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Chemical Compound Review

Alizarin     1,2-dihydroxyanthracene-9,10- dione

Synonyms: ALIZARINE, Alizarina, Hystazarin, Rubia, Alizarine B, ...
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Disease relevance of Alizarinprimeveroside

  • Turkey red blood cell passive haemagglutination assay as guideline for specific prevention of tetanus in injured persons [1].
  • Thereafter, alizarin red positive neurons started to decrease, but alizarin positive neurons were significantly increased in dying neurons 4 days after ischemia [2].
  • We also observed that the glycoside AlP was active at inducing UDS in PRH, but the compound was inactive in the Salmonella/microsome assay [3].
  • Alizarin-beta-d-glucoside was the most sensitive substrate tested and detected beta-glucosidase activity in 72% of Enterobacteriaceae strains and all enterococci and Listeria spp [4].
  • Biochemical responses of the aquatic higher plant Lemna gibba to a mixture of copper and 1,2-dihydroxyanthraquinone: synergistic toxicity via reactive oxygen species [5].

High impact information on Alizarinprimeveroside

  • Alizarin red-/Alcian blue-stained skeletons were prepared from embryos at 17.5, 15.5, and 13.5 days of gestation [6].
  • In addition to reduced mineralization as detected by alizarin staining, significant changes were also observed in the extracellular matrix of the embryonic bones [7].
  • Analysis by 32P-postlabelling revealed that lucidin, the glycoside mixture and Rubia Teep, but not alizarin, formed DNA adducts in all the tissues examined but that the adduct patterns were organ-specific [8].
  • This may at least partially be due to selective resistance of S-phase cells to DHA-caused cell loss [9].
  • No effects of DHA were observed in normal colorectal epithelial cells [9].

Chemical compound and disease context of Alizarinprimeveroside

  • Four weeks after implanting, 20 mg calcein green/kg body weight was administered intravenously, and 8 weeks after implanting, 20 mg alizarin/kg body weight was administered intravenously [10].
  • Conclusions: Alizarin-beta-d-glucoside is a highly sensitive substrate for detection of bacterial beta-glucosidase and compares favourably with existing substrates. beta-glucosides of 3',4'-dihydroxyflavone and 3-hydroxyflavone are effective substrates for the detection of beta-glucosidase in enterococci and Listeria spp [4].

Biological context of Alizarinprimeveroside

  • We established that in both bacterial species these genes were cotransducible with the neighboring histidine transport operon and were distally located relative to purF. pta mutants were sensitive to the dye alizarin yellow and were unable to grow on medium containing inositol as a carbon source [11].
  • Confocal laser scanning microscopic observations revealed the presence of calcein at the 14th day and only slight alizarin colour layer in the bone tissue at the 28th day, both indicating bone formation [12].
  • Recently we have shown that anthraquinone food pigments such as purpurin and alizarin suppress the genotoxic activities of several mutagens including heterocyclic amines and polycyclic aromatic hydrocarbons in the Drosophila DNA repair test and in the Ames test [13].
  • Since purpurin and alizarin suppressed the activity of MNU, a direct alkylating agent, there may also be a mechanism distinct from enzyme inhibitions in these anthraquinone-mediated suppressions of DNA damage [14].
  • To address this shortfall, the combined effects of an oxygenated PAH, 1,2-dihydroxyanthraquinone (1,2-dhATQ), and a heavy metal, Cu2+, on photosynthesis and growth of the duckweed (Lemna gibba) were evaluated [15].

Anatomical context of Alizarinprimeveroside


Associations of Alizarinprimeveroside with other chemical compounds

  • The reductive cleavage of AlP was also observed after treatment of this compound with rat liver enzymes (S9) and NADPH [3].
  • Anthracene inhibited photosynthesis at lower concentrations than 1,2-dihydroxyanthraquinone, which is consistent with the different modes of action and toxic strengths of these two contaminants [21].
  • To elucidate adsorption mechanism of alizarin red S (ARS), which is often used for staining bones in histology, adsorption of ARS on hydroxyapatite, Ca10(PO4)6(OH)2 (HAP), was investigated by a batch method, compared with alizarin, phenols, and benzenesulfonates [22].
  • The precision of estimates of central corneal endothelial density was studied in 16 human corneas stained by alizarine red and trypane blue [23].
  • Treatment of gravid hamsters with 60/mg of retinoic acid on the 8th day of pregnancy resulted in facial skeleton defects in 100% of the survivors examined by alizarin staining at term [24].

Gene context of Alizarinprimeveroside

  • The K(m) value of CYP1B1 was 11 microM, and the K(i) value of purpurin and alizarin against CYP1B1 was 0.7 microM(2) and 0.5 microM, respectively [13].
  • CYP1B1 was the most strongly affected CYP molecule by purpurin and alizarin among CYPs examined in this study [13].
  • Inhibition of human cytochrome P450 1B1, 1A1 and 1A2 by antigenotoxic compounds, purpurin and alizarin [13].
  • Altogether 27 fetuses with trisomy 16 and 118 chromosomally balanced siblings were examined radiographically and by alizarin staining on day 20 of gestation; the radiographs were analyzed by computer-aided densitometry and structural differentiation [25].
  • Adsorption of alizarin was also performed in order to show some particular features of the HDL [26].

Analytical, diagnostic and therapeutic context of Alizarinprimeveroside

  • Turkey red blood cell, beta 1-adrenergic receptors (BARs) were prepared to electrophoretic homogeneity by affinity chromatography, size exclusion high performance liquid chromatography, and preparative sodium dodecyl sulfate-polyacrylamide gel electrophoresis and used to prepare rabbit polyclonal anti-BAR antibodies [27].
  • The fetuses were removed by caesarian section on day 19 and examined by dissection and alizarin staining for gross structural and skeletal defects [28].
  • Bone formation was identified by light microscopy by the accumulation of matrix, staining with alizarin and calcein and by von Kossa's method, and confirmed by scanning electron microscopy (SEM) by using backscattered electron (BSE) and transmitted electron imaging of unembedded samples and BSE imaging of micro-milled embedded material [29].
  • Surface-enhanced Raman spectroscopy and UV-vis absorption spectroscopy were employed to study the interaction between the red dye alizarin and ovalbumin (OA), to check the effect of binding media usually employed when applying this pigment in painting practices based on egg tempera [30].
  • Two validated HPLC methods for the quantification of alizarin and other anthraquinones in Rubia tinctorum cultivars [31].


  1. Turkey red blood cell passive haemagglutination assay as guideline for specific prevention of tetanus in injured persons. Bistoni, F., Marconi, P., Perito, S., Bastianini, L., Antenucci, R., Pitzurra, M. Bull. World Health Organ. (1985) [Pubmed]
  2. Chronological alterations of neurofilament 150 immunoreactivity in the gerbil hippocampus and dentate gyrus after transient forebrain ischemia. Hwang, I.K., Do, S.G., Yoo, K.Y., Kim, D.S., Cho, J.H., Kwon, Y.G., Lee, J.Y., Oh, Y.S., Kang, T.C., Won, M.H. Brain Res. (2004) [Pubmed]
  3. Formation of genotoxic metabolites from anthraquinone glycosides, present in Rubia tinctorum L. Blömeke, B., Poginsky, B., Schmutte, C., Marquardt, H., Westendorf, J. Mutat. Res. (1992) [Pubmed]
  4. Evaluation of novel chromogenic substrates for the detection of bacterial beta-glucosidase. Perry, J.D., Morris, K.A., James, A.L., Oliver, M., Gould, F.K. J. Appl. Microbiol. (2007) [Pubmed]
  5. Biochemical responses of the aquatic higher plant Lemna gibba to a mixture of copper and 1,2-dihydroxyanthraquinone: synergistic toxicity via reactive oxygen species. Babu, T.S., Tripuranthakam, S., Greenberg, B.M. Environ. Toxicol. Chem. (2005) [Pubmed]
  6. Conditional deletion of the TGF-beta type II receptor in Col2a expressing cells results in defects in the axial skeleton without alterations in chondrocyte differentiation or embryonic development of long bones. Baffi, M.O., Slattery, E., Sohn, P., Moses, H.L., Chytil, A., Serra, R. Dev. Biol. (2004) [Pubmed]
  7. Calcium deficiency induces expression of cartilage-like phenotype in chick embryonic calvaria. Jacenko, O., Tuan, R.S. Dev. Biol. (1986) [Pubmed]
  8. Evaluation of DNA-binding activity of hydroxyanthraquinones occurring in Rubia tinctorum L. Poginsky, B., Westendorf, J., Blömeke, B., Marquardt, H., Hewer, A., Grover, P.L., Phillips, D.H. Carcinogenesis (1991) [Pubmed]
  9. Effect of anthraquinone-laxatives on the proliferation and urokinase secretion of normal, premalignant and malignant colonic epithelial cells. Schörkhuber, M., Richter, M., Dutter, A., Sontag, G., Marian, B. Eur. J. Cancer (1998) [Pubmed]
  10. The effect of combination of recombinant human bone morphogenetic protein-2 and basic fibroblast growth factor or insulin-like growth factor-I on dental implant osseointegration by confocal laser scanning microscopy. Lan, J., Wang, Z., Wang, Y., Wang, J., Cheng, X. J. Periodontol. (2006) [Pubmed]
  11. Isolation and Characterization of acetate kinase and phosphotransacetylase mutants of Escherichia coli and Salmonella typhimurium. LeVine, S.M., Ardeshir, F., Ames, G.F. J. Bacteriol. (1980) [Pubmed]
  12. Study of bone formation around dense hydroxyapatite implants using light microscopy, image processing and confocal laser scanning microscopy. Takeshita, F., Iyama, S., Ayukawa, Y., Akedo, H., Suetsugu, T. Biomaterials (1997) [Pubmed]
  13. Inhibition of human cytochrome P450 1B1, 1A1 and 1A2 by antigenotoxic compounds, purpurin and alizarin. Takahashi, E., Fujita, K., Kamataki, T., Arimoto-Kobayashi, S., Okamoto, K., Negishi, T. Mutat. Res. (2002) [Pubmed]
  14. Preventive effects of anthraquinone food pigments on the DNA damage induced by carcinogens in Drosophila. Takahashi, E., Marczylo, T.H., Watanabe, T., Nagai, S., Hayatsu, H., Negishi, T. Mutat. Res. (2001) [Pubmed]
  15. Synergistic effects of a photooxidized polycyclic aromatic hydrocarbon and copper on photosynthesis and plant growth: evidence that in vivo formation of reactive oxygen species is a mechanism of copper toxicity. Babu, T.S., Marder, J.B., Tripuranthakam, S., Dixon, D.G., Greenberg, B.M. Environ. Toxicol. Chem. (2001) [Pubmed]
  16. Fetal skeletal malformations associated with moderate zinc deficiency during pregnancy. Hickory, W., Nanda, R., Catalanotto, F.A. J. Nutr. (1979) [Pubmed]
  17. Radiation-induced double-strand modification in calf thymus DNA in the presence of 1,2-dihydroxy-9,10-anthraquinone and its Cu(II) complex. Das, S., Saha, A., Mandal, P.C. Environ. Health Perspect. (1997) [Pubmed]
  18. Pelvic pseudotumoral calcium pyrophosphate dihydrate deposition: an ultrastructural study. Maugars, Y.M., Peru, L.F., el Messaoudi, B., Michaud, G.O., Berthelot, J.M., Prost, A.M., Daculsi, G. J. Rheumatol. (1994) [Pubmed]
  19. Postnatal development of the fore- and hindlimbs in the grey short-tailed opossum, Monodelphis domestica. Martin, K.E., Mackay, S. J. Anat. (2003) [Pubmed]
  20. Formation of the knee joint after prenatal propyphenazone (isopropylantipyrine) administration. Burdan, F. Cells Tissues Organs (Print) (2002) [Pubmed]
  21. Intact and photomodified polycyclic aromatic hydrocarbons inhibit photosynthesis in natural assemblages of Lake Erie phytoplankton exposed to solar radiation. Marwood, C.A., Smith, R.E., Solomon, K.R., Charlton, M.N., Greenberg, B.M. Ecotoxicol. Environ. Saf. (1999) [Pubmed]
  22. Elucidation of adsorption mechanism of bone-staining agent alizarin red S on hydroxyapatite by FT-IR microspectroscopy. Moriguchi, T., Yano, K., Nakagawa, S., Kaji, F. Journal of colloid and interface science. (2003) [Pubmed]
  23. The precision of unbiased estimates of numerical density of endothelial cells in donor cornea. Sperling, S., Gundersen, H.J. Acta ophthalmologica. (1978) [Pubmed]
  24. Effects of retinoic acid on the development of the facial skeleton in hamsters: early changes involving cranial neural crest cells. Wiley, M.J., Cauwenbergs, P., Taylor, I.M. Acta anatomica. (1983) [Pubmed]
  25. Defects of skeletal morphology, density, and structure in mouse fetuses with trisomy 16. Sterz, H., Buselmaier, W., Bacchus, C., Gromier, L., Eppler, E. Teratology (1989) [Pubmed]
  26. Surface-charging behavior of Zn-Cr layered double hydroxide. Rojas Delgado, R., Arandigoyen Vidaurre, M., De Pauli, C.P., Ulibarri, M.A., Avena, M.J. Journal of colloid and interface science. (2004) [Pubmed]
  27. Immuno cross-reactivity suggests that catecholamine biosynthesis enzymes and beta-adrenergic receptors may be related. Shorr, R.G., Minnich, M.D., Varrichio, A., Strohsacker, M.W., Gotlib, L., Kruse, L.I., DeWolf, W.E., Crooke, S.T. Mol. Pharmacol. (1987) [Pubmed]
  28. Teratogenic activity and metabolism of primidone in the mouse. McElhatton, P.R., Sullivan, F.M., Toseland, P.A. Epilepsia (1977) [Pubmed]
  29. Simulation of bone resorption-repair coupling in vitro. Jones, S.J., Gray, C., Boyde, A. Anat. Embryol. (1994) [Pubmed]
  30. Surface-enhanced Raman scattering study of the interaction of red dye alizarin with ovalbumin. Cañamares, M.V., Sevilla, P., Sanchez-Cortes, S., Garcia-Ramos, J.V. Biopolymers (2006) [Pubmed]
  31. Two validated HPLC methods for the quantification of alizarin and other anthraquinones in Rubia tinctorum cultivars. Derksen, G.C., Lelyveld, G.P., van Beek, T.A., Capelle, A., de Groot, A.E. Phytochemical analysis : PCA. (2004) [Pubmed]
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