基本情報

所属

• 農学研究院　連携研究部門　連携推進分野

職名

• 准教授

学位

• 博士（農学）（北海道大学）

科研費研究者番号

• 60218906

J-Global ID

• 200901021221974676

研究キーワード

• 有機合成   過冷却促進物質   キラル誘導体化試薬   天然物化学   

研究分野

• 環境・農学 / 植物保護科学
• 環境・農学 / 植物保護科学
• ライフサイエンス / 生物有機化学

担当教育組織

•  学士課程　農学部
•  修士課程　農学院
•  博士課程　農学院

所属学協会

• アメリカ化学会   American Chemical Society   

研究活動情報

その他活動・業績

• 深過冷却するカツラ木部柔細胞由来の加水分解性ガロタンニンの過冷却活性に関する研究

  王 東暉, 春日 純, 桑原 慎子, 福士 幸治, 藤川 清三, 荒川 圭太 低温生物工学会誌 57 (2) 147 -151 2011年 [査読無し][通常論文]
   

  Xylem parenchyma cells (XPCs) of boreal trees adapt to subzero temperatures by deep supercooling. Previous studies suggested that intracellular substances were important for maintaining a supercooling state of cellular water at subzero temperatures in XPCs. In our recent studies, four kinds of flavonol glycosides and four kinds of hydrolyzable gallotannins were identified as supercooling-facilitating (SCF; anti-ice nucleation) substances in xylem extracts of katsura tree (Cercidiphyllum japonicum). In the present study, we examined SCF capabilities of the four kinds of hydrolyzable gallotannins in solutions containing different kinds of ice nucleators, including Erwinia ananas, Xanthomonas campestris, silver iodide, and 1,3,5-trihydroxybenzene (phloroglucinol). The results showed that all four gallotannins exhibited SCF capabilities in the solutions containing various kinds of ice nucleators, but capabilities were dependent on their concentrations and the type of ice nucleator used.
• Analysis of supercooling-facilitating (anti-ice nucleation) activity of flavonol glycosides

  Jun Kasuga, Yukiharu Fukushi, Chikako Kuwabara, Donghui Wang, Atsushi Nishioka, Emiko Fujikawa, Keita Arakawa, Seizo Fujikawa CRYOBIOLOGY 60 (2) 240 -243 2010年04月 [査読無し][通常論文]
   

  Deep Supercooling Xylem parenchyma cells (XPCs) of katsura tree (Cercidiphyllum japonicum) contain four kinds of flavonol glycosides with high supercooling-facilitating (anti-ice nucleation) activities These flavonol glycosides have very similar structures, but their supercooling-facilitating activities are very different In this study, we analyzed the supercooling-facilitating activities of 12 kinds of flavonol glycosides in order to determine the chemical structures that might affect supercooling-facilitating activity All of the flavonol glycosides tested showed supercooling-facilitating activity, although the magnitudes of activity differed among the compounds It was clear that the combination of the position of attachment of the glycosyl moiety, the kind of attached glycosyl moiety and the structure of aglycone determined the magnitude of anti-ice nucleation activity However, there is still some ambiguity preventing the exact identification of features that affect the magnitude of supercooling-facilitating activity. (C) 2009 Elsevier Inc. All rights reserved
• Do aphid galls provide good nutrients for the aphids?: Comparisons of amino acid concentrations in galls among Tetraneura species (Aphididae: Eriosomatinae)

  Debora K. Suzuki, Yukiharu Fukushi, Shin-ichi Akimoto ARTHROPOD-PLANT INTERACTIONS 3 (4) 241 -247 2009年12月 [査読無し][通常論文]
   

  Some aphid species induce leaf galls, in which the fundatrix parthenogenetically produces many nymphs. In order to ensure high performance, galls have to provide the aphids with sufficient nutrients, in particular, amino acids as a nitrogen source. We tested this hypothesis using six Tetraneura aphid species that induce closed galls. We extracted free amino acids from the whole gall tissues of unit weight and quantified the concentration of each amino acid. There were large differences in the total amino acid concentrations among galls of the Tetraneura species. Tetraneura species in which higher concentrations of total amino acids were found in the gall tended to produce larger numbers of offspring. Of the amino acids found, asparagine was predominant in the gall. The asparagine concentration in T. yezoensis galls was several hundred times as high as in control leaves. We discussed why such a high level of asparagine accumulates in aphid galls.
• Synthesis of Benzophenone Glucopyranosides from Phaleria macrocarpa and Related Benzophenone Glucopyranosides

  Phebe Hendra, Yukiharu Fukushi, Yasuyuki Hashidoko BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 73 (10) 2172 -2182 2009年10月 [査読無し][通常論文]
   

  The first total syntheses of benzophenone glucopyranosides reported from Phaleria macrocarpa and related benzophenone glucopyranosides were successfully carried out. The alkoxy groups present ortho to the carbonyl group in polyalkoxybenzophenones were selectively deprotected by AlCl3-PhNMe2 in high yields, leaving other alkoxy groups unaffected. It was concluded in the current synthetic study that all the reported benzophenone glucopyranosides possessed the same structure as 2,4',6-trihydroxy-4-methoxybenzophenone 2-O-beta-D-glucopyranoside.
• Efficient Synthesis of a New L-Shaped Dimer of Naphthalene, and Its Analogs

  Ken Yoshioka, Izumi Takaishi, Kazunari Shiozawa, Yukiharu Fukushi, Satoshi Tahara BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 72 (10) 2632 -2639 2008年10月 [査読無し][通常論文]
   

  Efficient syntheses of 14H-dinaphtho[1,8-bc:1',8'-fg]oxocin-14-one (2), 14H-dinaphtho[1,8-bc:1',2'-f[oxe-pin-14-one (3), and 2,2'(2H,2'H)-spirobi[naphtho[1,8-bc]furan] (9) are described. The putative structure of 2 has been reported previously, but the synthetic route was not reproducible. 7H-Dibenzo[c,h]xanthen-7-one (4), a known compound, was obtained by a different method. Possible reaction mechanism are proposed.
• Characterization of two O-methyltransferase-like genes in barley and maize

  Jian-Min Zhou, Yukiharu Fukushi, Eckhard Wollenweber, Ragai K. Ibrahim PHARMACEUTICAL BIOLOGY 46 (1-2) 26 -34 2008年01月 [査読無し][通常論文]
   

  Tricin (3',5'-dimethoxy-5,7,4'-trihydroxyflavone) is a characteristic flavone constituent of cereal grain plants that is credited for a variety of potential health benefits to humans. We have characterized the flavone-specific O-methyltransferase genes of barley (Hordent vulgare L., Gramineae), HvOMT1, and maize (Zea mays L., Gramineae), ZmOMT1, whose gene products use the flavone tricetin (5,7,3',4',5'-pentahydroxyflavone) as the preferred substrate and give rise to its 3',5'-dimethyl derivative, tricin, as the major product. The fact that homologous enzymes catalyze the same reaction also in wheat and rice suggests the existence in cereal grain plants of a flavone-specific O-methyltransferase multigene family. The natural occurrence of tricin in most monocot species implies the widespread occurrence of this gene family. The pharmacological significance of tricin as a naturally occurring constituent with a potential use as a nutraceutical, and the application of metabolic engineering methods to obtain tricin-enriched cereal grain products, are discussed.
• Isolation and structure elucidation of peronosporomycetes hyphal branching-inducing factors produced by Pseudomonas jessenii EC-S101

  Eduardo Hatano, Yasuyuki Hashidoko, Abhinandan Deora, Yukiharu Fukushi, Satoshi Tahara BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 71 (6) 1601 -1605 2007年06月 [査読無し][通常論文]
   

  Pseudomonas jessenii EC-S101 produced hyphal branching-inducing and mitosis-accelerating factors active towards Peronosporomycetes, Aphanomyces cochlioides hyphae. In searching for the active substances, EtOAc-solubles extracted from EC-S101 -cultured solid medium were fractionated under the guidance of a paper disc assay using an A. cochlioides mycelium. Two active substances were subsequently isolated and the structure was elucidated by spectroscopic analysis to be (+)-4,5-didehydroacaterin (1) and 3-[(1R)-hydroxyhexyl]-5-methylene-2(5H)-furanone (2), both of which accelerated the mitotic process of A. cochlioides hyphae along with excessive branching at 1.0 mu g per disc. These compounds are likely to affect the morphophysiological development of certain eukaryotic organisms in the terrestrial ecosystem.
• Characterization of a novel flavone O-methyltransferase gene in rice

  Jian-Min Zhou, Yukiharu Fukushi, Xiao-Feng Wang, Ragai K. Ibrahim NATURAL PRODUCT COMMUNICATIONS 1 (11) 981 -984 2006年 [査読無し][通常論文]
   

  We report the characterization of a novel flavone O-methyltransferase cDNA (OsOMTI) from the rice genome database. Its recombinant protein utilizes tricetin as the preferred substrate, catalyzing its stepwise methylation to the monomethyl- (selgin), dimethyl- (tricin), as the major product, and trimethyl ether derivatives. The use of this gene to increase tricin content in grain crops is discussed in relation to its potential health benefits.
• NMR determination of the absolute configuration of beta-chiral primary alcohols

  H Fukui, Y Fukushi, S Tahara TETRAHEDRON LETTERS 46 (30) 5089 -5093 2005年07月 [査読無し][通常論文]
   

  beta-Chiral primary alcohol was derivatized to an ester by the use of a new axially chiral reagent, 2'-methoxy-1,1'-binaphthatene-8-carboxylic acid (MBCA). The absolute configuration of the original beta-chiral primary alcohol was determined by the NOE correlation between the proton signals of the reagent moiety and those of the beta-chiral primary alcohol in the ester. (c) 2005 Elsevier Ltd. All rights reserved.
• Chemical response of Picea glehnii seed-epiphytic Penicillium species to Pythium vexans under in vitro competitive conditions for mycelial growth

  K Yamaji, Y Hashidoko, Y Fukushi, S Tahara JOURNAL OF CHEMICAL ECOLOGY 31 (4) 805 -817 2005年04月 [査読無し][通常論文]
   

  The potential protection of Picea glehnii seedlings from damping off by seed-epiphytic Penicillium species was investigated. We studied the chemical response of seed-epiphytic Penicillium species (Pen. cyaneum, Pen. damascenum, and Pen. implicatum) to Pythium vexans, a damping-off fungus, in vitro. Penicillium species were cultured singly or cocultured with Pyt. vexans for 14 or 18 d, and mycelial growth, pH of culture filtrate, antifungal activity of the culture filtrate against Pyt. vexans, and the amount of antifungal compound produced by each Penicillium species, were examined. The filtrate of both the single culture of Penicillium and the coculture of Penicillium and Pyt. vexans showed antifungal activity against Pyt. vexans. In a coculture with Pyt. vexans, Pen. cyaneum produced an antifungal compound (patulin) as in the single culture. Pen. damasceman cocultured with Pyt. vexans produced an antifungal compound (citrinin), as it did in the single culture and in larger amounts on day 10. Pen. implicatum produced two antifungal compounds, frequentin and palitantin, and the ratio of frequentin (with higher antifungal activity than palitantin) to palitantin was higher in the coculture with Pyt. vexans than in the single culture. Our results indicate that these Penicillium species have the ability to produce antifiangal compounds and to keep antifungal activity under competitive condition with Pyt. vexans. The chemical response of these Penicillium species to Pyt. vexans may contribute to protect P. glehnii seedlings from damage by Pyt. vexans.
• Production of enokipodins A, B, C, and D: A new group of antimicrobial metabolites from mycelial culture of Flammulina velutipes

  Noemia Kazue Ishikawa, Keiko Yamaji, Hiroshi Ishimoto, Kiyoshi Miura, Yukiharu Fukushi, Kunihide Takahashi, Satoshi Tahara Mycoscience 46 (1) 39 -45 2005年 [査読無し][通常論文]
   

  Antimicrobial compounds enokipodins A, B, C, and D were originally isolated from the culture filtrates of Flammulina velutipes mycelial culture. Analysis of antibacterial activity by the paper disk method and quantification of enokipodins A-D by high performance liquid chromatography (HPLC) showed that F. velutipes mycelia produced enokipodins A-D in their late growing phase. Great genetic variability in production of these compounds was observed among ten strains of F. velutipes in analyses of antimicrobial activity by the hole-plate diffusion method and quantification by HPLC. Enokipodins A-D demonstrated antimicrobial activity mainly against the grampositive bacteria Bacillus subtilis and Staphylococcus aureus. Evaluation of minimum inhibitory doses (MIDs) showed that MIDs of enokipodins A and C for B. subtilis were as low as that of the penicillin G antibiotic. © The Mycological Society of Japan and Springer-Verlag Tokyo 2005.
• Quantification of the particle method for chemotactic bioassay using Peronosporomycete zoospores

  T Takayama, Y Fukushi, MT Islam, S Tahara ZEITSCHRIFT FUR NATURFORSCHUNG C-A JOURNAL OF BIOSCIENCES 59 (11-12) 892 -896 2004年11月 [査読無し][通常論文]
   

  We estimated the amount of test solution absorbed by each Chromosorb W AW particle (60-80 mesh) using an isotopic technique to quantitate the particle method. C-14-Labeled standard compounds like carbendazim (MBC), 5-O-methylcochliophilin A, sucrose and proline were dissolved in several solvents, and Chromosorb carrier particles were treated with the solution to coat the particle with these test compounds. The ratios of the radioactivity of 5 mul of the test solution to that of 2 mg of carrier particles treated with the solution at some different concentrations were measured. It was found that each carrier particle holds approx. 3.8 nl of the test solution within a range of 2 x 10(-3) to 1 x 10(-7) m concentrations. Accordingly, it is now possible to widely use the particle method as a quantitative procedure to assay chemotaxis of Peronosporomycete zoospores.
• Non-pathogenic Fusarium strains protect the seedlings of Lepidium sativum from Pythium ultimum

  H Ishimoto, Y Fukushi, S Tahara SOIL BIOLOGY & BIOCHEMISTRY 36 (3) 409 -414 2004年03月 [査読無し][通常論文]
   

  Two root-colonizing Fusarium strains, Ls-F-in-4-1 and Rs-F-in-11, isolated from roots of Brassicaceae plants, induced the resistance in Lepidium sativum seedlings against Pythium ultimum. These strains caused an increase in the content of benzyl isothiocyanate, and of its precursor glucotropaeolin, in the roots of the host plants. The increased isothiocyanate content is one of the factors contributing to the resistance of L sativum against P. ultimum. To be transformed into the fungitoxic compound benzyl isothiocyanate, glucotropaeolin has to be hydrolyzed by myrosinase, which can be produced either by plants or microorganisms. The Fusarium strain Ls-F-in-4-1 has a myrosinase activity but the strain Rs-F-in-11 has not. These results suggest that both strains are able to trigger the metabolic pathway leading to benzyl isothiocyanate production in the plant. In the case of the myrosinase-negative strain Rs-F-in-11, hydrolyzation into isothiocyanate is only due to the myrosinase activity of the plant, and in the other case, the myrosinase produced by the strain Ls-F-in-11 also would contribute to the production of isothiocyanate. This paper reports a new mode of action of non-pathogenic Fusarium strains in controlling P. ultimum. (C) 2003 Elsevier Ltd. All rights reserved.
• Enzymatic nitration of phytophenolics: evidence for peroxynitrite-independent nitration of plant secondary metabolites

  Y Sakihama, R Tamaki, H Shimoji, T Ichiba, Y Fukushi, S Tahara, H Yamasaki FEBS LETTERS 553 (3) 377 -380 2003年10月 [査読無し][通常論文]
   

  Peroxynitrite (ONOO-), a reactive nitrogen species, is capable of nitrating tyrosine residue of proteins. Here we show in vitro evidence that plant phenolic compounds can also be nitrated by an ONOO--independent mechanism. In the presence of NaNO2, H2O2, and horseradish peroxidase (HRP), monophenolic p-coumaric acid (p-CA, 4-hydroxycinnamic acid) was nitrated to form 4-hydroxy-3-nitrocinnamic acid. The reaction was completely inhibited by KCN, an inhibitor for HRP. The antioxidant ascorbate suppressed p-CA nitration and its suppression time depended strongly on ascorbate concentration. We conclude that nitrogen dioxide radical (NO2), but not ONOO-, produced by a guaiacol peroxidase is the intermediate for phytophenolic nitration. (C) 2003 Published by Elsevier B.V. on behalf of the Federation of European Biochemical Societies.
• NMR determination of the absolute configuration of chiral 1,2-and 1,3-diols

  H Fukui, Y Fukushi, S Tahara TETRAHEDRON LETTERS 44 (21) 4063 -4065 2003年05月 [査読無し][通常論文]
   

  Each of the chiral 1,2- and 1,3-diols examined was derivatized exclusively to a single diastereomeric acetal by the use of a new axially chiral reagent, 2'-methoxy-1,1'-binaphthalene-8-carbaldehyde (MBC). The absolute configuration of the original 1,2- and 1,3-diols was determined by the NOE correlation between the proton signals of the reagent moiety and those of the diol moiety in the acetals. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Nicotinamide and structurally related compounds show halting activity against zoospores of the phytopathogenic fungus Aphanomyces cochlioides

  T Shimai, MT Islam, Y Fukushi, Y Hashidoko, R Yokosawa, S Tahara ZEITSCHRIFT FUR NATURFORSCHUNG C-A JOURNAL OF BIOSCIENCES 57 (3-4) 323 -331 2002年03月 [査読無し][通常論文]
   

  In a survey of plant secondary metabolites regulating the behavior of phytopathogenic Aphanomyces cochhoides zoospores, we found that leaf extracts of Amaranthus gangeticus and cotyledon extracts of pea (Pisum sativum) remarkably halted the motility of zoospores. Bioassay-directed fractionation of A. gangeticus and pea constituents revealed that the halting activity was dependent on a single chemical factor (halting factor). The active principle was identified as nicotinamide (1) by comparing its biological activity and spectroscopic properties with those of the authentic compound. Nicotinamide (1) showed potent halting activity toward the zoospores of A. cochhoides and A. euteiches, but it exhibited very less activity against other Oomycetes, Pythium aphanidermatum and Phytophthora infestans zoospores. Interestingly, the zoospores halted by nicotinamide (1) encysted within 10 - 15 min and then the resulting cystospores regenerated zoospores instead of germination. Nicotinamide (1) and related compounds were subjected to the halting activity bioassay to elucidate the structure-activity relationships. These bioassays revealed that part structures of (A) the aromatic ring containing at least one nitrogen atom, (13) carbonyl-like group adjacent to the aromatic ring and (C) hydrogen atoms on the amide group are responsible for the strong activity. So far, this is the first report of halting activity of nicotinamide (1) against fungal zoospores.
• Determination of absolute configuration of decipinone, a diterpenoid ester with a myrsinane-type carbon skeleton, by NMR spectroscopy

  AR Jassbi, Y Fukushi, S Tahara HELVETICA CHIMICA ACTA 85 (6) 1706 -1713 2002年 [査読無し][通常論文]
   

  The absolute configuration of decipinone (2), a myrsinane-type diterpene ester previously isolated from Euphorbia decipiens, has been determined by NMR study of its axially chiral derivatives (aR)(.) and (aS)-N-hydroxy-2'-methoxy-1,1'-binaphthalene-2-carboximidoyl chloride ((aR)(MBCC)-M-. (3a) and (aS)(MBCC)-M-. (3b)). The absolute configurations at C(7) and C(13) of 2 determined were (R) and (S), respectively Therefore, considering the relative configuration of 2, the absolute configuration determined was (2S,3S,4R,5R,6R,7R,11S,12R,13S,15R).
• NMR determination of the absolute configuration of chiral 1,2- and 1,3-diols

  FUKUI H, FUKUSHI Y, TAHARA S Tetrahedron Letters 44 (21) 4063 -4065 2002年 [査読無し][通常論文]
  
• Penicillium fungi from Picea glehnii seeds protect the seedlings from damping-off

  K Yamaji, Y Fukushi, Y Hashidoko, T Yoshida, S Tahara NEW PHYTOLOGIST 152 (3) 521 -531 2001年12月 [査読無し][通常論文]
   

  In a coinoculation test of seed-epiphytic Penicillium species and pathogenic Pythium vexans to Picea glehnii seedlings, the number of surviving seedlings which were inoculated with P. vexans 5 d after preinoculation with Penicillium damascenum PGS-O7 increased compared with those inoculated with P. vexans alone. The phytotoxicity of antifungal compounds to A glehnii seeds and seedlings was assessed in growth experiments, Production of these compounds was quantitatively analysed in the rhizosphere of the host seedlings using chromatography techniques. Dense mycelial growth of P. damascenum was observed microscopically around the roots of the inoculated seedlings. Furthermore, the antifungal and phytotoxic compound citrinin produced by P. damascenum was detected as a component released around the roots of the normally growing fungus-inoculated seedlings. We propose two possible mechanisms for the protection of P. glehnii seedlings by P. damascenum from P. vexans; first, chemical protection by an antibiotic agent, citrinin produced by P. damascenum, and second, the occupation of the space around the P. glehnii roots by the P. damascenum mycelia. (C) New Phytologist (2001).
• NMR determination of the absolute configuration of a macrophomate synthase inhibitor by using an axial chiral reagent

  H Fukui, Y Fukushi, S Ohashi, S Tahara BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 65 (8) 1920 -1923 2001年08月 [査読無し][通常論文]
   

  Macrophomate synthase catalyzes an extraordinary four-step transformation from oxalacetate and 2-pyrone to macrophomic acid by an intermolecular Diels-Alder reaction. The absolute configuration of the most potent macrophomate synthase inhibitor; (-)-2-carboxylmethyl-1-methoxybicyclo[2.2.2]oct-5-ene-2-carboxylic acid, was determined to be (1S, 2R, 4R) by using an axial chiral reagent.
• Antimicrobial cuparene-type sesquiterpenes, enokipodins C and D, from a mycelial culture of Flammulina velutipes

  NK Ishikawa, Y Fukushi, K Yamaji, S Tahara, K Takahashi JOURNAL OF NATURAL PRODUCTS 64 (7) 932 -934 2001年07月 [査読無し][通常論文]
   

  Two new cuparene-type sesquiterpenes, enokipodins C (1) and D (2), were isolated from culture medium of an edible mushroom, Flammulina velutipes, along with enokipodins A (3) and B (4). The structures of 1 and 2 were determined using spectroscopic methods (HRMS, H-1 and C-13, and 2D NMR). The absolute configuration of enokipodin C was determined from the observed IH NMR chemical shifts and NOEs in NOESY experiments after conversion into the corresponding esters with the chiral reagent 2-(2'-methoxy-1'-naphthyl)-3,4-dichlorobenzoic acid. All the metabolites showed antimicrobial activity against a fungus, Cladosporium herbarum, and Gram-positive bacteria, Bacillus subtilis and Staphylococcus aureus.
• Highly oxidized cuparene-type sesquiterpenes from a mycelial culture of Flammulina velutipes

  NK Ishikawa, K Yamaji, S Tahara, Y Fukushi, K Takahashi PHYTOCHEMISTRY 54 (8) 777 -782 2000年08月 [査読無し][通常論文]
   

  Cuparene-type sesquiterpenes were isolated from a culture broth of Flammulina velutipes (Curt.:Fr.) Sing. Using spectroscopic methods (HR-MS,H-1 and C-13 NMR, and 2D NMR, spectroscopy), their structures were determined to be 2,3,4,5-tetrahydro-2,7-dihydroxy-5,8,10,10-tetramethyl-2,5-methano-1-benzoxepin and 5-methyl-2-(3-oxo-1,2,2-trimethylcyclopentyl)benzoquinone. Both showed antimicrobial activity against Cladosporium herbarum and Bacillus subtilis. (C) 2000 Elsevier Science Ltd. All rights reserved.
• NMR determination of the absolute configuration of an alpha-exo-methylene-gamma-lactone

  H Fukui, Y Fukushi, S Tahara BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 64 (7) 1345 -1351 2000年07月 [査読無し][通常論文]
   

  Both the enantiomers of the axially chiral reagent, 2'-methoxy-1,1'-binaphthalene-2-carbohydroximoyl chloride (MBCC), were used to convert igalan, an alpha-exo-methylene-gamma-lactone, to yield 4,5-dihydroisoxazoles. The absolute configuration of igalan was determined to be (3aR,5R,6R,7aR)-6-ethenylhexahydro-6-methyl-3-methylene-5-(1-methylethenyl)-2(3H)-benzofuranone (IUPAC name) on the basis of NOE correlations in these derivatives. The absolute configurations of other alpha-exo-methylene-gamma-lactones can be determined by the same method.
• Rhizopus and Fusarium are Selected as the Dominant Fungal Gerera in Rhizospheres of Brassicaceae by Plant Secondary Metabolites

  Journal of Ecological Chemistry 26 (10) 2387 -2399 2000年 [査読無し][通常論文]
  
• Fungitoxic Alkaloids fromHokkaido Papaveraceae

  Fitoterapia 70 (5) 524 -531 2000年 [査読無し][通常論文]
  
• Phenolic glycosides from Eriosema tuberosum

  WG Ma, Y Fukushi, B Ducrey, K Hostettmann, S Tahara PHYTOCHEMISTRY 51 (8) 1087 -1093 1999年08月 [査読無し][通常論文]
   

  Three new phenolic glycosides named eriosemasides A-C, one novel (named eriosematin F) and four known phenolic constituents were isolated from the n-BuOH-soluble fraction of the roots of Eliosema tuberosum. Their structures were established by spectroscopic analyses and chemical methods. All the phenolic compounds were fungitoxic except the phenolic glycosides. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Fungitoxic alkaloids from Hokkaido Corydalis species

  WG Ma, Y Fukushi, S Tahara FITOTERAPIA 70 (3) 258 -265 1999年06月 [査読無し][通常論文]
   

  Two species of the genus Corydalis (C. incisa and C, ambigua) were phytochemically studied for their fungitoxic alkaloids. Thirteen alkaloids were isolated and identified by spectroscopic methods including mass and NMR techniques. Compounds 1 (corynoline) and 2 (acetylcorynoline) were found to be the main active compounds. The new compound 3 (named coryincine) has no fungitoxic activity. Structure-activity relationships among compounds 1-3 are discussed. (C) 1999 Elsevier Science B.V. All rights reserved.
• Conformational analysis of MNCB (MBNC) esters and amides: Promising chiral reagents for stereoselective applications

  SK Latypov, AV Aganov, S Tahara, Y Fukushi TETRAHEDRON 55 (23) 7305 -7318 1999年06月 [査読無し][通常論文]
   

  Calculations (MM, AM1/PM3, ab initio) and DNMR experiments indicate that 2-(2'-methoxy-1'-naphthyl)-3,5-dichlorobenzoic acid (MNCB) and 2'-methoxy-1,1'-binaphthyl-2-carboxylic acid (MBNC) esters and amides exist in solution as two conformers in equilibrium: one of them (sp) has synperiplanar Ar-1-Ar-2 and C=O bonds, and another one (op) has antiperiplanar bonds. Due to the close populations of the forms only a part of large shielding effects attributed to the ap form is transformed into observed high field shifts in NMR experiments. Thus, the low population of the "ap" conformer and the low selectivity of the aryl ring anisotropic influence on the alcohol (amine) moiety are limitations of the efficiency of MNCB (MBNC) in their use as reagents for absolute stereochemistry determination of alcohols and amines by NMR. The way to increase the efficiency of this type of reagent has been revealed on the basis of these findings. (C) 1999 Elsevier Science Ltd. All rights reserved.
• NMR determination of the absolute configuration of cyclic chiral alkenes

  H Fukui, Y Fukushi, S Tahara TETRAHEDRON LETTERS 40 (2) 325 -328 1999年01月 [査読無し][通常論文]
   

  By the use of a new axially chiral reagent, 2'-methoxy-1,1'-binaphthalene-2-carbohydroximoyl chloride (MBCC), chiral cyclic alkenes were stereoselectively derivatized into 4,5-dihydroisoxazoles. NOEs were observed between the protons of the reagent moiety and those of the alkene moiety in cycloadducts. The absolute configuration of the original alkenes was unambiguously determined by the NOE; correlation. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Tricyclic sesquiterpenes from Rudbeckia laciniata

  Y Fukushi, C Yajima, J Mizutani, S Tahara PHYTOCHEMISTRY 49 (2) 593 -600 1998年09月 [査読無し][通常論文]
   

  Three phytotoxic sesquiterpenes were isolated from the roots of Rudbeckia laciniata, of which one of these was designated as lacinan-8-ol. Its absolute configuration was established by the MNCB [2-(2'-methoxy-1'- naphthyl)-3,5-dichlorobenzoic acid] method. It was chemically transformed into the corresponding secondary allylic alcohol, whose absolute configuration was also determined by MNCB and CD (circular dichroism) allylic benzoate methods. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Isoflavonoid glycosides from Eriosema tuberosum

  WG Ma, Y Fukushi, K Hostettmann, S Tahara PHYTOCHEMISTRY 49 (1) 251 -254 1998年09月 [査読無し][通常論文]
   

  Five isoflavonoid glycosides together with the corresponding aglycones have been isolated from the n-BuOH-soluble fraction of a methanol extract of the roots of Eriosema tuberosum. One compound is new and its structure has been established by spectroscopic analyses and chemical methods as 5-O-methylgenistein 7-O-beta-D-apiofuranosyl-(1-->6)-O-beta-D-glucopyranoside. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Antiviral and antifungal activities of some naphthoquinones isolated from the roots of Lithospermum erythrorhizon

  CJ Li, Y Fukushi, J Kawabata, S Tahara, J Mizutani, Uyeda, I JOURNAL OF PESTICIDE SCIENCE 23 (1) 54 -57 1998年 [査読無し][通常論文]
  
• A catalytic amino acid and primary structure of active site in Aspergillus nigaer α-glucosidase

  Biosci. Biotech. Biochem. 61 (7) 1091 -1098 1997年 [査読無し][通常論文]
  
• Alloaromandendranes, bicyclogermacrane and 2,3-secoalloaromandendranes in cultured cells of the liverwort, Heteroscyphus planus

  K Nabeta, S Ohkubo, R Hozumi, Y Fukushi, H Nakai, K Katoh PHYTOCHEMISTRY 43 (1) 83 -93 1996年09月 [査読無し][通常論文]
   

  Novel ent-alloaromandendranes, planotriol and its acetates, and four ent-2,3-secoalloaromandendranes including two novel compounds in nature and one novel ent-bicyclogermacrene were isolated from cultured cells of the liverwort, Heteroscyphus planus. The absolute configuration of planotriol and its acetates were determined by a single X-ray analysis and H-1 NMR spectroscopy after derivatization with an axially chiral agent, 2-(2'-methoxy-1'-naphthyl)-3,5-dichlorobenzoic acid (MNCB). Planotriol diacetate was chemically converted into the known ent-2,3-secoalloaromandendrane, (-)-hanegokedial, suggesting that the 2,3-dihydroxy-alloaromandranes might be immediate precursors for 2,3-secoalloaromandendranes, The absolute stereochemistry of the bicyclogermacrane and the 2,3-secoalloaromandendranes was also determined by H-1 NMR analysis of the MNCB esters and chemical correlation. Copyright (C) 1996 Elsevier Science Ltd
• A new NMR chiral derivatizing reagent for determining the absolute configurations of carboxylic acids

  Y Fukushi, K Shigematsu, J Mizutani, S Tahara TETRAHEDRON LETTERS 37 (27) 4737 -4740 1996年07月 [査読無し][通常論文]
   

  Axially chiral 1,1'-binaphthalene-8,8'-diol (BNDO) was used as a chiral derivatizing reagent to determine the absolute configurations of alpha-chiral carboxylic acids by H-1 and C-13 NMR spectroscopy. Copyright (C) 1996 Elsevier Science Ltd
• Effects of lunularic acid analogs on the growth of liverwort, watercress and timothy grass

  NAKAYAMA T, FUKUSHI Y, MIZUTANI J, TAHARA S Biosci. Biotech. Biochem. 60 (5) 862 -865 1996年 [査読無し][通常論文]
  

特許

• Supercooling promoting agents.

  WO 2008007684
• 光学活性ビナフチル化合物からなるＮＭＲ用キラルシフト試薬

  特開2005-134365

共同研究・競争的資金等の研究課題

• NMRを用いた新しい絶対配置決定法の開発とその応用
• Development and application of new methods for NMR structure analyses

教育活動情報

主要な担当授業