Munjistin

Alizarin Purpurin Xanthopurpurin Munjistin Pseudopurpurin Other compounds... 

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, 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... 

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... 

Figure 13.4 Chromatographic signals of munjistin registered for mobile phases containing acetic acid (a) and formic acid (b)...

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].

Rubia chinensis Regel Maack R. cordifolia Thunb. R. cordifolia L. f. pratensis (Maxim.) Kitag. R. mungista Roxb. R. sylvatica (Maxim.) Nakai Qian Cao (Madder) (root) Rubierythrinic acid, alizarin, purpurin, pseudopurpurin, munjistin.3349 Hemostatic, shorten the blood clotting time, antibacterial, antitussive, stimulate uterine contractions. 

The dried root was also found to contain purpuroxanthin (II) formed by separation of CO2. from munjistin (VII). Pseudopurpurin (XXIII) is probably decarboxylated with formation of purpurin (XXI) when the madder root is dried. The dried madder root also contains the following hydroxyanthraquinone dyes in small amounts nordamna-canthal (VI), quinizarin (IX), 1,4-dihydroxy-2-hydroxymethylanthra-quinone (XI), quinizarin-2-carboxylic acid (XII), anthragallol (XVIII), and anthragallol-3-methyl ether (XX) (32, 34, 39). 

Constituents (See also table HI) The root or its bark contains as its principal dyes morindon (XXIII) and morindin (morindon-5-ruti-noside). Other constituents are soranjidiol (XIV), morindadiol, rubiadin (III) (partly as glycoside), purpuroxanthin (II), lucidin (5), munjistin (VII), and small amounts of alizarin (I), Morindanigrin... 

Figure 1. TLC of dyes of various madder types. 1, madder (Rubia tinc-torum L.) 2, wild madder (R. peregrina L.) 3, Indian madder (R. cor-difolia L.)i 4, Japanese madder (R. akane) 5, relbun root (Relbunium hypocarpium (L.) HEMSL.) 6, lady s bedstraw (Galium verum L.) 7, alizarin 8, purpurin + pseudopurpurin (lower spot) 9, munjistin.

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... 

Before the introduction of synthetic anthraquinone derivatives, natural anthraquinone dyes have been used for centuries. Apart from alizarin, madder also contains e.g. purpurin, pseudopurpurin, rubiadin and munjistin. 

Anthraquinoids (purpurin, munjistin) [154] Madder Greek painting materials, Hellenistic period (second to third century b.c.) and Roman period (second century a.d.) ESI operating in negative-ion mode, single qnadmpole analyzer with SIM acquisition mode... 

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. 

Quinones group Alizarin Aloe Aloe-emodin Aloin Carminic acid Chrysophanol Cochineal Emodin Frangulin Kermes Kermesic acid Lac Laccaic acid Lucidin Madder Morindone Munjistin Pseudopurpurin Purpurin Rhein Rubiadin Colour Index (1911) Hobson Wales (1998) 42—44... 

Madder is characterised by the presence of a series of key anthraquinone components, the most important of which are alizarin, purpurin and pseudopurpurin, molindone, xanthop-urpurin, rubiadin (qq.v.), although a large group of other anthraquinones is also present. Schweppe and Winter list the following additional components found in the various madder species munjistin, ibericin, lucidin, 2-hydroxyan-thraquinone, xanthopurpurin-3-methyl ether, alizarin-1-methyl... 

Munjistin, l,3-dihydroxyanthraquinone-2-carboxyhc acid, is an anthraquinone found as a component in roots of various Rubia, Relbunium and Morinda species it is therefore a major constituent of certain madder dyes (Schweppe and Winter, 1997). It is designated by the Colour Index as Cl 75370. 

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