Rubiadin

Madder, Armenian cochineal, lac dye historical samples pigment and wall painting Alizarin, munjistin, purpurin, xanthopurpurin, rubiadin, laccaic acid A, laccaic acid B, carminic acid, kermesic acid, flavokermesic acid HCI/MeOH/ h2o A H20 B ACN with TFA 275 nm/ESI ( ) HPLC optimization... 

Morinda citrifolia L. M. officinalis L. Je Shu Ba Ji Tian (root) Dihydroxy methyl anthraquinone, glucoside morindin, rubichloric acid, alizarin, alpha-methyl ether, rubiadin-I-methyl ether, tannins, morindadiol, masperuloside, soranjudiol, nordamnacanthal.50-424 Treat beri-beri, cancer, lumbago, cholecystitis, increase leukocyte count, stimulate endocrine system. 

Rubiadin-I-methyl ether Morinda citrifolia, M. officinalis... 

Constituents (See also table II) The dyes contained in the roots of these two plants are pseudopurpurin (XXII), its primveroside galiosin, purpurin (XXI) (formed in some cases from pseudopurpurin by decarboxylation), rubiadin (III), its 3-B-primveroside, lucidin (V) (jpartly as glycoside), purpuroxanthin (II), and alizarin (I) (partly as glycoside) (51). 

Constituents (See also table HI) Approx. 0,4% of hydroxyanthra-quinones the principal components are Morindon (XXIII) and Morindin (morindon-5-rutinoside). Other constituents are soranjidiol (XIV), morindadiol (1,5-dihydroxy-2(or 3)-methylanthraquinone), rubiadin... 

Rubia peregrina As the new, improved extraction method was used here, the pseudopurpurin spot is most prominent, and purpurin can also be clearly identified. Alizarin is only present in traces. The red spot may be rubiadin (III), until now not mentioned in the literature as a dye in Rubia peregrina. 

Rubia cordifolia In this case, too, the new extraction method was used. The pronouced spot is that of alizarin, and the second is that of pseudopurpurin. The red spot of (probably) rubiadin in contrast to Rubia peregrina cannot be found. 

Galium verum New extraction method. Pseudopurpurin is the main component, but purpurin, and in contrast to Rubia peregrina, alizarin can also be clearly identified. The red spot is, as in the case of Rubia peregrina, probably rubiadin. 

D-Glucosides of several hydroxyanthraquinones have been reported. For example, Schunk and Marchlewski isolated rubiadin D-glucoside from madder root. This compound was later synthesized by Jones and Robertson and shown to be 3-(/3-D-glucopyranosyloxy)-l-hydroxy-2-methyl-anthraquinone. 

Rubiadin. 1,3-Dthydroxy-2-methyl-9,I0-anthra-unedume l,3-dihydroxy-2-methylanthraquinone. C,sH10Ot mol wt 254.23. C 70.86%, H 3.96%. O 25.17%. From Rubio linciorum L Coprosma var, Morinda citrifolia Linn, Rubia-ceae Schunck, Ann. 87, 344 (1853) Briggs, Nicholls, J. 

After the first isolation of alizarin a lot of other anthraquinones were isolated from Rubia tinctorum for example purpurin, munjistin, rubiadin, pseudopurpurin, nordamnacanthal, lucidin, xanthopurpurin and anthra-gallol. 

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 ... 

Documented effects In vitro, ethanolic extracts of the plant showed low to moderate cytotoxic activity in human lympho-blastoid Raji cells (Spiridonov et al. 2005). Rubiadin exhibited antifungal and antituberculosis activity, as well as cytotoxicity to BC and NCI-H187 cancer cell lines (Kanokmedhakul et al. 2005). Asperuloside has laxative effects (Milkowska-Leyck et al. 1999). 

Phytochemistry The herb contains anthraglycosides and anthraquinones (galiosin, rubiadin, asperuloside, etc.), flavonoids, traces of essential oils, tannins, and dyeing substances. Rhizomes contain iridoids, steroid glycosides, coumarins, and flavonoids (Akopov 1990 Muzychkina 2000 Demirezer et al. 2006 Tamas et al. 2006 Zhao et al. 2008). Cultivated callus tissue produced a variety of different anthraquinones (Banthorpe and White 1995). 

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