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Chemical Compound Review

Chalcone     (E)-1,3-diphenylprop-2-en-1- one

Synonyms: Chalkone, Chalkon, Cinnamophenone, CHALCONE-CMPD, trans-Chalcone, ...
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Disease relevance of chalcone

  • However, the rppA gene from the Gram-positive, soil-living filamentous bacterium Streptomyces griseus encodes a 372-amino-acid protein that shows significant similarity to chalcone synthases [1].
  • Chalcone isomerase (CHI) catalyzes the intramolecular cyclization of chalcone synthesized by chalcone synthase (CHS) into (2S)-naringenin, an essential compound in the biosynthesis of anthocyanin pigments, inducers of Rhizobium nodulation genes, and antimicrobial phytoalexins [2].
  • The cDNA clone was identified on the basis of N-terminal sequence identity to purified S-adenosyl-L-methionine:isoliquiritigenin 2'-O-methyltransferase (chalcone OMT) and expression of enzymatically active chalcone OMT protein in Escherichia coli [3].
  • Xanthohumol, the main prenylated chalcone in hops, was investigated for its antiinvasive activity on human breast cancer cell lines (MCF-7 and T47-D) in vitro [4].
  • Direct and specific inactivation of rhinovirus by chalcone Ro 09-0410 [5].

High impact information on chalcone

  • Transgenic Petunia plants with a chsA coding sequence under the control of a 35S promoter sometimes lose endogene and transgene chalcone synthase activity and purple flower pigment through posttranscriptional chsA RNA degradation [6].
  • Ppr also regulates chalcone synthase gene expression in response to blue light with autophosphorylation inhibited in vitro by blue light [7].
  • The duplicated chalcone synthase genes C2 and Whp (white pollen) of Zea mays are independently regulated; evidence for translational control of Whp expression by the anthocyanin intensifying gene in [8].
  • Cloning of the two chalcone flavanone isomerase genes from Petunia hybrida: coordinate, light-regulated and differential expression of flavonoid genes [9].
  • In heterozygotes, niv-525 acts in trans to reduce the steady-state level of nivea transcript produced by its Niv+ homologue and hence the quantity of chalcone synthase protein [10].

Chemical compound and disease context of chalcone


Biological context of chalcone


Anatomical context of chalcone

  • We have combined in vivo genomic footprinting and light-induced transient expression of chalcone synthase promoter derivatives in parsley protoplasts to identify cis sequences regulating light activation [20].
  • The presence of chalcone synthase on these membranes was not caused by nonspecific adsorption or entrapment of proteins [21].
  • Biochemical, immunological, and immunocytochemical evidence for the association of chalcone synthase with endoplasmic reticulum membranes [21].
  • Addition of MeJA to soybean suspension cultures also increased mRNA levels for three wound-responsive genes (chalcone synthase, vegetative storage protein, and proline-rich cell wall protein) suggesting a role for MeJA/JA in the mediation of several changes in gene expression associated with the plants' response to wounding [22].
  • Immunocytochemical investigations with both a 5-nm and a 20-nm ImmunoGold conjugate showed that chalcone synthase was associated with the cytoplasmic face of rough (ribosome bearing) endoplasmic reticulum membranes [21].

Associations of chalcone with other chemical compounds

  • Glutathione and a UV light-induced glutathione S-transferase are involved in signaling to chalcone synthase in cell cultures [23].
  • RNA expression analysis of ripening fruit revealed that, with the exception of chalcone isomerase, all of the structural genes required for the production of kaempferol-type flavonols and pelargonidin-type anthocyanins were induced strongly by the LC/C1 transcription factors [24].
  • Enzyme activity measurement and immunoblots of buckwheat hypocotyl homogenates that were fractionated on linear sucrose density gradients and developed with a specific chalcone synthase antibody and a 20-nm ImmunoGold conjugate showed the presence of chalcone synthase in fractions enriched in endoplasmic reticulum membranes [21].
  • RNA blot hybridization with 32P-labeled cDNA sequences was used to demonstrate marked accumulation of phenylalanine ammonia-lyase and chalcone synthase mRNAs in excision-wounded hypocotyls of Phaseolus vulgaris L [25].
  • Stilbene (STS) and chalcone (CHS) synthases are homodimeric, related plant-specific polyketide synthases [26].

Gene context of chalcone

  • Analysis of gene expression in etiolated seedlings exposed to white light and in two putative regulatory mutants, ttg and tt8, demonstrated that the Arabidopsis F3H gene is coordinately expressed with chalcone synthase and chalcone isomerases is seedlings, whereas dihydroflavonol reductase expression is controlled by distinct regulatory mechanisms [27].
  • Together with chalcone polyketide reductase and cytochrome P450 2-hydroxyisoflavanone synthase, the chalcone isomerase (CHI) of leguminous plants is fundamental in the construction of these ecophysiologically active flavonoids [28].
  • Other families include the prokaryotic AKRs, the plant chalcone reductases, the Shaker channels, and the ethoxyquin-inducible aflatoxin B1 aldehyde reductase [29].
  • 2. At 10 microM, the prenylated chalcone, xanthohumol (XN), almost completely inhibited the 7-ethoxyresorufin O-deethylase (EROD) activity of CYP1A1 [30].
  • An enhancement in Fas/APO-1 and its two form ligands, membrane-bound Fas ligand (mFasL) and soluble Fas ligand (sFasL), was responsible for the apoptotic effect induced by chalcone [31].

Analytical, diagnostic and therapeutic context of chalcone


  1. A new pathway for polyketide synthesis in microorganisms. Funa, N., Ohnishi, Y., Fujii, I., Shibuya, M., Ebizuka, Y., Horinouchi, S. Nature (1999) [Pubmed]
  2. Structure and mechanism of the evolutionarily unique plant enzyme chalcone isomerase. Jez, J.M., Bowman, M.E., Dixon, R.A., Noel, J.P. Nat. Struct. Biol. (2000) [Pubmed]
  3. Molecular characterization and expression of alfalfa isoliquiritigenin 2'-O-methyltransferase, an enzyme specifically involved in the biosynthesis of an inducer of Rhizobium meliloti nodulation genes. Maxwell, C.A., Harrison, M.J., Dixon, R.A. Plant J. (1993) [Pubmed]
  4. Antiinvasive effect of xanthohumol, a prenylated chalcone present in hops (Humulus lupulus L.) and beer. Vanhoecke, B., Derycke, L., Van Marck, V., Depypere, H., De Keukeleire, D., Bracke, M. Int. J. Cancer (2005) [Pubmed]
  5. Direct and specific inactivation of rhinovirus by chalcone Ro 09-0410. Ishitsuka, H., Ninomiya, Y.T., Ohsawa, C., Fujiu, M., Suhara, Y. Antimicrob. Agents Chemother. (1982) [Pubmed]
  6. RNA-mediated RNA degradation and chalcone synthase A silencing in petunia. Metzlaff, M., O'Dell, M., Cluster, P.D., Flavell, R.B. Cell (1997) [Pubmed]
  7. Bacterial photoreceptor with similarity to photoactive yellow protein and plant phytochromes. Jiang, Z., Swem, L.R., Rushing, B.G., Devanathan, S., Tollin, G., Bauer, C.E. Science (1999) [Pubmed]
  8. The duplicated chalcone synthase genes C2 and Whp (white pollen) of Zea mays are independently regulated; evidence for translational control of Whp expression by the anthocyanin intensifying gene in. Franken, P., Niesbach-Klösgen, U., Weydemann, U., Maréchal-Drouard, L., Saedler, H., Wienand, U. EMBO J. (1991) [Pubmed]
  9. Cloning of the two chalcone flavanone isomerase genes from Petunia hybrida: coordinate, light-regulated and differential expression of flavonoid genes. van Tunen, A.J., Koes, R.E., Spelt, C.E., van der Krol, A.R., Stuitje, A.R., Mol, J.N. EMBO J. (1988) [Pubmed]
  10. A semi-dominant allele, niv-525, acts in trans to inhibit expression of its wild-type homologue in Antirrhinum majus. Coen, E.S., Carpenter, R. EMBO J. (1988) [Pubmed]
  11. Plant polyketide synthases: a chalcone synthase-type enzyme which performs a condensation reaction with methylmalonyl-CoA in the biosynthesis of C-methylated chalcones. Schröder, J., Raiber, S., Berger, T., Schmidt, A., Schmidt, J., Soares-Sello, A.M., Bardshiri, E., Strack, D., Simpson, T.J., Veit, M., Schröder, G. Biochemistry (1998) [Pubmed]
  12. Induction of apoptosis and cell cycle arrest by a chalcone panduratin A isolated from Kaempferia pandurata in androgen-independent human prostate cancer cells PC3 and DU145. Yun, J.M., Kweon, M.H., Kwon, H., Hwang, J.K., Mukhtar, H. Carcinogenesis (2006) [Pubmed]
  13. Grapevine stilbene synthase cDNA only slightly differing from chalcone synthase cDNA is expressed in Escherichia coli into a catalytically active enzyme. Melchior, F., Kindl, H. FEBS Lett. (1990) [Pubmed]
  14. Molecular cloning and heterologous expression of acridone synthase from elicited Ruta graveolens L. cell suspension cultures. Junghanns, K.T., Kneusel, R.E., Baumert, A., Maier, W., Gröger, D., Matern, U. Plant Mol. Biol. (1995) [Pubmed]
  15. Molecular basis of drug resistance to new antirhinovirus agents. Ishitsuka, H., Ninomiya, Y., Suhara, Y. J. Antimicrob. Chemother. (1986) [Pubmed]
  16. Identification and genetic regulation of the chalcone synthase multigene family in pea. Harker, C.L., Ellis, T.H., Coen, E.S. Plant Cell (1990) [Pubmed]
  17. Homodimeric and heterodimeric leucine zipper proteins and nuclear factors from parsley recognize diverse promoter elements with ACGT cores. Armstrong, G.A., Weisshaar, B., Hahlbrock, K. Plant Cell (1992) [Pubmed]
  18. Developmental and environmental regulation of a bean chalcone synthase promoter in transgenic tobacco. Schmid, J., Doerner, P.W., Clouse, S.D., Dixon, R.A., Lamb, C.J. Plant Cell (1990) [Pubmed]
  19. Tissue-specific gene silencing mediated by a naturally occurring chalcone synthase gene cluster in Glycine max. Tuteja, J.H., Clough, S.J., Chan, W.C., Vodkin, L.O. Plant Cell (2004) [Pubmed]
  20. Functional architecture of the light-responsive chalcone synthase promoter from parsley. Schulze-Lefert, P., Becker-André, M., Schulz, W., Hahlbrock, K., Dangl, J.L. Plant Cell (1989) [Pubmed]
  21. Biochemical, immunological, and immunocytochemical evidence for the association of chalcone synthase with endoplasmic reticulum membranes. Hrazdina, G., Zobel, A.M., Hoch, H.C. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  22. Jasmonic acid/methyl jasmonate accumulate in wounded soybean hypocotyls and modulate wound gene expression. Creelman, R.A., Tierney, M.L., Mullet, J.E. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  23. Glutathione and a UV light-induced glutathione S-transferase are involved in signaling to chalcone synthase in cell cultures. Loyall, L., Uchida, K., Braun, S., Furuya, M., Frohnmeyer, H. Plant Cell (2000) [Pubmed]
  24. High-flavonol tomatoes resulting from the heterologous expression of the maize transcription factor genes LC and C1. Bovy, A., de Vos, R., Kemper, M., Schijlen, E., Almenar Pertejo, M., Muir, S., Collins, G., Robinson, S., Verhoeyen, M., Hughes, S., Santos-Buelga, C., van Tunen, A. Plant Cell (2002) [Pubmed]
  25. Differential accumulation of plant defense gene transcripts in a compatible and an incompatible plant-pathogen interaction. Bell, J.N., Ryder, T.B., Wingate, V.P., Bailey, J.A., Lamb, C.J. Mol. Cell. Biol. (1986) [Pubmed]
  26. Reaction mechanisms of homodimeric plant polyketide synthase (stilbenes and chalcone synthase). A single active site for the condensing reaction is sufficient for synthesis of stilbenes, chalcones, and 6'-deoxychalcones. Tropf, S., Kärcher, B., Schröder, G., Schröder, J. J. Biol. Chem. (1995) [Pubmed]
  27. Analysis of flavanone 3-hydroxylase in Arabidopsis seedlings. Coordinate regulation with chalcone synthase and chalcone isomerase. Pelletier, M.K., Shirley, B.W. Plant Physiol. (1996) [Pubmed]
  28. A cluster of genes encodes the two types of chalcone isomerase involved in the biosynthesis of general flavonoids and legume-specific 5-deoxy(iso)flavonoids in Lotus japonicus. Shimada, N., Aoki, T., Sato, S., Nakamura, Y., Tabata, S., Ayabe, S. Plant Physiol. (2003) [Pubmed]
  29. A new nomenclature for the aldo-keto reductase superfamily. Jez, J.M., Flynn, T.G., Penning, T.M. Biochem. Pharmacol. (1997) [Pubmed]
  30. In vitro inhibition of human P450 enzymes by prenylated flavonoids from hops, Humulus lupulus. Henderson, M.C., Miranda, C.L., Stevens, J.F., Deinzer, M.L., Buhler, D.R. Xenobiotica (2000) [Pubmed]
  31. Chalcone inhibits the proliferation of human breast cancer cell by blocking cell cycle progression and inducing apoptosis. Hsu, Y.L., Kuo, P.L., Tzeng, W.S., Lin, C.C. Food Chem. Toxicol. (2006) [Pubmed]
  32. Inducible in vivo DNA footprints define sequences necessary for UV light activation of the parsley chalcone synthase gene. Schulze-Lefert, P., Dangl, J.L., Becker-André, M., Hahlbrock, K., Schulz, W. EMBO J. (1989) [Pubmed]
  33. A polyketide synthase in glycopeptide biosynthesis: the biosynthesis of the non-proteinogenic amino acid (S)-3,5-dihydroxyphenylglycine. Pfeifer, V., Nicholson, G.J., Ries, J., Recktenwald, J., Schefer, A.B., Shawky, R.M., Schröder, J., Wohlleben, W., Pelzer, S. J. Biol. Chem. (2001) [Pubmed]
  34. The role of cysteines in polyketide synthases. Site-directed mutagenesis of resveratrol and chalcone synthases, two key enzymes in different plant-specific pathways. Lanz, T., Tropf, S., Marner, F.J., Schröder, J., Schröder, G. J. Biol. Chem. (1991) [Pubmed]
  35. Purification and characterization of chalcone isomerase from soybeans. Bednar, R.A., Hadcock, J.R. J. Biol. Chem. (1988) [Pubmed]
  36. Molecular cloning of chalcone synthase cDNAs from Pisum sativum. Ichinose, Y., Kawamata, S., Yamada, T., An, C., Kajiwara, T., Shiraishi, T., Oku, H. Plant Mol. Biol. (1992) [Pubmed]
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