Lucidine

LC ESI MS allows also the identification of other anthraquinones in madder preparations. Based on structural information obtained by NI mass spectra and specific retention times (signals corresponding to quasi-molecular ions [M—H] and fragment ions [M—C02—H] ), pseudopurpurin (peaks at m/z 299.1 and 255.3) and munjistin (at m/z 283.1 and 239.3) are found in the natural material. Alizarin glycoside is identified by deprotonated quasi-molecular ions at m/z 401.1 and ions formed by the loss of glucose at m/z 239.1. Similar ions are found to be characteristic of lucidin... 

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... 

Madder lake, lac dye, cochineal Alizarin, purpurin, ruberythric acid, lucidin, laccaic acid A, carminic acid hci/h2o, n amyl alcohol, MeOH H20/MeOH with AcOH 250, 280 nm/ ESI( ) HPLC optimization... 

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... 

Detailed examination of another madder preparation proved that the sample can be premordanted with alum. [ 19] After hydrolysis performed with hydrochloric acid and extraction with M-amyl alcohol, only four colourants are found alizarin, purpurin, and probably lucidin and ruberythric acid. Additionally, signals at m/z 525 and 539 are observed in the mass spectrum. Analysis of the preparation by inductively coupled plasma mass spectrometry (ICP MS) shows that aluminium and calcium are the main inorganic components of the sample. This is why it was suggested that the signal at m/z 539 can be attributed to the complex of aluminium with alizarin, and the second one, observed at m/z 525, to an aluminium-calcium cluster. 

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].

Damnacanthol-3-0-(3-D-primeveroside (203) and lucidin 3-0-P-D-primeveroside (204), two anthraquinone isolates from -butanol soluble phase of the methanol extract of Morinda citrifolia L. (family Rubiaceae) roots, were evaluated to demonstrate a significant reduction of the blood glucose levels (p < 0.05) at 5 h after oral administration (100 mg/kg/body-weight). ... 

Abt. f. Allgemeine Toxikologie Universitatsklinik Eppendorf Grindelallee 117 D-20146 Hamburg Telefon (040) 4123-5277 Telefax (040) 4123-5328 Lucidin... 

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

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). 

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. 

Of the four species of Strychnos found in Australia, S. lucida R. Br. was found to contain strychnine (0.1%) and brucine (1.3%) as well as a further 0.5% of unresolved alkaloids (213). An alkaloid, lucidine-S, has been reported from the same source (214), but may be present only in the young plants, as its presence could not be confirmed in the older samples (213). The leaves of S. psilosperma F. Muell. were claimed to contain strychnine, brucine, and strychnicine (214) a later investigation (213) did not confirm this, but resulted in the isolation of two new alkaloids, strychnospermine (0.9%) and spermostrychnine 10.5%). 

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). 

S. lucida Strychnine, brucine, loganine, lucidine-S, lucidine-L [427,428]... 

---