---

● 2024

Tomonobu Toyomasu, So Oshikawa, Ayaka Naoe, Tomoka Moriya, Yuto Hasegawa, Momoko Nakasato, Yuga Ogawa, Hiroki Wakabayashi, Akira Itoh, Yuri Takeda-Kimura, Sho Miyazaki and Hiroshi Kawaide.
Gibberellin-biosynthetic ent-kaurene synthases in higher plants do not require their non-catalytic domains for the catalysis. Biochemical Journal (2024) doi:10.1042/BCJ20240162

S. Miyazaki,· H. Kawaide and Masatoshi Nakajima.
Inactivation Pathway of Diterpenoid Regulator in the Moss Physcomitrium patens. Journal of Plant Growth Regulation (2024) doi:10.1007/s00344-024-11301-2

---

● 2023

Takeru Shimada, Shiho Minato, Yuto Hasegawa, Koji Miyamoto, Yasumasa Minato, Matthew R Shenton, Kazunori Okada, Hiroshi Kawaide, Tomonobu Toyomasu
Characterization of diterpene synthase genes in Brachypodium distachyon, a monocotyledonous model plant,provides evolutionary insight into their multiple homologs in cereal
Bioscience, Biotechnology, and Biochemistry, zbad146, (2023) doi:10.1002/1873-3468.14691.

Rui Sun, Maiko Okabe, Sho Miyazaki, Toshiaki Ishida, Kiyoshi Mashiguchi, Keisuke Inoue, Yoshihiro Yoshitake, Shohei Yamaoka, Ryuichi Nishihama, Hiroshi Kawaide, Masatoshi Nakajima, Shinjiro Yamaguchi, Takayuki Kohchi
Biosynthesis of gibberellin-related compounds modulates far-red light responses in the liverwort Marchantia polymorpha
Plant Cell (2023) doi:10.1093/plcell/koad216

Kawakami, T. Miyazaki, S & Kawaide, H.
Molecular characterization of a moss isoprene synthase provides insight into its evolution
FEBS Letters (2023) doi:10.1002/1873-3468.14691.

Aizawa, M., Saito, H., Mitazaki, T., Taketani, T., Noguchi, K., Miyazaki, S., Kawaide, H. & Natsume, M.
Production of desmethyl-gregatin A, a possible causative toxin of brown stem rot in adzuki bean, by Phialophora gregata f. sp. adzukicola
J. Pestic. Sci.(2023) doi:10.1584/jpestics.D22-070

Takuya Hasegawa, Takatoshi Araki, Atsushi Okabe, Yusuke Kato, Atsushi Ooshiro, Sho Miyazaki, Hiroshi Kawaide & Masahiro Natsume
Contribution of ethyl β‐d‐glucoside, amino acids, and organic acids in tomato root exudates to the chemotaxis of Ralstonia pseudosolanacearum
Journal of General Plant Pathology(2023) doi:10.1007/s10327-023-01114-8

● 2022

---

● 2021

---

● 2020

Mao, L., Kawaide, H., Higuchi, T., Chen, M., Miyamoto, K., Hirata, Y., Kimura, H., Miyazaki, S., Teruya, M., Fujiwara, K., Tomita, K., Yamane, H., Hayashi, K., Nojiri, N., Jia, L., Qiu, J., Ye, C., Timko, M.P., Fan, L. & Okada, K..
Genomic evidence for convergent evolution of gene clusters for momilactone biosynthesis in land plants.
Proc. Natl. Acad. Sci. USA (2020) doi:10.1073/pnas.1914373117

Nakajima, M., Miyazaki, S. & Kawaide, H.
Hormonal diterpenoids distinct to gibberellins regurate protonema differentiation in the moss Physcomitrium patens.
Plant Cell Physiol. (2020) doi:10.1093/pcp/pcaa129

---

● 2019

Shiina, T., Nakagawa, K., Fujisaki, Y., Ozaki, T., Toyomasu, T., Hashimoto, M., Koshino, H., Minami A., Kawaide, H. & Oikawa, H.
Biosynthetic study of conidiation-inducing factor conidiogenone: Heterologous production and cyclization mechanism of a key bifunctional diterpene synthase.
Biosci.Biotechnol. Biochem (2019) doi:/10.1080/09168451.2018.1536518

---

Hasegawa, T., Kato, Y., Okabe, A., Itoi, C., Ooshiro, A., Kawaide, H. & Natsume, M.
Effect of Secondary Metabolites of Tomato (Solanum lycopersicum) on Chemotaxis of Ralstonia solanacearum, Pathogen of Bacterial Wilt Disease.
J Agric Food Chem. (2019) doi:/10.1021/acs.jafc.8b06245

---

Motoyama, K., Sobue, F., Kawaide, H., Yoshimura, T. & Hemmi, H.
Conversion of Mevalonate 3-Kinase into 5-Phosphomevalonate 3-Kinase by Single Amino Acid Mutations.
Appl. Environ. Microbiol. (2019) doi:/10.1128/AEM.00256-19

---

● 2018

Takuya Hasegawa, Atsushi Okabe, Yusuke Kato, Atsushi Ooshiro, Hiroshi Kawaide& Masahiro Natsume
Ethyl β-d-glucoside: a novel chemoattractant of Ralstonia solanacearum isolated from tomato root exudates by a bioassay-guided fractionation
Bioscience, Biotechnology, and Biochemistry (2018) doi:/10.1080/09168451.2018.1515618

---

Hajime Hayakawa, Kento Motoyama, Fumiaki Sobue, Tomokazu Ito, Hiroshi Kawaide, Tohru Yoshimura& Hisashi Hemmi
Modified mevalonate pathway of the archaeon Aeropyrum pernix proceeds via trans-anhydromevalonate 5-phosphate
Proc. Natl. Acad. Sci. USA (2018) doi:/10.1073/pnas.1809154115

---

Miyazaki S., Hara M., Ito S., Tanaka K., Asami T., Hayashi K.-i., Kawaide H.& Nakajima M
An ancestral gibberellin in a moss Physcomitrella patens
Molecular Plant (2018) doi:/10.1016/j.molp.2018.03.010

---

● 2017

Hasegawa, T., Okabe, A., Kato, Y., Ooshiro, A., Kawaide, H.& Natsume, M.
Bioassay-guided isolation of a novel chemoattractant for Ralstonia solanacearum in tomato root exudates.
Journal of General Plant Pathology (2017) doi:/10.1007/s10327-017-0752-5

---

Ye, Z., Yamazaki, K., Minoda, H., Miyamoto, K., Miyazaki, S., KAWAIDE, H., YAJIMA, A., NOJIRI, H., YAMANE, H.& OKADA, K.
In planta functions of cytochrome P450 monooxygenase genes in the phytocassane biosynthetic gene cluster on rice chromosome 2
Biosci. Biotechnol. Biochem. (2017) doi:/10.1080/09168451.2017.1398067

---

Noguchi, C., Miyazaki, S. Kawaide, H., Gotoh, M., Yoshida, Y.& Aoyama, Y.
Characterization of moss ent-kaurene oxidase (CYP701B1) using a highly purified preparation.
The Journal of Biochemistry (Tokyo) (2017) doi:/10.1093/jb/mvx063

---

Masahiro Natsume, Nobuya Tashiro, Akio Doi, Yatsuka Nishi& Hiroshi Kawaide
Effects of concanamycins produced by Streptomyces scabies on lesion type of common scab of potato.
Journal of General Plant Pathology (2017) doi:/10.1007/s10327-017-0696-9

---

YE, Zhongfeng, NAKAGAWA, Kazuya, NATSUME, Masahiro, NOJIRI,Hideaki, KAWAIDE, Hiroshi& OKADA, Kazunori.
Biochemical synthesis of uniformly 13C-labeled diterpene hydrocarbons and their bioconversion to diterpenoid phytoalexins in planta.
Biosci. Biotechnol. Biochem. (2017) doi:/10.1080/09168451.2017.1285689

---

Motoyama, K., Unno, H., hattori, A., Takaoka, T., Ishikita, H., Kawaide, H., Yoshimura, T.& Hennmo, H.
A single amino acid mutation converts (R)-5-diphosphomevalonate decarboxylase into a kinase.
J. Biol. Chem. (2017) doi:/10.1074%2Fjbc.M116.752535

---

● 2016

Toyomasu, T., Miyamoto, K., Shenton, M.R, Sakai, A., Sugawara, C., Horie, K., Kawaide, H., Hasegawa M., Chuba, M., Mitsuhashi, W., Yamane, H., Kurata, N.& Okada, K.
Characterization and evolutionary analysis of ent-kaurene synthase like genes from the wild rice species Oryza rufipogon.
Biochem. Biophys. Res. Commun. (2016) doi:/10.1016/j.bbrc.2016.10.062"

---

Okada, M., Matsuda, Y., Mitsuhashi, T., Hoshino, S., Mori, T., Nakagawa, K., Quan, Z., Qin, B., Zhang, H., Hayashi, F., Kawaide, H.& Abe, I
Genome-based discovery of an unprecedented cyclization mode in fungal sesterterpenoids biosynthesis.
J. Am. Chem. Soc. (2016) doi:/10.1021/jacs.6b05799

---

Miyamoto, K., Fujita, M., Shenton, M., Akashi, S., Sugawara, C., Sakai, A., Horie, K., Hasegawa, M., Kawaide, H., Mitsuhashi, W., Nojiri, H., Yamane, H., Kurata, N., Okada, K.& Toyomasu, T.
Evolutionary trajectory of phytoalexin biosynthetic gene clusters in rice.
Plant J. (2016) doi:/10.1111/tpj.13200

---

Kazunori Okada, Hiroshi Kawaide, Koji Miyamoto, Sho Miyazaki, Ryosuke Kainuma, Honoka Kimura, Kaoru Fujiwara, Masahiro Natsume, Hideaki Nojiri, Masatoshi Nakajima, Hisakazu Yamane, Yuki Hatano, Hiroshi Nozaki& Ken-ichiro Hayashi
HpDTC1, a Stress-Inducible Bifunctional Diterpene Cyclase Involved in Momilactone Biosynthesis, Functions in Chemical Defence in the Moss Hypnum plumaeforme.
Scientific Reports (2016) doi:/10.1038/srep25316

---

● 〜2015

Sugawara, S., Mashiguchi,K., Tanaka, K., Hishiyama, S., Sakai, T., Hanada, K., Kinoshita-Tsujimura, K., Yu, H., Dai, X., Takebayashi, Y., Takeda-Kamiya, N., Kakimoto, T., Kawaide, H., Natsume, M., Estelle, M., Zhao, Y.,Hayashi, K., Kamiya, Y.& Kasahara, H.
Distinct characteristics of indole-3-acetic acid and phenyl acetic acid, two common auxins in plants.
Plant & Cell Physiology (2015) doi:/10.1093/pcp/pcv088

---

川出　洋
菌類およびコケ・シダ類における生理活性ジテルペノイドの生合成研究
植物の生長調節 (2015) doi:/10.18978/jscrp.50.1_12

---

Miyazaki S., Kimura H., Natsume M., Asami T., Hayashi K., Kawaide H.& Nakajima M.
Analysis ot ent-kaurenoic acid by ultra performance liquid chromatography-tandem mass spectrometry.
Biochemistry and Biophysics Reports (2015) doi:/10.1016/j.bbrep.2015.05.010

---

Ogata, T., Okada, H., Kawaide, H., Takahashi, H., Seo, S., Matsuhara, I.& Matsushita, Y.
Involvement of NtERF3 in the cell death signaling pathway mediated by SIPK/WIPK and WRKY1 in tobacco plants.
Plant Biology (2015) doi:/10.1111/plb.12349

---

Shimane, M., Ueno, Y., Morisaki, K., Oogami, S., Natsume, M., Hayashi, K., Nozaki, H.&Kawaide, H.
Molecular evolution of the substrate specificity of ent-kaurene synthases to adapt to gibberellin biosynthesis in land plants.
Biochem. J. (2014) doi:/10.1042/BJ20140134

---

Tanaka, K., Hayashi, K., Natsume, M., Kamiya, Y., Sakakibara, H., Kawaide H.&Kasahara H.
UGT74D1 catalyzes the glucosylation of 2-oxindole-3-acetic acid inthe auxin metabolic pathway in Arabidopsis.
Plant Cell Physiol. (2014) doi:/10.1093/pcp/pct173

---

Kitaoka, N., Kawaide, H., Amano, N., Matsubara, T., Nabeta, K., Takahashi, K.&Matsuura, H.
CYP94B3 activity against jasmonic acid amino acid conjugates and the elucidation of 12-O-β-glucopyranosyl-jasmoyl-L-isoleucine as an additional metabolite.
Phytochemistry (2014) doi:/10.1016/j.phytochem.2013.12.019

---

Miyazaki, S., Toyoshima, H., Natsume, M., Nakajima, M.&Kawaide, H.
Blue-light irradiation up-regulates the ent-kaurene synthase gene and affects the avoidance response of protonemal growth in Physcomitrella patens.
Planta (2014) doi:/10.1007/s00425-014-2068-4

---

Azami, Y., Hattori, A., Nishimura, H., Kawaide, H., Yoshimura, T.&Hemmi, H.
(R)-mevalonate 3-phosphate is an intermediate of the mevalonate pathway in Thermoplasma acidophilum.
J. Biol. Chem. (2014) doi:/10.1074/jbc.M114.562686

---

Magome, H., Nomura, T., Hanada, A., Takeda-Kamiya, N., Ohnishi, T., Shinma, Y., Katsumata, T., Kawaide, H, Kamiya, Y.&Yamaguchi, S.
CYP714B1 and CYP714B2 encode gibberellin 13-oxidases that reduce gibberellin activity in rice.
(2013) Proc. Natl. Acad. Sci. USA doi:/10.1073/pnas.1215788110

---

Shimane, M., Sugai, Y., Kainuma, R., Natsume, M.& Kawaide, H.
Mevalonate-dependent enzymatic synthesis of amorphadiene driven by an ATP-regeneration system using polyphosphate kinase.
Biosci. Biotechnol. Biochem. (2012) doi:/10.1271/bbb.120177

---

Toyama, T., Tahara, M., Nagamune, K., Arimitsu, K., Hamashima, Y., Palacpac, N.M., Kawaide, H., Horii, T.&Tanabe, K.
Gibberellin biosynthetic inhibitors make human malaria parasite Plasmodium falciparum cells swell and rupture to death.
PLoS ONE (2012) doi:/10.1371/journal.pone.0032246

---

Aoki, Y., Matsumoto, D., Kawaide, H.& Natsume, M.
Physiological role of germicidins in spore germination and hyphal elongation in Streptomyces coelicolor A3(2)
J. Antibiot. (2011) doi:/10.1038/ja.2011.59

---

Hashimoto, M., Katsura, H., Kato, R., Kawaide, H&Natsume, M.
Effect of pamamycin-607 on secondary metabolite production by Streptomyces spp.
Biosci. Biotechnol. Biochem. (2011) doi:/0.1271/bbb.110251

---

Ooshiro, A., Kaji, M., Katoh, Y., Kawaide, H.& Natsume, M.
Antibacterial activity of alkyl gallates and related compounds against Ralstonia solanacearum.
J. Pestic. Sci. (2011) doi:/10.1584/jpestics.G10-84

---

Kawaide, H., Hayashi, K., Kawanabe, R., Sakigi, Y., Natsume, M.&Nozaki, H.
Identification of the single amino acid involved in quenching the ent-kauranyl cation by a water molecule in ent-kaurene synthase of Physcomitrella patens.
FEBS J. (2011) doi:/10.1111/j.1742-4658.2010.07938.x

---

Sugai, Y. Miyazaki, S., Mukai, S., Yumoto, I., Natsume, M.&Kawaide, H.
Enzymatic total synthesis of gibberellin A4 from acetate.
Biosci. Biotechnol. Biochem. (2011) doi:/10.1271/bbb.100733

---

Katsumata, T., Fukazawa, J., Magome, H., Jikumaru, Y., Kamiya, Y., Natsume, M., Kawaide, H& Yamaguchi, S.
Involvement of the CYP78A subfamily of cytochrome P450 monooxygenases in protonema growth and gametophore formation in the moss Physcomitrella patens.
Biosci. Biotechnol. Biochem. (2011) doi:/10.1271/bbb.100759

---

Miyazaki, S., Katsumata, T., Natsume, M.& Kawaide, H.
The CYP701B1 of Physcomitrella patens is an ent-kaurene oxidase that resists inhibition by uniconazole-P.
FEBS lett. (2011) doi:/10.1016/j.febslet.2011.04.057

---

Kitaoka, N., Matsubara, T., Sato, M., Takahashi, K., Wakuta, S., Kawaide, H., Matsui, H., Nabeta, K.&Matsuura, H.
Arabidopsis CYP94B3 encodes jasmonyl-L-isoleucine 12-hydroxylase, a key enzyme in the ocxidative catabolism of jasmonate.
Plant Cell Physiol. (2011) doi:/10.1093/pcp/pcr110

---

Mashiguchi, K., Tanaka, K., Sakai, T., Sugawara, S., Kawaide, H., Natsume, M., Hanada, A., Yaeno, T., Shirasu, K., Yao, H., McSteen, P., Zhao, Y., Hayashi, K., Kamiya, Y.&Kasahara, H.
The main auxin biosynthesis pathway in Arabidopsis.
Proc. Natl. Acad. Sci. USA (2011) doi:/0.1073/pnas.1108434108

---

Sugai, Y., Ueno, Y., Hayashi, K., Oogami, S., Toyomasu, T., Matsumoto, S., Natsume, M., Nozaki, H.&Kawaide, H.
Enzymatic 13C labeling and multidimensional NMR analysis of miltiradiene synthesized by bifunctional diterpene cyclase in Selaginella moellendorffii.
J. Biol. Chem. (2011) doi:/10.1074/jbc.M111.302703

---

Komatsu, T., Kawaide, H., Saito, C., Yamagami, A., Shimada, S., Nakazawa, M., Nakano, A., Tsujimoto, M., Natsume, M., Abe, H., Asami, T.& Nakano, T.
The Chloroplast protein BPG2 functions in brassinosteroid-mediated posttranscriptional accumulation of chloroplst rRNA.
Plant J. (2010) doi:/10.1111/j.1365-313X.2009.04077.x

---

Hayashi, K., Horie, K., Hiwatashi, Y., Kawaide, H., Yamaguchi, S., Hanada, A., Nakashima, T., Nakajima, M., Mander, L.N., Yamane, H., Hasebe, M.&Nozaki, H.
Endogenous diterpenes derived from ent-kaurene, a common gibberellin precursor, regulate protonema differentiation of the moss Physcomitrella patens.
Plant Phyisiol. (2010) doi:/10.1104/pp.110.157909

---

Kozone, I., Hashimoto, M., Graefe, U., Kawaide, H., Abe, H. &Natsume, M.
Structure-activity relationship of pamamycins: Effect of side chain length on aerial mycelium-inducing activity.
J. Antibiot. (2008) doi:/10.1038/ja.2008.118

---

Katsumata, T., Hasegawa, A., Fujiwara, T., Komatsu, T., Notomi, M., Abe, H., Natsume, M.&Kawaide, H.
Arabidopsis CYP85A2 catalyzes lactonization reactions in the biosynthesis of 2-deoxy-7-oxalactone brassinosteroids.
Biosci. Biotechnol. Biochem. (2008) doi:/10.1271/bbb.80192

---

Okada, K., Kasahara, H., Yamaguchi, S., Kawaide, H., Kamiya, Y., Nojiri, H.&Yamane, H.
Genetic evidence for the role of isopentenyl diphosphate isomerases in the mevalonate pathway and plant development in Arabidopsis.
Plant Cell Physiol. (2008) doi:/10.1093/pcp/pcn032

---

Sawada, Y., Katsumata, T., Kitamura, J., Kawaide, H., Nakajima, M., Asami, T., Nakaminami, K., Kurahashi, T., Mitsuhashi, W., Inoue, Y.&Toyomasu, T.
Germination of photoblastic lettuce seeds is regulated via the control of endogenous physiologically active gibberellin content, rather than of gibberellin responsiveness.
J. Exp. Bot. (2008) doi:/10.1093/jxb/ern192

---

Ko, KW., Lin, F., Katsumata, T., Sugai, Y., Miyazaki, S., Kawaide, H., Okada, K., Nojiri, H.&Yamane, H.
Functional identification of a rice ent-kaurene oxidase, OsKO2, using the Pichia pastoris expression system.
Biosci. Biotechnol. Biochem. (2008) doi:/10.1271/bbb.80427

---

Aoki, Y., Yoshida, M., Kawaide, H., Abe, H.&Natsume, M.
Structural determination of hypnosin, a spore germination inhibitor of phytopathogenic Streptomyces sp. causing root tumor in melon (Cucumis sp.).
J. Agric. Food Chem. (2007) doi:/10.1021/jf072719x

---

Aoki, Y., Yoshida, M., Kawaide, H., Abe, H.&Natsume, M.
Isolation and characterization of a spore germination inhibitor from Streptomyces sp. CB-1-1, a phytopathogen causing root tumor of melon.
Biosci. Biotechnol. Biochem. (2007) doi:/10.1271/bbb.60649

---

Nozaki, H., Hayashi, K., Nishimura, N., Kawaide, H., Matsuo, A.&Takaoka, D.
Momilactone A and B as allelochemicals from moss Hypnum plumaeforme: First occurrence in bryophytes.
Biosci. Biotechnol. Biochem. (2007) doi:/10.1271/bbb.70625

---

Kawaide, H.
Biochemical and molecular analyses of gibberellin biosynthesis in fungi.
Biosci. Biotechnol. Biochem. (2006) doi:/10.1271/bbb.70.583

---

Aoki, Y., Yoshida, Y., Yoshida, M., Kawaide, H., Abe, H.&Natsume, M.
Anthranilic acid, a spore germination inhibitor of phytopathogenic Streptomyces sp. B-9-1 causing root tumor of melon.
Actinomycetologica (2006) doi:/10.3209/saj.19.48

---

Hayashi, K., Kawaide, H., Notomi, M., Sakigi, Y., Matsuo, A.&Nozaki, H.
Identification and functional analysis of bifunctional ent-kaurene synthase from the moss Physcomitrella patens.
FEBS Lett. (2006) doi:/10.1016/j.febslet.2006.10.018

---

2024日本蘚苔類学会　優秀発表賞（2024年9月，宮崎）
  受賞題目: 顕花植物とは異なる進化を遂げた蘚類由来イソプレン合成酵素の進化起源の解明

---

日本農芸化学奨励賞（2024年1月，東京）
  受賞題目: 植物における新たな生活環制御に関わるテルペノイドの生合成研究

---

2023 日本農芸化学会関東支部 優秀発表賞(2023年8月,東京)
  受賞題目: 蘚類ハイゴケ由来のイソプレン合成酵素の同定

---

2023 日本蘚苔類学会 優秀発表賞(2023年8月,山形)
  受賞題目: 蘚類ハイゴケ由来のイソプレン合成酵素の同定

---

2014 Valent Bioscience Cooperation Best Poster Presentation Award (PGRSA/JSCRP 7th Joint Meeting)(2014年7月, サンフランシスコ)
  受賞題目: Substrate Recognition-Product Diversity of ent-kaurene synthases in land plants

---

植物化学調節学会第47回大会ポスタ－賞（2012年10月，山形）
  受賞題目: 黄麹菌Aspergillus oryzae由来キメラ型新規ジテルペン合成酵素の反応解析

---

社団法人 日本農芸化学会 欧文誌（Bioscience, Biotechnology and Biochemistry） 2011年BBB論文賞

---

植物化学調節学会第46回大会ポスタ－賞（2011年11月，宇都宮）
  受賞題目: 酵素合成法による完全C-13標識化と多次元NMRを組合わせたmiltiradiene合成酵素の機能解析

---

日本農芸化学会 日本農芸化学会２０１０年度大会トピックス賞（2010年3月，東京）
  受賞題目: 酢酸を原料とした活性型ジベレリンの酵素的全合成

---

TERPNET 2009 Good Presentation Award (9th International meeting: Biosynthesis and function of isoprenoids in plants, microorganisms and parasites)
  受賞題目: Biosynthetic enzyme-dependent synthesis and labeling of natural terpenoids.

---

植物化学調節学会第42回大会ポスタ－賞（2007年10月，静岡）
  受賞題目: 酢酸を出発原料としたゲラニルゲラニル二リン酸の酵素的合成

---