Open Access

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


Cite

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: 10.1080/01140671.1993.9513763.10.1080/01140671.1993.9513763Search in Google Scholar

Ahn Y.J., Lee S.B., Lee H.S., Kim G.H. 1998. Insec-ticidal and acaricidal activity of carvacrol and ß-thujaplicin derived from Thujopsis delabrata var. hondai sawdust. J. Chem. Ecol. 24: 81-90. DOI: 10.1023/A:1022388829078.10.1023/A:1022388829078Search in Google Scholar

Aladaileh S., Rodney P., Nair S.V., Raftos D.A. 2007. Characterization of phenoloxidase activity in Syd–ney rock oysters (Saccostrea glomerata). Comp. Biochem. Physiol. B 148: 470-480. DOI: 10.1016/j.cbpb.2007.07.089.10.1016/j.cbpb.2007.07.08917950018Search in Google Scholar

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 pathogenic Pseudomonas sp. causing seedling blight of rice. Ann. Phytopathol. Soc. Jpn. 51: 315-317.10.3186/jjphytopath.51.315Search in Google Scholar

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

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.379.10.1002/ps.37911561410Search in Google Scholar

Bentley R. 2008. A fresh look at natural tropolonoids. Nat. Prod. Rep. 25: 118-138. DOI: 10.1039/B711474E.10.1039/B711474E18250899Search in Google Scholar

Birkinshaw J.H., Chambers A.R., Raistrick H. 1942. Studies in the biochemistry of microorganisms. 70Stipitatic acid, C8H6O5, a metabolic product of Penicillium stipitatum Thorn. Biochem. J. 36: 242-251.Search in Google Scholar

Broothaerts W., McPherson J., Li B., Randall E., Lane W.D., Wiersma P.A. 2000. Fast apple (Malus x domestica) and tobacco (Nicotiana tabacum) leaf polyphenol oxidase activity easy for screening transgenic plants. J. Agric. Food Chem. 48: 5924-5928. DOI: 10.1021/jf000599m.10.1021/jf000599m11141262Search in Google Scholar

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/gki268.10.1093/nar/gki26855295615741178Search in Google Scholar

Chedgy R.J., Daniels C.R., Kadla J., Breuil C. 2007. Screening fungi tolerant to Western red cedar (Thujaplicata Donn) 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.2007.033.10.1515/HF.2007.033Search in Google Scholar

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.2013.06.029.10.1016/j.cbpa.2013.06.02923870699Search in Google Scholar

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.1205361109.10.1073/pnas.1205361109Search in Google Scholar

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.1201469109.10.1073/pnas.1201469109Search in Google Scholar

Diouf P.N., Delbarre N., Perrin D., Gérardin P., Rapin C., Jacquot J.P., Gelhaye E. 2002. Influence of tropo-lone on Poria placenta wood degradation. Appl. Environ. Microbiol. 68: 4377-4382. DOI: 10.1128/AEM.68.9.4377-4382.2002.10.1128/AEM.68.9.4377-4382.2002Search in Google Scholar

Doering W.E., Knox L.H. 1953. Synthesis of substituted tropolones. J. Am. Chem. Soc. 75: 297-303. DOI: 10.1021/ja01098a014.10.1021/ja01098a014Search in Google Scholar

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.10.1046/j.1365-2621.2002.00580.xSearch in Google Scholar

Dogan S., Turan P., Dogan M., Alkan M., Arslan O. 2007. Inhibition kinetic of Ocimum basilicum L. polyphenol oxidase. Int. J. Chem. Reac. Eng. 5: 1-12. DOI: 10.2202/1542-6580.1465.10.2202/1542-6580.1465Search in Google Scholar

Dogan S., Turan Y., Erturk H., Arslan O. 2005. Character–ization and purification of polyphenol oxidase from artichoke (Cynara scolymus L.). J. Agric. Food Chem. 53: 776-785. DOI: 10.1021/jf051646j.10.1021/jf051646jSearch in Google Scholar

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.10.1016/S0925-5214(02)00039-XSearch in Google Scholar

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.10.1016/0925-5214(92)90016-ISearch in Google Scholar

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/jf0526386.10.1021/jf052638616536622Search in Google Scholar

Fuji R., Ozaki K., Ino W., Watanabe H. 1995. Hinokitiol production in suspension cells of Thujopsis dolabrata var. hondai Makio. Plant Tiss. Cult. Lett. 12: 55-61. DOI: 10.5511/plantbiotechnology1984.12.55.10.5511/plantbiotechnology1984.12.55Search in Google Scholar

Fujisaki R., Kamei K., Yamamura M., Nishiya H., In-ouye S., Takahashi M., Abe S. 2012. In vitro and in vivo anti-plasmodial activity of essential oils, in–cluding hinokitiol. Southeast Asian J. Trop. Med. Public Health 43: 270-279.Search in Google Scholar

Furuya T., Asada Y., Matsuura Y., Mizobata S., Hamada H. 1997. Biotransformation of ß-thujaplicin by cultured cells of Eucalyptus perriniana. Phytochemistry 46: 1355-1358. DOI: 10.1016/S0031-9422(97)00463-9.10.1016/S0031-9422(97)00463-9Search in Google Scholar

Grohs B.-M., Kunz B. 1998. Fungitoxicity of chemical analogs with heartwood toxins. Curr. Microbiol. 37: 67-69. DOI: 10.1007/s002849900340.10.1007/s0028499003409625794Search in Google Scholar

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: 819-829.10.1051/forest:2000155Search in Google Scholar

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 de Thuja plicata Donn. Ann. For. Sci. 60: 271-276.10.1051/forest:2003018Search in Google Scholar

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 in Cupressus lusitanica cul–tured cells. Am. J. Plant Sci. 3: 268-275. DOI: 10.4236/ajps.2012.32032.10.4236/ajps.2012.32032Search in Google Scholar

Hori M. 2005. Development of repellent strips for con–trolling the cigarette beetle, Lasioderma serricorne (Fabricius) (Coleoptera: Anobiidae). Appl. Ento-mol. Zool. 40: 373-377.Search in Google Scholar

Hori M. 2004a. Evaluation of the practicability of hinoki-tiol as a repellent against the cigarette beetle, La-sioderma serricorne (Fabricius) (Coleoptera: Anobiidae). Appl. Entomol. Zool. 39: 699-704.Search in Google Scholar

Hori M. 2004b. Repellency of hinokitiol against the cig–arette beetle, Lasioderma serricorne (Fabricius) (Coleoptera: Anobiidae). Appl. Entomol. Zool. 39: 521-526.Search in Google Scholar

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.2013.06.007.10.1016/j.antiviral.2013.06.00723796982Search in Google Scholar

Inada S., Tsutsumi Y., Sakai K. 1993. Elicitor of the ß-thu-japlicin accumulation in callus cultures of Cupressus lusitanica. J. Fac. Agr. Kyushu U. 38: 119-126.10.5109/24044Search in Google Scholar

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.23.979.10.1248/bpb.23.97910963307Search in Google Scholar

Itose R., Sakai K. 1997. Improved culture conditions for the production of ß-thujaplicin by suspension cell cultures of Cupressus lusitanica. Plant Biotechnol. 14: 163-167.10.5511/plantbiotechnology.14.163Search in Google Scholar

Jeon J.-H., Lee S.-H., Kim M.-K., Lee H.-S. 2005. Lar-vicidal activity of Chamaecyparis obtusa and Thuja orientalis leaf oils against two mosquito species. Agr. Chem. Biotechnol. 48: 26-28.Search in Google Scholar

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)83152-0.10.1016/S0031-9422(00)83152-0Search in Google Scholar

Kahn V., Andrawis A. 1985a. Inhibition of mushroom ty-rosinase by tropolone. Phytochemistry 24: 905–908. DOI: 10.1016/S0031-9422(00)83150-7.10.1016/S0031-9422(00)83150-7Search in Google Scholar

Kahn V., Andrawis A. 1985b. Tropolone as a substrate for horseradish peroxidase. Phytochemistry 24: 909-913. DOI: 10.1016/S0031-9422(00)83151-9.10.1016/S0031-9422(00)83151-9Search in Google Scholar

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

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.10.1007/s00018-005-5054-y15968468Search in Google Scholar

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/S0365110X52001313.10.1107/S0365110X52001313Search in Google Scholar

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.2009.12.006.10.1016/j.ejmech.2009.12.00620045220Search in Google Scholar

Kwon S., Shimoda K., Hamada H., Ishihara K., Masuoka N., Hamada H. 2008. High production of ß-thu-japlicin glycosides by immobilized plant cells of Nicotiana tabacum. Acta Biol. Hung. 59: 347-355. DOI: 10.1556/ABiol.59.2008.3.8.10.1556/ABiol.59.2008.3.818839701Search in Google Scholar

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: 5312-5318.10.15376/biores.7.4.5312-5318Search in Google Scholar

Lim Y.W., Chedgy R.J., Amirthalingam S., Breuil C. 2007. Screening fungi tolerant to Western red cedar (Thuja plicata Donn) extractives. Part 2. Develop–ment of a feeder strip assay. Holzforschung 61: 195-200. DOI: 10.1515/HF.2007.034.10.1515/HF.2007.034Search in Google Scholar

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.2006.09.166.10.1016/j.bbrc.2006.09.16617055455Search in Google Scholar

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.2009.05.038.10.1016/j.canlet.2009.05.038Search in Google Scholar

Loubaud M., van Doorn W.G. 2004. Wound-induced and bacteria-induced xylem blockage in roses, Astilbe and Viburnum. Postharvest Biol. Technol. 32: 281-288. DOI: 10.1016/j.postharvbio.2003.12.004.10.1016/j.postharvbio.2003.12.004Search in Google Scholar

Madar Z., Gottlieb H.E., Cojocarn M., Riov J., Solel Z., Sztejnberg A. 1995. Antifungal terpenoids pro–duced by cypress after infection by Diplodia pinea f. sp. cupressi. Phytochemistry 38: 351-354. DOI: 10.1016/0031-9422(94)00575-E.10.1016/0031-9422(94)00575-ESearch in Google Scholar

Manter D.K., Karchesy J.J., Kelsey R.G. 2006. The sporicidal activity of yellow-cedar heartwood, essential oil and wood constituents towards Phytophthora ramorum in culture. For. Path. 36: 297-308. DOI: 10.1111/j.1439-0329.2006.00461.x.10.1111/j.1439-0329.2006.00461.xSearch in Google Scholar

Manter D.K., Kelsey R.G., Karchesy J.J. 2007a. Anti–microbial activity of extractable conifer heartwood compounds toward Phytophthora ramorum. J. Chem. Ecol. 33: 2133-2147. DOI: 10.1007/s10886-007-9368-0.10.1007/s10886-007-9368-0Search in Google Scholar

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 toward Phy-tophthora ramorum. Proceedings of the Sudden Oak Death Third Science Symposium, March 5-9, 2007, Santa Rosa, California, pp. 375-378.Search in Google Scholar

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

Mesa-Siverio D., Estévez-Braun A., Ravelo Á.G., Mur–guia J.R., Rodríguez-Afonso A. 2003. Novel DNA-damaging tropolone derivatives from Goupia gla–bra. Eur. J. Org. Chem. 2003: 4243-4247. DOI: 10.1002/ejoc.200300284.10.1002/ejoc.200300284Search in Google Scholar

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: 166-169.10.2503/jjshs.67.166Search in Google Scholar

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)01093-5.10.1016/S0031-9422(97)01093-5Search in Google Scholar

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

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

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: 1487-1490.10.1248/bpb.26.148714519960Search in Google Scholar

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 of Thujopsis dolabrata Sieb. et Zucc. hondai Mak. Biol. Pharm. Bull. 25: 981-985.Search in Google Scholar

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.2010.05.066.10.1016/j.bmc.2010.05.06620579888Search in Google Scholar

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.10.1039/c2ob26553bSearch in Google Scholar

Oh I., Yang W.-Y., Park J., Lee S., Mar W., Oh K.-B., Shin J. 2011. In vitro Na+/K+-ATPase inhibitory activity and antimicrobial activity of sesquiterpenes isolated from Thujopsis dolabrata. Arch. Pharm. Res. 34: 2141-2147. DOI: 10.1007/s12272-011-1218-5.10.1007/s12272-011-1218-5Search in Google Scholar

Okumura S., Hoshino M., Joshita K., Nishinomiya T., Murata M. 2011. Hinokitiol inhibits polyphenol ox–idase and enzymatic browning. Food Sci. Technol. Res. 17: 251-256.10.3136/fstr.17.251Search in Google Scholar

Ono M., Asai T., Watanabe H. 1998. Hinokitiol production in a suspension culture of Calocedrus formosana Florin. Biosci. Biotechnol. Biochem. 62: 1653-1659.10.1271/bbb.62.1653Search in Google Scholar

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: 137-143.10.2492/inflammregen.32.137Search in Google Scholar

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 leaves Chamaecyparis obtusa against Callosobruchus chinensis (L.) and Sitophi-lus oryzae (L.). J. Stored Prod. Res. 39: 375-384. DOI: 10.1016/S0022-474X(02)00030-9.10.1016/S0022-474X(02)00030-9Search in Google Scholar

Paul B., Gowda L.R. 2000. Purification and characteriza–tion of a polyphenol oxidase from the seeds of field bean (Dolichos lablab). J. Agric. Food Chem. 48: 3839-3846. DOI: 10.1021/jf000296s.10.1021/jf000296s10995279Search in Google Scholar

Pinto M.S.T., Siqueira F.P., Oliveira A.F.A., Fernandes K.V.S. 2008. A wounding-induced PPO from cowpea (Vigna unguiculata) seed–lings. Phytochemistry 69: 2297-2302. DOI: 10.1016/j.phytochem.2008.06.003.10.1016/j.phytochem.2008.06.00318675435Search in Google Scholar

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: 213-215.10.2503/jjshs.67.213Search in Google Scholar

Saniewska A., Jarecka A. 2008. The inhibitory effect of tropolone and hinokitiol on the growth and devel–opment of Fusarium oxysporum f. sp. tulipae. Phytopathol. Pol. 50: 33-41.Search in Google Scholar

Saniewska A., Saniewski M. 2007. The inhibitory effect of tropolone and hinokitiol on the mycelium growth of Phoma narcissi in vitro. Acta Agrobot. 60: 107-112.10.5586/aa.2007.013Search in Google Scholar

Saniewski M., Saniewska A., Horbowicz M., Kanlayanarat S. 2007. The inhibitory effect of hinokitiol and tropo-lone on reddish colouration in mechanically wounded scales of Hippeastrum x hybr. Hort. and on the development of Phoma narcissi, the patho–gen of Hippeastrum. Acta Hort. 755: 533-542.Search in Google Scholar

Saniewski M., Saniewska A., Kanlayanarat S. 2007. Biological activities of tropolone and hinokitiol: the tools in plant physiology and their use. Acta Hort. 755: 133-142.10.17660/ActaHortic.2007.755.17Search in Google Scholar

Shimizu C., Hori M. 2009. Repellency and toxicity of troponoid compounds against the adzuki bean beetle, Callosobruchus chinensis (L.) (Coleoptera: Bruchidae). J. Stored Prod. Res. 45: 49-53. DOI: 10.1016/j.jspr.2008.08.001.10.1016/j.jspr.2008.08.001Search in Google Scholar

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)70164-8.10.1016/S0315-5463(91)70164-8Search in Google Scholar

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

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.10.1111/j.1365-2621.2003.tb05687.xSearch in Google Scholar

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.2010.08.056.10.1016/j.bmc.2010.08.05620947360Search in Google Scholar

Trust T.J. 1975. Antibacterial activity of tropolone. Anti-microb. Agents Chemother. 7: 500-506. DOI: 10.1128/AAC.7.5.500.10.1128/AAC.7.5.5004291731147585Search in Google Scholar

Trust T.J., Bartlett K.H. 1975. Antibacterial activity of tropilidine and tropone. Antimicrob. Agents Chemother. 8: 381-383. DOI:10.1128/AAC.8.3.381.10.1128/AAC.8.3.3814293231167044Search in Google Scholar

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/jf00006a007.10.1021/jf00006a007Search in Google Scholar

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

Wang M., Hashimoto M., Hashidoko Y. 2013a. Repres–sion of tropolone production and induction of a Burkholderia plantarii pseudo-biofilm by carot-4-en-9, 10-diol, a cell-to-cell signaling disrupter produced by Trichoderma virens. PLOS ONE 8(11): e78024. DOI: 10.1371/journal.pone.0078024.10.1371/journal.pone.0078024381717124223754Search in Google Scholar

Wang M., Hashimoto M., Hashidoko Y. 2013b. Carot-4-en-9,10-diol, a conidiation-inducing sesquiter-pene diol produced by Trichoderma virens PS1-7 upon exposure to chemical stress from highly ac–tive iron chelators. Appl. Environ. Microbiol. 79: 1906-1914. DOI:10.1128/AEM.03531-12.10.1128/AEM.03531-12359223823315728Search in Google Scholar

Yamada J., Fujita K., Eto K., Sakai K. 2003. Cell growth and nutrient uptake by cell suspensions of Cupres-sus lusitanica. J. Wood Sci. 49: 5-10. DOI: 10.1007/s100860300001.10.1007/s100860300001Search in Google Scholar

Yamaguchi T., Fujita K., Sakai K. 1999. Biological ac–tivity of extracts from Cupressus lusitanica cell culture. J. Wood Sci. 45: 170-173. DOI: 10.1007/BF01192336.10.1007/BF01192336Search in Google Scholar

Yamasaki Y., Konno H., Noda K. 2008. Polyphenol oxi–dase from wheat bran is a serpin. Acta Biochim. Pol. 55: 325-328.10.18388/abp.2008_3079Search in Google Scholar

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/jm00080a010.10.1021/jm00080a010Search in Google Scholar

Yen T.-B., Chang H.-T., Hsieh C.-C., Chang S.-T. 2008. Antifungal properties of ethanolic extract and its active compounds from Calocedrus mac-rolepis var. formosana (Florin) heartwood. Biore-sour. Technol. 99: 4871-4877. DOI: 10.1016/j.biortech.2007.09.037.10.1016/j.biortech.2007.09.037Search in Google Scholar

Yu J.Q., Komada H. 1999. Hinoki (Chamaecyparis obtusa) bark, a substrate with antipathogen properties that suppress some root diseases of tomato. Sci. Hortic. 81: 13-24. DOI: 10.1016/S0304-4238(98)00262-3.10.1016/S0304-4238(98)00262-3Search in Google Scholar

Zhao J. 2007. Plant troponoids: Chemistry, biological ac–tivity, and biosynthesis. Curr. Med. Chem. 14: 2597-2621. DOI: 10.2174/092986707782023253.10.2174/09298670778202325317979713Search in Google Scholar

Zhao J., Fujita K., Sakai K. 2005. Oxidative stress in plant cell culture: A role in production of ß-thu-japlicin by Cupressus lusitanica suspension cul–ture. Biotechnol. Bioeng. 90: 621-631. DOI: 10.1002/bit.20465.10.1002/bit.2046515834951Search in Google Scholar

Zhao J., Fujita K., Yamada J., Sakai K. 2001. Improved ß-thujaplicin production in Cupressus lusitanica suspension cultures by fungal elicitor and methyl jasmonate. Appl. Microbiol. Biotechnol. 55: 301–305. DOI: 10.1007/s002530000555.10.1007/s00253000055511341310Search in Google Scholar

Zhao J., Fujita K., Sakai K. 2007. Reactive oxygen spe–cies, nitric oxide, and their interactions play dif–ferent roles in Cupressus lusitanica cell death and phytoalexin biosynthesis. New Phytol. 175: 215–229. DOI: 10.1111/j.1469-8137.2007.02109.x.10.1111/j.1469-8137.2007.02109.x17587371Search in Google Scholar

Zhao J., Guo Y., Fujita K., Sakai K. 2003. Involvement of cAMP signaling in elicitor-induced phyto-alexin accumulation in Cupressus lusitanica cell cultures. New Phytol. 161: 723-733. DOI: 10.1111/j.1469-8137.2004.00976.x.10.1111/j.1469-8137.2004.00976.x33873708Search in Google Scholar

Zhao J., Matsunga Y., Fujita K., Sakai K. 2006. Signal transduction and metabolic flux of ß-thujaplicin and monoterpene biosynthesis in elicited Cupres-sus lusitanica cell cultures. Metab. Eng. 8: 14-29. DOI: 10.1016/j.ymben.2005.09.002.10.1016/j.ymben.2005.09.00216242983Search in Google Scholar

Zhao J., Sakai K. 2003a. Multiple signaling pathways mediate fungal elicitor-induced ß-thujaplicin bio–synthesis in Cupressus lusitanica cell cultures. J. Exp. Bot. 54: 647-656. DOI: 10.1093/jxb/erg062.10.1093/jxb/erg06212554707Search in Google Scholar

Zhao J., Sakai K. 2003b. Peroxidases are involved in bi–osynthesis and biodegradation of ß-thujaplicin in fungal elicitor-treated Cupressus lusitanica. New Phytol. 159: 719-731. DOI: 10.1046/j.1469-8137.2003.00841.x.10.1046/j.1469-8137.2003.00841.x33873588Search in Google Scholar

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

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 in Cupressus lusitanica cell cultures. J. Exp. Bot. 55: 1003-1012. DOI: 10.1093/jxb/erh127.10.1093/jxb/erh12715047767Search in Google Scholar

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: 10.3109/14756360903476398.10.3109/1475636090347639820578978Search in Google Scholar

eISSN:
2300-5009
Language:
English
Publication timeframe:
2 times per year
Journal Subjects:
Life Sciences, Biotechnology, Plant Science, Ecology, other