the whole plant of Oldenlandia umbellata L. (Schweppe, 1992). 

The term retzel is foimd in formulas in German texts from the middle ages. It is a term for madder root, Rubia tinctorum L. (Floss, 1962). 

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