★論文

2018

Shiina, T., Nakagawa, K., Fujisaki, Y., Ozaki, T., Liu, C., Toyomasu, T., Hashimoto, M., Koshino, H., Minami, A., Kawaide, H. and Oikawa, H.: Biosynthetic study of conidiation-inducing factor conidiogenone: heterologous production and cyclization mechanism of a key bifunctional diterpene synthase. Biosci Biotechnol Biochem. doi: 10.1080/09168451.2018.1536518. (2018)

Toyomasu, T., Goda, C., Sakai, A., Miyamoto, K., Shenton, M.R., Tomiyama, S., Mitsuhashi, W., Yamane, H., Kurata. N. and Okada, K.: Characterization of diterpene synthase genes in the wild rice species Oryza brachyatha provides evolutionary insight into rice phytoalexin biosynthesis. Biochem. Biophys. Res. Commun. 503: 1221-1227 (2018).

Wagatsuma, T., Maejima, E., Watanabe, T., Toyomasu, T., Kuroda, M., Muranaka, T., Ohyama, K., Ishikawa, A., Usui, M., Khan, S. H., Maruyama, H., Tawaraya, K., Kobayashi, Y, and Koyama, H.: Dark conditions enhance aluminum tolerance in several rice cultivars via multiple modulations of membrane sterols. J. Exp. Bot. 69: 567-577 (2018).

2017

Shinde, S. S., Minami, A., Chen, Z., Tokiwano, T., Toyomasu, T., Kato, N., Sassa, T., and Oikawa, H.: Cyclization mechanism of phomopsene synthase:mass spectrometry based analysis of various site-specifically labeled terpenes. J. Antibiot. 70: 632-638 (2017).

2016

Toyomasu, T., Miyamoto, K., Matthew R. Shenton, R.S., Sakai, A., Sugawara, C., Horie, K., Kawaide, H., Hasegawa, M., Chuba, M., Mitsuhashi, W., Yamane, H., Kurata, N. and Okada, K.: Characterization and evolutionary analysis of ent-kaurene synthase like genes from the wild rice species Oryza rufipogon. Biochem. Biophys. Res. Commun. 480: 402-408 (2016).

Miyamoto, K., Fujita, M., Matthew, R.S., Akashi, S., Sugawara, C., Sakai, A., Horie, K., Hasegawa, M., Kawaide, H., Mitsuhashi, W., Nojiri, H.,Yamane, H., Kurata, N., Okada, K., and Toyomasu, T.: Evolutionary trajectory of phytoalexin biosynthetic gene clusters in rice. Plant J. 87: 293-304 (2016).

Chen, M., Chou, W.K.W., Toyomasu, T., Cane, D.E., Christianson, D.W.: Structure and function of fusicoccadiene synthase, a hexameric bifunctional ditrepene synthase. ACS Chem. Biol. 11: 889-899 (2016).

2015

Tezuka, D., Ito, A., Mitsuhashi, W., Toyomasu, T., and Imai, R.: The rice ent-KAURENE SYNTHASE LIKE 2 encodes a functional ent-beyerene synthase. Biochem. Biophys. Res. Commun. 460: 766-771 (2015).

Wagatsuma, T., Khan, M.S.H., Watanabe, T., Maejima, E., Sekimoto, H., Yokota, T., Nakano, T., Toyomasu, T., Tawaraya, K., Koyama, H., Uemura M., Ishikawa, S., Ikka, T., Ishikawa, A., Kawamura, T., Murakami, S., Ueki, N., Umetsu, A., and Kannari, T.: Higher sterol content regulated by CYP51 with concomitant lower phospholipid content in membranes is a common strategy for aluminium tolerance in several plant species. J. Exp. Bot. 66: 907-918 (2015).

Toyomasu, T., Usui, M., Sugawara, C., Kanno, Y., Sakai, A., Takahashi, H., Nakazono, M., Kuroda, M., Miyamoto, K., Morimoto, Y., Mitsuhashi, W., Okada, K., Yamaguchi, S., and Yamane, H.: Transcripts of two ent-copalyl diphosphate synthase genes differentially localize in rice plants according to their distinct biological roles. J. Exp. Bot. 66: 369-376 (2015).

2014

Toyomasu, T., Usui, M., Sugawara, C., Otomo, K., Hirose, Y., Miyao, A., Hirochika, H., Okada, K., Shimizu, T., Koga, J., Hasegawa, M., Chuba, M., Kawana, Y., Kuroda, M., Minami, E., Mitsuhashi, W., and Yamane, H.: Reverse-genetic approach to verify physiological roles of rice phyyoalexins: characterization of a knockdown mutant of OsCPS4 phytoalexin biosynthetic gene in rice. Physiol. Plant. 150: 55-61 (2014).

2013

Ueda, K., Tawaraya, K., Murayama, H., Sato, S., Nishizawa, T., Toyomasu, T., Murayama, T., Shiozawa, S., and Yasuda, H.: Effects of arbuscular mycorrhizal fungi on the abundance of foliar-feeding insects and their natural enemy. Appl. Entomol. Zool., 48: 79-85 (2013).

2012

Zhou, K., Xu, M., Tiernan, M., Xie, Q., Toyomasu, T., Sugawara, C., Oku, M., Usui, M., Mitsuhashi, W., Chono, M., Chandler, P. M., Peters, R. J.: Functional characterization of wheat ent-kaurene(-like) synthases indicates continuing evolution of labdane-related diterpenoid metabolism in the cereals. Phytochemistry, 84: 47-55 (2012).

Wu, Y., Zhou, K., Toyomasu, T., Sugawara C., Oku M., Abe S., Usui M., Mitsuhashi W., Chono M., Chandler P. M., and Peters, R. J.: Functional characterization of wheat copalyl diphosphate synthases sheds light on the early evolution of labdane-related diterpenoid metabolism in the cereals. Phytochemistry, 84: 40-46 (2012).

T

awaraya, K., Shiozawa, S., Ueda, K., Murayama, H., Nishizawa, T., Toyomasu, T., Murayama, T., Sato, S., Wagatsuma, T., and Yasuda, H.: Leaf herbivory by Spodoptera litura increases arbuscular mycorrhizal colonization in roots of soybean. Soil Sci. Plant Nutr., 58: 445-449 (2012).

Noike, M., Ono, Y., Araki, Y., Tanio, R., Higuchi, Y., Nitta, H., Hamano, Y., Toyomasu, T., Sassa, T., Kato, N., and Dairi, T.: Molecular breeding of a fungus producing a precursor diterpene suitable for semi-synthesis by dissection of the biosynthetic machinery. PLOS ONE, 7: e42090 (2012).

Noike, M., Liu, C., Ono, Y., Hamano, Y., Toyomasu, T., Sassa, T., Kato, N., and Dairi, T.: An enzyme catalyzing O-prenylation of the glucose moiety of fusicoccin A, a diterpene glucoside produced by fungus Phomopsis amygdali. ChemBioChem, 13: 566-573 (2012).

Sawada, Y., Umetsu, A., Komatsu, Y., Kitamura, J., Suzuki, H., Asami, T., Fukuda, M., Honda, I., Mitsuhashi, W., Nakajima, M., and Toyomasu, T.: An unusual spliced variant of DELLA protein, a negative regulator of gibberellin signaling, in lettuce. Biosci. Biotechnol. Biochem., 76: 544-550 (2012).

2011

Umetsu, A., Sawada Y., Mitsuhashi, W., Mazier, M., and Toyomasu, T.: Characterization of a loss-of-function mutant of gibberellin biosynthetic gene LsGA3ox1 in lettuce. Biosci. Biotechnol. Biochem., 75: 2398-2400 (2011).

Sugai, Y., Ueno, Y., Hayashi, K., Oogami, S., Toyomasu, T., Matsumoto, S., Natsume, M., Nozaki, H., and Kawaide, H.: Enzymatic 13C labeling and multidimensional NMR analysis of miltiradiene synthesized by bifunctional diterpene cyclase in Selaginella moellendorffii. J. Biol. Chem., 286: 42840-42847 (2011).

Hillwig, M. L., Xu, M., Toyomasu, T., Tiernan, M. S., Wei, G., Cui, G., Huang, L., and Peters, R. J.: Domain loss has independently occurred multiple times in plant terpene synthase evolution. Plant J., 68: 1051-1060 (2011).

Ono, Y., Minami, A., Noike, A., Higuchi, Y., Toyomasu, T., Sassa, T., Kato, N., and Dairi, T.: Dioxygenases, key enzymes to determine the aglycon structures of fusicoccin and brassicicene, diterpene compounds produced by fungi. J. Am. Chem. Soc., 133: 2548-2555 (2011).

2010

Nakano, C., Hoshino, T., Sato, T., Toyomasu, T., Dairi, T., and Sassa, T.: Substrate specificity of the CYC2 enzyme from Kitasatospora griseola: production of sclarene, biformene and novel bicyclic diterpenes by the enzymatic reactions of labdane- and halimane-type diterpene diphosphate. Tetrahedron Lett., 51: 125-128 (2010).

2009

Fukuda, M., Matsuo, S., Kikuchi, K., Mituhashi, W., Toyomasu, T., and Honda, I.: Up-regulation of endogenous level of a bioactive gibberellin through LsGA3ox1 expression during stem elongation stimulated by higher temperature in lettuce. J. Plant Physiol., 166: 2077-2084 (2009).

Hashimoto, M., Higuchi, Y., Takahashi, S., Osada, H., Sakaki, T., Toyomasu, T., Sassa, T., Kato, N., and Dairi, T.: Functional analyses of cytochrome P450 genes responsible for the early steps of brassicicene C biosynthesis. Bioorg. Med. Chem. Lett., 19: 5640-5643 (2009).

Toyomasu, T., Tsukahara, M., Kenmoku, H., Anada, M., Nitta, H., Mitsuhashi, W., Sassa, T., and Kato, N.: Transannular proton transfer in the cyclization of geranylgeranyl diphosphate to fusicoccadiene, a biosynthetic intermediate of fusicoccins. Org. Lett., 11: 3044-3047 (2009).

Toyomasu, T., Kagahara, T., Hirose, Y. Usui, M., Abe, S., Okada, K., Koga, J., Mitsuhashi, W., and Yamane, H.: Cloning and characterization of cDNAs encoding ent-copalyl diphosphate synthases in wheat: insight into the evolution of rice phytoalexin biosynthetic genes. Biosci. Biotechnol. Biochem. 73: 772-775 (2009).

Murayama, H., Arikawa, M., Sasaki, Y., Dal Cin, V., Mitusuhashi, W., and Toyomasu, T.: Effect of ethylene treatment on expression of polyuronide-modifying genes and solubilization of polyuronides during ripening in two peach cultivars having different softening characteristics. Postharvest Biol. Technol. 52: 196-201 (2009).

Toyomasu, T., Kaneko, A., Tokiwano, T., Kanno, Y., Kanno, Y., Niida, R., Miura, S., Nishioka, T., Ikeda, C., Mitsuhashi, W., Dairi, T., Kawano, T., Oikawa, H., Kato, N., and Sassa, T.: Biosynthetic gene-based secondary metabolite screening: a new diterpene, methyl phomopsenonate, from the fungus Phomopsis amygdali. J. Org. Chem., 74: 1541-1548 (2009).

Minami, A., Tajima, N., Higuchi, Y., Toyomasu, T., Sassa, T., Kato, N., and Dairi, T.: Identification and functional analysis of brassicicene C biosynthetic gene cluster in Alternaria brassicicola. Bioorg. Med. Chem. Lett., 19: 870-874 (2009).

2008

Endo, A., Sawada, Y., Takahashi, H., Okamoto, M., Ikegami, K., Koiwai, H., Seo. M., Toyomasu, T., Mitsuhashi, W., Shinozaki, K., Nakazono, M., Kamiya, Y., Koshiba, T., and Nambara, E.: Drought induction of Arabidopsis 9-cis-epoxycarotenoid dioxygenase occurs in vascular parenchyma cells. Plant Physiol., 147: 1984-1993 (2008).

Sawada, Y., Katsumata, T., Kitamura, J., Kawaide, H., Nakajima, M., Asami, T., Nakaminami, K., Kurahashi, T., Mitsuhashi, W., Inoue, Y., and Toyomasu, T.: Germination of photoblastic lettuce seeds is regulated via the control of endogenous physiologically active gibberellin contents, rather than of gibberellin responsiveness. J. Exp. Bot., 59: 3383-3393 (2008).

Toyomasu, T., Niida, R., Kenmoku, H., Kanno, Y., Miura, S., Nakano, C., Shiono, Y., Mitsuhashi, W., Toshima, H., Oikawa, H., Hoshino, T., Dairi, T., Kato, N., and Sassa, T.: Identification of diterpene biosynthetic gene clusters and functional analysis of labdane-related diterpene cyclases in Phomopsis amygdali. Biosci. Biotechnol. Biochem., 72: 1038-1047 (2008).

Sawada, Y., Aoki, M., Nakaminami, K., Mitsuhashi, W., Tatematsu, K., Kushiro, T., Koshiba, T., Kamiya, Y., Inoue, Y., Nambara, E., and Toyomasu, T.: Phytochrome- and gibberellin-mediated regulation of abscisic acid metabolism during germination of photoblastic lettuce seeds. Plant Physiol. 146: 1386-1396 (2008).

Toyomasu, T., Kagahara, T., Okada, K., Koga, J., Hasegawa, M., Mitsuhashi, W., Sassa, T., and Yamane, H.: Diterpene phytoalexins are biosynthesized in and exuded from roots of rice seedlings Biosci. Biotechnol. Biochem. 72: 562-567 (2008).

Hayashi, Y., Toyomasu, T., Hirose, Y., Onodera, Y., Mitsuhashi, W., Yamane, H., Sassa, T., and Dairi, T.: Comparison of the enzymatic properties of ent-copalyl diphosphate synthases in the biosynthesis of phytoalexins and gibberellins in rice. Biosci. Biotechnol. Biochem. 72: 523-530 (2008).

2007

Nemoto, T., Okada, A., Okada, K., Shibuya, N., Toyomasu, T., Nojiri, H., and Yamane, H.: Promoter analysis of the rice stemar-13-ene synthase gene OsDTC2, which is involved in the biosynthesis of the phytoalexin oryzalexin S. Biochim. Biophys. Acta, 1769: 678-683 (2007).

Shimura, K., Okada, A., Okada, K., Jikumaru, Y., Ko, K.-W., Toyomasu, T., Sassa, T., Hasegawa, M., Kodama, O., Shibuya, N., Koga, J., Nojiri, H., and Yamane, H.: Identification of a biosynthetic gene cluster in rice for momilactones. J. Biol. Chem., 282: 34013-34018 (2007).

Gao, M., Matsuta, N., Toyomasu, T., Mitsuhashi, W., Dandekar, A. M., Tao, R., and Nishimura, K.: Gene expression and ethylene production in transgenic pear (Pyrus communis cv. 'La France') with sense and antisense cDNA encoding ACC oxidase. Plant Science, 173: 32-42 (2007).

Toyomasu, T., Tsukahara, M., Kaneko, A., Niida, R., Mitsuhashi, W., Dairi, T., Kato, N. and Sassa, T.: Fusicoccins are biosynthesized by an unusual chimera diterpene synthase in fungi. Proc. Natl. Acad. Sci. USA. 104: 3084-3088 (2007).

2006

Murayama, H., Sekine, D., Yamauchi, Y., Gao, M., Mitsuhashi, W., and Toyomasu, T.: Effect of girdling above the abscission zone of fruit on 'Bartlett' pear ripening on the tree. J. Exp. Bot., 57: 3679-3686 (2006).

Kanno, Y., Otomo, K., Kenmoku, H., Mitsuhashi, W., Yamane, H., Oikawa, H., Toshima, H., Matsuoka, M., Sassa, T. and Toyomasu, T.: Characterization of a rice gene family encoding type-A diterpene cyclases. Biosci. Biotechnol. Biochem., 70: 1702-1710 (2006).

Sekine, D., Munemura, I., Gao, M., Mitsuhashi, W., Toyomasu, T. and Murayama, H.: Cloning of cDNAs encoding cell-wall hydrolases from pear (Pyrus communis) fruit and their involvement in fruit softening and development of melting texture. Physiol. Plant., 126: 163-174 (2006).

2004

Otsuka, M., Kenmoku, H., Ogawa, M., Okada, K., Mitsuhashi, W., Sassa, T., Kamiya, Y., Toyomasu, T. and Yamaguchi, S.: Emission of ent-kaurene, a diterpenoid hydrocarbon precursor for gibberellins, into the headspace from plants. Plant Cell Physiol., 45: 1129-1138 (2004).

Otomo, K., Kanno, Y., Motegi, A., Kenmoku, H., Yamane, H., Mitsuhashi, W., Oikawa, H,. Toshima, H., Itoh, H., Matsuoka, M., Sassa, T. and Toyomasu, T.: Diterpene cyclases responsible for the biosynthesis of phytoalexins, momilactones A, B, and oryzalexins A-F in rice. Biosci. Biotechnol. Biochem., 68: 2001-2006 (2004).

Itoh, H., Tatsumi, T., Sakamoto, T., Otomo, K., Toyomasu, T., Kitano, H., Ashikari, M., Ichihara, S. and Matsuoka, M.: A rice semi-dwarf gene, Tan-Ginbozu (D35), encodes the gibberellin biosynthesis enzyme, ent-kaurene oxidase. Plant Mol. Biol., 54: 533-547 (2004).

Otomo, K., Kenmoku, H., Oikawa, H., Konig, W. A., Toshima, H., Mitsuhashi, W., Yamane, H., Sassa, T. and Toyomasu, T.: Biological functions of ent- and syn-copalyl diphosphate synthases in rice: key enzymes for the branch point of gibberellin and phytoalexin biosynthesis. Plant J. 39: 886-893 (2004).

Nemoto, T., Cho, E. M., Okada, A., Okada, K., Otomo, K., Kanno, Y., Toyomasu, T., Mitsuhashi, W., Sassa T., Minami E., Shibuya, N., Nishiyama, M., Nojiri, H. and Yamane, H.: Stemar-13-ene synthase, a diterpene cyclase involved in the biosynthesis of the phytoalexin oryzalexin S in rice. FEBS Lett., 571, 182-186 (2004).

Koiwai, H., Nakaminami, K., Seo, M., Mitsuhashi, W., Toyomasu, T. and Koshiba, T.: Tissue-specific localization of an abscisic acid biosynthetic enzyme, AAO3, in Arabidopsis. Plant Physiol., 134: 1697-1707 (2004).

Mitsuhashi, W., Sasaki, S., Kanazawa, A., Yang Y.-Y., Kamiya, Y. and Toyomasu, T.: Differential expression of acid invertase genes during seed germination in Arabidopsis thaliana. Biosci. Biotechnol. Biochem. 68: 602-608 (2004).

Mitsuhashi, W., Yamashita, T., Toyomasu, T., Kashiwagi, Y. and Konnai, T.: Sequential development of cystein proteinase activities and gene expression during somatic embryogenesis in carrot. Biosci. Biotechnol. Biochem. 68: 705-713 (2004).

Cho, E.M., Okada, A., Kenmoku, H., Otomo, K., Toyomasu, T., Mitsuhashi, W., Sassa, T., Yajima, A., Yabuta, G., Mori, K., Oikawa, H., Toshima, H., Shibuya, N., Nojiri, H., Omori, T., Nishiyama, M. and Yamane, H.: Molecular cloning and characterization of a cDNA encoding ent-cassa-12,15-diene synthase, a putative diterpenoid phytoalexin biosynthetic enzyme, from suspension-cultured rice cells treated with a chitin elicitor. Plant J. 37: 1-8 (2004).

Toyomasu, T., Nakaminami, K., Toshima, H., Mie, T., Watanabe, K., Ito, H., Matsui, H., Mitsuhashi, W., Sassa, T. and Oikawa, H.: Cloning of a gene cluster responsible for the biosynthesis of diterpene aphidicolin, a specific inhibitor of DNA poloymerase a. Biosci. Biotechnol. Biochem. 68: 146-152 (2004).

2003

Mitsuhashi, W., Toyomasu, T., Masui, H., Katho T., Nakaminami, K., Kashiwagi, Y., Akutsu, M., Kenmoku, H., Sassa, T., Yamaguchi, S., Kamiya, Y. and Kamada, H.: Gibberellin is essentially required for carrot (Daucus carota L.) somatic embryogenesis: Dynamic regulation of gibberellin 3-oxidase gene expressions. Biosci. Biotechnol. Biochem. 67: 2438-2447 (2003).

Nakaminami, K., Sawada, Y., Suzuki, M., Kenmoku, H., Kawaide, H., Mitsuhashi, W., Sassa, T., Inoue, Y., Kamiya, Y. and Toyomasu, T.: Deactivation of gibberellin by 2-oxidation during germination of photoblastic lettuce seeds. Biosci. Biotechnol. Biochem. 67: 1551-1558 (2003).

2002

Karlson, D., Nakaminami, K., Toyomasu, T. and Imai, R.: A cold-regulated nucleic acid-binding protein of winter wheat shares a domain with bacterial cold shock proteins. J. Biol. Chem., 277: 35248-35256 (2002).

Oikawa, H., Nakamura, K., Toshima, H., Toyomasu, T. and Sassa, T.: Proposed mechanism for the reaction catalyzed by a diterpene cyclase, aphidicolan-16b-ol synthase: experimental results on biomimetic cyclization and examination of the cyclization pathway by ab initio calculations. J. Am. Chem. Soc., 124: 9145-9153 (2002).

Toshima, H., Oikawa, H., Yada, H., Ono, H., Toyomasu, T. and Sassa, T.: Total synthesis of (±)-syn-copalol. Biosci. Biotech. Biochem., 66, 2504-2510 (2002).

Kenmoku, H., Shimai, T., Toyomasu, T., Kato, N. and Sassa, T.: Erinacine Q, a new erinacine from Hericium erinaceum, and its biosynthetic route to erinacine C in the basidiomycete. Biosci. Biotech. Biochem., 66, 571-575 (2002).

2001

Toshima, H., Oikawa, H., Toyomasu, T. and Sassa, T.: Total synthesis of (+)-albicanol and (±)-albicanyl acetate. Biosci. Biotech. Biochem., 65, 1244-1247 (2001).

Oikawa, H., Toyomasu, T., Toshima, H., Ohashi, S., Kawaide, H., Kamiya, Y., Ohtsuka, M., Shinoda, S., Mitsuhashi, W. and Sassa, T.: Cloning and functional expression of cDNA encoding aphidicolan-16b-ol synthase: A key enzyme responsible for formation of an unusual diterpene skelton in biosynthesis of aphidicolin. J. Am. Chem. Soc., 123: 5154-5155 (2001).

2000

Toyomasu, T., Kawaide, H., Ishizaki, A., Shinoda, S., Otsuka, M., Mitsuhashi, W. and Sassa, T.: Cloning of a full-length cDNA encoding ent-kaurene synthase from Gibberella fujikuroi: functional analysis of a bifunctional diterpene cyclase. Biosci. Biotechnol. Biochem. 64: 660-664 (2000).

Toshima, H., Oikawa, H., Toyomasu, T. and Sassa, T.: Total synthesis of both enantiomers of copalol via optical resolution of a general synthetic intermediate for drimane sesquiterpenes and labdane diterpenes. Tetrahedron, 56: 8443-8450 (2000).

1998

Toyomasu, T., Kawaide, H., Mitsuhashi, W., Inoue, Y. and Kamiya, Y.: Phytochrome regulates gibberellin biosynthesis during germination of photoblastic lettuce seeds. Plant Physiol., 118: 1517-1523 (1998).

1997

Toyomasu, T., Kawaide, H., Sekimoto, H., Numers, C., Phillips, A.L., Hedden, P. and Kamiya, Y.: Cloning and characterization of a cDNA encoding gibberellin 20-oxidase from rice (Oryza sataiva L.) seedlings. Physiol. Plant., 99: 111-118 (1997).