Skip to main content
Have a personal or library account? Click to login
The Biological Activities of Troponoids and Their Use in Agriculture A Review Cover

The Biological Activities of Troponoids and Their Use in Agriculture A Review

Journal of Horticultural Research
Volume 22 (2014): Issue 1 (June 2014)
By: ,   and    
Open Access
|Sep 2014
References

References

  1. Aharoni Y., Copel A., Fallik E. 1993. Hinokitiol (ß -thujaplicin), for postharvest decay control on ‘Galia’ melons. New Zeal. J. Crop Hort. 21: 165–169. DOI: 10.1080/01140671.1993.9513763.
    Open DOISearch in Google Scholar
  2. Ahn Y.J., Lee S.B., Lee H.S., Kim G.H. 1998. Insec-ticidal and acaricidal activity of carvacrol and ß-thujaplicin derived fromvar.sawdust. J. Chem. Ecol. 24: 81-90. DOI: 10.1023/A:1022388829078.
    Open DOISearch in Google Scholar
  3. Aladaileh S., Rodney P., Nair S.V., Raftos D.A. 2007. Characterization of phenoloxidase activity in Syd–ney rock oystersComp. Biochem. Physiol. B 148: 470-480. DOI: 10.1016/j.cbpb.2007.07.089.
    Open DOISearch in Google Scholar
  4. Azegami K., Nishiyama K., Watanabe Y., Suzuki T., Yo-shida M., Nase K., Toda S. 1985. Tropolone as a root growth-inhibitor produced by a plant pathogenicsp. causing seedling blight of rice. Ann. Phytopathol. Soc. Jpn. 51: 315-317.
    Open DOISearch in Google Scholar
  5. Barret R. 2002. Characterisation of apricot polyphenoloxi-dase during fruit development. Adelaide Research and Scholarship. http:/hdl.handle.net/2440/37978.
    Search in Google Scholar
  6. Baya M., Soulounganga P., Gelhaye E., Gérardin P. 2001. Fungicidal activity of ß-thujaplicin analogues. Pest Manag. Sci. 57: 833-838. DOI: 10.1002/ps.379.
    Open DOISearch in Google Scholar
  7. Bentley R. 2008. A fresh look at natural tropolonoids. Nat. Prod. Rep. 25: 118-138. DOI: 10.1039/B711474E.
    Open DOISearch in Google Scholar
  8. Birkinshaw J.H., Chambers A.R., Raistrick H. 1942. Studies in the biochemistry of microorganisms. 70Stipitatic acid, C8H6O5, a metabolic product ofThorn. Biochem. J. 36: 242-251.
    Search in Google Scholar
  9. Broothaerts W., McPherson J., Li B., Randall E., Lane W.D., Wiersma P.A. 2000. Fast applexand tobaccoleaf polyphenol oxidase activity easy for screening transgenic plants. J. Agric. Food Chem. 48: 5924-5928. DOI: 10.1021/jf000599m.
    Open DOISearch in Google Scholar
  10. Budihas S.R., Gorshkova I., Gaidamakov S., Wamiru A., Bona M.K., Parniak M.A., Crouch R.J., McMahon J.B., Beutler J.A., Le Grice S.F.J. 2005. Selective inhibition of HIV-1 reverse transcriptase-associ-ated ribonuclease H activity by hydroxylated tropolones. Nucleic Acids Res. 33: 1249-1256. DOI: 10.1093/nar/gki268.
    Open DOISearch in Google Scholar
  11. Chedgy R.J., Daniels C.R., Kadla J., Breuil C. 2007. Screening fungi tolerant to Western red cedarDonn) extractives. Part I. Mild extrac–tion by ultrasonication and quantification of extrac–tives by reverse-phase HPLC. Holzforschung 61: 190-194. DOI: 10.1515/HF.2007.033.
    Open DOISearch in Google Scholar
  12. Constabel C.P., Yip L., Patton J.J., Christopher M.E. 2000. Polyphenol oxidase from hybrid poplar. Cloning and expression in response to wounding and herbivory. Plant Physiol. 124: 285-296. DOI: 10.1104/pp.124.1.285. Cox R.J., Al-Fahad A. 2013. Chemical mechanisms in–volved during the biosynthesis of tropolones. Curr. Opin. Chem. Biol. 17: 532-536. DOI: 10.1016/j.cbpa.2013.06.029.
    Open DOISearch in Google Scholar
  13. Crawford J.M., Clardy J. 2012. Microbial genome min–ing answers longstanding biosynthetic questions. Proc. Natl. Acad. Sci. USA 109(20): 7589-7590. DOI: 10.1073/pnas.1205361109.
    Open DOISearch in Google Scholar
  14. Davison J., Al Fahad A., Cai M., Song Z., Yehia S.Y., Laz–arus C.M., Bailey A.M., Simpson T.J., Cox R.J. 2012. Genetic, molecular, and biochemical basis on fungal tropolone biosynthesis. Proc. Natl. Acad. Sci. USA 109(20): 7642-7647. DOI: 10.1073/pnas.1201469109.
    Open DOISearch in Google Scholar
  15. Diouf P.N., Delbarre N., Perrin D., Gérardin P., Rapin C., Jacquot J.P., Gelhaye E. 2002. Influence of tropo-lone onwood degradation. Appl. Environ. Microbiol. 68: 4377-4382. DOI: 10.1128/AEM.68.9.4377-4382.2002.
    Open DOISearch in Google Scholar
  16. Doering W.E., Knox L.H. 1953. Synthesis of substituted tropolones. J. Am. Chem. Soc. 75: 297-303. DOI: 10.1021/ja01098a014.
    Open DOISearch in Google Scholar
  17. Dogan M., Arslan O., Dogan S. 2002. Substrate speci–ficity, heat inactivation and inhibition of polyphe-nol oxidase from different aubergine cultivars. Int. J. Food Sci. Tech. 37: 415-423. DOI: 10.1046/j.1365-2621.2002.00580.x.
    Open DOISearch in Google Scholar
  18. Dogan S., Turan P., Dogan M., Alkan M., Arslan O. 2007. Inhibition kinetic ofL. polyphenol oxidase. Int. J. Chem. Reac. Eng. 5: 1-12. DOI: 10.2202/1542-6580.1465.
    Open DOISearch in Google Scholar
  19. Dogan S., Turan Y., Erturk H., Arslan O. 2005. Character–ization and purification of polyphenol oxidase from artichokeL.). J. Agric. Food Chem. 53: 776-785. DOI: 10.1021/jf051646j.
    Open DOISearch in Google Scholar
  20. van Doorn W.G., Vaslier N. 2002. Wounding-induced xylem occlusion in stems of cut chrysanthemum flowers, roles of peroxidase and cathechol oxidase. Postharvest Biol. Technol. 26: 275-284. DOI: 10.1016/S0925-5214(02)00039-X.
    Open DOISearch in Google Scholar
  21. Fallik E., Grinberg S. 1992. Hinokitiol: a natural sub–stance that controls postharvest diseases in eggplant and pepper fruits. Postharvest Biol. Technol. 2: 137-144. DOI: 10.1016/0925-5214(92)90016-I.
    Open DOISearch in Google Scholar
  22. Fuerst E.P., Anderson J.V., Morris C.F. 2006. Delineating the role of polyphenol oxidase in the darkening of alkaline wheat noodles. J. Agric. Food Chem. 54: 2378-2384. DOI: 10.1021/jf0526386.
    Open DOISearch in Google Scholar
  23. Fuji R., Ozaki K., Ino W., Watanabe H. 1995. Hinokitiol production in suspension cells ofvar.Makio. Plant Tiss. Cult. Lett. 12: 55-61. DOI: 10.5511/plantbiotechnology1984.12.55.
    Open DOISearch in Google Scholar
  24. Fujisaki R., Kamei K., Yamamura M., Nishiya H., In-ouye S., Takahashi M., Abe S. 2012.andanti-plasmodial activity of essential oils, in–cluding hinokitiol. Southeast Asian J. Trop. Med. Public Health 43: 270-279.
    Search in Google Scholar
  25. Furuya T., Asada Y., Matsuura Y., Mizobata S., Hamada H. 1997. Biotransformation of ß-thujaplicin by cultured cells ofPhytochemistry 46: 1355-1358. DOI: 10.1016/S0031-9422(97)00463-9.
    Open DOISearch in Google Scholar
  26. Grohs B.-M., Kunz B. 1998. Fungitoxicity of chemical analogs with heartwood toxins. Curr. Microbiol. 37: 67-69. DOI: 10.1007/s002849900340.
    Open DOISearch in Google Scholar
  27. Haluk J.-P., Roussel C. 2000. Caractérisation et origine des tropolones responsables de la durabilité na–turelle des Cupressacées. Application potentielle en préservation du bois. Ann. For. Sci. 57: 819-829.
    Open DOISearch in Google Scholar
  28. Haluk J.P., Roussel-Bousta C. 2003. Biosynthèse de tropolones dans les cals et les suspension cellu–laires à partir d’ébauches foliaires de plantules deDonn. Ann. For. Sci. 60: 271-276.
    Open DOISearch in Google Scholar
  29. Harada T., Harada E., Sakamoto R., Ashitani T., Fujita K., Kuroda K. 2012. Regio- and substrate- specific oxidative metabolism of terpinolene by cytochrome P450 monooxygenases incul–tured cells. Am. J. Plant Sci. 3: 268-275. DOI: 10.4236/ajps.2012.32032.
    Open DOISearch in Google Scholar
  30. Hori M. 2005. Development of repellent strips for con–trolling the cigarette beetle,(Fabricius) (Coleoptera: Anobiidae). Appl. Ento-mol. Zool. 40: 373-377.
    Search in Google Scholar
  31. Hori M. 2004a. Evaluation of the practicability of hinoki-tiol as a repellent against the cigarette beetle,(Fabricius) (Coleoptera: Anobiidae). Appl. Entomol. Zool. 39: 699-704.
    Search in Google Scholar
  32. Hori M. 2004b. Repellency of hinokitiol against the cig–arette beetle,(Fabricius) (Coleoptera: Anobiidae). Appl. Entomol. Zool. 39: 521-526.
    Search in Google Scholar
  33. Hu Y., Cheng X., Cao F., Huang A., Tavis J.E. 2013. ß-Thujaplicinol inhibits hepatitis B virus replication by blocking the viral ribonuclease H activity. Antiviral Res. 99: 221-229. DOI: 10.1016/j.antiviral.2013.06.007.
    Open DOISearch in Google Scholar
  34. Inada S., Tsutsumi Y., Sakai K. 1993. Elicitor of the ß-thu-japlicin accumulation in callus cultures ofJ. Fac. Agr. Kyushu U. 38: 119-126.
    Open DOISearch in Google Scholar
  35. Inamori Y., Sakagami Y., Morita Y., Shibata M., Sugiura M., Kumeda Y., Okabe T., Tsujibo H., Ishida N. 2000. Antifungal activity of hinokitiol-related com–pounds on wood-rotting fungi and their insecticidal activities. Biol. Pharm. Bull. 23: 995-997. DOI: 10.1248/bpb.23.979.
    Open DOISearch in Google Scholar
  36. Itose R., Sakai K. 1997. Improved culture conditions for the production of ß-thujaplicin by suspension cell cultures ofPlant Biotechnol. 14: 163-167.
    Open DOISearch in Google Scholar
  37. Jeon J.-H., Lee S.-H., Kim M.-K., Lee H.-S. 2005. Lar-vicidal activity ofandleaf oils against two mosquito species. Agr. Chem. Biotechnol. 48: 26-28.
    Search in Google Scholar
  38. Kahn V. 1985. Tropolone - a compound that can aid in differentiating between tyrosinase and peroxidase. Phytochemistry 24: 915-920. DOI: 10.1016/S0031-9422(00)83152-0.
    Open DOISearch in Google Scholar
  39. Kahn V., Andrawis A. 1985a. Inhibition of mushroom ty-rosinase by tropolone. Phytochemistry 24: 905–908. DOI: 10.1016/S0031-9422(00)83150-7.
    Open DOISearch in Google Scholar
  40. Kahn V., Andrawis A. 1985b. Tropolone as a substrate for horseradish peroxidase. Phytochemistry 24: 909-913. DOI: 10.1016/S0031-9422(00)83151-9.
    Open DOISearch in Google Scholar
  41. Katsumata R., Ikue Y., Noriko N., Kanako M., Yutaka K., Kenji T., Kan K. 2003. Preservation of jams employing hinokitiol. J. Antibact. Antifung. Agents 31: 59-67.
    Search in Google Scholar
  42. Kim Y.-J., Uyama H. 2005. Tyrosinase inhibitors from natural and synthetic sources: structure, inhibition mechanism and perspective for the future. Cell. Mol. Life Sci. 62: 1707-1723. DOI: 10.1007/s00018-005-5054-y.
    Open DOISearch in Google Scholar
  43. King M.V., de Vries J.L., Pepinsky R. 1952. An x-ray diffraction determination of the chemical structure of colchicine. Acta Cryst. B 5: 437-440. DOI: 10.1107/S0365110X52001313.
    Open DOISearch in Google Scholar
  44. Koufaki M., Theodorou E., Alexi X., Nikoloudaki F., Alexis M.N. 2010. Synthesis of tropolone deriva–tives and evaluation of their in vitro neuroprotective activity. Eur. J. Med. Chem. 45: 1107-1112. DOI: 10.1016/j.ejmech.2009.12.006.
    Open DOISearch in Google Scholar
  45. Kwon S., Shimoda K., Hamada H., Ishihara K., Masuoka N., Hamada H. 2008. High production of ß-thu-japlicin glycosides by immobilized plant cells ofActa Biol. Hung. 59: 347-355. DOI: 10.1556/ABiol.59.2008.3.8.
    Open DOISearch in Google Scholar
  46. Li S., Freitag C.M., Morrell J.J., Okabe T. 2012. Antifun-gal effects of hinokitiol and its sodium salt for wood protection. BioRes. 7: 5312-5318.
    Open DOISearch in Google Scholar
  47. Lim Y.W., Chedgy R.J., Amirthalingam S., Breuil C. 2007. Screening fungi tolerant to Western red cedarDonn) extractives. Part 2. Develop–ment of a feeder strip assay. Holzforschung 61: 195-200. DOI: 10.1515/HF.2007.034.
    Open DOISearch in Google Scholar
  48. Liu S., Yamauchi H. 2006. Hinokitiol, a metal chelator de–rived from natural plants, suppresses cell growth and disrupts androgen receptor signaling in prostate carci–noma cell lines. Biochem. Biophys. Res. Commun. 351: 26-32. DOI: 10.1016/j.bbrc.2006.09.166.
    Open DOISearch in Google Scholar
  49. Liu S., Yamauchi H. 2009. p-27Associated G1 arrest induced by hinokitiol in human malignant mela–noma cells is mediated via down-regulation of pRb, Skp2 ubiquitin ligase, and impairment of Cdk2 function. Cancer Lett. 286: 240-249. DOI: 10.1016/j.canlet.2009.05.038.
    Open DOISearch in Google Scholar
  50. Loubaud M., van Doorn W.G. 2004. Wound-induced and bacteria-induced xylem blockage in roses,andPostharvest Biol. Technol. 32: 281-288. DOI: 10.1016/j.postharvbio.2003.12.004.
    Open DOISearch in Google Scholar
  51. Madar Z., Gottlieb H.E., Cojocarn M., Riov J., Solel Z., Sztejnberg A. 1995. Antifungal terpenoids pro–duced by cypress after infection byf. sp.Phytochemistry 38: 351-354. DOI: 10.1016/0031-9422(94)00575-E.
    Open DOISearch in Google Scholar
  52. Manter D.K., Karchesy J.J., Kelsey R.G. 2006. The sporicidal activity of yellow-cedar heartwood, essential oil and wood constituents towardsin culture. For. Path. 36: 297-308. DOI: 10.1111/j.1439-0329.2006.00461.x.
    Open DOISearch in Google Scholar
  53. Manter D.K., Kelsey R.G., Karchesy J.J. 2007a. Anti–microbial activity of extractable conifer heartwood compounds towardJ. Chem. Ecol. 33: 2133-2147. DOI: 10.1007/s10886-007-9368-0.
    Open DOISearch in Google Scholar
  54. Manter D.K., Kelsey R.G., Karchesy J.J. 2007b. Antimi–crobial activity of extracts and select compounds in the heartwood of seven western conifers towardProceedings of the Sudden Oak Death Third Science Symposium, March 5-9, 2007, Santa Rosa, California, pp. 375-378.
    Search in Google Scholar
  55. Marshall M.R., Kim J., Wei C.-I. 2000. Enzymatic brown–ing in fruits, vegetables and seafoods. FAO, pp. 1-49.
    Search in Google Scholar
  56. Mesa-Siverio D., Estévez-Braun A., Ravelo Á.G., Mur–guia J.R., Rodríguez-Afonso A. 2003. Novel DNA-damaging tropolone derivatives fromEur. J. Org. Chem. 2003: 4243-4247. DOI: 10.1002/ejoc.200300284.
    Open DOISearch in Google Scholar
  57. Mizutani F., Rabbany A.B.M.G., Akiyoshi H. 1998a. Inhibition of ethylene production by tropolone compounds in young excised peach seeds. J. Jpn. Soc. Hortic. Sci. 67: 166-169.
    Open DOISearch in Google Scholar
  58. Mizutani F., Rabbany A.B.M.G., Akiyoshi H. 1998b. Inhibition of ethylene production and 1-aminocyclo-propane-1-carboxylate oxidase activity by tropolo-nes. Phytochemistry 48: 31-34. DOI: 10.1016/S0031-9422(97)01093-5.
    Open DOISearch in Google Scholar
  59. Morita Y., Matsumura E., Okabe T., Fukui T., Ohe T., Ishida N., Inamori Y. 2004a. Biological activity of ß-dolabrin, y-thujaplicin, and 4-acetyltropolone, hi-nokitiol - related compounds. Biol. Pharm. Bull. 27: 1666-1669.
    Search in Google Scholar
  60. Morita Y., Matsumura E., Okabe T., Fukui T., Shibata M., Sugiura M., Ohe T., Tsujibo H., Ishida N., In–amori Y. 2004b. Biological activity of a-thu-japlicin, the isomer of hinokitiol. Biol. Pharm. Bull. 27: 899-902.
    Search in Google Scholar
  61. Morita Y., Matsumura E., Okabe T., Shibata M., Sugiura M., Ohe T., Tsujibo H., Ishida N., Inamori Y. 2003. Biological activity of tropolone. Biol. Pharm. Bull. 26: 1487-1490.
    Open DOISearch in Google Scholar
  62. Morita Y., Matsumura E., Tsujibo H., Yasuda M., Okabe T., Sakagami Y., Kumeda Y., Ishida N., Inamori Y. 2002. Biological activity of 4-acetyltropolone, the minor component ofSieb. et Zucc.Mak. Biol. Pharm. Bull. 25: 981-985.
    Search in Google Scholar
  63. Najda-Bernatowicz A., Krawczyk M., Stankiewicz-Drogoń A., Bretner M., Boguszewska-Chachulska A.M. 2010. Studies on the anti-hepatitis C virus activ–ity of newly synthesized tropolone derivatives: identification of NS3 helicase inhibitors that spe–cifically inhibit subgenomic HCV replication. Bioorg. Med. Chem. 18: 5129-5136. DOI: 10.1016/j.bmc.2010.05.066.
    Open DOISearch in Google Scholar
  64. Oblak E.Z., Bolstad E.S., Ononye S.N., Priestley N.D., Hadden M.K., Wright D.L. 2012. The furan route to tropolones: probing the antiproliferative effects of ß-thujaplicin analogs. Org. Biomol. Chem. 10(43): 8597-8604. DOI: 10.1039/C2OB26553B.
    Open DOISearch in Google Scholar
  65. Oh I., Yang W.-Y., Park J., Lee S., Mar W., Oh K.-B., Shin J. 2011.Na+/K+-ATPase inhibitory activity and antimicrobial activity of sesquiterpenes isolated fromArch. Pharm. Res. 34: 2141-2147. DOI: 10.1007/s12272-011-1218-5.
    Open DOISearch in Google Scholar
  66. Okumura S., Hoshino M., Joshita K., Nishinomiya T., Murata M. 2011. Hinokitiol inhibits polyphenol ox–idase and enzymatic browning. Food Sci. Technol. Res. 17: 251-256.
    Open DOISearch in Google Scholar
  67. Ono M., Asai T., Watanabe H. 1998. Hinokitiol production in a suspension culture ofFlorin. Biosci. Biotechnol. Biochem. 62: 1653-1659.
    Open DOISearch in Google Scholar
  68. Ooka S., Sato T., Arito M., Nakano H., Takakuwa Y., Suematsu N., Okamoto K., Kurokawa M., Ozaki S., Kato T. 2012. The effects of hinokitiol on human cells revealed by a proteomic approach. Inflamm. Regen. 32: 137-143.
    Open DOISearch in Google Scholar
  69. Park I.K. Lee S.G., Choi D.H., Park J.D., Ahn Y.J. 2003. Insecticidal activities of constituents identified in the essential oil from leavesagainst(L.) and(L.). J. Stored Prod. Res. 39: 375-384. DOI: 10.1016/S0022-474X(02)00030-9.
    Open DOISearch in Google Scholar
  70. Paul B., Gowda L.R. 2000. Purification and characteriza–tion of a polyphenol oxidase from the seeds of field beanJ. Agric. Food Chem. 48: 3839-3846. DOI: 10.1021/jf000296s.
    Open DOISearch in Google Scholar
  71. Pinto M.S.T., Siqueira F.P., Oliveira A.F.A., Fernandes K.V.S. 2008. A wounding-induced PPO from cowpeaseed–lings. Phytochemistry 69: 2297-2302. DOI: 10.1016/j.phytochem.2008.06.003.
    Open DOISearch in Google Scholar
  72. Rabbany A.B.M.G., Mizutani F. 1998. Effect of tropo-lone and hinokitiol on in vitro activities of 1-ami-nocyclopropane-carboxylate synthase and oxidase in wounded winter squash mesocarps. J. Jpn. Soc. Hortic. Sci. 67: 213-215.
    Open DOISearch in Google Scholar
  73. Saniewska A., Jarecka A. 2008. The inhibitory effect of tropolone and hinokitiol on the growth and devel–opment off. sp.Phytopathol. Pol. 50: 33-41.
    Search in Google Scholar
  74. Saniewska A., Saniewski M. 2007. The inhibitory effect of tropolone and hinokitiol on the mycelium growth ofin vitro. Acta Agrobot. 60: 107-112.
    Open DOISearch in Google Scholar
  75. Saniewski M., Saniewska A., Horbowicz M., Kanlayanarat S. 2007. The inhibitory effect of hinokitiol and tropo-lone on reddish colouration in mechanically wounded scales ofxHort. and on the development ofthe patho–gen ofActa Hort. 755: 533-542.
    Search in Google Scholar
  76. Saniewski M., Saniewska A., Kanlayanarat S. 2007. Biological activities of tropolone and hinokitiol: the tools in plant physiology and their use. Acta Hort. 755: 133-142.
    Open DOISearch in Google Scholar
  77. Shimizu C., Hori M. 2009. Repellency and toxicity of troponoid compounds against the adzuki bean beetle,(L.) (Coleoptera: Bruchidae). J. Stored Prod. Res. 45: 49-53. DOI: 10.1016/j.jspr.2008.08.001.
    Open DOISearch in Google Scholar
  78. Sholberg P.L., Shimizu B.N. 1991. Use of the natural plant products, hinokitiol to extend shelf-life of peaches. Can. Inst. Food Sci. Technol. J. 24: 273–277. DOI: 10.1016/S0315-5463(91)70164-8.
    Open DOISearch in Google Scholar
  79. Sung B.K., Kim M.K., Lee S.H., Son J.G., Lee H.S. 2004. Acaricidal activity of essential oils derived from 10 Cupressaceae species against stored food and house dust mites. Food Sci. Biotechnol. 13: 376-380.
    Search in Google Scholar
  80. Suppakul P., Miltz J., Sonneveld K., Bigger S.W. 2003. Active packaging technologies with an emphasis on antimicrobial packaging and its applications. J. Food Sci. 68: 408-420. DOI: 10.1111/j.1365-2621.2003.tb05687.x.
    Open DOISearch in Google Scholar
  81. Takahashi S., Kamiya T., Saeki K., Nezu T., Takeuchi S., Takasawa R., Sunaga S., Yoshimori A., Ebizuka S., Abe T., Tanuma S. 2010. Structural insights into the hot spot amino acid residues of mushroom tyrosinase for the bindings of thujaplicins. Bioorg. Med. Chem. 18: 8112-8118. DOI: 10.1016/j.bmc.2010.08.056.
    Open DOISearch in Google Scholar
  82. Trust T.J. 1975. Antibacterial activity of tropolone. Anti-microb. Agents Chemother. 7: 500-506. DOI: 10.1128/AAC.7.5.500.
    Open DOISearch in Google Scholar
  83. Trust T.J., Bartlett K.H. 1975. Antibacterial activity of tropilidine and tropone. Antimicrob. Agents Chemother. 8: 381-383. DOI:10.1128/AAC.8.3.381.
    Open DOISearch in Google Scholar
  84. Valero E., Garcia-Moreno M., Varón R., Garcia-Carmona F. 1991. Time-dependent inhibition of grape poly–phenol oxidase by tropolone. J. Agric. Food Chem. 39: 1043-1046. DOI: 10.1021/jf00006a007.
    Open DOISearch in Google Scholar
  85. Wakabayashi H., Yokoyama K., Hashiba K., Hashimoto K., Kikuchi H., Nishikawa H., Kurihara T., Satoh K., Shioda S., Muto S., Terakubo S., Nakashima H., Motohashi N., Sakagami H. 2003. Cytotoxic activ–ity of tropolones against human oral tumor cell lines. Anticancer Res. 23: 4757-4763.
    Search in Google Scholar
  86. Wang M., Hashimoto M., Hashidoko Y. 2013a. Repres–sion of tropolone production and induction of apseudo-biofilm by carot-4-en-9, 10-diol, a cell-to-cell signaling disrupter produced byPLOS ONE 8(11): e78024. DOI: 10.1371/journal.pone.0078024.
    Open DOISearch in Google Scholar
  87. Wang M., Hashimoto M., Hashidoko Y. 2013b. Carot-4-en-9,10-diol, a conidiation-inducing sesquiter-pene diol produced byPS1-7 upon exposure to chemical stress from highly ac–tive iron chelators. Appl. Environ. Microbiol. 79: 1906-1914. DOI:10.1128/AEM.03531-12.
    Open DOISearch in Google Scholar
  88. Yamada J., Fujita K., Eto K., Sakai K. 2003. Cell growth and nutrient uptake by cell suspensions ofJ. Wood Sci. 49: 5-10. DOI: 10.1007/s100860300001.
    Open DOISearch in Google Scholar
  89. Yamaguchi T., Fujita K., Sakai K. 1999. Biological ac–tivity of extracts fromcell culture. J. Wood Sci. 45: 170-173. DOI: 10.1007/BF01192336.
    Open DOISearch in Google Scholar
  90. Yamasaki Y., Konno H., Noda K. 2008. Polyphenol oxi–dase from wheat bran is a serpin. Acta Biochim. Pol. 55: 325-328.
    Open DOISearch in Google Scholar
  91. Yamato M., Ando J., Sakaki K., Hashigaki K., Wataya Y., Tsukagoshi S., Tashiro T., Tsuruo T. 1992. Syn-thesis and antitumor activity of tropolone deriva–tives. 7. Bistropolones containing connecting meth–ylene chains. J. Med. Chem. 35: 2670-273. DOI: 10.1021/jm00080a010.
    Open DOISearch in Google Scholar
  92. Yen T.-B., Chang H.-T., Hsieh C.-C., Chang S.-T. 2008. Antifungal properties of ethanolic extract and its active compounds fromvar.(Florin) heartwood. Biore-sour. Technol. 99: 4871-4877. DOI: 10.1016/j.biortech.2007.09.037.
    Open DOISearch in Google Scholar
  93. Yu J.Q., Komada H. 1999. Hinokibark, a substrate with antipathogen properties that suppress some root diseases of tomato. Sci. Hortic. 81: 13-24. DOI: 10.1016/S0304-4238(98)00262-3.
    Open DOISearch in Google Scholar
  94. Zhao J. 2007. Plant troponoids: Chemistry, biological ac–tivity, and biosynthesis. Curr. Med. Chem. 14: 2597-2621. DOI: 10.2174/092986707782023253.
    Open DOISearch in Google Scholar
  95. Zhao J., Fujita K., Sakai K. 2005. Oxidative stress in plant cell culture: A role in production of ß-thu-japlicin bysuspension cul–ture. Biotechnol. Bioeng. 90: 621-631. DOI: 10.1002/bit.20465.
    Open DOISearch in Google Scholar
  96. Zhao J., Fujita K., Yamada J., Sakai K. 2001. Improved ß-thujaplicin production insuspension cultures by fungal elicitor and methyl jasmonate. Appl. Microbiol. Biotechnol. 55: 301–305. DOI: 10.1007/s002530000555.
    Open DOISearch in Google Scholar
  97. Zhao J., Fujita K., Sakai K. 2007. Reactive oxygen spe–cies, nitric oxide, and their interactions play dif–ferent roles incell death and phytoalexin biosynthesis. New Phytol. 175: 215–229. DOI: 10.1111/j.1469-8137.2007.02109.x.
    Open DOISearch in Google Scholar
  98. Zhao J., Guo Y., Fujita K., Sakai K. 2003. Involvement of cAMP signaling in elicitor-induced phyto-alexin accumulation incell cultures. New Phytol. 161: 723-733. DOI: 10.1111/j.1469-8137.2004.00976.x.
    Open DOISearch in Google Scholar
  99. Zhao J., Matsunga Y., Fujita K., Sakai K. 2006. Signal transduction and metabolic flux of ß-thujaplicin and monoterpene biosynthesis in elicitedcell cultures. Metab. Eng. 8: 14-29. DOI: 10.1016/j.ymben.2005.09.002.
    Open DOISearch in Google Scholar
  100. Zhao J., Sakai K. 2003a. Multiple signaling pathways mediate fungal elicitor-induced ß-thujaplicin bio–synthesis incell cultures. J. Exp. Bot. 54: 647-656. DOI: 10.1093/jxb/erg062.
    Open DOISearch in Google Scholar
  101. Zhao J., Sakai K. 2003b. Peroxidases are involved in bi–osynthesis and biodegradation of ß-thujaplicin in fungal elicitor-treatedNew Phytol. 159: 719-731. DOI: 10.1046/j.1469-8137.2003.00841.x.
    Open DOISearch in Google Scholar
  102. Zhao X., Sugawara T., Kuroda S., Arisawa J., Kimura K. 2009. Antimicrobial activity of ß-thujaplicin (hinoki-tiol) on heterotrophic bacteria isolated from reverse osmosis water using for the preparation of hemodial-ysis fluids. In: Dössel O. and Schlegel W.C. (Eds.), WC 2009, IFMBE Proceedings/25/VII, pp. 30-33.
    Search in Google Scholar
  103. Zhao J., Zheng S.-H., Fujita K, Sakai K. 2004. Jasmonate and ethylene signaling and their interaction are in–tegral parts of the elicitor signaling pathway lead–ing to ß-thujaplicin biosynthesis incell cultures. J. Exp. Bot. 55: 1003-1012. DOI: 10.1093/jxb/erh127.
    Open DOISearch in Google Scholar
  104. Zhu Y.J., Qiu L., Zhou J.J., Guo H.Y., Hu Y.H., Li Z.C., Wang Q., Chen Q.X., Liu B. 2010. Inhibitory effect of hinokitiol on tyrosinase activity and melanin bi–osynthesis and its antimicrobial activities. J. En–zyme Inhib. Med. Chem. 25: 798-803. DOI: 10.3109/14756360903476398.
    Open DOISearch in Google Scholar
DOI: https://doi.org/10.2478/johr-2014-0001 | Journal eISSN: 2353-3978 (formerly 2300-5009) | Journal ISSN: 2300-5009
Journal RSS Feed
Language: English
Page range: 5 - 19
Submitted on: May 19, 2014
Accepted on: Jun 11, 2014
Published on: Sep 10, 2014
Published by: National Institute of Horticultural Research
In partnership with: Paradigm Publishing Services
Keywords:
Cupressaceae,
ß-thujaplicin,
tropolone,
polyphenol oxidase,
biosynthesis antibacterial,
anti-fungal,
insecticidal activity
Related subjects:
Life sciences,
Biotechnology,
Plant science,
Ecology,
Life sciences, other

© 2014 Marian Saniewski, Marcin Horbowicz, Sirichai Kanlayanarat, published by National Institute of Horticultural Research
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Volume 22 (2014): Issue 1 (June 2014)
Next article