Rubia tinctorum lucidin from

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].

The major constituent in the extract of madder, Rubia tinctorum (Rubiaceae), was identified as lucidin-3-O-primeveroside (342), a commonly used food pigment. It exhibited antifeedant activity against the carpet beetle, Attagenus japonicus 50 This opens the window for using dyes from either R. akane or R. tinctorum to protect textile against these textile pests. 

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). 

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. 

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... 

Alizarin, Pseudopurpurin, Purpurin as well as Lucidin, Morindone, Munjistin and Rubiadin in Madder and other closely related dyestuffs of natural origin from plant species such as Rubia tinctorum L. and other R. species, Odenlandia species, Morinda species and Galium species. 

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