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Chemical Compound Review

AC1L92W6     2-(3,4-dihydroxyphenyl)-7H- chromene-3,5,7...

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Disease relevance of Cyanidol


High impact information on Cyanidol


Chemical compound and disease context of Cyanidol

  • Overall, these results demonstrate that Dp, Pt, and Cy affect plasminogen activation, thus leading to the inhibition of glioblastoma cell migration and therefore they may be helpful for the development of new strategies for cancer prevention and therapy [3].

Biological context of Cyanidol

  • The different effects exerted by DP as compared with CY suggest that the presence of the three hydroxyl groups on the beta ring in the molecular structure of DP may be important for its greater biological activity [11].
  • In this study, we have shown the gene expression profile in human adipocytes treated with anthocyanins (cyanidin 3-glucoside; C3G or cyanidin; Cy) [12].
  • Cyanidin ACNs were metabolized via methylation and glucuronidation as well as by formation of both derivatives on the same ACN molecule [13].
  • [reaction: see text] A novel and efficient synthesis of cyanidin 3-O-beta-D-glucoside (1) was accomplished the first time by a biomimetic oxidation route [14].
  • However, anticancer effects of peonidin 3-glucoside have not been clearly demonstrated, with only limited studies being available concerning the inhibitory effect of cyanidin 3-glucoside for tumor cell growth [15].

Anatomical context of Cyanidol


Associations of Cyanidol with other chemical compounds


Gene context of Cyanidol


Analytical, diagnostic and therapeutic context of Cyanidol

  • The results of this study demonstrate that cyanidin glycosides of freeze-dried black raspberries are bioactive compounds which could account for at least some of the chemopreventive activity observed in animal models [27].
  • Cyanidin 3-O-beta-D-glucoside was reacted with 2,2'-azobis(2,4-dimet hylvaleronitrile) to generate the alkylperoxyl radicals, and the reaction products were isolated by high-performance liquid chromatography [28].
  • Two anthocyanins, cyanidin 3-glucoside and cyanidin 3-rutinoside, were identified in the leaves and flowers of both cultivars and quantified by HPLC analysis [29].
  • We previously determined that five rather hydrophobic metabolites appeared in blood plasma after oral administration of cyanidin 3-O-beta-D-glucopyranoside, but a group of hydrophilic metabolites still remained unidentified [30].
  • In neutral aqueous solution, the crude extract from A. reptans flower cell cultures and the major anthocyanin cyanidin 3-(di-p-coumaroyl)sophoroside-5-malonylglucoside were more stable than cyanidin 3-glucoside, and also prevented more efficiently peroxidation than did the latter [31].


  1. Dietary cyanidin 3-O-beta-D-glucoside-rich purple corn color prevents obesity and ameliorates hyperglycemia in mice. Tsuda, T., Horio, F., Uchida, K., Aoki, H., Osawa, T. J. Nutr. (2003) [Pubmed]
  2. Protective effects of dietary cyanidin 3-O-beta-D-glucoside on liver ischemia-reperfusion injury in rats. Tsuda, T., Horio, F., Kitoh, J., Osawa, T. Arch. Biochem. Biophys. (1999) [Pubmed]
  3. Anthocyanidins inhibit migration of glioblastoma cells: Structure-activity relationship and involvement of the plasminolytic system. Lamy, S., Lafleur, R., B??dard, V., Moghrabi, A., Barrette, S., Gingras, D., B??liveau, R. J. Cell. Biochem. (2007) [Pubmed]
  4. Tart cherry anthocyanins inhibit tumor development in Apc(Min) mice and reduce proliferation of human colon cancer cells. Kang, S.Y., Seeram, N.P., Nair, M.G., Bourquin, L.D. Cancer Lett. (2003) [Pubmed]
  5. Cyanidin attenuates PGE2 production and cyclooxygenase-2 expression in LNCaP human prostate cancer cells. Muñoz-Espada, A.C., Watkins, B.A. J. Nutr. Biochem. (2006) [Pubmed]
  6. A new petunia flower colour generated by transformation of a mutant with a maize gene. Meyer, P., Heidmann, I., Forkmann, G., Saedler, H. Nature (1987) [Pubmed]
  7. Engineering secondary metabolism in maize cells by ectopic expression of transcription factors. Grotewold, E., Chamberlin, M., Snook, M., Siame, B., Butler, L., Swenson, J., Maddock, S., Clair, G., Bowen, B. Plant Cell (1998) [Pubmed]
  8. Reaction mechanism from leucoanthocyanidin to anthocyanidin 3-glucoside, a key reaction for coloring in anthocyanin biosynthesis. Nakajima , J., Tanaka, Y., Yamazaki, M., Saito, K. J. Biol. Chem. (2001) [Pubmed]
  9. Functional genomics by integrated analysis of metabolome and transcriptome of Arabidopsis plants over-expressing an MYB transcription factor. Tohge, T., Nishiyama, Y., Hirai, M.Y., Yano, M., Nakajima, J., Awazuhara, M., Inoue, E., Takahashi, H., Goodenowe, D.B., Kitayama, M., Noji, M., Yamazaki, M., Saito, K. Plant J. (2005) [Pubmed]
  10. Reduction of light-induced anthocyanin accumulation in inoculated sorghum mesocotyls. Implications for a compensatory role in the defense response. Lo, S.C., Nicholson, R.L. Plant Physiol. (1998) [Pubmed]
  11. Anthocyanins induce cell cycle perturbations and apoptosis in different human cell lines. Lazzè, M.C., Savio, M., Pizzala, R., Cazzalini, O., Perucca, P., Scovassi, A.I., Stivala, L.A., Bianchi, L. Carcinogenesis (2004) [Pubmed]
  12. Microarray profiling of gene expression in human adipocytes in response to anthocyanins. Tsuda, T., Ueno, Y., Yoshikawa, T., Kojo, H., Osawa, T. Biochem. Pharmacol. (2006) [Pubmed]
  13. Aglycones and sugar moieties alter anthocyanin absorption and metabolism after berry consumption in weanling pigs. Wu, X., Pittman, H.E., McKay, S., Prior, R.L. J. Nutr. (2005) [Pubmed]
  14. Novel and efficient synthesis of cyanidin 3-O-beta-D-glucoside from (+)-catechin via a flav-3-en-3-ol as a key intermediate. Kondo, T., Oyama, K., Nakamura, S., Yamakawa, D., Tokuno, K., Yoshida, K. Org. Lett. (2006) [Pubmed]
  15. Cyanidin 3-glucoside and peonidin 3-glucoside inhibit tumor cell growth and induce apoptosis in vitro and suppress tumor growth in vivo. Chen, P.N., Chu, S.C., Chiou, H.L., Chiang, C.L., Yang, S.F., Hsieh, Y.S. Nutrition and cancer. (2005) [Pubmed]
  16. Anthocyanins are efficiently absorbed from the small intestine in rats. Talavéra, S., Felgines, C., Texier, O., Besson, C., Manach, C., Lamaison, J.L., Rémésy, C. J. Nutr. (2004) [Pubmed]
  17. Absorption and metabolism of cyanidin 3-O-beta-D-glucoside in rats. Tsuda, T., Horio, F., Osawa, T. FEBS Lett. (1999) [Pubmed]
  18. Delphinidin and cyanidin inhibit PDGF(AB)-induced VEGF release in vascular smooth muscle cells by preventing activation of p38 MAPK and JNK. Oak, M.H., Bedoui, J.E., Madeira, S.V., Chalupsky, K., Schini-Kerth, V.B. Br. J. Pharmacol. (2006) [Pubmed]
  19. Effect of cyanidin 3-O-beta-glucopyranoside on micronucleus induction in cultured human lymphocytes by four different mutagens. Fimognari, C., Berti, F., Cantelli-Forti, G., Hrelia, P. Environ. Mol. Mutagen. (2004) [Pubmed]
  20. Neurotensin-and EGF-induced metabolic activation of colon carcinoma cells is diminished by dietary flavonoid cyanidin but not by its glycosides. Briviba, K., Abrahamse, S.L., Pool-Zobel, B.L., Rechkemmer, G. Nutrition and cancer. (2001) [Pubmed]
  21. A blend of polyphenolic compounds explains the stimulatory effect of red wine on human endothelial NO synthase. Wallerath, T., Li, H., Gödtel-Ambrust, U., Schwarz, P.M., Förstermann, U. Nitric Oxide (2005) [Pubmed]
  22. Flavonols and anthocyanins of bush butter, Dacryodes edulis (G. Don) H.J. Lam, fruit. changes in their composition during ripening. Ella Missang, C., Guyot, S., Renard, C.M. J. Agric. Food Chem. (2003) [Pubmed]
  23. Bioavailability of anthocyanidin-3-glucosides following consumption of red wine and red grape juice. Frank, T., Netzel, M., Strass, G., Bitsch, R., Bitsch, I. Can. J. Physiol. Pharmacol. (2003) [Pubmed]
  24. Anthocyanidin synthase from Gerbera hybrida catalyzes the conversion of (+)-catechin to cyanidin and a novel procyanidin. Wellmann, F., Griesser, M., Schwab, W., Martens, S., Eisenreich, W., Matern, U., Lukacin, R. FEBS Lett. (2006) [Pubmed]
  25. Potential functional foods in the traditional Maori diet. Cambie, R.C., Ferguson, L.R. Mutat. Res. (2003) [Pubmed]
  26. Dietary cyanidin 3-O-beta-D-glucoside increases ex vivo oxidation resistance of serum in rats. Tsuda, T., Horio, F., Osawa, T. Lipids (1998) [Pubmed]
  27. Identification of cyanidin glycosides as constituents of freeze-dried black raspberries which inhibit anti-benzo[a]pyrene-7,8-diol-9,10-epoxide induced NFkappaB and AP-1 activity. Hecht, S.S., Huang, C., Stoner, G.D., Li, J., Kenney, P.M., Sturla, S.J., Carmella, S.G. Carcinogenesis (2006) [Pubmed]
  28. Oxidation products of cyanidin 3-O-beta-D-glucoside with a free radical initiator. Tsuda, T., Ohshima, K., Kawakishi, S., Osawa, T. Lipids (1996) [Pubmed]
  29. Relationship of light quantity and anthocyanin production in Pennisetum setaceum Cvs. rubrum and red riding hood. Beckwith, A.G., Zhang, Y., Seeram, N.P., Cameron, A.C., Nair, M.G. J. Agric. Food Chem. (2004) [Pubmed]
  30. Extended glucuronidation is another major path of cyanidin 3-O-beta-D-glucopyranoside metabolism in rats. Ichiyanagi, T., Shida, Y., Rahman, M.M., Hatano, Y., Konishi, T. J. Agric. Food Chem. (2005) [Pubmed]
  31. Acylated anthocyanidin 3-sophoroside-5-glucosides from Ajuga reptans flowers and the corresponding cell cultures. Terahara, N., Callebaut, A., Ohba, R., Nagata, T., Ohnishi-Kameyama, M., Suzuki, M. Phytochemistry (2001) [Pubmed]
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