トシマ ヒロアキ
戸嶋 浩明教授
Hiroaki TOSHIMA

■研究者基本情報

組織

  • 地球・地域環境共創機構  地球・地域環境共創機構長
  • 農学部 食生命科学科
  • 農学研究科(修士課程) 農学専攻 実践農食科学コース
  • 応用生物学野 食生命科学領域

研究分野

  • ライフサイエンス, 応用生物化学, 有機合成化学
  • ライフサイエンス, 生物有機化学, 有機合成化学
  • ライフサイエンス, 生物有機化学, 生物有機化学

研究キーワード

  • 天然物、コロナチン、ジャスモン酸、ジテルペン、合成、生合成、プローブ、花芽誘導、KODA

学位

  • 1990年03月 理学博士(慶應義塾大学)

経歴

  • 2022年04月 - 現在, 茨城大学地球・地域環境共創機構(GLEC)機構長
  • 2018年04月 - 2022年03月, 茨城大学農学部長・農学研究科長
  • 2016年04月 - 2018年03月, 全学教育機構 副機構長(共通教育部門長)
  • 2011年04月 - 2014年03月, 茨城大学大学教センター 副センター長(企画実施部長)
  • 2008年04月, 茨城大学教授農学部
  • 2007年04月 - 2008年03月, 茨城大学准教授農学部
  • 2001年04月 - 2007年03月, 茨城大学助教授農学部
  • 2001年10月, 東京農工大学大学院連合農学研究科(併任)
  • 1999年04月 - 2001年03月, 北海道大学大学院助手農学研究科
  • 1991年04月 - 1999年03月, 北海道大学助手農学部
  • 1990年04月 - 1991年03月, 田辺製薬株式会社(有機化学研究所)

委員歴

  • 2017年04月 - 2019年03月, 農薬デザイン研究会委員, 日本農薬学会 農薬デザイン研究会
  • 2011年04月 - 2017年03月, 編集委員, 日本農薬学会
  • 2011年04月 - 2015年03月, 英文誌編集委員, 日本農芸化学会
  • 2011年03月 - 2013年02月, 編集委員, 有機合成化学協会

■研究活動情報

受賞

  • 2000年04月, 2000年度農芸化学奨励賞(日本農芸化学会), 植物の病害および生理機能に関与する生理活性物質の合成研究

論文

  • Identification of an aldehyde synthase involved in indole-3-acetic acid biosynthesis in the galling sawfly (Pontania sp.) and screening of an inhibitor
    Miyata; U.; Arakawa; K.; Takei; M.; Asami; T.; Asanbou; K.; Toshima; H.; Suzuki; Y., Indole-3-acetic acid (IAA), a phytohormone auxin, may be involved in insect gall induction. We previously proposed that the IAA biosynthetic pathway is Trp → indole-3-acetaldoxime → indole-3-acetaldehyde (IAAld) → IAA or Trp → IAAld → IAA. In this study, we surveyed galling sawfly enzymes responsible for the rate-limiting steps using a heterologous protein expression system and identified PonAAS2, an aromatic aldehyde synthase, that catalyzed the conversion of Trp to IAAld. The PonAAS2 gene was highly expressed in early- and mid-stage larvae that contained high concentrations of IAA, but the expression level was almost negligible in larvae that had escaped from their gall in autumn and contained very low concentrations of IAA. An inhibitor of PonAAS2, obtained by screening a chemical library, inhibited IAA production in sawfly enzyme solution by 80%, suggesting the important role of this enzyme in IAA biosynthesis in sawfly., Elsevier
    Insect Biochemistry and Molecular Biology, 2021年08月18日, [査読有り]
  • Heterologous biosynthesis of fungal indole sesquiterpene sespendole
    Kosei Kudo; Chengwei Liu; Tomoyuki Matsumoto; Atsushi Minami; Taro Ozaki; Hiroaki Toshima; Katsuya Gomi; Hideaki Oikawa, Indole sesquiterpene sespendole, which has been isolated from the filamentous fungus Pseudobotrytis terrestris FKA-25, is a specific inhibitor of lipid droplet synthesis in mouse macrophages. The biosynthetic pathway that involves genes encoding six enzymes (spdEMBQHJ) was elucidated through heterologous expression of spd genes in Aspergillus oryzae, biotransformation experiments, and in vitro enzymatic reactions with a recombinant protein, thereby revealing the mechanism underlying the characteristic modification on the indole ring, catalyzed by a set of prenyltransferase (SpdE)/cytochrome P450 (SpdJ) enzymes. Functional analysis of the homologous genes encoding these enzymes involved in the biosynthesis of lolitrem allowed a biosynthetic pathway for the bicyclic ring skeleton fused to the indole ring to be proposed., Wiley-VCH
    ChemBioChem, 2018年05月02日, [査読有り]
  • Xylosylated Detoxification of the Rice Flavonoid Phytoalexin Sakuranetin by the Rice Sheath Blight Fungus Rhizoctonia solani
    S. Katsumata; H. Toshima; M. Hasegawa, Sakuranetin (1) is a rice flavanone-type phytoalexin. We have already reported that the metabolites from the detoxification of 1 by Pyricularia oryzae are naringenin (2) and sternbin. In this study, we investigated whether the rice sheath blight fungus Rhizoctonia solani, another major rice pathogen, can detoxify 1. The extract of R. solani suspension culture containing 1 was analyzed by LC-MS to identify the metabolites of 1. Three putative metabolites of 1 were detected in the extract from the R. solani suspension culture 12 h after the addition of 1, and they were identified as 2, sakuranetin-4-O-β-D-xylopyranoside (3), and naringenin-7-O-β-D-xylopyranoside (4) by NMR, LC-MS/MS, and GC-MS analyses. The accumulation of 2, 3, and 4 reached their maximum levels 9–12 h after the addition of 1, whereas the content of 1 decreased to almost zero within 9 h. The antifungal activities of 3 and 4 against R. solani were negligible, and 2 showed weaker antifungal activity than 1. We concluded that 2, 3, and 4 are metabolites from the detoxification of 1 by R. solani. Xylosylation is a rare and efficient detoxification method for phytoalexins., MDPI AG
    Molecules, 2018年01月29日, [査読有り]
  • Identification of sternbin and naringenin as detoxified metabolites from the rice flavanone phytoalexin sakuranetin by Pyricularia oryzae
    S. Katsumata; K. Hamana; K. Horie; H. Toshima; M. Hasegawa, Sakuranetin (1) is a flavanone phytoalexin that has been reported to play an important role in disease resistance in rice plants. The rice blast fungus Pyricularia oryzae (syn. Magnaporthe oryzae) has been reported to metabolize 1 to lower its antifungal activity. Here, two flavanones, sternbin (2) and naringenin (3), were identified as metabolites of 1 in P.oryzae suspension culture by liquid chromatography tandem mass spectrometry (LC/MS/MS). The inhibition of 1, 2, and 3 on P.oryzae mycelial growth were 45%, 19%, and 19%, respectively, at a concentration of 100m. Thus, 2 and 3 are detoxified metabolites of 1 by P.oryzae., WILEY-V C H VERLAG GMBH
    Chemistry & Biodiversity, 2017年02月14日, [査読有り]
  • Ultraviolet-induced amides and casbene diterpenoids from rice leaves
    Kiyotaka Horie; Kengo Sakai; Misaki Okugi; Hiroaki Toshima; Morifumi Hasegawa, To discover new phytoalexins, an 80% MeOH extract of UV-irradiated rice leaves was analyzed using LC-MS, resulting in the detection of three unidentified compounds. We isolated the compounds from the UV-irradiated rice leaves using chromatographic methods and identified the compounds as N-benzoyltyramine (1), and two casbene-type diterpenes, 5-dihydro-ent-10-oxodepresssin (2) and 5-deoxo-ent-10-oxodepressin (3), using spectroscopic methods. Additionally, we compared the accumulation levels of major UV-inducible compounds in response to Magnaporthe oryzae inoculation and the antifungal activities of the compounds against M. oryzae colony growth. Although 1-3 showed negligible antifungal activity against M. oryzae, the compounds significantly accumulated in M. oryzaeinoculated rice leaves. Furthermore, we confirmed that N-benzoyltryptamine and N-cinnamoyltryptamine also accumulated after M. oryzae inoculation and have relatively high antifungal activity against M. oryzae to the same extent as phytocassanes. These results strongly support the hypothesis that the two amides are rice phytoalexins. (C) 2015 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved., ELSEVIER SCIENCE BV
    PHYTOCHEMISTRY LETTERS, 2016年03月, [査読有り]
  • Identification of UV-Induced Diterpenes Including a New Diterpene Phytoalexin, Phytocassane F, from Rice Leaves by Complementary GC/MS and LC/MS Approaches
    Kiyotaka Horie; Yasuno Inoue; Miki Sakai; Qun Yao; Yosuke Tanimoto; Jinichiro Koga; Hiroaki Toshima; Morifumi Hasegawa, Rice phytoalexins are regarded as one of the most important weapons against pathogenic microorganisms. We attempted to identify novel phytoalexins and their derivatives using GC/MS and LC/MS analyses. Diterpene derivatives, 9 beta-pimara-7,15-diene-3 beta,6 beta,19-triol, 1, stemar-13-en-2 alpha-ol, 2, and 1 alpha,2 alpha-dihydroxy-ent-12,15-cassadiene-3,11-dione, 3, were isolated from UV-irradiated rice leaves by chromatographic methods. These structures were confirmed by 1D- and 2D-NMR and MS analyses. Interestingly, all three compounds were accumulated following an infection by the rice blast pathogen. Magnaporthe oryzae. Compounds 1 and 2 exhibited weak antifungal activity and may be the biosynthetic intermediates of rice phytoalexins momilactones and oryzalexin S, respectively. Compound 3 exhibited relatively high inhibitory activity against the fungal mycelial growth of M. oryzae to the same extent as the known phytoalexin phytocassane A. We conclude that 3 is a member of the cassane-type phytoalexin family and propose the name phytocassane F., AMER CHEMICAL SOC
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2015年04月, [査読有り]
  • Biosynthetic pathway of the phytohormone auxin in insects and screening of its inhibitors
    Hiroyoshi Suzuki; Junpei Yokokura; Tsukasa Ito; Ryoma Arai; Chiaki Yokoyama; Hiroaki Toshima; Shinji Nagata; Tadao Asami; Yoshihito Suzuki, Insect galls are abnormal plant tissues induced by galling insects. The galls are used for food and habitation, and the phytohormone auxin, produced by the insects, may be involved in their formation. We found that the silkworm, a non-galling insect, also produces an active form of auxin, indole-3-acetic acid (IAA), by de novo synthesis from tryptophan (Trp). A detailed metabolic analysis of IAA using IAA synthetic enzymes from silkworms indicated an IAA biosynthetic pathway composed of a three-step conversion: Trp → indole-3-acetaldoxime → indole-3-acetaldehyde (IAAld) → IAA, of which the first step is limiting IAA production. This pathway was shown to also operate in gall-inducing sawfly. Screening of a chemical library identified two compounds that showed strong inhibitory activities on the conversion step IAAld → IAA. The inhibitors can be efficiently used to demonstrate the importance of insect-synthesized auxin in gall formation in the future. © 2014 Elsevier Ltd., Elsevier Ltd
    Insect Biochem. Mol. Biol., 2014年08月08日, [査読有り]
  • Regiospecificities and prenylation mode specificities of the fungal indole diterpene prenyltransferases AtmD and PaxD
    Chengwei Liu; Atsushi Minami; Motoyoshi Noike; Hiroaki Toshima; Hideaki Oikawa; Tohru Dairi, We recently reported the function of paxD, which is involved in the paxilline (compound 1) biosynthetic gene cluster in Penicillium paxilli. Recombinant PaxD catalyzed a stepwise regular-type diprenylation at the 21 and 22 positions of compound 1 with dimethylallyl diphosphate (DMAPP) as the prenyl donor. In this study, atmD, which is located in the aflatrem (compound 2) biosynthetic gene cluster in Aspergillus flavus and encodes an enzyme with 32% amino acid identity to PaxD, was characterized using recombinant enzyme. When compound 1 and DMAPP were used as substrates, two major products and a trace of minor product were formed. The structures of the two major products were determined to be reversely monoprenylated compound 1 at either the 20 or 21 position. Because compound 2 and β-aflatrem (compound 3), both of which are compound 1-related compounds produced by A. flavus, have the same prenyl moiety at the 20 and 21 position, respectively, AtmD should catalyze the prenylation in compound 2 and 3 biosynthesis. More importantly and surprisingly, AtmD accepted paspaline (compound 4), which is an intermediate of compound 1 biosynthesis that has a structure similar to that of compound 1, and catalyzed a regular monoprenylation of compound 4 at either the 21 or 22 position, though the reverse prenylation was observed with compound 1. This suggests that fungal indole diterpene prenyltransferases have the potential to alter their position and regular/reverse specificities for prenylation and could be applicable for the synthesis of industrially useful compounds. © 2013, American Society for Microbiology.
    Applied and Environmental Microbiology, 2013年12月, [査読有り]
  • Reconstitution of Biosynthetic Machinery for Indole-Diterpene Paxilline in Aspergillus oryzae
    Koichi Tagami; Chengwei Liu; Atsushi Minami; Motoyoshi Noike; Tetsuya Isaka; Shuhei Fueki; Yoshihiro Shichijo; Hiroaki Toshima; Katsuya Gomi; Tohru Dairi; and Hideaki Oikawa, Indole-diterpenes represented by paxilline share a common pentacyclic core skeleton derived from indole and geranylgeranyl diphosphate. To shed light on the detailed biosynthetic mechanism of the paspaline-type hexacyclic skeleton, we examined the reconstitution of paxilline biosynthetic machinery in Aspergillus oryzae NSAR1 Stepwise introduction of the six pax genes enabled us to isolate all biosynthetic intermediates and to synthesize paxilline. In vitro and in vivo studies on the key enzymes, prenyltransferase PaxC and cyclase PaxB, allowed us to elucidate actual substrates of these enzymes. Using the isolated and the synthesized epoxide substrates, the highly intriguing stepwide epoxidation/cyclization mechanism for the construction of core structure has been confirmed. In addition, we also demonstrated "tandem transformation" to simultaneously introduce two genes using a single vector (paxG/paxB, pAdeA; paxP/paxQ pUNA). This may provide further option for the reconstitution strategy to synthesize more complex fungal metabolites., AMER CHEMICAL SOC
    J. Am. Chem. Soc., 2013年01月13日, [査読有り]
  • Identification of a novel casbane-type diterpene phytoalexin, ent-10-oxodepressin, from rice leaves Bioscience, Biotechnology, and Biochemistry
    Yasuno Inoue; Miki Sakai; Qun Yao; Yosuke Tanimoto; Hiroaki Toshima; Morifumi Hasegawa, A 70% methanol extract of UV-irradiated rice leaves (400 g) was separated by chromatographic methods to give UV-induced compound 1 (2.1 mg) which showed a possible molecular ion at m/z 300 in the GC/MS analysis. Its structure was determined by NMR and MS methods. The H-1- and C-13-NMR spectra of 1 were identical to those of 10-oxodepressin (2), a casbane-type diterpene derived from the soft coral, Sinularia depressa. The specific rotation of 1 was positive, whereas that of 2 was negative. We therefore established 1 as ent-10-oxodepressin. The accumulation of 1 was also induced by an inoculation of the rice blast fungus. Compound 1 inhibited spore germination (IC50 30 ppm) and germ tube growth (IC50 10 ppm) of the rice blast fungus. We thus concluded that 1 was a novel rice phytoalexin., TAYLOR & FRANCIS LTD
    Bioscience, Biotechnology, and Biochemistry, 2013年, [査読有り]
  • Stereoselective Synthesis of Promising Flower-inducing KODA Analog, (9R,12S,13R,15Z)-9-Hydroxy-12,13-methylene-10-oxooctadec-15-enoic acid
    Shin Shimomura; Shuho Oyama; Kyouhei Nakano; Morifumi Hasegawa; Hiroaki Toshima, 責任著者, Stereoselective synthesis of a promising flower-inducing 9,10-ketol octadecadienoic acid (KODA) analog, (9R,12S,13R,15Z)-9-hydroxy-12,13-methylene-10-oxooctadec-15-enoic acid, was designed to obtain the desired stereoisomer via coupling between chiral sulfone and aldehyde segments. A known chiral cyclopropane derivative was converted to the sulfone segment via carbon-chain elongation and sulfonylation. Dec-9-en-1-ol was converted to the aldehyde segment, whose C-9 configuration was introduced by Sharpless asymmetric dihydroxylation. Coupling of the both segments and subsequent assembly gave the desired (9R,12S,13R,15Z)analog. The (9S,12S,13R,15Z)-analog was also synthesized by using the enatiomeric aldehyde segment. This strategy made it possible to synthesize the remaining stereoisomeric analogs., TAYLOR & FRANCIS LTD
    Bioscience, Biotechnology, and Biochemistry, 2013年, [査読有り]
  • Identification of a degradation intermediate of the momilactone A rice phytoalexin by the rice blast fungus.
    Imai T; Ohashi Y; Mitsuhara I; Seo S; Toshima H; Hasegawa M
    Bioscience, Biotechnology, and Biochemistry, 2012年, [査読有り]
  • Identification of a degradation intermediate of a rice phytoalexin, momilactone A               
    Takuya Imai; Yuko Ohashi; Ichiro Mitsuhara; Shigemi Seo; Hiroaki Toshima; Morifumi Hasegawa
    Biosci. Biotechnol. Biochem., 2012年, [査読有り]
  • Biomimetic cyclization of epoxide precursors of indole mono-, sesqui- and diterpene alkaloids by Lewis acids.
    Tetsuya Isaka; Morifumi Hasegawa; and Hiroaki Toshima, 責任著者, Cyclization of the synthesized epoxide precursors of indole mono-, sesqui- and diterpene alkaloids was performed to elucidate the mechanism for biomimetic cationic cyclization to polycyclic structures. 3-(6,7-Epoxygeranyl)indole (11), 3-(10,11-epoxyfarnesyl)indole (2) and 3-(14,15-epoxygeranylgeranyl)indole (3) were respectively synthesized from geraniol, farnesol and geranylgeraniol in 6 or 7 steps. Four Lewis acids (MeAlCl2, BF3 center dot OEt2, TiCl4 and SnCl4) were applied for biomimetic cyclization of the synthesized epoxide precursors. The cyclization products (one product from 11, four products from 2, and three products from 3) were isolated after separation by chromatography. Their structures were determined by using NMR (COSY, HSQC, HMBC, NOESY, etc.) and HRMS analyses. The results show that biomimetic cyclization gave new polycyclic compounds similar to natural indole terpene alkaloids. We conclude that the stability of cation intermediates should determine the preference for product formation by biomimetic cyclization when using a Lewis acid., TAYLOR & FRANCIS LTD
    Biosci. Biotechnol. Biochem., 2011年, [査読有り]
  • Synthesi of Optically Active γーValerolactone bad δーNonanolactone via Optical Resolution Using Chiral Amine Derived from Amino Acid
    Kenichi Yumoto; Morifumi Hasegawa; Hiroaki Toshima, 責任著者, Optically active gamma-valerolactone and gamma-nonanolactone have been synthesized via optical resolution using a newly developed chiral airline derived from L-phenylalanine. Both racemic gamma-lactones were transformed to corresponding diastereomeric amides by amidation with the optical resolution agent. Fractional crystallization of diastereomeric amides, recrystallization of each diastereomer, and Subsequent hydrolysis gave optically active gamma-valerolactone and gamma-nonanolactone with Sufficient enantiomeric excess and isolated yield. The optical resolution agent was recovered after hydrolysis., PERGAMON-ELSEVIER SCIENCE LTD
    Heterocycles, 2010年, [査読有り]
  • Nocardioides sp. strain WSN05-2, isolated from a wheat field, degrades deoxynivalenol, producing the novel intermediate 3-epi-deoxynivalenol               
    Ikunaga, Y; Sato, I; Grond, S; Numaziri, N; Yoshida. S; Yamaya, H; Hiradate, S; Hasegawa, M; Toshima, H; Koitabashi, M; Ito, M; Karlovsky, P; Tsushima, S
    Appl Microbiol Biotechnol, 2010年, [査読有り]
  • Identification of diterpene biosynthetic gene clusters and functional analysis of labdane-related diterpene cyclases in Phomopsis amygdali.
    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., Two diterpene biosynthesis gene clusters in the fusicoccin-producing fungus, Phomopsis amygdali, were identified by genome walking from PaGGS1 and PaGGS4 which encode the geranylgeranyl diphosphate (GGDP) synthases. The diterpene cyclase-like genes, PaDC1 and PaDC2, were respectively located proximal to PaGGS1 and PaGGS4. The amino acid sequences of these two enzymes were similar to those of fungal labdane-related diterpene cyclases. Recombinant PaDC1 converted GGDP mainly into phyllocladan-16 alpha-ol via (+)-copalyl diphosphate (CDP) and trace amounts of several labdane-related hydrocarbons which had been identified from the P. amygdali F6 mycelia. Since phyllocladan-16 alpha-ol had not been identified in P. amygdali F6 mycelia, we isolated phyllocladan-16 alpha-ol from the mycelia. Recombinant PaDC2 converted GGDP into (+)-CDP. Furthermore, we isolated the novel diterpenoid, phyllocladan-11 alpha,16 alpha,18-triol, which is a possible metabolite of phyllocladan-16 alpha-ol in the mycelia. We propose that genome walking offers a useful strategy for the discovery of novel natural products in fungi., TAYLOR & FRANCIS LTD
    Biosci. Biotechnol. Biochem., 2008年, [査読有り]
  • Cloning of the gene cluster responsible for the biosynthesis of brasulicardin A, a unique diterpenoid
    Hayashi; Y.; Matsuura; N.; Toshima; H.; Itoh; N.; Ishikawa; J.; Mikami; Y.; and Dairi; T., Brasilicardin A (BCA), produced by Nocardia brasiliensis IFM 0406 (currently referred to as N. terpenica), has a unique structure consisting of a diterpene skeleton with L-rhamnose, N-acetylglucosamine, amino acid, and 3-hydroxybenzoate moieties, and exhibits potent biological activities. To understand the biosynthetic machinery of this unique compound, we have cloned the corresponding gene cluster. Firstly, we cloned a gene by PCR that encodes geranylgeranyl diphosphate synthase (GGPPS), which produces a direct precursor of diterpene compounds. We obtained four candidate genes and one of the genes was confirmed to encode a GGPPS. By sequence analysis of regions flanking the GGPPS gene, we identified eleven genes (bra1-11), all oriented in the same direction. We did not, however, detect any genes related to L-rhamnose and N-acetylglucosamine biosyntheses in the flanking regions. A gene disruption experiment did indeed show that this gene cluster was responsible for BCA biosynthesis., JAPAN ANTIBIOTICS RESEARCH ASSOC
    J. Antibiot, 2008年, [査読有り]
  • Characterization of rice gene family encoding tape-A diterpene cyclases               
    Kanno; Y.; Otomo; K.; Kenmoku; H.; Mitsuhashi; W.; Yamane; H.; Oikawa; H.; Toshima; H.; Matsuoka; M.; Sassa; T.; and Toyomasu; T.
    Biosci. Biotechnol. Biochem, 2006年, [査読有り]
  • Volatile emission by [N-(-)-jasmonoyl]-alanylleucine from rice leaves (Oryza sativa L.)
    Tamogami; S.; Suzuki; M.; Toshima; H.; Hasegawa; M.; Kodama; O.; and Noma; M., A dipeptide conjugate of jasmonic acid, [N-(-)-jasmonoyl]-L-alanyl-L-leucine, was prepared and its biological activities were investigated. The conjugate was active in the emission of linalool from rice leaves, while [N-(-)-jasmonoyl]-D-alanyl-L-leucine was not. Neither conjugate was active in the production of sakuranetin. This is the first report of a biologically active dipeptide conjugate of jasmonic acid. (c) Pesticide Science Society of Japan., PESTICIDE SCI SOC JAPAN
    J. Pestic. Sci., 2005年, [査読有り]
  • 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
    Cho; E.; Okada; A.; Kenmoku; H.; Otomo; K.; Toyomasu; T.; Mitsuhashi; W.; Sassa; T.; Yajima; A.; Yabuta; G.; Mori; K.; Oikawa; H.; Toshima; H.; Shibuya; N.; Omori; T.; Nishiyama; M. and Yamane; H., We have isolated and characterized a cDNA encoding a novel diterpene cyclase, OsDTC1, from suspension-cultured rice cells treated with a chitin elicitor. OsDTC1 functions as ent-cassa-12,15-diene synthase, which is considered to play a key role in the biosynthesis of (-)-phytocassanes recently isolated as rice diterpenoid phytoalexins. The expression of OsDTC1 mRNA was also confirmed in ultraviolet (UV)-irradiated rice leaves. In addition, we identified ent-cassa-12,15-diene, a putative diterpene hydrocarbon precursor of (-)-phytocassanes, as an endogenous compound in the chitin-elicited suspension-cultured rice cells and the UV-irradiated rice leaves. The OsDTC1 cDNA isolated here will be a useful tool to investigate the regulatory mechanisms of the biosyntheis of (-)-phytocassanes in rice., WILEY-BLACKWELL
    Plant J., 2004年, [査読有り]
  • Cloning of a Gene Cluster Responsible for the Biosynthesis of Diterpene Aphidicolin, a Specific Inhibitor of DNA Polymerase a.
    Toyomasu; T.; Nakaminami; K.; Toshima; H.; Mie; T.; Watanabe; K.; Ito; H.; Matsui; H.; Mitsuhashi; W.; Sassa; T.; and Oikawa; H., The fungal diterpene, aphidicolin, is a well-known specific inhibitor of DNA polymerase alpha. Terpenoids are an important class of natural products. However, identification of the biosynthetic gene cluster in terpenoids is relatively rare compared with another important class of natural products, polyketides. To explore a reliable identification method for the biosynthetic gene cluster in fungal diterpenoids, cloning of the biosynthetic gene cluster of aphidicolin was employed. The application of a simple PCR method for genome walking based on the sequence of cDNA encoding aphidicolan-16beta-ol synthase (ACS) allowed us to analyze a 15.6-kb region of the Phoma betae genomic DNA. Six ORFs, PbGGS, ACS, PbP450-1, PbP450-2, PbTP, and PbTF were found in this region, and respectively expected to encode geranylgeranyl diphosphate synthase, diterpene synthase, two cytochrome P-450s, the transporter and transcription factor. Their amino acid sequences and introns were deduced by a corresponding cDNA analysis. This study shows that simple PCR-based genome walking without constructing a genomic DNA library is useful for identification of a small gene cluster. We propose a general strategy for the cloning the biosynthetic genes of fungal diterpenoids by using fungal GGS., TAYLOR & FRANCIS LTD
    Biosci. Biotechnol. Biochem, 2004年, [査読有り]
  • Structure and expression of 12-oxophytodienoate reductase (subgroup I) genes in pea, and characterization of the oxidoreductase activities of their recombinant products.
    Matsui; H.; Nakamura; G.; Ishiga; Y.; Toshima; H.; Inagaki; Y.; Toyoda; K.; Shiraishi; T.; Ichinose; Y., Recently, we observed that expression of a pea gene (S64) encoding an oxophytodienoic acid reductase (OPR) was induced by a suppressor of pea defense responses, secreted by the pea pathogen Mycosphaerella pinodes. Because it is known that OPRs are usually encoded by families of homologous genes, we screened for genomic and cDNA clones encoding members of this putative OPR family in pea. We isolated five members of the OPR gene family from a pea genomic DNA library, and amplified six cDNA clones, including S64, by RT-PCR (reverse transcriptase-PCR). Sequencing analysis revealed that S64 corresponds to PsOPR2, and the amino acid sequences of the predicted products of the six OPR-like genes shared more than 80% identity with each other. Based on their sequence similarity, all these OPR-like genes code for OPRs of subgroup I, i.e., enzymes which are not required for jasmonic acid biosynthesis. However, the genes varied in their exon/intron organization and in their promoter sequences. To investigate the expression of each individual OPR-like gene, RT-PCR was performed using gene-specific primers. The results indicated that the OPR-like gene most strongly induced by the inoculation of pea plants with a compatible pathogen and by treatment with the suppressor from M. pinodes was PsOPR2. Furthermore, the ability of the six recombinant OPR-like proteins to reduce a model substrate, 2-cyclohexen-1-one (2-CyHE), was investigated. The results indicated that PsOPR1, 4 and 6 display robust activity, and PsOPR2 has a most remarkable ability to reduce 2-CyHE, whereas PsOPR3 has little and PsOPR5 does not reduce this compound. Thus, the six OPR-like proteins can be classified into four types. Interestingly, the gene structures, expression profiles, and enzymatic activities used to classify each member of the pea OPR-like gene family are clearly correlated, indicating that each member of this OPR-like family has a distinct function., SPRINGER-VERLAG
    Genet. Genomics, 2004年, [査読有り]
  • Biosynthesis of Indole Diterpenes, Emindole, and Paxilline: Involvement of a Common Intermediate
    Fueki; S.; Tokiwano; T.; Toshima; H.; and Oikawa; H., The key step for construction of the carbon skeleton in the indole diterpenes, paxilline, and emindole DA was examined. Intact incorporation of multiply H-2-labeled 3-geranylgeranylindole into two different fungal metabolites proves 3-geranylgeranylindole to be a biosynthetic intermediate. These results give evidence that indole diterpenes are biosynthesized via epoxidation of a common intermediate, and the subsequent cationic cyclization, analogous to those in the steroid biosynthesis., AMER CHEMICAL SOC
    Org. Lett., 2004年, [査読有り]
  • Dihydrocoronatine, Promising Candidate for a Chemical Probe to Study Coronatine-, Jasmonoid- and Octadecanoid-binding Protein.
    Suzuki; M.; Hasegawa; M.; Kodama; O.; and Toshima; H., 責任著者, Coronatine (1), its synthetic analogs (6-13) and jasmonic acid induced various volatiles in rice leaves. In the range of 0.01-0.1 mm, dihydrocoronatine (7) exhibited 4-687 times higher activity for linalool emission than that of 1. The radioactive derivative of 7, [4,5-H-3]-7, was employed to identify the putative coronatine-binding protein in rice leaves. 7 would be a promising candidate for a chemical probe to study cornatine-binding protein related to the jasmonoid and octadecanoid signaling pathway in higher plants. A detailed study of coronatine-binding protein in rice leaves and cell culture with [4,5-H-3]-7 is now in progress., TAYLOR & FRANCIS LTD
    Biosci. Biotechnol. Biochem., 2004年, [査読有り]
  • Selective Synthesis of Dehydroamino Acids from Threonines
    Nakamura; K.; Isaka; T.; Toshima; H.; and Kodaka; M., Dehydropeptides containing dehydroamino acid (DeltaAA) are frequently found in natural resources with important biological activity. Herein, we report the selective synthesis of Z- and E-DeltaAbu from L- and L-allo-threonine as starting materials through selenation and oxidative elimination. The detailed reaction mechanism of phosphine-assisted selenoether formation is also discussed. (C) 2004 Elsevier Ltd. All rights reserved., PERGAMON-ELSEVIER SCIENCE LTD
    Tetrahedron Lett., 2004年, [査読有り]
  • Biological Function of ent- and syn-Copalyl Diphosphate Synthases in Rice: Key Enzymes for the Branch Point of Gibberellin and Phytoalexin Biosynthesis
    Otomo; K.; Kenmoku; H.; Oikawa; H.; Koning; W. A.; Toshima; H.; Mitsuhashi; W.; Yamane; H.; Sassa; T.; and Toyomasu; T., Rice (Oryza sativa L.) produces ent-copalyl diphosphate (ent-CDP) and syn-CDP as precursors for several classes of phytoalexins and the phytohormones, gibberellins (GAs). It has recently been shown that a loss-of-function mutation of OsCPS1, a gene encoding a putative ent-CDP synthase, results in a severely GA-deficient dwarf phenotype in rice. To clarify the biological functions of the ent- and syn-CDP synthases involved in the biosynthesis of phytoalexins and/or GAs, we isolated two cDNAs, OsCyc1 and OsCyc2, encoding putative diterpene cyclases from ultraviolet (UV)-irradiated rice leaves (cv. Nipponbare). The production of phytoalexins in rice leaves is known to be highly induced by UV treatment. Using a bacterial expression system, we demonstrated that OsCyc1 encodes syn-CDP synthase and that OsCyc2 and OsCPS1 encode ent-CDP synthase. The level of expression of the OsCyc1 and OsCyc2 transcripts in rice leaves increased drastically in response to UV treatment, whereas expression of the OsCPS1 transcript was not induced by UV light. These results suggest that OsCyc1, OsCyc2 and OsCPS1 are responsible for the biosynthesis of momilactones A and B and oryzalexin S, oryzalexins A-F and phytocassanes A-E, and GAs, respectively. Our results strongly suggest the presence of two ent-CDP synthase isoforms in rice, one that participates in the biosynthesis of GAs and a second that is involved in the biosynthesis of phytoalexins., BLACKWELL PUBLISHING LTD
    Plant J., 2004年, [査読有り]
  • Diterpene Cyclases Responsible for the Biosynthesis of Phytoalexins, Momilactones A, B and Oryzalexins A-F, in Rice.
    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., Rice (Oryza sativa L.) produces diterpene phytoalexins, such as momilactones, oryzalexins, and phytocassanes. Using rice genome information and in vitro assay with recombinant enzymes, we identified genes (OsKS4 and OsKS10) encoding the type-A diterpene cyclases 9beta-pimara-7,15-diene synthase and ent-sandaracopimara-diene synthase which are involved in the biosynthesis of momilactones A, B and oryzalexins A-F respectively. Transcript levels of these two genes increased remarkably after ultraviolet (UV) treatment, which is consistent with elevated production of phytoalexins by UV. These two genes might prove powerful tools for understanding plant defense mechanisms in rice., TAYLOR & FRANCIS LTD
    Biosci. Biotechnol. Biochem, 2004年
  • Simultaneous Analysis of Phytohormones, Phytotoxins and Volatile Organic Compounds in Plants
    Schmelz; E. A.; Engelberth; J.; Alborn; H. T.; OユDonnell; P.; Sammons; M.; Toshima; H.; and Tumlinson; J. H., Phytohormones regulate the protective responses of plants against both biotic and abiotic stresses by means of synergistic or antagonistic actions referred to as signaling crosstalk. A bottleneck in crosstalk research is the quantification of numerous interacting phytohormones and regulators. The chemical analysis of salicylic acid, jasmonic acid, indole-3-acetic acid, and abscisic acid is typically achieved by using separate and complex methodologies. Moreover, pathogen-produced phytohormone mimics, such as the phytotoxin coronatine (COR), have not been directly quantified in plant tissues. We address these problems by using a simple preparation and a GC-MS-based metabolic profiling approach. Plant tissue is extracted in aqueous 1-propanol and mixed with dichloromethane. Carboxylic acids present in the organic layer are methylated by using trimethylsilylcliazomethane; analytes are volatilized under heat, collected on a polymeric absorbent, and eluted with solvent into a sample vial. Analytes are separated by using gas chromatography and quantified by using chemical-ionization mass spectrometry that produces predominantly [M+H](+) parent ions. We use this technique to examine levels of COR, phytohormones, and volatile organic compounds in model systems, including Arabidopsis thaliana during infection with Pseudomonas syringae pv. tomato DC3000, corn (Zea mays) under herbivory by corn earworm (Helicoverpa zea), tobacco (Nicotiana tabacum) after mechanical damage, and tomato (Lycopersicon esculentum) during drought stress. Numerous complex changes induced by pathogen infection, including the accumulation of COR, salicylic acid, jasmonic acid, indole-3-acetic acid, and abscisic acid illustrate the potential and simplicity of this approach in quantifying signaling crosstalk interactions that occur at the level of synthesis and accumulation., NATL ACAD SCIENCES
    Proc. Natl. Acad. Sci. USA, 2003年, [査読有り]
  • Proposed Mechanism for the Reaction Catalyzed by a Diterpene Cyclase, Aphidecolan-16β-ol synthase: Experimental Results on Biomimetic Cyclization and Examination of the Cyclization Pathmay by ab Initio Calculations
    Oikawa, H; Nakamura, K; Toshima, H; Toyomasu, T; Sassa, T, To examine the mechanism of the cyclization reaction catalyzed by aphidicolan-16beta-ol synthase (ACS), which is a key enzyme in the biosynthesis of diterpene aphidicolin, a specific inhibitor of DNA polymerase alpha, skeletal rearrangement of 2a and biomimetic cyclization of 4b were employed. The structures of the reaction products, which reflect penultimate cation intermediates, allowed us to propose a detailed reaction pathway for the Lewis acid-catalyzed cyclizations and rearrangements. Isolation of these products in an aphidicolin-producing fungus led us to speculate that the mechanism of the ACS-catalyzed cyclization reaction is the same as that of a nonenzymatic reaction. Ab initio calculations of the acid-catalyzed reaction intermediates and the transition states indicate that the overall reaction catalyzed by ACS is an exothermic process though the reaction proceeds via an energetically disfavored secondary cation-like transition state. In coni. unction with the solvent effect in the acid-catalyzed reactions, this indicates that the actual role of ACS is to provide a template which enforces conformations of the intermediate cations leading to the productive cyclization although it has been believed that the cation-pi interaction between cation intermediates and aromatic amino acid residues in the active site is important for the enzymatic catalysis. This study provided important information on the role of various cationic species, especially secondary cation-like structures, in both nonenzymatic and enzymatic reactions., AMER CHEMICAL SOC
    J. Am. Chem. Soc, 2002年, [査読有り]
  • Total Synthesis of (+,-)-syn-Copalol
    Toshima; H.; Oikawa; H.; Yada; H.; Ono; H.; Toyomasu; T.; and Sassa; T., 筆頭著者, The labdane diterpene derivative, syn-copalol [ (+)-5] is the alcohol part of syn-copalyl diphosphate [ (+)-4] In this paper, racemic ()-5 was synthesized from a known racemic lactone in 8 steps. The current and our previous syntheses provide all four copalol derivatives [ (+)-3, (-)-3 and (+/-)-51 which are required for the biosynthetic study of polycyclic diterpenes., TAYLOR & FRANCIS LTD
    Biosci. Biotechnol. Biochem., 2002年, [査読有り]
  • (-)-Semivioxanthin, A New Abscisic Active Compound against Hinoki Cypress Leaves Isolated from Cryptosporiopsis abietina
    Yada; H.; Sato; H.; Toshima; H.; Deura; M. and Ichihara; A., The new naphthopyrone, (-)-semivioxanthin (1) was isolated from Cryptosporiopsis abietina. The structure of I was determined as the reversed optical isomer of semivioxanthin by comparing its spectroscopic data with those of semivioxanthin. Compound 1 exhibited abscisic activity against Hinoki cypress leaves and antifungal activity against Cladosporium herbarum., TAYLOR & FRANCIS LTD
    Biosci. Biotechnol. Biochem., 2001年, [査読有り]
  • Total Synthesis of (+)-Albicanol and (+)-Albicanyl Acetate
    Toshima; H.; Oikawa; H.; Toyomasu; T. and Sassa; T., 筆頭著者, The drimane sesquiterpenes, (+)-albicanol (2) and (+)-albicanyl acetate (3), mere synthesized from an optically active bicyclic diol [ (+)-1] that had been obtained via the recently developed optical resolution of a general synthetic intermediate for drimane sesquiterpenes, The crucial step in the previous syntheses was markedly improved by the modified Wittig methylenation of a silyloxy ketone (7), The high overall yield (77% in 4 or 5 steps from (+)-1) by this total synthesis makes it possible to synthesize the other biologically active drimane sesquiterpenes., TAYLOR & FRANCIS LTD
    Biosci. Biotechnol. Biochem., 2001年, [査読有り]
  • Structural Confirmation of 15-Norlubiminol and 15-Norepi-Lubiminol, Isolated from Solanum aethiopicum, by Chemical Conversion from Lubimin and Epilubimin, and their Antifungal Activity
    Watanabe; A.; Toshima; H.; Nagase; H.; Nagaoka; T. and Yoshihara; T., 15-Norlubiminol and 15-norepilubiminol were obtained from Solanum aethiopicum as an inseparable 1:1 mixture in a relatively poor yield to that of the major phytoalexins, lubimin and epilubimin. Their structures were confirmed by chemical conversion starting from lubimin and epilubimin. Baeyer-Villiger oxidation of the protected lubimins with m-chloroperoxybenzoic acid provided the desired formates. Deoxygenation with triphenylphosphine selenide and subsequent methanolysis provided 15-norlubiminols, whose H-1-NMR spectra were respectively identical with that of the corresponding isomer in the natural 15-norlubiminol mixture. The antifungal activity of 15-norlubiminols would be weaker than that of lubimins., TAYLOR & FRANCIS LTD
    Biosci. Biotechnol. Biochem., 2001年, [査読有り]
  • Diversity of Diterpene Hydrocarbons in Fungus Phoma betae
    Oikawa; H.; Toshima; H.; Ohashi; S.; Konig; W. A.; Kenmoku; H. and Sassa; T., Isolation and examination of diterpene hydrocarbons produced by the fungus Phoma betae allowed us to determine the structures of eight compounds. Analysis by capillary GC with a cyclodextrin derived chiral stationary phase allowed us to determine the absolute configuration of the diterpenes. The occurrence of aphidicolenes, stemar-13-ene, pimara- and isopimaradienes demonstrates the diversity of diterpenes found in this fungus. (C) 2001 Elsevier Science Ltd. All rights reserved., PERGAMON-ELSEVIER SCIENCE LTD
    Tetrahedron Lett., 2001年, [査読有り]
  • Syntheses of β-Resorcylic Acid Derivatives, Novel Potato Micro-tuber Inducing Substances Isolated from Lasiodiplodia theobromae
    Qing, Y; Toshima, H; Yoshihara, T, The syntheses of beta -resorcylic acid derivatives 1 and 2, isolated from fungus Lasiodiplodia theobromae, and their dimethyl ethers were accomplished. (R)-(-)-1,3-Butanediol was used as a chiral source of the side chain C-6-synthon. The dianion of the benzoic acid moiety was alkylated with C-6-bromide to give the desired skeleton. Several beta -resorcylic acid derivatives including 1 and 2 were synthesized via hydrogenation, lactonization, demethylation and esterification. The (R)-configuration of the stereogenic center in the side chain was proved by this synthesis. It is confirmed that two phenolic hydroxy groups are required for 1 and 2 to exhibit potato micro-tuber inducing activity. (C) 2001 Elsevier Science Ltd. All rights reserved., PERGAMON-ELSEVIER SCIENCE LTD
    Tetrahedron, 2001年, [査読有り]
  • Cloning and Functional Expression of cDNA Encoding Aphidicolan-16β-of Synthase : A Key Enzyme Responsible for Formation of an Unusual Diterpene Skeleton in Biosynthesis of Aphidicolin
    Oikawa, H; Toyomasu, T; Toshima, H; Ohashi, S; Kawaide, H; Kamiya, Y; Ohtsuka, M; Shinoda, S; Mitsuhashi, W; Sassa, T, AMER CHEMICAL SOC
    J. Am. Chem. Soc., 2001年, [査読有り]
  • Wound-induced Expression of a Tabacco Peroxidase Is Not Enhanced by Ethephon and Suppressed by Methyl Jasmorate and Coronatine
    Hiraga; S.; Ito; H.; Sasaki; K.; Yamakawa; H.; Mitsuhara; I.; Toshima; H.; Matsui; H.; Honma; M. and Ohashi; Y., In tobacco plants, wounding induces production of a set of defense-related proteins such as basic pathogenesis-related (PR) proteins and proteinase inhibitors (PIs) via the jasmonate/ethylene pathway. Although class III plant peroxidase (POX) is also wound-inducible, the regulatory mechanism for its wound-induced expression is not fully understood. Here, we describe that a tobacco POX gene (tpoxN1), which is constitutively expressed in roots, is induced locally 30 min after wounding and then systemically in tobacco plants. Infection of necrotizing virus also induced tpoxN1 gene. The wound-induced expression was not enhanced by known wound-signal compounds such as methyl jasmonate (MeJA) and ethephon in contrast to other wound-inducible genes such as basic PR-1 and PI-II genes. And treatment with MeJA and coronatine, biological analogs of jasmonate, rather suppressed the tpoxN1 expression. Salicylic acid, an antagonist of jasmonate-based wound signaling, did not suppress the wound-induced expression of tpoxN1, Only spermine, which is reported as an endogenous inducer for acidic PR genes in tobacco mosaic virus-infected tobacco leaves, could induce tpoxN1 gene expression, These results suggest that,wound-induced expression of the tpoxN1 gene is regulated differently from that of the basic PR and PI-II genes., JAPANESE SOC PLANT PHYSIOLOGISTS
    Plant Cell Physiol., 2000年, [査読有り]
  • Syntheses of Stereochemically Restricted Lactone-type Analognes of Jasmonic Acids
    Toshima; H.; Aramaki; H. and Ichihara; A., 筆頭著者, 5-Oxa-7-epi-jasmonic acid and 5-oxa-jasmonic acid, which are stereochemically restricted lactone-type analogues of jasmonic acids, were synthesized via three-component coupling of 2(5H)-furanone, tert-butyl acetate and 1-bromo-2-pentyne. After acidic deprotection of the tert-butyl esters, the (Z)-olefin was introduced by catalytic partial reduction with the Lindlar catalyst to give the desired analogues., TAYLOR & FRANCIS LTD
    Biosci. Biotechnol. Biochem., 2000年, [査読有り]
  • Synthesis and Potato Cell Expansion-inducing Activity of the Stereochemically Restricted Bicyclic Analogue of 7-Epi-jasmonic Acid
    Toshima; H.; Nara; S.; Fujino; Y. and Ichihara; A., 筆頭著者, The stereochemically restricted bicyclic analogue of 7-epi-jasmonic acid was synthesized from a known bicyclo[3.3.0]octane derivative. The enol triflate derived from the bicyclic compound was subjected to palladium-catalyzed coupling with allyltributyltin to give the desired carbon skeleton. Selective catalytic hydrogenation and subsequent acidic hydrolysis gave a new bicyclic analogue of 7-epi-jasmonic acid. The ACC conjugate of the bicyclic analogue was also synthesized. This ACC conjugate exhibited only slightly weaker potato cell expansion-inducing activity than that of the JA standard., TAYLOR & FRANCIS LTD
    Biosci. Biotechnol. Biochem., 2000年, [査読有り]
  • Total Synthesis of Both Enantiomers of Copalol via Optical Resolution of a General Synthetic Intermediate for Drimane Sesquiterpenes and Labdane Diterpenes
    Toshima; H.; Oikawa; H.; Toyomasu; T. and Sassa; T., 筆頭著者, The total synthesis of both enantiomers of copalol (6) was accomplished via the optical resolution of a racemic diol [ (+/-)-4] which is a general synthetic intermediate for drimane sesquiterpenes and labdane diterpenes. Esterification between (+/-)-4 and Boc-L-proline gave the diastereomeric pair of monoesters (5a and 5b) which could be readily separated by flash column chromatography. PDC-oxidation of the resolved 5a and 5b, and subsequent beta -elimination gave optically active enones (9 and ent-9). Both enones were respectively converted into (+)-6 in 36% yield and (-)-6 in 26% yield in five steps: (1) Sakurai reaction (TiCl4-promoted conjugate addition of allylsilane), (2) Wittig methylenation, (3) Wacker oxidation, (4) Horner-Emmons reaction, and (5) DIBAL-H reduction. (C) 2000 Elsevier Science Ltd. All rights reserved., PERGAMON-ELSEVIER SCIENCE LTD
    Tetrahedron, 2000年, [査読有り]
  • Study on Fungitoxic 3-Amino-2-piperidinone-containing Lipids : Revised Structure of Cepaciamide A and Structural Determination of its Closely Related Lipid, Cepaciamide B
    Toshima; H.; Maru; K.; Jiao; Y.; Yoshihara; T. and Ichihara; A., 筆頭著者, The structure of cepaciamide A was revised to be (3R,3'S,2"S,11"S,12"R)-3-[3'-(2"-hydroxy-11", 12"-methyleneoctadecanoyloxy)hexadecamido]-2-piperidinone with respect to the absolute configuration of the C-3'- and C-2"-positions and the position of the cyclopropane ring by using synthetic methods. The structure of cepaciamide B was also determined to be (3R,3'S,2"S,11"Z)-3-[3'-(2"-hydroxy-11"-octadecenoyloxy)hexadecamido]-2-piperidinone. (C) 1999 Elsevier Science Ltd. All rights reserved., PERGAMON-ELSEVIER SCIENCE LTD
    Tetrahedron Lett., 1999年, [査読有り]
  • Study on Fungitoxic 3-Amino-2-piperidinone-containing Lipids : Total Syntheses of Cepaciamides A and B
    Toshima; H.; Maru; K.; Saito; M. and Ichihara; A., 筆頭著者, Total syntheses of cepaciamides A and B were accomplished In the preparation of two fatty acid segments, (S)-malic acid was used as a chiral source to introduce (2S)-configuration. A known chiral cyclopropane derivative was introduced in the segment of cepaciamide A. The formation of (Z)-olefin in the segment of cepaciamide B was achieved by means of partial reduction of the acetylenic bond Esterification between fatty acid segments and amide segment with DCC/DMAP and subsequent oxidative deprotection of the MPM group with CAN gave cepaciamides. (C) 1999 Elsevier Science Ltd. All rights reserved., PERGAMON-ELSEVIER SCIENCE LTD
    Tetrahedron Lett., 1999年
  • Total Synthesis of(2S, 3R, 5S)-(-)-Dihydroxytetradecun-5-olide, A New Biologically Active δ-Lactone Produced by ┣DBSeiridium(/)-┫DB ┣DBunicorne(/)-┫DB
    Toshima, H; Sato, H; Ichihara, A, 筆頭著者, The first total synthesis of (2S,3R,5S)-(-)-2,3-dihydroxytetradecan-5-olide (1), a new biologically active delta-lactone produced by Seiridium unicome, was accomplished from (R)-malic acid In connection with the determination of the absolute configuration of 1, (2R,3S,5R)-(+)-2,3-dihydroxytetradecan-5-olide (ent-1) was also synthesized from D-glucose. (C) 1999 Elsevier Science Ltd. All rights reserved., PERGAMON-ELSEVIER SCIENCE LTD
    Tetrahedron, 1999年, [査読有り]
  • Total Synthesis of(+)-(2S, 3R)-Piscidic Acid ┣DBvia(/)-┫DB Catalytic Asymmetric Dihydroxylation of A Trisubstituted Olefin
    Toshima, H; Saito; M. and Y; Yoshihara, T, 筆頭著者, (+)-(2S,3R)-Piscidic acid was efficiently synthesized with high optical purity (90% e.e.) via Sharpless catalytic asymmetric dihydroxylation of a trisubstituted olefin in only 6 steps from commercially available 4-hydroxyphenyl-pyruvic acid as the starting material. The reaction proceeded with high optical purity by using the chiral ligands, dihydroquinidine 2,5-diphenyl-4,6-pyrimidinediyl diether or dihydroquinidine 1,4-anthraquinonediyl diether., TAYLOR & FRANCIS LTD
    Biosci. Biotechnol. Biochem., 1999年, [査読有り]
  • Synthetic Study on Naturally Occurring Acetylenic Spiroacetal Enol Ethers : The First Access to Optically Active 3,4-Diacetoxy 2-formylmethylene-1,6-dioxaspiro[4.5]decanes
    Toshima; H.; Aramaki; H. and Ichihara; A., 筆頭著者, Optically active 3,4-diacetoxy-2-formylmethylene-1,6-dioxaspiro[4.5]decanes have been synthesized from an acyclic keto-alcohol possessing an unsaturated aldehyde part via intramolecular conjugate addition. The C3- and C4-stereogenic centers were introduced via Sharpless asymmetric dihydroxylation of an acyclic conjugated ketone with modified AD-mix-alpha in high enantioselectivity (96% e.e.). This is the first access to optically active spiroacetal 2-enol ethers. (C) 1999 Elsevier Science Ltd. All rights reserved., PERGAMON-ELSEVIER SCIENCE LTD
    Tetrahedron Lett., 1999年, [査読有り]
  • Total Syntheses of Cepaciamides A and B, Novel Fungitoxic 3-Amino-2-piperidinone-containing Lipids Produced by Psendomonas cepacia D-202
    Toshima; H.; Maru; K.; Saito; M. and Ichihara; A., 筆頭著者, Total syntheses of cepaciamides A and B were accomplished (R)-3-Amino-2-piperidinone was obtained via cyclization of (R)-ornithine. The common amide-linked fatty acid was synthesized via Sharpless AD as the key step. Amide-formation was achieved with DEPC. In the preparation of two fatty acid segments, (S)-malic acid was used as the chiral source to introduce (2S)-configuration. A known chiral cyclopropane derivative was introduced in the segment of cepaciamide A. The formation of (Z)-olefin in the segment of cepaciamide B was achieved by means of partial reduction of the acetylenic bond Esterification between the fatty acid-segments and the amide-segment with DCC/DMAP and subsequent oxidative deprotection of the MPM group with CAN gave cepaciamides. (C) 1999 Elsevier Science Ltd. All rights reserved., PERGAMON-ELSEVIER SCIENCE LTD
    Tetrahedron, 1999年, [査読有り]
  • Syntheses and Tuber-inducing Activities of Unnafural Long Chain OPC-9 : 0 and OPC-10 : 0
    Toshima; H.; Takano; Y.; Ichihara; A.; Koda; Y. and Kikuta; Y., 筆頭著者, The unnatural long-chain OPCs, OPC-9:0 and OPC-10:0, were respectively synthesized from the ethyl eaters of OPC-7:0 and OPC-8:0, C-2-carbon elongation was achieved via alkylation of the enolate of tert-butyl acetate. The potato tuber-inducing activity of OPC-10:0, as well as OPC-8:0, -6:0 and -4:0, was similar to that of jasmonic acid. OPC-9:0 also exhibited weak tuber-inducing activity., TAYLOR & FRANCIS LTD
    Biosci. Biotechnol. Biochem., 1999年, [査読有り]
  • Total Synthesis of All Four Stereoisomers of Piscidic Acid via Catalytic Asymmetric Dihydroxylation of (Z)-and(E)-Trisubstituted Olefins
    Toshima; H.; Saito; M. and Yoshihara; T., 筆頭著者, All four stereoisomers of (2S, 3R)-(+)-piscidic acid were synthesized with high optical purity via Sharpless catalytic asymmetric dihydroxylation of (Z)- and (E)-trisubstituted olefins in 6 steps from (4-hydroxyphenyl)pyruvic acid. The Wittig reaction of methyl (4-hydroxyphenyl)pyruvate with (carbomethoxymethylene)triphenylphosphorane gave (Z)- and (E)-trisubstituted olefins in a 3:1 ratio. After protecting the phenolic hydroxyl group as the tert-butyl-dimethylsilyl ether, the (Z)-olefin was subjected to asymmetric dihydroxylation by using the chiral ligand, dihydroquinidine 1,4-anthraquinonediyl diether, and the reaction proceeded with 89% e.e. Desilylation and subsequent alkaline hydrolysis gave (2S, SR) (+)-piscidic acid. The optical purity was increased to >99% e.e. by recrystallization. The use of dihydroquinine 1,4-anthraquinonediyl diether enable (2R, 3S)-(-)-piscidic acid to be obtained. In the asymmetric dihydroxylation of the (E)-olefin, phthalazine ligands (dihydroquinidine and dihydroquinine 1,4-phthalazinediyl diethers) gave high e.e. values. Via the same deprotection procedure, (2S, 3S)-(+)-3-epi-piscidic acid and (2R, 3R)-(-)3-epi-piscidic acid were respectively obtained., TAYLOR & FRANCIS LTD
    Biosci. Biotechnol. Biochem., 1999年, [査読有り]
  • Improved synthesis of the C-8-C-23 segment of aplysiatoxins via asymmetric dihydroxylation of the chiral homoallylic alcohol
    H Toshima; A Ichihara, Important intermediate 2 of the segment (3) possessing four sequential asymmetric centers (C-9-C-12) of aplysiatoxins was synthesized via dihydroxylation of 5 in only 7 steps from methyl (S)-3-hydroxy-2-methylpropionate. Another promising compound (10a) was also synthesized in only 6 steps via asymmetric dihydroxylation of chiral homoallylic alcohol 4 as the key step., TAYLOR & FRANCIS LTD
    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1998年03月, [査読有り]
  • Syntheses and Potato Tuber-inducing Activity of Coronafacic Acid Analogues
    Toshima; H.; Nara; S.; Ichihara; A.; Koda; Y. and Kikuta; Y., 筆頭著者, Coronafacic acid (1) is an acid component of coronatine, and has been isolated from several pathovars of Pseudomonas syringae. Syntheses of C-6-non- and C-6-alkyl-substituted analogues of 1 were accomplished via intramolecular 1,6-conjugate addition as the key step. Among them, 1 and four C-6-alkyl-substituted analogues exhibited potato tuber-inducing activity, but the C-6-non-substituted analogue did not. It was revealed that a certain length of the C-6-alkyl group was necessary to exhibit activity., TAYLOR & FRANCIS LTD
    Biosci. Biotechnol. Biochem., 1998年, [査読有り]
  • Syntheses of 3-Oxa-OPC and 2-Fluoro-OPC Homologues
    Toshima; H.; Fujino; Y.; Ichihara; A.; Koda; Y. and Kikuta; Y., 筆頭著者, 3-Oxa-OPC and 2-fluoro-OPC homologues which do not undergo beta-oxidation were synthesized from esters of odd-numbered OPC homologues by a short-step procedure. The 3-oxa-OPC homologues were synthesized via etherification of an alcohol with tert-butyl bromoacetate under phase-transfer conditions. The 2-fluoro-OPC homologues were synthesized via the addition of the trichloromethyl anion to an aldehyde and subsequent fluorination., TAYLOR & FRANCIS LTD
    Biosci. Biotechnol. Biochem., 1998年, [査読有り]
  • Highly Stereoselective Syntheses of Spiroacetal Enol Ethers, (E)-and (Z)-Methoxycarbonylmethylene 1,6-dioxaspiro[4,5]decanes
    Toshima; H.; Aramaki; H.; Furumoto; Y.; Inamura; S. and Ichihara; A., 筆頭著者, (E)- and (Z)-2-methoxycarbonylmethylene-1,6-dioxaspiro[4.5]decanes have been synthesized from an acyclic keto alcohol possessing an alkynoate part via intramolecular conjugate addition. Under thermodynamically controlled conditions using t-BuOK in THF, the (E)-isomer could be obtained in 52:1 ratio. When a catalytic amount of Pd(OAc)(2) was used in benzene, the (Z)isomer could be obtained in 95:1 ratio. (C) 1998 Elsevier Science Ltd. All rights reserved., PERGAMON-ELSEVIER SCIENCE LTD
    Tetrahedron, 1998年, [査読有り]
  • Isolation, Structural Determination, and Total Synthesis of A New Biologically Active δ-Lactone Produced by
    Toshima, H; Watanabe, A; Sato, H; Ichihara, A, 筆頭著者, The structure of a new biologically active delta-lactone, produced by Seiridium unicome, was determined to be (2S,3R,5S)-(-)-2,3-dihydroxytetradecan-5-olide. The relative configuration was elucidated from NMR experiments. The synthesis of the enantiomer from D-glucose revealed the absolute configuration. The total synthesis of the natural form was also achieved from (R)-malic acid. (C) 1998 Elsevier Science Ltd. All rights reserved., PERGAMON-ELSEVIER SCIENCE LTD
    Tetrahedron Lett., 1998年, [査読有り]
  • Asymmetric Total Syntheses of (+)-Coronafacic Acid and (+)-Coronatine
    Toshima; H.; Nara; S. and Ichihara; A., 筆頭著者, An asymmetric total synthesis of (+)-coronafacic acid, starting from (R)-(+)-3-acetoxy-2-cyclopen-1-one as a chiral source, was accomplished, Construction of the 1-hydrindanone framework was carried out by using intramolecular 1,6-conjugate addition as the key step, Coupling between (+)-coronafacic acid and protected coronamic acid, and subsequent deprotection provided (+)-coronatine, This is the first asymmetric total synthesis of (+)-coronatine., TAYLOR & FRANCIS LTD
    Biosci. Biotechnol. Biochem., 1997年, [査読有り]
  • Asymmetric Total Syntheses of (+)-Coronafacic Acid and (+)-Coronatine, Phytotoxins isolated from Pseudomonas Syringae Pathovars
    Nara; S.; Toshima; H. and Ichihara; A., Asymmetric total synthesis of (+)-coronafacic acid (2), was accomplished via intramolecular 1, 6-conjugate addition as the key step. The chiral ester (+)-7 was prepared via two approaches: starting from (R)-(+)-4-acetoxy-2-cyclopenten-1-one (12), and using catalytic asymmetric Michael reactions promoted by heterobimetallic BINOL complexes. Coupling between (+)-2 and the protected coronamic acid 8 and subsequent deprotection by hydrogenolysis provided (+)-coronatine (1). This is the first asymmetric total synthesis of (+)-1. (C) 1997 Elsevier Science Ltd., PERGAMON-ELSEVIER SCIENCE LTD
    Tetrahedron, 1997年, [査読有り]
  • Efficient Syntheses of the OPC Homologous series, OPC-1 : 0, -3 : 0, -4 : 0, -5 : 0, -6 : 0, -7 : 0, and -8 : 0
    Toshima; H.; Nara; S.; Aramaki; H.; Ichihara; A.; Koda; Y. and Kikuta; Y., 筆頭著者, The OPC homologous series was synthesized from 2-[ (Z)-2-pentenyl]cyclopenten-1-one in short steps and with high yields. The carbon-carbon bond information was achieved by the 1,4-conjugate addition approach. This method makes it possible to supply a sufficient amount of OPC homologues which would enable significant information to be collected for plant physiological studies., TAYLOR & FRANCIS LTD
    Biosci. Biotechnol. Biochem., 1997年, [査読有り]
  • Similarites of the Biological Activities of Coronatine and Coronafacic Acid to those of Jasmonic Acid
    Koda; Y.; Takahashi; K.; Kikuta; Y.; Greulich; F.; Toshima; H. and Ichihara; A., Coronatine, a phytotoxin produced by Pseudomonas syringae pv. atropurpurea and an amide of coronafacic acid and coronamic acid, is known to induce the expansion of cells in potato tubers just as jasmonic acid (JA) does. Furthermore, the chemical structure of coronafacic acid resembles that of JA to some extent. These observations led us to postulate that coronatine and related compounds might have biological activities similar to those of JA. We compared the biological activities of coronatine and coronafacic acid to those of JA in four jasmonate-responsive assay systems, namely, in assays for tuber-inducing activity (with single-node segments of potato stems), for cell expansion-inducing activity (with cells of potato tubers), for cell division-inhibiting activity (with soybean callus) and for senescence-promoting activity (with oat leaves). Coronatine had a positive effect in all these assays and its activity was 100 to 10 000 times higher than that of JA in terms of the threshold concentration for activity. Coronafacic acid also gave a positive result in all the assays, but its activity was slightly weaker than that of JA in two assay systems. These results suggest that the special configuration of side chains with respect to the plane of the cyclopentanone ring, namely, the 1R, 2S configuration in JA and the 3aS, 7aR configuration in coronatine and coronafacic acid, is necessary for these various biological activities., PERGAMON-ELSEVIER SCIENCE LTD
    Phytochemistry, 1996年, [査読有り]
  • Synthesis of Spiroacetal Enol Ethers ┣DBvia(/)-┫DB Intramolecular Conjugate Addition of Hemiacetal Alkoxides to Alkynoates
    Toshima, H; Furumoto, Y; Inamura, S; Ichihara, A, 筆頭著者, (E)- and (Z)-2-Methoxycarbonylmethylene-1,6-dioxaspiro[4.5]decane (12E, 12Z) have been constructed from the acyclic keto alcohol 11a possessing an alkynoate part under the basic conditions. By the thermodynamic control, 12E could be obtained in high selectivity. Under several basic and acidic conditions, 12Z could be isomerized to 12E. Copyright (C) 1996 Elsevier Science Ltd, PERGAMON-ELSEVIER SCIENCE LTD
    Tefrahedron Lett., 1996年, [査読有り]
  • Intramolecular 1,6-Conjugate Addition Approach for Construction of the Hydrindane Framework : Total Synthesis of(±)-Coronafacic Acid
    Nara, S; Toshima, H; Ichihara, A, A new approach for the construction of the hydrindane framework has been achieved by intramolecular 1, 6-conjugate addition under some basic conditions. The precursors, alpha, beta, gamma, delta-unsaturated esters (11a-11d) were synthesized from the ester 8 and acrolein derivatives (6a-6d) via aldol condensation. This methodology was applied to the total synthesis of (+/-)coronafacic acid and its analogues. Copyright (C) 1996 Elsevier Science Ltd, PERGAMON-ELSEVIER SCIENCE LTD
    Tetrahedron Lett., 1996年, [査読有り]
  • Practical Stereoselective Syntheses of All Four Stereoisomers of Coronamic Acid (2-Ethyl-1-amino-cyclopropane-1-carboxylic acid)
    Toshima; H. and Ichihara; A., 筆頭著者, All four stereoisomers of coronamic acid were synthesized from both enantiomers of 1,2-butanediol. Cyclopropanation of cyclic sulfate with the dibenzyl malonate anion gave cyclopropane dibenzyl ester in a quantitative yield. Transformation into a protected amino acid was achieved by stereoselective hydrolysis and Curtius rearrangement as the key steps. Saponification and subsequent acidic hydrolysis in one pot and ion exchange gave a free amino acid in a high yield., TAYLOR & FRANCIS LTD
    Biosci. Biotechnol. Biochem., 1995年, [査読有り]
  • Total Syntheses of Oscillatoxin D and 30-Methyloscillatoxin D
    Toshima; H.; Goto; T. and Ichihara; A., 筆頭著者, The first total syntheses of oscillatoxin D (1a) and 30-methyloscillatoxin D (1b) have been accomplished. The construction of the spiroether has been achieved by intramolecular Michael-type addition as a key step based on a possible biomimetic pathway., PERGAMON-ELSEVIER SCIENCE LTD
    Tetrahedron Lett., 1995年, [査読有り]
  • SYNTHETIC STUDY ON OSCILLATOXIN-D - CONSTRUCTION OF THE C-1-C-26 SPIROETHER SEGMENT BY INTRAMOLECULAR ALDOL CONDENSATION AND MICHAEL-TYPE ADDITION
    H TOSHIMA; T GOTO; A ICHIHARA, The C-1-C-7 segment (10) and the C-8-C-21 segment (14) of oscillatoxin D have been synthesized efficiently. The acyclic compound obtained by coupling of these two segments, has been converted int the C-1-C-26 spiroether (18) possessing the same stereogenic centers of oscillatoxin D. The construction of the spiroether has been achieved by intramolecular aldol condensation and Michael-type addition as key steps., PERGAMON-ELSEVIER SCIENCE LTD
    TETRAHEDRON LETTERS, 1994年06月, [査読有り]
  • Inhibitory Effect of Coronanic Acid Derivatives on Senescence in Cut Carnation Flowers
    Toshima; H.; Niwayama; Y.; Nagata; H.; Greulich; F. and Ichihara; A., 筆頭著者, (+)-(1R,2S)-Allocoronamic acid, (-)-(1S,2R)-allocoronamic acid, and their racemate showed an inhibitory effect on senesence in cut carnation flowers. This antisenescent activity was based on the inhibition of endogenous ethylene formation catalyzed by an ethylene-forming enzyme., TAYLOR & FRANCIS LTD
    Biosci. Biotechnol. Biochem., 1993年, [査読有り]
  • Synthetic Study on Aplysiatoxins, Highly Inflammatory Agents and Tumor Promoters : Synthesis of Three Optically Active Segments
    Toshima; H.; Yoshida; S.; Suzuki; T.; Nishiyama; S. and Yamamura; S., PERGAMON-ELSEVIER SCIENCE LTD
    Tetrahedron Lett., 1989年, [査読有り]
  • Synthetic Study on Aplysiatoxins, Highly Inflammatory Agents and Tumor Promoters : Synthesis of 3-Deoxydebromoaplysiatoxin
    Toshima; H.; Suzuki; T.; Nishiyama; S. and Yamamura; S., 筆頭著者, PERGAMON-ELSEVIER SCIENCE LTD
    Tetrahedron Lett., 1989年, [査読有り]
  • Total Synthesis and Absolute Configuration of Aurovertin B, An Acute neurotoxic Metabolite
    Nishiyama; S.; Toshima; H.; Kanai; H. and Yamamura; S., PERGAMON-ELSEVIER SCIENCE LTD
    Tetrahedron, 1988年, [査読有り]
  • Isolation, Structural Elucidation, and Total Synthesis of Epiisocitreovinidinol
    Nishiyama; S.; Shizuri; Y.; Toshima; H.; Ozaki; M.; Yamamura; S.; Kawai; K.; Kawai; N. and Furukawa; H., CHEMICAL SOC JAPAN
    Chem. Lett., 1987年, [査読有り]
  • Total Synthesis and Absolute Configuration of Aurovertin B
    1) Nishiyama; S.; Toshima; H.; Kanai; H. and Yamamura; S., PERGAMON-ELSEVIER SCIENCE LTD
    Tetrahedron Lett., 1986年, [査読有り]
  • Total Synthesis of Citreoviridinol and Neccitreoviridinol               
    Nishiyama, S; Toshima, H; Yamamura, S
    Chem. Lett., 1986年, [査読有り]

MISC

書籍等出版物

  • 植物生理現象解明の鍵化学物質コロナチン               
    戸嶋浩明, 共著
    大学教育出版, 2005年
  • Coronatine: Chemistry and Biological Activities               
    A. Ichihara; H. Toshima, 共著
    CRC Press LLC, 1999年
  • 植物病原菌由来の植物成長調節物質               
    市原耿民; 吉原照彦; 戸嶋浩明, 共著
    学会出版センター, 1997年
  • Total Synthesis of Bioactive Natural Spiroethers, Tautomycin and Oscillatoxin D               
    A. Ichihara; H. Oikawa; H. Toshima, 共著
    Elsevier Science B.V., 1996年

講演・口頭発表等

  • ホウレンソウ葉のフラボン型ファイトアレキシン               
    村田悠夏、鳥井 潤一郎、戸嶋 浩明、長谷川 守文
    日本農芸化学会 2023 年度大会, 2023年03月15日
  • ゴール形成ハバチ(Pontania sp.)のIAA生合成酵素PonAAS2の解析               
    宮田海; 阿讃坊和也; 戸嶋浩明; 藤本瑞; 鈴木義人
    植物化学調節学会第 56 回大会, 2021年11月13日, 植物化学調節学会
  • ホウレンソウ葉における塩化銅ストレス誘導性化合物の同定               
    鳥井 潤一郎、戸嶋 浩明、長谷川 守文
    日本農芸化学会 2021 年度大会, 2021年03月19日
  • ジャスモン酸メチルによってイネ根部で誘導されるジテルペノイドファイトアレキシン類の探索               
    早川優介,手塚大介; 菊地爽太; 今井亮三; 豊増知伸; 戸嶋浩明,長谷川守文
    日本農薬学会第46回大会, 2021年03月09日
  • イネフェニルアミド型フィトアレキシンのイネ病原真菌による解毒代謝               
    隠塚修平、Surono Dwi Saputra、戸嶋浩明、長谷川守文
    日本農薬学会第45回大会, 2020年03月08日
  • イネのアミド型ファイトアレキシンの病原真菌による代謝               
    隠塚修平,木村塁,香川明慶,西脇萌,戸嶋浩明,長谷川 守文
    日本農芸化学会 2019 年度大会, 2019年03月24日
  • イネフィトアレキシンであるモミラクトンAのイネ病原真菌による代謝               
    隠塚修平、勝間田駿、武山恵典、戸嶋浩明、長谷川守文
    日本農薬学会第43回大会, 2018年05月26日
  • イネ紋枯病菌によるフィトアレキシン代謝産物の構造決定及び抗菌活性               
    勝間田駿、隠塚修平、戸嶋浩明、長谷川守文
    日本農芸化学会2018年度大会, 2018年03月16日
  • 植物病原菌に対するイネフィトアレキシンの抗菌活性               
    勝間田駿、大橋佳奈、戸嶋浩明、長谷川守文
    日本農芸化学会2017年度大会(2017), 2017年03月18日
  • イネフィトアレキシン モミラクトンAのイネいもち病菌による代謝産物の同定               
    武山 恵典、平石 由貴、遠藤 尚、今井 卓也、戸嶋 浩明、長谷川 守文
    日本農芸化学会2016年度大会(2016), 2016年03月28日
  • シクロペンタン導入型KODA類縁体の合成研究               
    渡辺 美聡、横山 峰幸、長谷川 守文、戸嶋 浩明
    日本農芸化学会2016年度大会(2016), 2016年03月28日
  • 紫外線照射イネ葉に蓄積するアミド化合物とイネいもち病菌に対する抗菌活性               
    堀江清孝,酒井健伍,奥木美咲,戸嶋浩明,長谷川守文
    日本農芸化学会2015年度大会(2015), 2015年03月27日
  • イネのフィトアレキシンであるサクラネチンのいもち病菌による代謝               
    濱名一穂、戸嶋浩明、長谷川守文
    日本農芸化学会2014年度大会(2014), 2014年03月29日
  • 紫外線照射イネ葉からの新規ファイトカサン類縁体の同定               
    井上靖乃、堀江清孝、戸嶋浩明、長谷川守文
    日本農芸化学会2014年度大会(2014), 2014年03月29日
  • インドールジテルペンの生合成に関与するプレニル基転移酵素に関する研究-1               
    劉成偉、南篤志、野池基義、戸嶋浩明、及川英秋、大利徹
    日本農芸化学会2014年度大会(2014), 2014年03月28日
  • 抗β―酸化型CP-KODA(30x0-CP-KODA)の合成研究               
    大山秀芳、中山ともみ、長谷川守文、戸嶋浩明
    日本農芸化学会2013年度大会(2013), 2013年03月26日
  • インドールジテルペン・パキシリンの酵素的全合成               
    田上紘一、劉成偉、南篤志、野池基義、井坂哲也、笛木周平、七条好宏、戸嶋浩明、五味勝也、大利徹、及川英秋
    日本農芸化学会2013年度大会(2013), 2013年03月26日
  • 生合成類似環化反応による新規インドールテルペン類の合成研究               
    井坂哲也、長谷川守文、戸嶋浩明
    日本農芸化学会2012年度大会(2012), 2012年03月24日
  • イネフィトアレキシン モミラクトンBのいもち病菌による代謝産物の同定               
    今井卓也、戸嶋浩明、長谷川守文
    植物化学調節学会46回大会, 2011年11月02日
  • 紫外線照射イネ葉からの新奇ジテルペン化合物ent-10-oxodepressinの単離               
    井上靖乃、阪井美紀、姚群、谷本洋輔、戸嶋浩明、長谷川守文
    植物化学調節学会46回大会, 2011年11月02日
  • ルイス酸を用いた環化反応によるインドールテルペン類の合成研究               
    井坂哲也、長谷川守文、戸嶋浩明
    日本農芸化学会2011年度大会(2011), 2011年03月26日
  • シクロプロパン環導入型KODA類縁体の立体異性体選択的合成               
    下村伸、長谷川守文、横山峰幸、伊福欧二、山村庄亮、戸嶋浩明
    日本農芸化学会2011年度大会(2011), 2011年03月26日
  • イネフィトアレキシン モミラクトンAのいもち病菌による代謝産物の同定               
    今井卓也、大橋祐子、光原一朗、瀬尾茂美、戸嶋浩明、長谷川守文
    植物化学調節学会45回大会, 2010年11月
  • ルイス酸を用いた環化反応による非天然型インドールアルカロイドの合成               
    井坂哲也、長谷川守文、戸嶋浩明
    日本化学会 第4回関東支部大会(2010), 2010年08月30日
  • シクロプロパン環導入型KODA類縁体の立体異性体選択的合成法に関する研究               
    下村伸、長谷川守文、横山峰幸、伊福欧二、山村庄亮、戸嶋浩明
    日本化学会 第4回関東支部大会(2010), 2010年08月30日
  • シクロプロパン環導入型KODA類縁体の立体選択的合成法に関する研究               
    下村伸、長谷川守文、横山峰幸、伊福欧二、山村庄亮、戸嶋浩明
    日本農芸化学会2010年度大会, 2010年03月
  • イネフィトアレキシン モミラクトンAのいもち病菌による代謝               
    今井卓也、大橋祐子、光原一朗、瀬尾茂美、戸嶋浩明、長谷川守文
    日本農芸化学会2010年度大会, 2010年03月
  • イチゴ葉の温湯処理による炭疽病菌抵抗性の誘導               
    佐々木克宗、Widiastuti Ani、長谷川守文、戸嶋浩明、 佐藤達雄
    植物化学調節学会第44回大会, 2009年10月
  • 紫外線照射によって誘導されるイネ葉片中のジテルペン化合物の同定および定量               
    長谷川守文、姚群、古池秀平、戸嶋浩明
    日本農芸化学会2009年度大会, 2009年03月
  • アミノ酸修飾型キラルアミンによるγ−およびδ−ラクトンの光学分割               
    湯本賢一、長谷川守文、戸嶋浩明
    日本農芸化学会2009年度大会, 2009年03月
  • 生合成類似反応によるインドールジテルペンの合成研究(2)               
    井坂哲也、星野力、及川英秋、戸嶋浩明
    日本農芸化学会2008年度大会, 2008年03月
  • 光学活性syn-Copalolの合成               
    中嶋春菜、及川英秋、豊増知伸、佐々武史、戸嶋浩明
    日本農芸化学会2008年度大会, 2008年03月
  • 紫外線照射イネ葉片からのストレス誘導性化合物の精製               
    姚群、阪井美紀、戸嶋浩明、長谷川守文
    日本農芸化学会2008年度大会, 2008年03月
  • インドールジテルペノイドの生合成               
    戸嶋浩明
    日本農芸化学会 薮田セミナー「新領域を拓く微生物・植物の二次代謝テルペノイド生合成研究」, 2007年05月, [招待有り]
  • 生合成類似反応によるインドールジテルペン類の合成研究               
    井坂哲也、中嶋春菜、戸嶋浩明
    日本農芸化学会2006年度大会, 2006年03月
  • コムギのB型ジテルペン環化酵素遺伝子               
    豊増知伸、廣瀬裕子、加賀原拓真、菅野裕理、大友一子、三橋渉、及川英秋、戸嶋浩明、佐々武史
    日本農芸化学会2006年度大会, 2006年03月
  • コロナチン結合タンパク質解明を目指した分子プローブの開発               
    鈴木宗典、長谷川守文、渡邊吉則、児玉治、戸嶋浩明
    日本農芸化学会2005年度大会, 2005年03月
  • イネのジテルペン型ファイトアレキシン生合成酵素遺伝子について               
    大友一子、菅野裕理、茂木彰宏、太田和哉、加賀原拓真、兼目裕允、山根久和、三橋渉、及川英秋、戸嶋浩明、伊藤博紀、松岡信、佐々武史、豊増知伸
    日本農芸化学会2005年度大会, 2005年03月
  • コロナチン-、ジャスモノイド-、及びオクタデカノイド結合タンパク質解明プローブ、ジヒドロコロナチン               
    鈴木宗典、長谷川守文、児玉治、戸嶋浩明
    植物化学調節学会第39回大会, 2004年10月
  • イネファイトアレキシン、モミラクトンA,BとオリザレキシンA-Fの生合成に関与するジテルペン環化酵素               
    菅野裕理、大友一子、茂木彰宏、兼目裕允、山根久和、三橋渉、及川英秋、戸嶋浩明、伊藤博紀、松岡信、佐々武史、豊増知伸
    植物化学調節学会第39回大会, 2004年10月
  • イネ葉中のジャスモノイル-CoAチオエステラーゼ活性               
    長谷川守文、坂本雄紀、戸嶋浩明、児玉治
    植物化学調節学会第38回大会, 2003年10月
  • イネのコパリル二リン酸合成酵素遺伝子について               
    大友一子、豊増知伸、三橋渉、及川英秋、戸嶋浩明、伊藤博紀、松岡信、佐々武史
    植物化学調節学会第38回大会, 2003年10月
  • 植物毒素由来の合成プローブから解き明かす植物生理現象               
    戸嶋浩明
    日本農芸化学会関東支部会2003年度大会, 2003年10月, [招待有り]
  • イネ葉におけるファイトアレキシン生合成に関与するジテルペン環化酵素遺伝子のクローニングと機能解析               
    大友一子、豊増知伸、三橋渉、兼目裕允、及川英秋、戸嶋浩明、佐々武史
    日本農芸化学会2003年度大会, 2003年04月
  • 植物毒素コロナチンの構造活性相関研究               
    鈴木宗典、児玉治、戸嶋浩明
    日本農芸化学会2003年度大会, 2003年04月
  • ヒノキ鱗片葉脱離活性を有するδ-lactoneの構造活性相関研究               
    斎藤淳、児玉治、戸嶋浩明
    日本農芸化学会関東支部会2002年度大会, 2002年10月
  • イネ葉におけるファイトアレキシン生合成に関与するジテルペン環化酵素遺伝子のクローニングと機能解析               
    大友一子、豊増知伸、三橋渉、兼目裕允、及川英秋、戸嶋浩明、佐々武史
    植物化学調節学会第37回大会, 2002年10月
  • イネ培養細胞におけるファイトアレキシン生合成に関与するジテルペン環化酵素遺伝子OsDTC1のcDNAクローニングと機能解析               
    趙銀敏、岡田敦、兼目裕允、豊増知伸、及川英秋、戸嶋浩明、佐々武史、矢島新、薮田五郎、森謙治、渋谷直人、大森俊雄、西山真、山根久和
    植物化学調節学会第37回大会, 2002年10月
  • ファイトアレキシンモミラクトンAの生合成に関する研究               
    Anotai Atawong、張智強、長谷川守文、戸嶋浩明、児玉治
    日本農薬学会第27回大会, 2002年03月

所属学協会

  • 2002年04月 - 現在, 日本農薬学会
  • 1995年04月 - 現在, 植物化学調節学会
  • 1992年04月 - 現在, 日本農芸化学会
  • 1987年03月 - 現在, 有機合成化学協会
  • 1985年04月 - 現在, 日本化学会