Research Update:Rubia Root.

  seminal trace...Rubia cordifolia L.extract.Rubia Root,Qian Cao,Indian Madder Root Extract.5:1...

 


   Phytochemical info of Rubia Root.

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 Definition:Rubia Root are majorly composed of
 Chemical information disclosed as following table:


   Research Update:Rubia Root.

  A novel bicyclic hexapeptide, RA-XVIII, from Rubia cordifolia: Structure, semi-synthesis, and cytotoxicity.:Bioorg Med Chem Lett. 2007 Nov 17;

 A new bicyclic peptide of RA-series, RA-XVIII (3), was isolated from the roots of Rubia cordifolia L. Its structure was established to be a hydroxylated derivative of RA-VII by the semi-synthesis of 3 from deoxybouvardin, and its cytotoxicity against P-388 cells was 0.012mug/mL.

  Individual and combined effects of the rolA, B and C genes on anthraquinone production in Rubia cordifolia transformed calli.:Biotechnol Bioeng. 2007 Nov 19;Shkryl YN, Veremeichik GN, Bulgakov VP, Tchernoded GK, Mischenko NP, Fedoreyev SA, Zhuravlev YN.Institute of Biology and Soil Science, Far East Branch of Russian Academy of Sciences, Vladivostok, 690022, Russia.

 It is known that the rolA, rolB and rolC genes of Agrobacterium rhizogenes T-DNA affect processes of plant development and activate the synthesis of secondary metabolites in transformed plant cells. Although a synergistic activity of the rol genes on root formation is well-documented, little is known about their individual and combined action on secondary metabolism. In the present investigation, we provide evidence indicating that individual rolA, rolB and rolC genes are capable of increasing biosynthesis of anthraquinones (AQs) in transformed calli of Rubia cordifolia. The stimulatory effect was due to the increased transcription of a key gene of AQ biosynthesis, the isochorismate synthase (ICS) gene. The strongest AQ-stimulating activity was shown for an R. cordifolia culture expressing rolB at high levels, where rolB ensured a 15-fold increase of AQ accumulation compared with the control, non-transformed calli. A tyrosine phosphatase inhibitor abolished the rolB-induced increase of AQ production, thus indicating the involvement of tyrosine (de)phosphorylation in the rolB-mediated AQ stimulation. The rolA-and rolC-expressing cultures produced 2.8-fold and 4.3-fold higher levels of AQs, respectively, when compared with the control calli. However, the effect of rolA, rolB and rolC on AQ biosynthesis was not synergistic because rolA and rolC apparently attenuated the stimulatory effect of rolB on AQ biosynthesis. Therefore, the rolgene-mediated signals that promote root formation and those which activate biosynthesis of secondary metabolites seem to have a point of divergence.

  A 13-week subchronic toxicity study of madder color in F344 rats.:Food Chem Toxicol. 2008 Jan;46(1):241-52. Epub 2007 Aug 14.

 A 13-week repeated oral dose toxicity study of madder color (MC), a natural food colorant extracted from the roots of Rubia tinctorum L., was performed using F344 rats. Five groups of animals, each consisting of 10 males and 10 females, were fed diet containing 0, 0.6, 1.2, 2.5 or 5.0% MC for 13 weeks. During the experiment, lower body weight was evident from the 2.5% dose. Hematologically, fluctuation in red blood cell (RBC) parameters suggestive of weak anemia (females), and slight increases of platelet counts (both sexes) and white blood cell (WBC) counts (males) were observed at higher doses. Serum biochemically, slight fluctuations were observed in many parameters, including increased total protein (TP), conjugated bilirubin, Ca, and inorganic phosphate, and decrease of the albumin/globulin (A/G) ratio in both sexes, with dose-dependence for TP and A/G from 0.6% in females. Histopathological changes were mainly observed in the renal proximal tubules, such as microvesicular vacuolar degeneration in the cortex and karyomegaly in the outer medulla involving both sexes, lesions being evident even with 0.6%. In the outer medulla, elevation of cell proliferation activity as assessed with proliferating cell nuclear antigen was observed in males from 2.5%. Severity of focal necrosis of hepatocytes was increased only in females at 5.0%, while the increased relative liver weight as with the increased conjugated bilirubin was evident in both sexes from 1.2%. The results thus suggest that MC exerts mild toxicity, targeting liver, kidneys, and possibly RBCs and WBCs, some renal changes being evident from 0.6% in diet, that is attributable to be the lowest-observed adverse effect level (305.8-309.2mg/kg body weight/day).

  Role of Rubia cordifolia Linn. in radiation protection.:Indian J Exp Biol. 2007 Jul;45(7):620-5.Tripathi YB, Singh AV.Department of Medicinal Chemistry, Institute of Medical Sciences, Banaras Hindu University, Varanasi-221 005, India. yaminiok@yahoo.com

 The radioprotective potential of alcoholic extract of root of R. cordifolia, was studied by survival, hemopoietic cell protection and micronucleus assay. The LD50 value for the alcoholic root extract was found to be 1200 mg/kg body weight at 72 hr post irradiation. A significant radiation protection (67%) as assessed by increased animal survival was observed when R. cordifolia (RC) extract was administered intraperitoneally, 90 min. before the radiation exposure. Besides, the extract also inhibited radiation induced lipid peroxidation measured by the inhibition of thiobarbituric acid reactive substance (TBARS). The RC extract at a selected dose of 460 mg/kg body weight was effective in protecting the radiation induced suppression of endogenous colony forming units in spleen. A significant inhibition of radiation (2 Gy) induced micronuclei formation was observed when RC extract was administered 90 min prior to irradiation. Thus, it appears that the alcoholic root extract of R. cordifolia provides significant protection against radiation induced lipid peroxidation, hemopoietic injury and genotoxicity. The mechanism of action of RC extract appears to be through its anti-oxidant, metal chelation and anti-inflammatory property.

  An effective high-speed countercurrent chromatographic method for preparative isolation and purification of mollugin directly from the ethanol extract of the Chinese medicinal plant Rubia cordifolia.:J Sep Sci. 2007 Jun;30(9):1313-7. Lu Y, Liu R, Sun C, Pan Y.Department of Chemistry, Zhejiang University, Hangzhou, China.

 The medicinal plant Rubia cordifolia has been used widely in traditional Chinese medicine (TCM) for its antibacterial, antioxidant and anti-inflammatory activities. In this study, a preparative high-speed countercurrent chromatography (HSCCC) method for isolation and purification of the bioactive component mollugin directly from the ethanol extract of R. cordifolia was successfully established by using light petroleum (bp 60-90 degrees C)/ethanol/diethyl ether/water as the two-phase solvent system. The upper phase of light petroleum/ethanol/diethyl ether/water (5:4:3:1 v/v) was used as the stationary phase of HSCCC. Under the optimum conditions, 46 mg of mollugin at 98.5% purity, as determined by HPLC, could be yielded from 500 mg of the crude extract in a single HSCCC separation. The peak fraction of HSCCC was identified by 1H NMR and 13C NMR.


  A spectrometric and chromatographic approach to the study of ageing of madder (Rubia tinctorum L.) dyestuff on wool.:Anal Chim Acta. 2007 Jul 16;596(1):46-54. Epub 2007 May 31.Clementi C, Nowik W, Romani A, Cibin F, Favaro G.Dipartimento di Chimica, Universit¨¤ di Perugia, Via Elce di Sotto 8, 06123 Perugia, Italy.

 In this work, the lightfastness of wool textile samples, dyed with madder and its principal components alizarin and purpurin, was investigated using two complementary experimental techniques: absorption and emission UV-vis spectroscopy and chromatography (HPLC-PDA). Spectroscopic techniques were used to follow the time course of ageing, whereas chromatography was applied to determine relative compositional changes that occurred after exposure of wool dyed samples to natural and artificial ageing. The results from the two techniques integrate well each other and provide complementary and useful indications about the sensitivity of the dyed textiles to ageing, showing that purpurin is the principal component responsible for the spectral and chromatic properties of madder as well as for its degradation. The fading of both the fibre and dye is reduced in the presence of alum and in the absence of oxygen. The multi-analytical approach used highlights the potential of the UV-vis spectroscopy for the investigation of dyes on textiles. The great sensitivity of the spectrofluorimetry makes this technique particularly promising for a non-destructive study of dyes on works of art.

  9,10-Anthraquinones and other biologically active compounds from the genus Rubia.:Chem Biodivers. 2004 Sep;1(9):1241-64. Review. Singh R; Geetanjali, Chauhan SM.Department of Chemistry, University of Delhi, Delhi-110 007, India. singh_dr_ram@yahoo.com

 The secondary metabolites isolated from Rubia species, their biological activities, and colouration properties have been reviewed. Over 150 chemical constituents belonging to different classes of bioactive compounds such as anthraquinones and their glycosides, naphthoquinones and glycosides, terpenes, bicyclic hexapeptides, iridoids, and carbohydrates are listed together with their source(s) and corresponding references.

  Antihyperglycemic, antistress and nootropic activity of roots of Rubia cordifolia Linn.:Indian J Exp Biol. 2006 Dec;44(12):987-92.Patil RA, Jagdale SC, Kasture SB.MAEERs Maharashtra Institute of Pharmacy, Kothrud, Pune 411 038, India.

 Effect of alcoholic extract of roots of Rubia cordifolia was studied on elevated blood glucose level in alloxan treated animals. The extract reduced the blood sugar level raised by alloxan. Effect of alcoholic extract was also investigated on cold restraint induced stress and on scopolamine-induced memory impairment. Alcoholic extract enhanced brain gamma-amino-n-butyric acid (GABA) levels and decreased brain dopamine and plasma corticosterone levels. Acidity and ulcers caused due to cold restraint stress were inhibited by alcoholic extract. Animals treated with alcoholic extract spent more time in open arm in elevated plus maze model. It also antagonized scopolamine induced learning and memory impairment. Baclofen induced catatonia was potentiated by alcoholic extract.

  Identification and quantification of the constituents of madder root by gas chromatography and high-performance liquid chromatography.:J Chromatogr A. 2006 Nov 10;1133(1-2):259-74. Epub 2006 Sep 8.Boldizs¨¢r I, Szucs Z, F¨¹zfai Z, Moln¨¢r-Perl I.Department of Plant Anatomy, L. E?tv?s University, P¨¢zm¨¢ny P¨¦ter s¨¦t¨¢ny 1/C, Budapest 1117, Hungary.

 The possibilities in the identification and quantitation of the constituents of Rubia tinctorum L.'s root, called also madder root, was described and compared by gas chromatography (GC)-MS, high-performance liquid chromatography (HPLC)-UV/photodiode array detection (DAD) and HPLC-MS: chromatographic analyses were carried out in parallel, from the same samples/extracts/hydrolyzates. Anthraquinone glycosides, anthraquinones, carboxylic acids and sugars were determined directly in the presence of the matrix and in its extracts without and subsequently to hydrolyses. Hydrolyses were performed as a function of time, with hydrochloric and trifluoroacetic acids, as well as enzymatically. Data revealed that as hydrolyzing agent trifluoroacetic acid is to be preferred. Madder root's anthraquinones (pseudopurpurin/purpurin, alizarin, lucidin, munjistin, nordamnacanthal) were identified on the basis of their absorption spectra (HPLC-DAD) and fragmentation patterns by GC-MS and HPLC-MS, equally. Reproducibility of anthraquinone's quantitation, by HPLC-DAD and GC-MS, in the concentration ranges of 4 x 10(-5) to 3 x 10(-2)g/g dried sample, provided an average reproducibility of 4.2% (varying between 0.9 and 9.4% relative standard deviation (RSD percentages)). Carboxylic acids (malic, citric, quinic, rosmarinic acids) and saccharides (xylose, ribose, fructose, glucose, sucrose, primverose) were quantified as their trimethylsilyl (oxime) ether/ester derivatives by GC-MS, in the concentration ranges of 10(-5)g to 10(-2)g/g dried sample, with an average reproducibility of 4.7% RSD.

  Evaluation of nitric oxide scavenging activity, in vitro and ex vivo, of selected medicinal plants traditionally used in inflammatory diseases.:Phytother Res. 2006 Oct;20(10):896-900. Basu S, Hazra B.Department of Pharmaceutical Technology, Jadavpur University, Calcutta 700032, India.

 Steroidal and non-steroidal antiinflammatory drugs, despite their various side effects, are in great demand worldwide. Alternatively, herbal formulations provide relief to a large percentage of the population suffering from inflammatory diseases. Therefore, such practices need to be rationalized through a mechanistic approach. Thus, four traditional medicinal plants, namely Ventilago madraspatana Gaertn., Rubia cordifolia Linn., Lantana camara Linn. and Morinda citrifolia Linn. were selected for a study on the inhibition of nitric oxide (NO*), a key mediator in the phenomenon of inflammation, signifying the presence of effective antiinflammatory constituents therein. Plant samples were extracted with different solvents for evaluation of their inhibitory activity on NO* produced in vitro from sodium nitroprusside, and in LPS-activated murine peritoneal macrophages, ex vivo. Further, the inhibition of NO* synthesis was correlated with the reduction of iNOS protein expression through Western blot. Notable NO* scavenging activity was exhibited in vitro by some extracts of V. madraspatana, R. cordifolia and L. camara (IC(50) < 0.2 mg/mL). Most of them showed marked inhibition (60%-80%), ex vivo, at a dose of 80 microg/mL without appreciable cytotoxic effect on the cultured macrophages. Immunoblot analysis confirmed that the modulatory effect of the samples had occurred through suppression of iNOS protein.


  The mutagenic potential of madder root in dyeing processes in the textile industry.:Mutat Res. 2006 Jun 16;605(1-2):22-29. Epub 2006 May 4.J?ger I, Hafner C, Welsch C, Schneider K, Iznaguen H, Westendorf J.Hydrotox GmbH, B?tzinger Stra?e 29, D-79111 Freiburg, Germany.

 The roots of Rubia tinctorum L. have a long tradition of being used in dyeing processes of textiles from centuries ago until the present time. The colouring principles belong to the class of hydroxyanthraquinones. Concern arose because several of these compounds were recognised as mutagenic in vitro and even carcinogenic in rodents. To assess the possible risk to humans caused by coloured textiles, mutagenicity was investigated with two madder root samples of different origin (Iran and Bhutan) along the entire dyeing process from root extracts to the dyed wool. The Salmonella/microsome test (Ames assay) with the strains TA98, TA100 and TA1537 was used. Significant mutagenic effects could be detected in madder root extracts and also in the final product, the dyed wool. Madder root from Iran showed considerably higher mutagenic responses than samples from Bhutan. Analytical investigations of the extracts by HPLC showed the presence of a spectrum of anthraquinones typical for madder root. Three mutagenic compounds, lucidine, rubiadine and purpuroxanthine, together with the non-mutagenic alizarine could be detected. The mutagenic response of the different samples was positively correlated with the concentration of the mutagenic anthraquinones, and with lucidine in particular. Based on these investigations a risk to dye-house workers and users of textiles dyed with R. tinctorum must be anticipated.

  Antimicrobial activity of common madder (Rubia tinctorum L.).:Phytother Res. 2006 Jun;20(6):490-2.Kalyoncu F, Cetin B, Saglam H.Department of Biology, Faculty of Science and Arts, Celal Bayar University, Manisa, Turkey.

 In this study, ethanol, methanol, ethyl acetate and water extracts of Rubia tinctorum L. (Rubiaceae) were tested for antimicrobial activity by the disc diffusion method. From the present study it was found that Rubia tinctorum L. revealed antimicrobial activity against some Gram (+) and Gram (-) bacteria, yeasts, filamentous fungi and actinomycetes.

  Rubiae Radix suppresses the activation of mast cells through the inhibition of Syk kinase for anti-allergic activity.:J Pharm Pharmacol. 2006 Apr;58(4):503-12.

 The effect of extracts from various Oriental medicinal herbs on mast-cell-mediated allergic reactions was investigated in this study. Of these extracts, the medicinal herb Rubiae Radix exhibited the most potent activity in the cells, with an IC50 value (concentration necessary to obtain 50% inhibition of the response) of approximately 35 +/- 2.1 microg mL(-1), and its inhibition of compound-48/80-induced systemic anaphylaxis by 48.6 +/- 8.5% at 300 mg kg(-1) in mice. It also inhibited the expression of the pro-inflammatory mediator tumour necrosis factor-alpha (TNF-alpha). As for its mechanism of action, Rubiae Radix suppressed the activating phosphorylation of Syk, a key enzyme in mast-cell signalling processes, and that of Akt in a dose-dependent manner. It also inhibited the MAP kinase ERK1/2, which is critical for the production of inflammatory cytokines in mast cells, as indicated by the suppression of the activating phosphorylation of ERK1/2. These results suggest that Rubiae Radix suppresses the activation of mast cells through the inhibition of Syk for anti-allergic activity.

  Pericyclic reactions of prenylated naphthoquinones: biomimetic syntheses of mollugin and microphyllaquinone.:Org Lett. 2005 Dec 22;7(26):5865-8.Lumb JP, Trauner D.Department of Chemistry, University of California, Berkeley, California 94720, USA

 A total synthesis of the bioactive naphthohydroquinone mollugin and the related naphthoquinone dimer microphyllaquinone is described. Both syntheses exploit the propensity of prenylated quinones to undergo tautomerization/oxa 6pi-electrocyclizations.

  Examination of the anthraquinone composition in root-stock and root samples of Rubia tinctorium L. plants of different origins.:Acta Pharm Hung. 2004;74(3):142-8. Hungarian.Boldizs¨¢r I, L¨¢szl¨®-Bencsik A, Szucs Z, D¨¢nos B.E?tv?s Lor¨¢nd Tudom¨¢nyegyetem N?v¨¦nyszervezettani Tansz¨¦k, Budapest, P¨¢zm¨¢ny P¨¦ter s¨¦t¨¢ny 1/C. - 1117

 The aim of our work was to identify the anthraquinone derivatives in the underground organs (root-stock and root) of the madder root live plant sortiment Rubia tinctorium L, furthermore to isolate populations the anthraquinone compostitions of which are optimal from therapeutical point of view. In the course of the examinations, we studied the anthraquinone composition in root-stock and root samples of plants originating from 11 different habitats. The identification of the anthraquinone derivatives we carried out after the hydrolysis of these samples with HCl solution, by HPLC method and by use of UV-VIS spectrophotometric and mass spectrometric detection. In the samples we identified 6 anthraquinone-aglicones. The main components were alizarin (9.6-21.8 mg/g), purpurin (3.7-12.3 mg/g), and lucidin (1.8-5.7 mg/g). The total anthraquinone-derivative content varied between 15.6 and 39.4 mg/g. After the evaluation of the results it can be stated that from therapeutical point of view the most favourable biggest ratio of total anthraquinone amount/lucidin amount (11.97) and one of the biggest total anthraquinone-derivative contents (38.1 mg/g) are found in the Rubia tinctorium sample marked R02 originating from Aachen (Germany). These results enable us at the same time to find--through the establishment of further collections and through the exploration of the biodiversity of these--basic material with more favourable composition than at present, especially in relation to lucidin derivatives which are risk factors.


  Evaluation of the antibacterial activity of Ventilago madraspatana Gaertn., Rubia cordifolia Linn. and Lantana camara Linn.: isolation of emodin and physcion as active antibacterial agents.:Phytother Res. 2005 Oct;19(10):888-94. Basu S, Ghosh A, Hazra B.Department of Pharmaceutical Technology, Jadavpur University, Calcutta 700 032, India.

 The antibacterial activity of the extracts of Ventilago madraspatana stem-bark, Rubia cordifolia root and Lantana camara root-bark, prepared with solvents of different polarity, was evaluated by the agar-well diffusion method. Twelve bacteria, six each of gram-positive and gram-negative strains, were used in this study. Chloroform and ethanol extracts of V. madraspatana showed broad-spectrum activity against most of the bacteria except S. aureus, E. coli and V. cholerae. On the other hand, the activity of the chloroform and methanol extracts of R. cordifolia and L. camara was found to be more specific towards the gram-positive strains, although gram-negative P. aeruginosa was also inhibited by the methanol extracts of both these plants in a dose dependent manner. The water extracts of V. madraspatana and L. camara were found to be inactive, while that of R. cordifolia was significantly active against B. subtilis and S. aureus compared with streptomycin and penicillin G used as standards. In the course of bio-assay guided fractionation, emodin and physcion were isolated for the first time from the stem-bark of V. madraspatana. It was noteworthy to find the MICs of emodin in the range 0.5-2.0 microg/mL against three Bacillus sp. Both the anthraquinonoid compounds inhibited P. aeruginosa, emodin being more effective, showing an MIC of 70 microg/mL.

  Hepatoprotective effects of rubiadin, a major constituent of Rubia cordifolia Linn.:J Ethnopharmacol. 2006 Feb 20;103(3):484-90. Epub 2005 Oct 5.Rao GM, Rao CV, Pushpangadan P, Shirwaikar A.Pharmacognosy and Ethnopharmacology Division, National Botanical Research Institute, Lucknow 226 001, Uttarpradesh, India. mmraos@rediffmail.com

 The hepatoprotective effects of rubiadin, a major constituent isolated from Rubia cordifolia Linn., were evaluated against carbon tetrachloride (CCl4)-induced hepatic damage in rats. Rubiadin at a dose of 50, 100 and 200 mg/kg was administered orally once daily for 14 days. The substantially elevated serum enzymatic activities of serum glutamic oxaloacetic transaminase (SGOT), serum glutamate pyruvate transaminase (SGPT), serum alkaline phosphatase (SALP) and gamma-glutamyltransferase (gamma-GT) due to carbon tetrachloride treatment were dose dependently restored towards normalization. Meanwhile, the decreased activities of glutathione S-transferase and glutathione reductase were also restored towards normalization. In addition, rubiadin also significantly prevented the elevation of hepatic malondialdehyde formation and depletion of reduced glutathione content in the liver of CCl4 intoxicated rats in a dose dependent manner. Silymarin used as standard reference also exhibited significant hepatoprotective activity on post treatment against carbon tetrachloride induced hepatotoxicity in rats. The biochemical observations were supplemented with histopathological examination of rat liver sections. The results of this study strongly indicate that rubiadin has a potent hepatoprotective action against carbon tetrachloride induced hepatic damage in rats.

  In vitro anticancer activity of twelve Chinese medicinal herbs.:Phytother Res. 2005 Jul;19(7):649-51.Shoemaker M, Hamilton B, Dairkee SH, Cohen I, Campbell MJ.Department of Surgery, University of California, San Francisco, CA 94115, USA.

 Aqueous extracts of 12 Chinese medicinal herbs, Anemarrhena asphodeloides, Artemisia argyi, Commiphora myrrha, Duchesnea indica, Gleditsia sinensis, Ligustrum lucidum, Rheum palmatum, Rubia cordifolia, Salvia chinensis, Scutellaria barbata, Uncaria rhychophylla and Vaccaria segetalis were evaluated for their antiproliferative activity on eight cancer cell lines as well as on normal human mammary epithelial cells. Five human and three murine cancer cell lines representing different tissues (breast, lung, pancreas and prostate) were used. All the crude aqueous extracts demonstrated growth inhibitory activity on some or all of the cancer cell lines, but only two showed activity against the normal mammary epithelial cells. Overall, the murine cell lines tended to be more sensitive to most of the extracts compared with the human cell lines. Among the human cell lines, cell type specificity was observed for two extracts. These results indicate the potential use of traditional Chinese medicinal herbs as antineoplastic agents and suggest that further studies evaluating their mechanism(s) of action and the isolation of active antitumor compounds are warranted.

  Plant medicines of Indian origin for wound healing activity: a review.:Int J Low Extrem Wounds. 2003 Mar;2(1):25-39.Biswas TK, Mukherjee B.Department of Sharira Kriya, J. B. Roy State Ayurvedic Medical College and Hospital.

 Research on wound healing drugs is a developing area in modern biomedical sciences. Scientists who are trying to develop newer drugs from natural resources are looking toward the Ayurveda, the Indian traditional system of medicine. Several drugs of plant, mineral, and animal origin are described in the Ayurveda for their wound healing properties under the term Vranaropaka. Most of these drugs are derived from plant origin. Some of these plants have been screened scientifically for the evaluation of their wound healing activity in different pharmacological models and patients, but the potential of most remains unexplored. In a few cases, active chemical constituents were identified. Some Ayurvedic medicinal plants, namely, Ficus bengalensis, Cynodon dactylon, Symplocos racemosa, Rubia cordifolia, Pterocarpus santalinus, Ficus racemosa, Glycyrrhiza glabra, Berberis aristata, Curcuma longa, Centella asiatica, Euphorbia nerifolia, and Aloe vera, were found to be effective in experimental models. This paper presents a limited review of plants used in Ayurvedic medicine.

  Antioxidant phenolic constituents in roots of Rheum officinale and Rubia cordifolia: structure-radical scavenging activity relationships.:J Agric Food Chem. 2004 Dec 29;52(26):7884-90.

 The phenolic constituents in the roots of Rheum officinale and Rubia cordifolia were identified with the aid of high-performance liquid chromatography and liquid chromatography-mass spectrometry and by comparison with authentic standards. A total of 17 hydroxyanthraquinones, gallic acid, and tannins were separated, and 14 of them were identified, being the main phenolic constituents present. Their antioxidant activity (Trolox equivalent antioxidant capacity) was evaluated using the improved 2,2-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)diammonium salt method. Hydroxyanthraquinones were the predominant antioxidant phenolic constituents in the roots of R. cordifolia, and tannins and gallic acid were the predominant antioxidant phenolic constituents in the roots of R. officinale. The structure-radical scavenging activity relationships of the tested hydroxyanthraquinones were systematically demonstrated as follows: Hydroxy groups on one benzene ring of the anthraquinone structure were essential for hydroxyanthraquinones to show activity, the ortho-dihydroxy structure in the hydroxyanthraquinone molecules could greatly enhance their radical scavenging effect, and glycosylation of the hydroxyanthraquinones reduced activity.


  Two validated HPLC methods for the quantification of alizarin and other anthraquinones in Rubia tinctorum cultivars.:Phytochem Anal. 2004 Nov-Dec;15(6):397-406.Derksen GC, Lelyveld GP, van Beek TA, Capelle A, de Groot AE.Laboratory of Organic Chemistry, Natural Products Chemistry Group, Wageningen University, Dreijenplein 8, 6703 HB Wageningen, The Netherlands.

 Direct and indirect HPLC-UV methods for the quantitative determination of anthraquinones in dried madder root have been developed, validated and compared. In the direct method, madder root was extracted twice with refluxing ethanol-water. This method allowed the determination of the two major native anthraquinone glycosides lucidin primeveroside and ruberythric acid. In the indirect extraction method, the anthraquinone glycosides were first converted into aglycones by endogenous enzymes and the aglycones were subsequently extracted with tetrahydrofuran-water and then analysed. In this case the anthraquinones alizarin, purpurin and nordamnacanthal may be determined. The content of nordamnacanthal is proportional to the amount of lucidin primeveroside originally present. The indirect extraction method is easier to apply. Different madder cultivars were screened for their anthraquinone content.

  Effect of Rubia cordifolia, Fagonia cretica linn, and Tinospora cordifolia on free radical generation and lipid peroxidation during oxygen-glucose deprivation in rat hippocampal slices.:Biochem Biophys Res Commun. 2004 Nov 12;324(2):588-96.Rawal A, Muddeshwar M, Biswas S.SMV Center for Biotechnology, Sindhu Mahavidyalaya, Panchpaoli, Nagpur, MS 440017, India.

 The major damaging factor during and after the ischemic/hypoxic insult is the generation of free radicals, which leads to apoptosis, necrosis, and ultimately cell death. Rubia cordifolia (RC), Fagonia cretica linn (FC), and Tinospora cordifolia (TC) have been reported to contain a wide variety of antioxidants and have been in use in the eastern system of medicine for various disorders. Hippocampal slices were subjected to oxygen-glucose deprivation (OGD) and divided into three groups, control, OGD, and OGD+drug treated. Cytosolic reduced glutathione (GSH), nitric oxide [NO, measured as nitrite (NO2)]. EPR was used to establish the antioxidant effect of RC, FC, and TC with respect to superoxide anion (O*2-), hydroxyl radicals (*OH), nitric oxide (NO) radical, and peroxynitrite anion (ONOO-) generated from pyrogallol, menadione, DETA-NO, and Sin-1, respectively. RT-PCR was performed for the three herbs to assess their effect on the expression of gamma-glutamylcysteine ligase (GCLC), iNOS, and GAPDH gene expression. All the three herbs were effective in elevating the GSH levels and expression of the GCLC. The herbs also exhibited strong free radical scavenging properties against reactive oxygen and nitrogen species as revealed by electron paramagnetic resonance spectroscopy, diminishing the expression of iNOS gene. RC, FC, and TC therefore attenuate oxidative stress mediated cell injury during OGD and exert the above effects at both the cytosolic as well as at gene expression levels and may be effective therapeutic tool against ischemic brain damage.

  Rubia cordifolia, Fagonia cretica linn and Tinospora cordifolia exert neuroprotection by modulating the antioxidant system in rat hippocampal slices subjected to oxygen glucose deprivation.:BMC Complement Altern Med. 2004 Aug 13;4:11.Rawal AK, Muddeshwar MG, Biswas SK.SMV Center for Biotechnology, Sindhu Mahavidyalaya, Panchpaoli, Nagpur-440017, MS, India. akrawal@rediffmail.com

 BACKGROUND: The major damaging factor during and after the ischemic/hypoxic insult is the generation of free radicals, which leads to apoptosis, necrosis and ultimately cell death. Rubia cordifolia (RC), Fagonia cretica linn (FC) and Tinospora cordifolia (TC) have been reported to contain a wide variety of antioxidants and have been in use in the eastern system of medicine for various disorders. However, their mechanism of action was largely unknown. We therefore selected these herbs for the present study to test their neuroprotective ability and the associated mechanism in rat hippocampal slices subjected to oxygen-glucose deprivation (OGD). METHODS: Hippocampal Slices were subjected to OGD (oxygen glucose deprivation) and divided into 3 groups: control, OGD and OGD + drug treated. Cytosolic Cu-Zn superoxide dismutase (Cu-Zn SOD), reduced glutathione (GSH), glutathione peroxidase (GPx), nitric oxide (NO) was measured as nitrite (NO2) in the supernatant and protein assays were performed in the respective groups at various time intervals. EPR was used to establish the antioxidant effect of RC, FC and TC with respect to superoxide anion (O2.-), hydroxyl radicals (. OH), nitric oxide (NO) radical and peroxynitrite anion (ONOO) generated from pyrogallol, menadione, DETA-NO and Sin-1 respectively. RT-PCR was performed for the three groups for GCLC, iNOS, Cu-Zn SOD and GAPDH gene expression. RESULTS: All the three herbs were effective in elevating the GSH levels, expression of the gamma-glutamylcysteine ligase and Cu-Zn SOD genes. The herbs also exhibited strong free radical scavenging properties against reactive oxygen and nitrogen species as studied by electron paramagnetic resonance spectroscopy. In addition all the three herbs significantly diminished the expression of iNOS gene after 48 hours which plays a major role in neuronal injury during hypoxia/ischemia. CONCLUSIONS: RC, FC and TC therefore attenuate oxidative stress mediated cell injury during OGD and exert the above effects at both the cytosolic as well as at gene expression level and may be an effective therapeutic tool against ischemic brain damage.

  Synthesis of [Gly-1]RA-VII, [Gly-2]RA-VII, and [Gly-4]RA-VII. Glycine-containing analogues of RA-VII, an antitumor bicyclic hexapeptide from Rubia plants.:J Org Chem. 2004 Mar 5;69(5):1481-6.

 Three analogues of RA-VII (1), an antitumor bicyclic hexapeptide from Rubia plants, were synthesized. Three analogues, [Gly-1]RA-VII (4), [Gly-2]RA-VII (5), and [Gly-4]RA-VII (6), in which one of the three alanine residues in 1 was replaced by a glycine residue, were prepared by linking of the cycloisodityrosine unit, obtained by degradation of 1, to three different glycine-containing tetrapeptides followed by macrocyclization. Of these three analogues, analogue 4 showed the highest cytotoxic activity. The NMR study revealed that in solution the conformer structures and their ratios of analogue 4 were very similar to those of natural peptide 1, suggesting that the methyl groups at Ala-2 and Ala-4 should be essential for producing the bioactive conformation, whereas that at D-Ala-1 is not essential.

  Bioactive constituents from Chinese natural medicines. XI. inhibitors on NO production and degranulation in RBL-2H3 from Rubia yunnanensis: structures of rubianosides II, III, and IV, rubianol-g, and rubianthraquinone.:Chem Pharm Bull. 2003 Jun;51(6):654-62.

 Three new arborinane-type triterpene glycosides, rubianosides II, III, and IV, a new arborinane-type triterpene, rubianol-g, and a new anthraquinone, rubianthraquinone, were isolated from a Chinese natural medicine, the roots of Rubia yunnanensis. The structures of the new constituents including their absolute configurations were determined on the basis of chemical and physicochemical evidence. The inhibitory effects of the isolated constituents on nitric oxide production in lipopolysaccharide-activated macrophages were examined. Among them, a cyclic peptide constituent, RA-XII and its aglycon, RA-V (deoxybouvadin), potently inhibited overproduction of nitric oxide and induction of inducible nitric oxide synthase. In addition, an anthraquinone constituent, 2-methyl-1,3,6-trihydroxy-9,10-anthraquinone, was found to show inhibitory effects on the release of beta-hexosaminidase in RBL-2H3 cells.


  Two new anthraquinones from the roots of Rubia cordifolia Linn.:Pharmazie. 2003 Mar;58(3):216-7. Abdullah ST, Ali A, Hamid H, Ali M, Ansari SH, Alam MS.Faculty of Science, Jamia Hamdard, Hamdard Nagar, New Delhi, India.

 Two new anthraquinones, named cordifoliol and cordifodiol, have been isolated from the roots of Rubia cordifolia. Their structures have been established as 1-hydroxy-3-ethyl-9,10-anthraquinone (1) and 1,8-dihydroxy-11, 20 (15-pentyl-naphthaquinonyl) phenanthrene (2) on the basis of spectral data analyses and chemical reactions.

  Screening of Chinese herbal drug extracts for inhibitory activity on nitric oxide production and identification of an active compound of Zanthoxylum bungeanum.:J Ethnopharmacol. 2001 Oct;77(2-3):209-17.

 Sixty-eight water and methanol extracts from 34 Chinese herbal drugs, most of which are used for inflammatory diseases, were screened for their inhibitory effects on nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated J774.1 macrophages and in LPS/interferon (IFN)-gamma-stimulated mouse peritoneal exudate macrophages. Among the extracts, methanol extracts of Myristica fragrans, Plantago asiatica, Rubia cordifolia, and Zanthoxylum bungeanum showed significant inhibition in J774.1 macrophages, while in mouse peritoneal exudate macrophages, water extracts of Ru. cordifolia and Scutellaria baicalensis and methanol extracts of Angelica megaphylla, My. fragrans, and Z. bungeanum inhibited the NO production. Among them, inhibition of water extract of Sc. baicalensis was found to be mainly due to direct scavenging of NO radicals, through an examination of its scavenging activity on PAPA NONOate-generated NO radicals, while water extract of Ru. cordifolia and methanol extracts of An. megaphylla, My. fragrans, P. asiatica, and Z. bungeanum showed inhibition on iNOS mRNA expression. At last, an inhibitory compound on iNOS mRNA expression was isolated from a methanol extract of Z. bungeanum and identified as 4-O-beta-D-glucopyranosyldihydroferulic acid by NMR spectral analyses and chemical synthesis.

  A 90-day repeated dose toxicity study of madder color in F344 rats: a preliminary study for chronic toxicity and carcinogenicity studies.:

 A 90-day toxicity study of madder color was performed in F344 rats by feeding the pellet diet containing 0, 0.6, 1.2, 2.5 and 5.0% of test substance to clarify its toxic potential and to determine the dose levels for the following chronic toxicity/carcinogenicity studies. Body weight gain and food consumption were dose-dependently decreased at 1.2% or more in males and at 2.5% or more in females throughout the experimental period. All animals were survived until the end of experiment and subjected to autopsy. Hematologically, the following parameters were fluctuated in relation to the treatment: decreases in the red blood cells, hemoglobin, and hematocrit in females at 2.5% or more; increase of platelets in males at 2.5% or more, and in females at 5%; increase in white blood cells in males at 5%. Serum protein parameters were also affected by the treatment in males at 1.2% or more and in females at all doses. Increase in the serum calcium level was observed in males at 2.5% or more and in females at 5%. Serum inorganic phosphorus level was also increased in males at 1.2% or more and in females at 2.5% or more. At autopsy, both absolute and relative kidney weights of females increased dose-dependently at 0.6% or more. Relative liver weight in females also increased at 1.2% or more. Histopathologically, microvesicular vacuolar degeneration of proximal tubules was observed in the kidney of both sexes (males at 1.2% or more; females at 0.6% or more). In addition, mononuclear cell infiltration (both sexes) and hyaline casts and tubular regeneration (male) appeared in the kidney at 5%. In the female liver, focal liver cell necrosis associated with mononuclear cell infiltration was evident at 5%. The results demonstrate the toxic effects of madder color on the liver (in females at 5%) and kidney (in males at 1.2% or more; in females at 0.6% or more) of F344 rats when treated orally for 90 days. In addition, toxicities in hematopoietic system and/or bone would probably be appeared when rats are treated with 1.2% or more of madder color for long-term over 90 days. NOAEL was determined to be 0.6% in males, but could not be determined in females under the condition of this study. Based on the results of this study, the dose levels for subsequent chronic toxicity and carcinogenicity studies were determined to be 0.2, 1.0 and 5.0%, and 2.5 and 5.0%, respectively.

  Anticonvulsant and behavioral actions of triterpene isolated from Rubia cordifolia Linn.:Indian J Exp Biol. 2000 Jul;38(7):675-80.Kasture VS, Deshmukh VK, Chopde CT.M.V.P. Samaj's College of Pharmacy, Gangapur Road, Nashik 422 002, India.

 Effect of a triterpene isolated from the acetone soluble part of petroleum ether extract of R. cordifolia was studied on convulsions induced by maximum electro shock (MES), electrical kindling and various chemoconvulsants in rats and mice. The effect of triterpene was also investigated on behavior and gamma-aminobutyric acid (GABA) and serotonin (5-HT) content in mouse brain. Triterpene inhibited seizures induced by MES, electrical kindling, pentylenetetrazol (PTZ), and lithium-pilocarpine. However, seizures induced by strychnine were not inhibited. Triterpene reduced locomotion as well as rearing. Pentobarbitone induced sleep was potentiated and amphetamine induced stereotypy was inhibited. The triterpene was found to possess anxiogenic activity. Brain GABA and 5-HT contents were raised by the compound. The study suggests that the triterpene isolated from R. cordifolia bear a potential for further study.

  Further quinoidal derivatives from Rubia cordifolia L.:Pharmazie. 2000 Apr;55(4):317-9.Hassanean HA, Ibraheim ZZ, Takeya K, Itorawa H.Department of Pharmacognosy, Faculty of Pharmacy, Assiut University, Egypt

 Two new quinoidal dimers, a new naphthohydroquinone anhydride, a known naphthoic acid ester derivative and two known benzoic acid derivatives were isolated from the chloroform fraction of a chloroform-methanol (1:1) extract of Rubia cordifolia L. The identification of these compounds was based on spectral analysis.


  Comparison of the antioxidant action of the alcoholic extract of Rubia cordifolia with rubiadin.:Indian J Biochem Biophys. 1998 Oct;35(5):313-6.Tripathi YB, Sharma M.Department of Medicinal Chemistry, Banaras Hindu University, Varanasi, India.

 The inhibition of FeSO4 induced lipid peroxidation in rat liver by alcoholic extract of Rubia cordifolia and by one of its constituent rubiadin (1, 3-dihydroxy-2-methyl anthraquinone) (pure form) has been compared. Both have been found to inhibit lipid peroxidation in a dose dependent manner. Whereas the former shows both oxidising and reducing properties with Fe2+ and Fe3+, the latter shows oxidising property only by converting Fe2+ to Fe3+. The former inhibits the oxidation of reduced glutathione while the latter does not.

  Rubiadin, a new antioxidant from Rubia cordifolia.:Indian J Biochem Biophys. 1997 Jun;34(3):302-6.Tripathi YB, Sharma M, Manickam M.Department of Medicinal Chemistry, Banaras Hindu University, Varanasi, India.

 Rubiadin, a dihydroxy anthraquinone, isolated from alcoholic extract of Rubia cordifolia, possesses potent antioxidant property. It prevents lipid peroxidation induced by FeSO4 and t-butylhydroperoxide (t-BHP) in a dose dependent manner. The per cent inhibition was more in the case of Fe2+ induced lipid peroxidation. The antioxidant property of the preparation has been found to be better than that of EDTA, Tris, mannitol, Vitamin E and p-benzoquinone.

  Inhibition of hepatitis B surface antigen secretion on human hepatoma cells. Components from Rubia cordifolia.:J Nat Prod. 1996 Mar;59(3):330-3.

 The antiviral activity in the roots of Rubia cordifolia was examined, and three naphthohydroquinones, furomollugin (1), mollugin (2), and rubilactone (3), were isolated from it. Compounds 1 and 2 strongly suppressed the secretion of hepatitis B surface antigen (HBsAg), both with IC50 = 2.0 micrograms/mL, in human hepatoma Hep3B cells while having little effect on the viability of the cells. Evaluation of structurally related derivatives of 1 and 2 revealed that a 6-hydroxy group and a pyran or furan ring contribute to this suppressive effect.

  Possible presence of calcium channel blocker(s) in Rubia cordifolia: an indigenous medicinal plant..:J Pak Med Assoc. 1994 Apr;44(4):82-5.Gilani AH, Janbaz KH, Zaman M, Lateef A, Suria A, Ahmed HR.Department of Pharmacology, Aga Khan University Medical College, Karachi.

 Crude extract of Rubia cordifolia (RC) was tested in isolated tissue preparations for its possible calcium channel antagonistic activity. RC suppressed the spontaneous contractions of guinea-pig atria, rabbit jejunum and rat uterus in a concentration dependent manner (0.1-3 mg/ml). In rabbit aorta, it inhibited norepinephrine (10 microM) and KCl (80 mM) induced contractions. Replacement of physiological salt solution with calcium free solution abolished the spontaneous movements of rabbit jejunum. However, addition of calcium (25 micrograms/ml) in the tissue bath restored the spontaneous movements. When the tissues were pretreated with plant extract (1 mg/ml) or verapamil (0.5 microgram/ml), addition of calcium failed to restore spontaneous contractions. These results indicate that the plant extract exhibits spasmolytic activity similar to that of verapamil suggestive of presence of calcium channel blocker like constituent(s) in this plant.

  Protective effect of Rubia cordifolia on lipid peroxide formation in isolated rat liver homogenate.:Indian J Exp Biol. 1994 Mar;32(3):180-3.Pandey S, Sharma M, Chaturvedi P, Tripathi YB.Department of Medicinal Chemistry, Banaras Hindu University, Varanasi, India.

 Rubia cordifolia Linn. (Rubiaceae) is an important component of the ayurvedic system of medicine. It has a variety of uses such as blood purifier, immunomodulant, antiinflammatory and anti-PAF. In this report the anti-peroxidative property of the solvent free alcoholic extract of R. cordifolia has been studied in rat liver homogenate. It prevents the cumene hydroperoxide induced malondialdehyde formation in the dose and time dependent manner. This effect is accompanied by the maintained reduced glutathione level even in the presence of above toxin.


  Study of cardiac function in first stage examination of RA-700. RA-700 Clinical Study Group.:

 There are many studies in the literature on the subject of anti-neoplastic drugs for acute and chronic cardiac toxic function. It is important to check previously the cardiac toxicity of the new anti-neoplastic drugs. Now we have had a chance to study the first stage examination of RA-700, isolated from Rubia akane or Rubia cordifolia. Then we tried to study several kinds of parameters, for instance ECG, ultrasonic cardiograms and arterio-grams on cardiac toxicities of RA-700. We injected the first group of neoplastic patients only once with RA-700, while in the second group, we injected them with RA-700 for 5 consecutive days (see our previous report.) In the present study, we made some conclusions about the administration of RA-700. 1) Changes in cardiac function were noted in both groups. 2) Changes in blood pressure, sigma QRS, ejection fraction, and fractional shortening of the second group tended to be more extreme than those of the first group. Care for continuity is a concern with long-term and high doses of RA-700. 3) Because of the small sample, we could find no relationship between the changes in cardiac function and the injection doses of RA-700. 4) Therefore, the cardiac function must be checked by giving anti-neoplastic drugs to neoplastic patients.

  Anthraquinones, naphthohydroquinones and naphthohydroquinone dimers from Rubia cordifolia and their cytotoxic activity.:

 Further investigation of the roots of Rubia cordifolia resulted in the isolation of four new naphthohydroquinones and two naphthohydroquinone dimers, and one known naphthohydroquinone, one naphthoquinone, two anthraquinones and one naphthohydroquinone dimer. The structures of these compounds were established by various chemical and spectroscopic methods including two dimensional NMR techniques. Also, the isolated compounds were submitted to a bio-assay for cytotoxic and antitumor activity.

  Anti-platelet activating factor property of Rubia cordifolia Linn.:Indian J Exp Biol. 1993 Jun;31(6):533-5.Tripathi YB, Pandey S, Shukla SD.Department of Medicinal Chemistry, Banras Hindu University, Varanasi, India.

 Rubia cordifolia is clinically used for the purification of blood by the physicians of the Indian System of Medicine. For the first time, the effect of the partially purified fraction of this whole plant has been studied on rabbit platelets. It inhibits the platelet aggregation induced by PAF (platelet activating factor) but not thrombin. It also inhibits the binding of 3H-PAF to the platelets in the dose-dependent manner. Thus it appears that R. cordifolia inhibits action of PAF at its receptor level either by it's blocking or by desensitization.

  Two antitumour bicyclic hexapeptides from Rubia cordifolia.:Phytochemistry. 1993 Jun;33(3):613-5.

 Two novel antitumour bicyclic hexapeptides, named RA-XV and -XVI, were isolated from Rubia cordifolia and their structures were characterized by spectroscopic and chemical means.

  Conformational recognition of RA-XII by 80S ribosomes: a differential line broadening study in 1H NMR spectroscopy.:Chem Pharm Bull. 1993 Apr;41(4):781-3.

 1H NMR spectroscopy has been used to demonstrate specific binding of rat 80S ribosomes to the major conformer of an antitumor bicyclic hexapeptidic glucoside, RA-XII, isolated from Rubia cordifolia, in a fast exchange process.


  Determination of trace elements in several hemostatic medicinal plants and their boiling water extracts.:Zhongguo Zhong Yao Za Zhi. 1993 Apr;18(4):223-4, 254-5. Chinese.Lin XY, Li XL, Yang Y.Faculty of Pharmacy, Xi' an Medical University.

 The experimental results indicate that the amounts of Cu, Zn, Fe and Mn in Rubia cordifolia and Agrimonia pilosa var. japonica are very small in boiling water extracts (only 6%). But after digestion they may rise to 30%. It was found that the amounts of four trace elements decreased with the increase of extracting time, but the ratios of Mn/Zn and Zn/Cu were almost the same.

  Structures and conformations of metabolites of antitumor cyclic hexapeptides, RA-VII and RA-X.:Chem Pharm Bull. 1992 Nov;40(11):2984-9.

 Metabolites of antitumor cyclic hexapeptides, RA-VII and -X which were isolated from Rubia cordifolia were studied by hepatic microsomal biotransformation in rats and in bile juice of rabbits to which these drugs were administered intravascularly. Their structures and conformations were elucidated by two-dimensional nuclear magnetic resonance techniques, temperature effect on NH protons and nuclear Overhauser effect experiments. Specific N-demethylation of Tyr-3, O-demethylation and hydroxylation at aromatic rings of Tyr-3 and -5 were observed. Compared with metabolites of RA-VII, most of RA-X was excreted unchanged in the bile juice. Relationship among their structures, conformations and antitumor activities is also discussed.

  New antitumor bicyclic hexapeptides, RA-XI, -XII, -XIII and -XIV from Rubia cordifolia.:Chem Pharm Bull. 1992 May;40(5):1352-4.

 Four new bicyclic hexapeptides, named as RA-XI, -XII, XIII and -XIV were isolated from Rubia cordifolia and showed potent antitumor activities against P-388. The structures were elucidated from spectroscopic and chemical evidences. RA-XII, XIII and -XIV were proved to be unique bicyclic hexapeptidic glucosides.

  Studies on naphthoic acid esters from the roots of Rubia cordifolia L.:Yao Xue Xue Bao. 1992;27(4):279-82. Chinese.Hua HM, Wang SX, Wu LJ, Li X, Zhu TR.Research Department of Natural Drugs, Shenyang College of Pharmacy.

 Four naphthoic acid esters including a new compound were isolated from the roots of Rubia cordifolia L. The new one was named as rubilactone and its structure was elucidated as 3'-carbomethoxy-4'-hydroxy-naphtho[1',2'-2,3] pyran-6-one (I) based on the physicochemical properties and spectrometric analyses (UV, IR, MS, 1HNMR and 13CNMR). The other three were 3'-carbomethoxy-4'-hydroxy-naphtho [1',2'-2,3] furan (II), dihydromollugin (III) and 3-carbomethoxy-2-(3'-hydroxy)isopentyl-1,4-naphthohydroquinone-1-O -beta-D-glucoside (IV).

  Studies on anthraquinones from the roots of rubia cordifolia l.:Yao Xue Xue Bao. 1992;27(10):743-7. Chinese.Wang SX, Hua HM, Wu LJ, Li X, Zhu TR.Research Department of Natural Drugs, Shenyang College of Pharmacy.

 Seven anthraquinones were isolated from the ethyl alcohol extracts of the roots of Rubia Cordifolia L. By means of spectrometric data combined with physico-chemical properties, six of them were identified as 2-methyl-1,3,6-trihydroxy-9,10-anthraquinone (I), 1-hydroxy-9,10-anthraquinone(II), 1,2,4-trihydroxy-9,10-anthrequinone(III), 2-methyl-1,3,6-trihydroxy-9,10-anthraquinone-3-O-beta-D-glucoside(IV), 1,2-dijhydroxy-9,10-anthraquinone-2-O-beta-D-xylosyl(1-->6)-beta-D -glucoside(V) and 1,3-dihydroxy-2-hydroxymethyl1-9,10-anthraquinone-3-O-beta-D- xylosyl(1-->6)-beta-D-glucoside(VI). VII is a new compound. Its structure was elucidated to be 2-methyl-1,3,6-trihydroxy-9,10-anthraquinone-3-O-beta-D-xylosyl(1-->2)-b eta-D- (6'-O-acetyl)glucoside.


  Studies on antibacterial constituents from the roots of Rubia cordifolia L..:Yao Xue Xue Bao. 1990;25(11):834-9. Chinese.Qiao YF, Wang SX, Wu LJ, Li X, Zhu TR.Department of National Products, Shenyang College of Pharmacy.

 Twelve compounds were isolated from the roots of Rubia cordifolia L.. Nine of them were established by chemical and spectroscopic methods to be alizarin (I),1-hydroxy-2-methyl-9,10-anthraquinone(II),1,3,6-trihydroxy-2-methyl- 9,10-anthra-quinone-3-O-(6'-O-acetyl)-alpha-L-rhamnosyl(1--- -2)-beta-D- glucoside(III),1,3,6-trihydroxy-2-methyl-9,10-anthraqueinone-3-O-a lpha- L-rhamnosyl(1----2)-beta-D-glucoside(IV),1,3,6-trihydrozy-2- methyl-9,10- anthraquinone-3-O-(6'-O-acetyl)-beta-D-glucoside(V),2-carbomethyoxy++ +-3-prenyl- 1,4-naphthohydroquinone di-beta-D-glucoside(VI),rubimallin(VII),beta- sitosterol(VIII) and daucosterol(IX), among them, V is a nwe compound and IX was obtained from this genus for the first time, III, VI and VII showed certain antibacterial activities.

  Antitumor activity and toxicity in mice of RA-700, a cyclic hexapeptide.:Anticancer Res. 1987 May-Jun;7(3 Pt B):329-34.

 The antitumor activity of RA-700, a cyclic hexapeptide isolated from Rubia Cordifolia, was evaluated in comparison with deoxy-bouvardin and vincristine (VCR). As regards the proliferation of L1210 cultured cells, the cytotoxicity of RA-700 was similar to that of VCR but superior to that of deoxy-bouvardin. The IC50 value of RA-700 was 0.05 mcg/ml under our experimental conditions. RA-700 inhibited the incorporation of 14C-leucine at a concentration at which no effects were observed on the incorporation of 3H-thymidine and 3H-uridine in L1210 culture cells in vitro. The antitumor activity of RA-700 was similar to that of deoxy-bouvardin and VCR against P388 leukemia. Daily treatment with RA-700 at an optimal dose resulted in 118% ILS. As with deoxy-bouvardin and VCR, the therapeutic efficacy of RA-700 depends on the time schedule. RA-700 showed marginal activity against L1210 leukemia (50% ILS), similar to that of deoxy-bouvardin but inferior to that of VCR. RA-700 inhibited Lewis tumor growth in the early stage after tumor implantation, whereas deoxy-bouvardin and VCR did not. As regards toxicity, a slight reduction of peripheral WBC counts was observed with the drug, but no reduction of RBC and platelet counts. BUN, creatinine, GPT and GOT levels in plasma did not change with the administration of the drug.

  Cell growth-inhibitory effects of derivatives of antitumor cyclic hexapeptide RA-V obtained from Rubiae radix (V).:Gann. 1984 Oct;75(10):929-36.

 Alkylehter and ester derivatives of the antitumor cyclic hexapeptide RA-V obtained from the roots of Rubia cordifolia (Rubiaceae) were synthesized and bioassayed for activity against cultured tumor cells. RA-V and its n-hexylether showed significant effects against human nasopharynx carcinoma (KB), P388 lymphocytic leukemia and MM2 mammary carcinoma cells. The activity values (log 1/IC50) of ether derivatives of RA-V gave an upward parabolic or bilinear relationship when plotted against log P (P: partition coefficient determined with the 1-octanol/water system) as the carbon number of the side chain at the phenol moiety of RA-V was increased, the optimum log P values being in the range from 3.5 to 4.9. The ester derivatives showed a similar relationship, the optimum log P values being 6.3-6.7, which is higher than that of the ether derivatives. The lethal effect of RA-V on KB cells was clearly different from that of mitomycin C, and RA-V was concluded to be a "time-dependent drug" like vinblastine.


  Scientific References:

  1.Research Update:Rubia Root.