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Chemical Compound Review

beta-Jonone     4-(2,6,6-trimethyl-1- cyclohexenyl)but-3-en...

Synonyms: beta-IRISONE, SureCN23954, AGN-PC-00S3G5, AG-F-20325, CTK3J2478, ...
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Disease relevance of BETA-IONONE


High impact information on BETA-IONONE


Biological context of BETA-IONONE

  • Together, these observations indicate that in bleach-adapted rods beta-ionone activates phototransduction in the dark [2].
  • These more polar products are presumed to result from multiple hydroxylations on the beta-ionone ring [10].
  • From this recombinant strain the enzyme was purified by immuno-affinity chromatography and its cyclization activity characterized as a two-step reaction in which both sides of the lycopene molecule are cyclized to beta-ionone rings with the monocyclic gamma-carotene as an intermediate [11].
  • The biotransformation of therapeutic retinoids containing the beta-ionone ring system is likely to involve the microsomal ATRA 4-hydroxylase P450 [12].
  • From the N-BuOH soluble fraction of an MeOH extract of DENDRANTHEMA SHIWOGIKU, two new beta-ionone glucosides and roseoside were isolated, the structures of the new compounds elucidated were 2 and 3, respectively, on the basis of spectroscopic data and the results of an enzymic hydrolysis of 2 [13].

Anatomical context of BETA-IONONE


Associations of BETA-IONONE with other chemical compounds


Gene context of BETA-IONONE

  • Both beta-ionone and geraniol inhibited CDK 2 activity and dose-dependently decreased the expression of cyclins D1, E, and A, and CDK 2 and 4, without changing the expression of p21cip1 or p27kip1 [3].
  • W(thereby the oxygen diffusion-concentration product) is larger in the meta II-enriched sample than in rhodopsin, indicating light-induced conformational changes of opsin around the beta-ionone binding site [20].
  • However, the levels of TIMP-1 and TIMP-2 transcripts were elevated in cells treated with beta-ionone in a dose-dependent manner [22].
  • CONCLUSION: beta-ionone can inhibit the proliferation of SGC-7901 cells, upregulate the expression of TIMP-1 and TIMP-2 expression, and may influence metastasis of cancer [22].
  • The effects of beta-ionone on MMP-2 and MMP-9 activities in SGC-7901 cells were not observed [22].

Analytical, diagnostic and therapeutic context of BETA-IONONE


  1. Activation of mislocalized opsin kills rod cells: a novel mechanism for rod cell death in retinal disease. Alfinito, P.D., Townes-Anderson, E. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  2. Occupancy of the chromophore binding site of opsin activates visual transduction in rod photoreceptors. Kefalov, V.J., Carter Cornwall, M., Crouch, R.K. J. Gen. Physiol. (1999) [Pubmed]
  3. Geraniol and beta-ionone inhibit proliferation, cell cycle progression, and cyclin-dependent kinase 2 activity in MCF-7 breast cancer cells independent of effects on HMG-CoA reductase activity. Duncan, R.E., Lau, D., El-Sohemy, A., Archer, M.C. Biochem. Pharmacol. (2004) [Pubmed]
  4. Stereo- and regioselective hydroxylation of alpha-ionone by Streptomyces strains. Lutz-Wahl, S., Fischer, P., Schmidt-Dannert, C., Wohlleben, W., Hauer, B., Schmid, R.D. Appl. Environ. Microbiol. (1998) [Pubmed]
  5. Apoptosis of human gastric adenocarcinoma cells induced by beta-ionone. Liu, J.R., Chen, B.Q., Yang, B.F., Dong, H.W., Sun, C.H., Wang, Q., Song, G., Song, Y.Q. World J. Gastroenterol. (2004) [Pubmed]
  6. Existence of a beta-ionone ring-binding site in the rhodopsin molecule. Matsumoto, H., Yoshizawa, T. Nature (1975) [Pubmed]
  7. The biochemical characterization of two carotenoid cleavage enzymes from Arabidopsis indicates that a carotenoid-derived compound inhibits lateral branching. Schwartz, S.H., Qin, X., Loewen, M.C. J. Biol. Chem. (2004) [Pubmed]
  8. Mechanism of rhodopsin activation as examined with ring-constrained retinal analogs and the crystal structure of the ground state protein. Jang, G.F., Kuksa, V., Filipek, S., Bartl, F., Ritter, E., Gelb, M.H., Hofmann, K.P., Palczewski, K. J. Biol. Chem. (2001) [Pubmed]
  9. Circadian regulation of the PhCCD1 carotenoid cleavage dioxygenase controls emission of beta-ionone, a fragrance volatile of petunia flowers. Simkin, A.J., Underwood, B.A., Auldridge, M., Loucas, H.M., Shibuya, K., Schmelz, E., Clark, D.G., Klee, H.J. Plant Physiol. (2004) [Pubmed]
  10. HPLC-MS/MS analysis of the products generated from all-trans-retinoic acid using recombinant human CYP26A. Chithalen, J.V., Luu, L., Petkovich, M., Jones, G. J. Lipid Res. (2002) [Pubmed]
  11. Expression, purification and properties of lycopene cyclase from Erwinia uredovora. Schnurr, G., Misawa, N., Sandmann, G. Biochem. J. (1996) [Pubmed]
  12. All-trans-retinoic acid 4-hydroxylation in human liver microsomes: in vitro modulation by therapeutic retinoids. Nadin, L., Murray, M. British journal of clinical pharmacology. (1996) [Pubmed]
  13. Structural Elucidation of Dendranthemosides A and B: Two New beta-Ionone Glucosides from Dendranthema shiwogiku. Otsuka, H., Takeda, Y., Yamasaki, K., Takeda, Y. Planta Med. (1992) [Pubmed]
  14. The ring of the rhodopsin chromophore in a hydrophobic activation switch within the binding pocket. Spooner, P.J., Sharples, J.M., Goodall, S.C., Bovee-Geurts, P.H., Verhoeven, M.A., Lugtenburg, J., Pistorius, A.M., Degrip, W.J., Watts, A. J. Mol. Biol. (2004) [Pubmed]
  15. Relative orientation between the beta-ionone ring and the polyene chain for the chromophore of rhodopsin in native membranes. Spooner, P.J., Sharples, J.M., Verhoeven, M.A., Lugtenburg, J., Glaubitz, C., Watts, A. Biochemistry (2002) [Pubmed]
  16. Immunosuppression induced by acute exposure to cocaine is dependent on metabolism by cytochrome P-450. Jeong, T.C., Jordan, S.D., Matulka, R.A., Stanulis, E.D., Park, S.S., Holsapple, M.P. J. Pharmacol. Exp. Ther. (1996) [Pubmed]
  17. Differences in the pharmacological activation of visual opsins. Isayama, T., Chen, Y., Kono, M., Degrip, W.J., Ma, J.X., Crouch, R.K., Makino, C.L. Vis. Neurosci. (2006) [Pubmed]
  18. EPR spin trapping detection of carbon-centered carotenoid and beta-ionone radicals. Konovalova, T.A., Kispert, L.D., Polyakov, N.E., Leshina, T.V. Free Radic. Biol. Med. (2000) [Pubmed]
  19. Specific reaction of 9-cis-retinoyl fluoride with bovine opsin. Wong, C.G., Rando, R.R. Biochemistry (1984) [Pubmed]
  20. Oxygen diffusion-concentration product in rhodopsin as observed by a pulse ESR spin labeling method. Subczynski, W.K., Renk, G.E., Crouch, R.K., Hyde, J.S., Kusumi, A. Biophys. J. (1992) [Pubmed]
  21. Apoptosis and cell-cycle arrest in human and murine tumor cells are initiated by isoprenoids. Mo, H., Elson, C.E. J. Nutr. (1999) [Pubmed]
  22. Inhibition of beta-ionone on SGC-7901 cell proliferation and upregulation of metalloproteinases-1 and -2 expression. Liu, J.R., Yang, B.F., Chen, B.Q., Yang, Y.M., Dong, H.W., Song, Y.Q. World J. Gastroenterol. (2004) [Pubmed]
  23. Bleached pigment activates transduction in salamander cones. Cornwall, M.C., Matthews, H.R., Crouch, R.K., Fain, G.L. J. Gen. Physiol. (1995) [Pubmed]
  24. Interactions of the beta-ionone ring with the protein in the visual pigment rhodopsin control the activation mechanism. An FTIR and fluorescence study on artificial vertebrate rhodopsins. Jäger, F., Jäger, S., Krütle, O., Friedman, N., Sheves, M., Hofmann, K.P., Siebert, F. Biochemistry (1994) [Pubmed]
  25. Role of metabolism by esterase and cytochrome P-450 in cocaine-induced suppression of the antibody response. Jeong, T.C., Jordan, S.D., Matulka, R.A., Stanulis, E.D., Kaminski, E.J., Holsapple, M.P. J. Pharmacol. Exp. Ther. (1995) [Pubmed]
  26. Induction of liver cytochrome P450 2B1 by beta-ionone in Sprague Dawley rats. Jeong, T.C., Kim, H.J., Yun, C.H., Lee, S.S., Yang, K.H., Han, S.S., Roh, J.K. Biochem. Biophys. Res. Commun. (1995) [Pubmed]
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