norisoprenoids

Summary

Summary: Thirteen-carbon butene cyclohexene degradation products formed by the cleavage of CAROTENOIDS. They contribute to the flavor of some FRUIT. Ionone should not be confused with the similarly named ionol.

Top Publications

  1. Rubio A, Rambla J, Santaella M, Gómez M, Orzaez D, Granell A, et al. Cytosolic and plastoglobule-targeted carotenoid dioxygenases from Crocus sativus are both involved in beta-ionone release. J Biol Chem. 2008;283:24816-25 pubmed publisher
    ..In addition, the location and precise timing of beta-ionone synthesis, together with its known activity as a fragrance and insect attractant, suggest that this volatile may have a role in Crocus pollination...
  2. Jerkovic I, Marijanović Z. Volatile composition screening of Salix spp. nectar honey: benzenecarboxylic acids, norisoprenoids, terpenes, and others. Chem Biodivers. 2010;7:2309-25 pubmed publisher
    ..g., high percentage of phenylacetic acid) and several norisoprenoids (?-isophorone and 4-oxoisophorone)...
  3. Jerkovic I, Tuberoso C, Tuberso C, Gugić M, Bubalo D. Composition of sulla (Hedysarum coronarium L.) honey solvent extractives determined by GC/MS: norisoprenoids and other volatile organic compounds. Molecules. 2010;15:6375-85 pubmed publisher
    ..These procedures have permitted the identification of 56 compounds that include norisoprenoids, benzene derivatives, aliphatic compounds and Maillard reaction products...
  4. Mathieu S, Terrier N, Procureur J, Bigey F, Gunata Z. A carotenoid cleavage dioxygenase from Vitis vinifera L.: functional characterization and expression during grape berry development in relation to C13-norisoprenoid accumulation. J Exp Bot. 2005;56:2721-31 pubmed
    ..A significant induction of the gene expression approaching véraison was observed in both cultivars. In parallel, the C(13)-norisoprenoid level increased from véraison to maturity in both cultivars. ..
  5. Simkin A, Underwood B, Auldridge M, Loucas H, Shibuya K, Schmelz E, et al. Circadian regulation of the PhCCD1 carotenoid cleavage dioxygenase controls emission of beta-ionone, a fragrance volatile of petunia flowers. Plant Physiol. 2004;136:3504-14 pubmed
    ..beta-Ionone emission by flowers occurred principally during daylight hours, paralleling PhCCD1 expression in corollas. The results indicate that PhCCD1 activity and beta-ionone emission are likely regulated at the level of transcript. ..
  6. Simkin A, Schwartz S, Auldridge M, Taylor M, Klee H. The tomato carotenoid cleavage dioxygenase 1 genes contribute to the formation of the flavor volatiles beta-ionone, pseudoionone, and geranylacetone. Plant J. 2004;40:882-92 pubmed publisher
  7. Mahattanatawee K, Rouseff R, Valim M, Naim M. Identification and aroma impact of norisoprenoids in orange juice. J Agric Food Chem. 2005;53:393-7 pubmed
    Four norisoprenoids, alpha-ionone, beta-ionone, beta-cyclocitral, and beta-damascenone, along with their putative carotenoid precursors, were identified in Valencia orange juice using time-intensity GC-O, GC-MS, and photodiode array HPLC...
  8. Kim M, Moon D, Kang C, Kwon T, Choi Y, Kim G. beta-Ionone enhances TRAIL-induced apoptosis in hepatocellular carcinoma cells through Sp1-dependent upregulation of DR5 and downregulation of NF-kappaB activity. Mol Cancer Ther. 2010;9:833-43 pubmed publisher
    ..Taken together, these data suggest that ION is a useful agent for TRAIL-based cancer treatments. Mol Cancer Ther; 9(4); 833-43. (c)2010 AACR. ..
  9. Yamamoto M, Akita T, Koyama Y, Sueyoshi E, Matsunami K, Otsuka H, et al. Euodionosides A-G: megastigmane glucosides from leaves of Euodia meliaefolia. Phytochemistry. 2008;69:1586-96 pubmed publisher
    ..Their structures were elucidated through a combination of spectroscopic analyses and application of the modified Mosher's method. ..

More Information

Publications62

  1. Spooner P, Sharples J, Verhoeven M, Lugtenburg J, Glaubitz C, Watts A. Relative orientation between the beta-ionone ring and the polyene chain for the chromophore of rhodopsin in native membranes. Biochemistry. 2002;41:7549-55 pubmed
    ..The more precise distance measurement made here between C8 and C18 (2.95 A) predicts that the chain is twisted out-of-plane with respect to the ring by a modest amount (C5-C6-C7-C8 torsion angle = -28 +/- 7 degrees ). ..
  2. Jones S, Fernandes N, Yeganehjoo H, Katuru R, Qu H, Yu Z, et al. ?-ionone induces cell cycle arrest and apoptosis in human prostate tumor cells. Nutr Cancer. 2013;65:600-10 pubmed publisher
    ..ionone, individually or in combination with other HMG CoA reductase suppressors, may have potential in prostate cancer chemoprevention and/or therapy. ..
  3. Lalko J, Lapczynski A, McGinty D, Bhatia S, Letizia C, Api A. Fragrance material review on trans-beta-ionone. Food Chem Toxicol. 2007;45 Suppl 1:S248-50 pubmed
    ..A toxicologic and dermatologic review of trans-beta-Ionone when used as a fragrance ingredient is presented. ..
  4. Uddin A, Labuda I, Burns F. A novel mechanism of filaggrin induction and sunburn prevention by ?-damascenone in Skh-1 mice. Toxicol Appl Pharmacol. 2012;265:335-41 pubmed publisher
    ..Damascenone protected against sunburn by activating a sebaceous gland-based pathway that fortified and thickened the cornified envelope plus sebum layer in a way that previously has been observed to occur only in keratinocytes. ..
  5. Yan J, Ding L, Shi X, Donkor P, Chen L, Qiu F. Megastigmane glycosides from leaves of Eucommia ulmoides Oliver with ACE inhibitory activity. Fitoterapia. 2017;116:121-125 pubmed publisher
    ..The results showed that the isolates (2, 3, 4, 5, 7) had moderate inhibitory effects on ACE in vitro compared with captopril. ..
  6. Liu J, Sun X, Dong H, Sun C, Sun W, Chen B, et al. beta-Ionone suppresses mammary carcinogenesis, proliferative activity and induces apoptosis in the mammary gland of the Sprague-Dawley rat. Int J Cancer. 2008;122:2689-98 pubmed publisher
    ..These results demonstrate the potent capacity of dietary beta-ionone to suppress DMBA-initiated mammary cancer in rats. ..
  7. Collin S, Nizet S, Claeys Bouuaert T, Despatures P. Main odorants in Jura flor-sherry wines. Relative contributions of sotolon, abhexon, and theaspirane-derived compounds. J Agric Food Chem. 2012;60:380-7 pubmed publisher
    ..With an extraction dedicated to hydrophilic compounds, the key role of sotolon was confirmed (112-387 ?g/kg; FD = 256-1024). This procedure enabled us to also evidence its ethyl analogue, abhexon (31-74 ?g/kg; FD = 64-256). ..
  8. Pirona R, Vecchietti A, Lazzari B, Caprera A, Malinverni R, Consolandi C, et al. Expression profiling of genes involved in the formation of aroma in two peach genotypes. Plant Biol (Stuttg). 2013;15:443-51 pubmed publisher
    ..In particular, a subset of 12 transcripts involved in metabolism of esters, norisoprenoids, phenylpropanoids and lactones, varied in expression during ripening and between Bolero and OroA.
  9. Kaczor A, Reva I, Fausto R. Influence of cage confinement on the photochemistry of matrix-isolated E-?-ionone: FT-IR and DFT study. J Phys Chem A. 2013;117:888-97 pubmed publisher
  10. Bezman Y, Mayer F, Takeoka G, Buttery R, Ben Oliel G, Rabinowitch H, et al. Differential effects of tomato (Lycopersicon esculentum mill) matrix on the volatility of important aroma compounds. J Agric Food Chem. 2003;51:722-6 pubmed
    ..If a matrix effect is found, analysis of the odorant molecule contents in the headspace rather than in the food is recommended in order to better evaluate their access to the olfactory receptors. ..
  11. Lee T, Wang G, Lee C, Kuo Y, Chou C. Inhibitory effects of glycosides from the leaves of Melaleuca quinquenervia on vascular contraction of rats. Planta Med. 2002;68:492-6 pubmed
    ..The rank-order potency (EC 50 value) of vasorelaxing activities of these compounds is 4 > 2 > 2a > 3 > 1. ..
  12. González Pombo P, Farina L, Carrau F, Batista Viera F, Brena B. Aroma enhancement in wines using co-immobilized Aspergillus niger glycosidases. Food Chem. 2014;143:185-91 pubmed publisher
    A major fraction of monoterpenes and norisoprenoids in young wines is conjugated to sugars representing a significant reservoir of aromatic precursors...
  13. D Abrosca B, Dellagreca M, Fiorentino A, Monaco P, Oriano P, Temussi F. Structure elucidation and phytotoxicity of C13 nor-isoprenoids from Cestrum parqui. Phytochemistry. 2004;65:497-505 pubmed
    ..All the structures have been determined by spectroscopic means and chemical correlations. The compounds showed phytotoxic effect on the germination and growth of Lactuca sativa L...
  14. Wang J, Zhang N, Beuve A, Townes Anderson E. Mislocalized opsin and cAMP signaling: a mechanism for sprouting by rod cells in retinal degeneration. Invest Ophthalmol Vis Sci. 2012;53:6355-69 pubmed
    ..We propose that in retinal disease, mislocalized rod opsin gains access to cAMP signaling, which leads to neuritic sprouting. ..
  15. Brandi F, Bar E, Mourgues F, Horváth G, Turcsi E, Giuliano G, et al. Study of 'Redhaven' peach and its white-fleshed mutant suggests a key role of CCD4 carotenoid dioxygenase in carotenoid and norisoprenoid volatile metabolism. BMC Plant Biol. 2011;11:24 pubmed publisher
    ..To investigate the regulation of carotenoid metabolism, as related to norisoprenoids and other volatile compounds in peach (Prunus persica L. Batsch...
  16. Wu Y, Liu J, Yang L, Chen H, Zhang S, Zhao H, et al. Allelopathic control of cyanobacterial blooms by periphyton biofilms. Environ Microbiol. 2011;13:604-15 pubmed publisher
    ..In addition, this work provides significant insights into the competitive relationships between algae and biofilms. ..
  17. Kanchanapoom T, Kasai R, Chumsri P, Hiraga Y, Yamasaki K. Megastigmane and iridoid glucosides from Clerodendrum inerme. Phytochemistry. 2001;58:333-6 pubmed
    ..The structural elucidations were based on analyses of physical and spectroscopic data. ..
  18. Liu D, Xu M, Wu L, Deng Z, Lin W. Norisoprenoids from the marine sponge Spheciospongia sp. J Asian Nat Prod Res. 2009;11:811-6 pubmed publisher
    ..b>Norisoprenoids were found from the sponge genus Spheciospongia for the first time, and were suggested to be the chemical ..
  19. Yang Y, Zhang F, Feng Z, Jiang J, Zhang P. Two new compounds from the roots of Rhodiola crenulata. J Asian Nat Prod Res. 2012;14:862-6 pubmed publisher
    ..Their structures were determined on the basis of various spectroscopic methods, including IR, HR-ESI-MS, 1D and 2D NMR, and chemical evidences. The cytotoxicity of these two compounds was evaluated by using MTT method. ..
  20. Yu Q, Beyer P. Reaction specificities of the ?-ionone-forming lycopene cyclase from rice (Oryza sativa) elucidated in vitro. FEBS Lett. 2012;586:3415-20 pubmed publisher
    ..It was also found that 5-cis-lycopene, which was thought to be decisive for ?-cyclization, was not involved in the reaction, with OsLCYe acting as an exclusion filter for this naturally occurring isomer. ..
  21. Ma J, Yang J, Ji T, Wang A, Su Y. [Chemical constituents from Hypericum perforatum]. Zhongguo Zhong Yao Za Zhi. 2012;37:2408-12 pubmed
    ..5 micromol x L(-1). compound 10 was new, compounds 2-4, 7 were obtained from Hypericum for the first time and compounds 5-6 was isolated from this plant for the first time. Compound 8 showed remarkable PTP1B inhibitory activity. ..
  22. Willner B, Granvogl M, Schieberle P. Characterization of the key aroma compounds in Bartlett pear brandies by means of the sensomics concept. J Agric Food Chem. 2013;61:9583-93 pubmed publisher
    ..In 15 commercial Bartlett pear brandies ethyl (E,Z)-2,4-decadienoate and (E,E)-2,4-decadienoate eliciting a pear-like aroma showed a reasonable correlation of their concentrations with the overall aroma quality. ..
  23. Ding Y, Nguyen H, Choi E, Bae K, Kim Y. Rhusonoside A, a new megastigmane glycoside from Rhus sylvestris, increases the function of osteoblastic MC3T3-E1 cells. Planta Med. 2009;75:158-62 pubmed publisher
    ..39 %, 171.27 %, and 134.25 %, respectively, of the basal value at 10 muM ( P < 0.05). In addition, 0.1 muM of compound 1 significantly increased mineralization of MC3T3-E1 cells to 142.78 % ( P < 0.05) of the basal value. ..
  24. Cooper C, Davies N, Menary R. Changes in some carotenoids and apocarotenoids during flower development in Boronia megastigma (Nees). J Agric Food Chem. 2009;57:1513-20 pubmed publisher
    ..The understanding of these processes may assist in optimizing harvest and postharvest processes useful to the boronia extraction industry. ..
  25. Kanchanapoom T, Chumsri P, Kasai R, Otsuka H, Yamasaki K. Lignan and megastigmane glycosides from Sauropus androgynus. Phytochemistry. 2003;63:985-8 pubmed
    ..The structural elucidations were bases on analyses of physical and spectroscopic data. ..
  26. Hu K, Qin Y, Tao Y, Zhu X, Peng C, Ullah N. Potential of Glycosidase from Non-Saccharomyces Isolates for Enhancement of Wine Aroma. J Food Sci. 2016;81:M935-43 pubmed publisher
    ..uvarum strain exhibited catalytic specificity for aromatic glycosides of C13 -norisoprenoids and some terpenes, enhancing fresh floral, sweet, berry, and nutty aroma characteristics in wine.
  27. Suzuki M, Matsumoto S, Mizoguchi M, Hirata S, Takagi K, Hashimoto I, et al. Identification of (3S, 9R)- and (3S, 9S)-megastigma-6,7-dien-3,5,9-triol 9-O-beta-D-glucopyranosides as damascenone progenitors in the flowers of Rosa damascena Mill. Biosci Biotechnol Biochem. 2002;66:2692-7 pubmed
    ..Compound 2b gave damascenone (1), 3-hydroxy-beta-damascone (3) and 4b upon heating under acidic conditions. ..
  28. Gomes Carneiro M, Dias D, Paumgartten F. Study on the mutagenicity and antimutagenicity of beta-ionone in the Salmonella/microsome assay. Food Chem Toxicol. 2006;44:522-7 pubmed
    ..Therefore, antagonism of CP-and AFB1-induced mutagenic effects by BIO could have been mediated-at least in part-by the inhibition of CYP2B enzymes. ..
  29. Castro Vazquez L, Díaz Maroto M, Pérez Coello M. Volatile composition and contribution to the aroma of spanish honeydew honeys. Identification of a new chemical marker. J Agric Food Chem. 2006;54:4809-13 pubmed
    ..A total of 15 volatile compounds presented odor activity values (OAVs) greater than 1, with phenylacetaldehyde and beta-damascenone being those with the highest OAVs. ..
  30. Sueyoshi E, Liu H, Matsunami K, Otsuka H, Shinzato T, Aramoto M, et al. Bridelionosides A-F: Megastigmane glucosides from Bridelia glauca f. balansae. Phytochemistry. 2006;67:2483-93 pubmed
    ..Their structures were determined by a combination of spectroscopic analyses and by application of the modified Mosher's method. ..
  31. Sugihara M, Buss V, Entel P, Elstner M, Frauenheim T. 11-cis-retinal protonated Schiff base: influence of the protein environment on the geometry of the rhodopsin chromophore. Biochemistry. 2002;41:15259-66 pubmed
    ..The dihedral angle about the C12-C13 bond is +170 degrees from planar s-cis, which imparts a positive helicity on the chromophore, in agreement with earlier considerations based on theoretical and spectroscopic evidence. ..
  32. Lapczynski A, Lalko J, McGinty D, Bhatia S, Letizia C, Api A. Fragrance material review on methyl-beta-ionone. Food Chem Toxicol. 2007;45 Suppl 1:S290-3 pubmed
    ..A toxicologic and dermatologic review of methyl-beta-ionone when used as a fragrance ingredient is presented. ..
  33. Lalko J, Lapczynski A, McGinty D, Bhatia S, Letizia C, Api A. Fragrance material review on dihydro-alpha-ionone. Food Chem Toxicol. 2007;45 Suppl 1:S221-4 pubmed
    ..A toxicologic and dermatologic review of dihydro-alpha-ionone when used as a fragrance ingredient is presented. ..
  34. Yoshimitsu H, Nishida M, Nohara T. Two labdane diterpene and megastigmane glycosides from Aquilegia hybrida. Chem Pharm Bull (Tokyo). 2008;56:1009-12 pubmed
    ..Their structures were determined on the basis of spectroscopic data and chemical evidence...
  35. Jeong H, Chun Y, Yun C, Moon C, Lee H, Han S, et al. Induction of cytochrome P450 1A and 2B by alpha- and beta-ionone in Sprague Dawley rats. Arch Pharm Res. 2002;25:197-201 pubmed
  36. Lalko J, Lapczynski A, McGinty D, Bhatia S, Letizia C, Api A. Fragrance material review on ionone. Food Chem Toxicol. 2007;45 Suppl 1:S251-7 pubmed
    ..A toxicologic and dermatologic review of ionone when used as a fragrance ingredient is presented. ..
  37. Liu J, Chen B, Yang B, Dong H, Sun C, Wang Q, et al. Apoptosis of human gastric adenocarcinoma cells induced by beta-ionone. World J Gastroenterol. 2004;10:348-51 pubmed
    ..Apoptosis was also shown in beta-ionone-treated SGC-7901 cells by the TUNEL assay. beta-ionone can inhibit cell proliferation and induce apoptosis of SGC-7901 cells. However, the mechanism needs to be further investigated. ..
  38. Shu P, Wei X, Xue Y, Li W, Zhang J, Xiang M, et al. Wilsonols A-L, megastigmane sesquiterpenoids from the leaves of Cinnamomum wilsonii. J Nat Prod. 2013;76:1303-12 pubmed publisher
    ..Compound 13 exhibited IC50 values ranging from 2.5 to 12 ?M and selectivity indices of >10 against SMMC-7721, A-549, and MCF-7 cell lines. Selected compounds were evaluated for in vitro immunomodulatory activity. ..
  39. Lalko J, Lapczynski A, McGinty D, Bhatia S, Letizia C, Api A. Fragrance material review on isodamascone (isomer unspecified). Food Chem Toxicol. 2007;45 Suppl 1:S263-6 pubmed
    ..A toxicologic and dermatologic review of isodamascone when used as a fragrance ingredient is presented. ..
  40. Ito H, Kobayashi E, Li S, Hatano T, Sugita D, Kubo N, et al. Megastigmane glycosides and an acylated triterpenoid from Eriobotrya japonica. J Nat Prod. 2001;64:737-40 pubmed
  41. de Pinho P, Valentão P, Gonçalves R, Sousa C, Andrade P. Volatile composition of Brassica oleracea L. var. costata DC leaves using solid-phase microextraction and gas chromatography/ion trap mass spectrometry. Rapid Commun Mass Spectrom. 2009;23:2292-300 pubmed publisher
    ..Fertilizations with higher levels of sulfur produced Brassica leaves with more sulfur volatiles. In opposition, N and S fertilization led to leaves with lower levels of norisoprenoids and terpenes.
  42. Appel D, Lutz Wahl S, Fischer P, Schwaneberg U, Schmid R. A P450 BM-3 mutant hydroxylates alkanes, cycloalkanes, arenes and heteroarenes. J Biotechnol. 2001;88:167-71 pubmed
    ..We here report that this triple mutant indeed is capable to hydroxylate a respectable range of other substrates, all of which bear little or no resemblance to the fatty acid substrates of the native enzyme. ..
  43. Jaeger S, McRae J, Bava C, Beresford M, Hunter D, Jia Y, et al. A Mendelian trait for olfactory sensitivity affects odor experience and food selection. Curr Biol. 2013;23:1601-5 pubmed publisher
    ..These studies demonstrate that an OR variant that influences olfactory sensitivity can affect how people experience and respond to foods, beverages, and other products. ..
  44. Zhang H, Song G, Shao J, Xiang X, Li Q, Chen Y, et al. Dynamics and polyphasic characterization of odor-producing cyanobacterium Tychonema bourrellyi from Lake Erhai, China. Environ Sci Pollut Res Int. 2016;23:5420-30 pubmed publisher
    ..It was interesting to observe the coincidence of the occurrence of T. bourrellyi with slightly eutrophicated waters since Lake Erhai had been regarded as an early phase of eutrophicated lake. ..
  45. Asokkumar S, Naveenkumar C, Raghunandhakumar S, Kamaraj S, Anandakumar P, Jagan S, et al. Antiproliferative and antioxidant potential of beta-ionone against benzo(a)pyrene-induced lung carcinogenesis in Swiss albino mice. Mol Cell Biochem. 2012;363:335-45 pubmed publisher
    ..Overall findings suggested that the ION effectively ameliorated the lung carcinogenesis, which is attributed to the antiproliferative and antioxidant potential through free radical scavenging property. ..
  46. Huang C, Lyu S, Hu M. Synergistic effects of the combination of ?-ionone and sorafenib on metastasis of human hepatoma SK-Hep-1 cells. Invest New Drugs. 2012;30:1449-59 pubmed publisher
    ..2 cells, indicating the selective cytotoxicity of this combination on tumor cells. The combination of SF and BI could be a potential therapeutic strategy against human hepatoma cells. ..
  47. Lalko J, Lapczynski A, McGinty D, Bhatia S, Letizia C, Api A. Fragrance material review on beta-ionone. Food Chem Toxicol. 2007;45 Suppl 1:S241-7 pubmed
    ..A toxicologic and dermatologic review of beta-ionone when used as a fragrance ingredient is presented. ..
  48. Makino C, Riley C, Looney J, Crouch R, Okada T. Binding of more than one retinoid to visual opsins. Biophys J. 2010;99:2366-73 pubmed publisher
    ..Therefore, both blue- and green-sensitive rod rhodopsins have at least one allosteric binding site for retinoid, but ?-ionone binds to the latter type of rhodopsin with low affinity and low efficacy. ..
  49. Shitamoto J, Matsunami K, Otsuka H, Shinzato T, Takeda Y. Crotalionosides A-C, three new megastigmane glucosides, two new pterocarpan glucosides and a chalcone C-glucoside from the whole plants of Crotalaria zanzibarica. Chem Pharm Bull (Tokyo). 2010;58:1026-32 pubmed
    ..The aglycones of pterocarpan glucosides were found to be melilotocarpan B and the absolute structure of the chalcone C-glucoside was determined by comparison of the CD spectral behavior with the reported values. ..
  50. Jung M, Mo H, Elson C. Synthesis and biological activity of beta-ionone-derived alcohols for cancer chemoprevention. Anticancer Res. 1998;18:189-92 pubmed
    ..We have found several derivatives which show higher growth inhibitory properties and are promising candidates for further improvement of activity. ..
  51. Zhou J, Geng G, Shi Q, Sauriol F, Wu J. Design and synthesis of androgen receptor antagonists with bulky side chains for overcoming antiandrogen resistance. J Med Chem. 2009;52:5546-50 pubmed publisher
    ..Molecular modeling indicates 6 adopts a "Y"-shape conformation and forms multiple hydrogen bonds with AR backbone. ..
  52. Zhou J, Geng G, Wu J. Synthesis and in vitro characterization of ionone-based chalcones as novel antiandrogens effective against multiple clinically relevant androgen receptor mutants. Invest New Drugs. 2010;28:291-8 pubmed publisher
    ..The results suggest that chalcone 17 could be a good candidate for further pre-clinical development as a novel antiandrogen for advanced prostate cancer. ..
  53. Yamano Y, Ito M. Synthesis of optically active vomifoliol and roseoside stereoisomers. Chem Pharm Bull (Tokyo). 2005;53:541-6 pubmed
    ..Simultaneous separation of these stereoisomers by HPLC was also performed. ..