Faculty Profiles - IZUMI Minoru

Papers - IZUMI Minoru

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A Combination of Unnatural Phosphatidyl Acceptor and Tandem Electrospray Ionization Mass Spectrometry for Tracing Phospholipase D Activity Reviewed

ODA Keiichi, IMURA Megumi, UEDA Yoshimi, HOSOKAWA Miho, KOBAYASHI Michiyo, MATSUBARA Junko, SATO Mizuho, KUMURA Naokazu, IZUMI Minoru, NAKAJIMA Shuhei, SUGIO Tsuyoshi, BABA Naomichi

Agricultural and Biological Chemistry 73 ( 5 ) 1233 - 1237 2009.5

Language：English Publishing type：Research paper (scientific journal) Publisher：Japan Society for Bioscience, Biotechnology, and Agrochemistry

Phospholipase D (PLD) is a biocatalyst in the synthesis of bioactive compounds and a key enzyme in a variety of biological signal transductions. A combination of unnatural phosphatidyl acceptor, N,N,N-triethyl-N-2-hydroxyethylammonium bromide 6, as a substrate for PLD, and tandem electrospray ionization mass spectrometry (ESI MS) was found to provide information as to whether a given phospholipid serves as a substrate for the PLD-catalyzed reaction. Thus 2-(13′-hydroperoxy-octadecadienoyl)-1-palmitoylglycerophosphocholine 1, and its degradation products 2-(13′-oxo-octadecadienoyl)-1-palmitoylglycerophosphocholine 9 and 2-(13′-hydroxy-octadecadienoyl)-1-palmitoylglycerophosphocholine 11, in a mixture were found to be a substrate of the PLD-catalyzed transphosphatidylation. The sensitivity of this method was exemplified by the observation that PLD activity in cabbage leaves was detected using a small amount of crude crushed leaves with little pretreatment. This simple method can be used in screening for PLD activity and searching for inhibitors of the enzyme from various natural sources.

DOI： 10.1271/bbb.90093

Other Link： https://jlc.jst.go.jp/DN/JALC/00331263150?from=CiNii

Identification of a chemical probe for NAADP by virtual screening Reviewed

Edmund Naylor, Abdelilah Arredouani, Sridhar R. Vasudevan, Alexander M. Lewis, Raman Parkesh, Akiko Mizote, Daniel Rosen, Justyn M. Thomas, Minoru Izumi, A. Ganesan, Antony Galione, Grant C. Churchill

NATURE CHEMICAL BIOLOGY 5 ( 4 ) 220 - 226 2009.4

Language：English Publishing type：Research paper (scientific journal) Publisher：NATURE PUBLISHING GROUP

Research into the biological role of the Ca(2+)-releasing second messenger NAADP (nicotinic acid adenine dinucleotide phosphate) has been hampered by a lack of chemical probes. To find new chemical probes for exploring NAADP signaling, we turned to virtual screening, which can evaluate millions of molecules rapidly and inexpensively. We used NAADP as the query ligand to screen the chemical library ZINC for compounds with similar three-dimensional shape and electrostatic properties. We tested the top-ranking hits in a sea urchin egg bioassay and found that one hit, Ned-19, blocks NAADP signaling at nanomolar concentrations. In intact cells, Ned-19 blocked NAADP signaling and fluorescently labeled NAADP receptors. Moreover, we show the utility of Ned-19 as a chemical probe by using it to demonstrate that NAADP is a key causal link between glucose sensing and Ca(2+) increases in mouse pancreatic beta cells.

DOI： 10.1038/nchembio.150

A Combination of Molecular Probe-Tandem Electrospray Ionization Mass Spectrometry: A Technique for Tracing Structural Changes in Phospholipid Hydroperoxides Reviewed

Rumiko Shimizu, Ai Nagai, Hiroko Tominaga, Megumi Imura, Arnold N. Onyango, Minoru Izumi, Shuhei Nakajima, Shoichi Tahara, Takao Kaneko, Naomichi Baba

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 73 ( 3 ) 781 - 784 2009.3

Language：English Publishing type：Research paper (scientific journal) Publisher：TAYLOR & FRANCIS LTD

An ethyl-labeled phosphatidylcholine hydroperoxide (PC-OOH/Et 2) was synthesized as a molecular probe for naturally occurring PC-OOH 1. Applying the precursor ion scan mode in tandem ESI mass spectrometry at m/z 198, a signal of the PC-OOH/Et 2 alone could be selectively detected even in the presence of a large excess of a complex mixture of phospholipids in the blood. Furthermore, molecular species that formed from PC-OOH/Et 2 by its degradation in the blood were also observed in the same spectrum. Since the molecular probe-and-mass spectrometry-assisted analytical method presented herein requires no separation process by HPLC or TLC and is speedy, requiring less than I h, it. may be useful in lipid analysis.

DOI： 10.1271/bbb.80672

Synthesis of Novel Conjugates of Tetraoxane Endoperoxide with Bis(Quaternary Ammonium Salts) Reviewed

Naokazu Kumura, Hirotaka Furukawa, Michiyo Kobayashi, Arnold N. Onyango, Minoru Izumi, Shuhei Nakajima, Hye-Sook Kim, Yusuke Wataya, Naomichi Baba

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 73 ( 1 ) 217 - 220 2009.1

Language：English Publishing type：Research paper (scientific journal) Publisher：TAYLOR & FRANCIS LTD

Novel water-soluble conjugates of 1,2,4,5-tetraoxane bis(quaternary ammonium salts) were synthesized in a relatively stable crystalline form via four steps starting from methyltrioxorhenium-catalyzed endo-peroxidation of ethyl 4-oxocyclohexanecarboxylate with hydrogen peroxide in hexafluoro-2-propanol. The assay for the in vitro toxicity of water-soluble tetraoxanes 5a-5d to malaria parasites indicate that they were inactive against the Plasmodium falciparum FCR-3 strain.

DOI： 10.1271/bbb.80571

Cyclomaltodextrin Glucanotransferase-Catalyzed Transglycosylation from Dextrin to Alkanol Maltosides Reviewed

Halsuo Zhao, Hiroyuki Naito, Yoshimi Ueda, Katsuhide Okada, Kenji Sadagane, Minoru Izumi, Shuhel Nakajima, Naomichi Baba

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 72 ( 11 ) 3006 - 3010 2008.11

Language：English Publishing type：Research paper (scientific journal) Publisher：TAYLOR & FRANCIS LTD

Maltosides of butanol, octanol, and lauryl alcohol were found for the first time to serve as substrates for cyclomaltodextrin glucanotransferase (CGTase), and glycosyl residue was transfered from dextrin to the substrate affording novel maltosides with 3-4 glucose units.

DOI： 10.1271/bbb.80295

A New Catch-and-release Purification Method Using a Levulinyl Group as a Tag and Its Application to Oligosaccharide Synthesis Reviewed

Minoru Izumi, Ritsu Okamoto, Mizuho Sato, Shuhei Nakajima, Naomichi Baba, Koichi Fukase

CHEMISTRY LETTERS 37 ( 10 ) 1030 - 1031 2008.10

Authorship：Lead author,　Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：CHEMICAL SOC JAPAN

Products possessing a levulinyl group were selectively isolated from reaction Mixtures using a new resin-capture method and a polymer-supported aminooxy group. Successive treatment with NaOH in MeOH readily liberated purified products from the resins. Applications of this method to oligosaccharide syntheses are described.

DOI： 10.1246/cl.2008.1030

Synthesis and biological evaluation of alkoxycoumarins as novel nematicidal constituents Reviewed

Kazuto Takaishi, Minoru Izumi, Naomichi Baba, Kazuyoshi Kawazu, Shuhei Nakajima

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS 18 ( 20 ) 5614 - 5617 2008.10

Language：English Publishing type：Research paper (scientific journal) Publisher：PERGAMON-ELSEVIER SCIENCE LTD

We synthesized all of the monomethoxycoumarins, 5-alkoxycoumarins and their derivatives, and investigated their nematicidal activity against the phytopathogenic nematode, Bursaphelenchus xylophilus. Among the compounds, 5-ethoxycoumarin showed the highest nematicidal activity. Furthermore, 5-ethoxycoumarin was comparatively harmless against both the brine shrimps, Artemia salina, and the Japanese killifish, Oryzias latipes. (C) 2008 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.bmcl.2008.08.102

Antinematodal activities of ingenane diterpenes from Euphorbia kansui and their derivatives against the pine wood nematode (Bursaphelenchus xylophilus) Reviewed

Jianxiao Shi, Zhixuan Li, Teruhiko Nitoda, Minoru Izumi, Hiroshi Kanzaki, Naomichi Baba, Kazuyoshi Kawazu, Shuhei Nakajima

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION C-A JOURNAL OF BIOSCIENCES 63 ( 1-2 ) 59 - 65 2008.1

Language：English Publishing type：Research paper (scientific journal) Publisher：VERLAG Z NATURFORSCH

Under the bioassay-guided method, two diterpenes, 3-O-(2",3"-dimethylbutanoyl)-13-O-dodecanoylingenol (1) and 3-O-(2",3"-dimethylbutanoyl)-13-O-decanoylingenol (2) isolated from Euphorbia kansui, showed a pronounced antinematodal activity against the nematode Bursaphelenchus xylophilus at the same minimum effective dose (MED) of 5 mu g per cotton ball and still displayed antinematodal activity at a dose of 2.5 mu g per cotton ball. Compounds 3-6 were obtained, and the structure of the new compound 6 was elucidated based on 1D- and 2D-NMR analyses and physicochemical data. Preliminary structure-biological activity relationships of ingenane-type compounds were deduced.

Termiticidal activity of Diterpenes from the roots of Euphorbia kansui Reviewed

Jianxiao Shi, Zhixuan Li, Minoru Izumi, Naomichi Baba, Shuhei Nakajima

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION C-A JOURNAL OF BIOSCIENCES 63 ( 1-2 ) 51 - 58 2008.1

Language：English Publishing type：Research paper (scientific journal) Publisher：VERLAG Z NATURFORSCH

Five ingenane compounds, 1-5, kansuinins A and B, isolated from Euphorbia kansui, and their derivatives 7 and 9 were tested for termiticidal activity against the Japanese termite, Reticulitermes speratus. At 72 hours after treatment, the ingenane compounds 1 to 5 caused 100% mortality in R. speratus at 50, 25 and 12.5 mu g/disk, respectively, except for compound 1, which gave a mortality rate of (93.06 +/- 5.56)% at 12.5 mu g/disk. At 36, 48 and 60 hours after treatment, compounds I to 5 showed more termiticidal activity than kansuinins A and B and their derivatives. The kansuinins showed no or only slight activity against termites in the filter paper bioassay under the conditions tested compared with a solvent control.

Repellent from traditional chinese medicine, Periploca sepium Bunge Reviewed

Jianxiao Shi, Tomoko Yamashita, Ayumi Todo, Teruhiko Nitoda, Minoru Izumi, Naomichi Baba, Shuhei Nakajima

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION C-A JOURNAL OF BIOSCIENCES 62 ( 11-12 ) 821 - 825 2007.11

Language：English Publishing type：Research paper (scientific journal) Publisher：VERLAG Z NATURFORSCH

By using a new bioassay-guided method, 2-hydroxy-4-methoxybenzaldehyde isolated from the root bark of Periploca sepium, a traditional Chinese medicine, showed repellent activity against the olive weevil (Dyscerus perforatus) at 62.5, 125, 250 and 500 mu g/disc, respectively. In addition, it also exhibited antinematodal activity against Bursaphelenchus xylophilus at a minimum effective dose of 200 mu g/ball. The three related compounds obtained were also evaluated for the above-mentioned bioactivities.

Three antinematodal diterpenes from Euphorbia kansui Reviewed

Jian-Xiao Shi, Zhi-Xuan Li, Teruhiko Nitoda, Minoru Izumi, Hiroshi Kanzaki, Naomichi Baba, Kazuyoshi Kawazu, Shuhei Nakajima

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 71 ( 4 ) 1086 - 1089 2007.4

Language：English Publishing type：Research paper (scientific journal) Publisher：TAYLOR & FRANCIS LTD

Three compounds, 20-O-acetyl-[3-O-(2'E,4'Z)-deca-dienoyl]-ingenol (1), 20-O-acetyl-[5-O-(2'E,4'Z)-decadienoyl]-ingenol (2) and 3-O-(2'E,4'Z)-decadienoylingenol (3), were isolated from Euphorbia kansui under the bioassay-guided method. Each compound showed the same antinematodal activity against the nematode, Bursaphelenchus xylophilus, at a minimum effective dose (MED) of 5 mu g/cotton ball.

DOI： 10.1271/bbb.60677

Synthesis of lipid derivatives of pyrrole polyamide and their biological activity Reviewed

Masahiko Yamamoto, Changjin Zhu, Lui Yi, Zheng Rong, Yoshie Miura, Minoru Izumi, Shuhei Nakajima, Ken-ichi Tanamoto, Sakayu Shimizu, Naomichi Baba

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 71 ( 4 ) 1078 - 1082 2007.4

Language：English Publishing type：Research paper (scientific journal) Publisher：TAYLOR & FRANCIS LTD

Novel fatty acyl and phospholipid derivatives of pyrrole polyamide were synthesized. Their cytotoxicity against a cancer cell line of MT-4 cells and those infected by human immunodeficiency virus (HIV) was examined. Although no anti-HIV activity was found, their cytotoxicitty against the cancer cells was significantly enhanced by introducing a lipophilic group into the pyrrole polyamide.

DOI： 10.1271/bbb.60650

Glucosylation of Sucrose Laurate with Cyclodextrin Glucanotransferase Reviewed

OKADA Katsuhide, ZHAO Haisuo, IZUMI Minoru, NAKAJIMA Shuhei, BABA Naomichi

Agricultural and Biological Chemistry 71 ( 3 ) 826 - 829 2007.3

Language：English Publishing type：Research paper (scientific journal) Publisher：Japan Society for Bioscience, Biotechnology, and Agrochemistry

Sucrose monolauroyl esters were found to serve as substrates for cyclodextrin glucanotransferase (CGTase)-catalyzed transglucosidation reactions, affording new sucrose esters that have an additional 1-3 glucose residues on the pyranose ring of the sucrose moiety in the ester.

DOI： 10.1271/bbb.60646

Other Link： http://ousar.lib.okayama-u.ac.jp/34238

Synthesis and biological activity of fatty acid derivatives of quinine Reviewed

N Kumura, M Izumi, S Nakajima, S Shimizu, HS Kim, Y Wataya, N Baba

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 69 ( 11 ) 2250 - 2253 2005.11

Language：English Publishing type：Research paper (scientific journal) Publisher：TAYLOR & FRANCIS LTD

Derivatives of quinine with fatty acids including polyunsaturated fatty acids were prepared. They showed moderate antimalarial activity as compared with quinine itself using Plasmodium falciparum. The activities were not dependent on whether the fatty acyl group was saturated or unsaturated. On the other hand, the derivatives showed significantly higher cytotoxicity against a mammary tumor cell line FM3A than quinine itself. Calculating from these data, an acetyl derivative of quinine with the shortest acyl group was found to give the highest selectivity.

DOI： 10.1271/bbb.69.2250

Chlorotrimethylsilane as a mild and effective source of acid catalyst in reductive benzylation

M Izumi, K Fukase

CHEMISTRY LETTERS 34 ( 4 ) 594 - 595 2005.4

Authorship：Lead author,　Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：CHEMICAL SOC JAPAN

New reductive benzylation of hydroxy functions was effected by using the combination of benzaldehyde, TMSCl, and Et3SiH. TMSCl first reacts with alcohols to form HCl, which is probably the ultimate catalyst for this reaction system. TMSCl can also trap water and thus effectively promote dehydration reactions when more than stoichiometric amount of TMSCl is used. Although excess TMSCl was required for the foregoing reactions, TMSCl could be readily removed by simple evaporation.

DOI： 10.1246/cl.2005.594

Preparation of monosaccharide having (mercaptomethyl)diacetylene compounds using solid-support as a thiol source Reviewed

M Izumi, M Shibakami

SYNLETT ( 10 ) 1395 - 1398 2003.8

Authorship：Lead author Language：English Publishing type：Research paper (scientific journal) Publisher：GEORG THIEME VERLAG KG

This paper describes the efficient synthesis of monosaccharides having (mercaptomethyl)diacetylene using Novabiochem(TM) thiol 2-chlorotrityl resin. Coupling of an acetylene-terminated monosaccharide with the propargyl group that is attached to the solid-support afforded diacetylene-linked monosaccharide. The desired thiol compounds were obtained by cleavage of the chlorotrityl group in good yields. Preparation of the gold nano-particles having the monosaccharides via gold-thiol reaction is briefly discussed.

Sonogashira Coupling Reaction on the Surface of Gold Nanoparticles: Introduction of Multiple Carbohydrate Ligands

Minoru Izumi, toshiyuki takagi, Motonari Shibakami

ITE Letters on Batteries, New Technologies & Medicine (with News) 3 ( 6 ) 707 - 712 2002.10

Solid-phase synthesis of oligosaccharides using novel alkyne-type linkers: Selection of reactive sites on the support by Sonogashira reaction Reviewed

M Izumi, K Fukase, S Kusumoto

SYNLETT ( 9 ) 1409 - 1416 2002.9

Authorship：Lead author Language：English Publishing type：Research paper (scientific journal) Publisher：GEORG THIEME VERLAG KG

Two new alkyne-type linkers having alkynylmethyloxy moieties were elaborated for solid-phase synthesis of oligosaccharides. A propargyl glycoside-type linker between a sugar residue and a solid support was formed by the Sonogashira reaction of a propargyl glycoside with polymer-supported iodobenzene. A propargyl ester-type linker was also constructed by the same reaction of a 4-(proparygy1oxycarbonyl)benzyl glycoside with the latter. Both linkers are stable against acids such as TFA but can be readily cleaved with this acid after conversion to the corresponding alkyne-cobalt complex by treatment with Co-2(CO)(8). The latter ester linker is generally advantageous in that mild cleavage liberates a product as its carboxybenzyl glycoside which is readily purified. The Sonogashira reaction was found to proceed only at spatially reactive sites on the solid support where the reagent accesses readily, so that the subsequent reactions including glycosylation on solid phase proceeded smoothly to result in high total yields of the desired oligosaccharides.

A direct continuous spectrophotometric assay for glycosidases with 3-nitro-2-pyridyl glycosides by tautomerization of 2-hydroxy-3-nitropyridine Reviewed

SJ Ma, J Hiratake, Y Nakai, M Izumi, K Fukase, S Kusumoto, K Sakata

ANALYTICAL BIOCHEMISTRY 302 ( 2 ) 291 - 297 2002.3

Language：English Publishing type：Research paper (scientific journal) Publisher：ACADEMIC PRESS INC ELSEVIER SCIENCE

Two kinds of 3-nitro-2-pyridyl glycosides were synthesized and evaluated as substrates for continuous spectrophotometric assay for glycosidases. The liberated aglycon, 2-hydroxy-3-nitropyridine, immediately tautomerized to 3-nitro-2(1H)-pyridone, causing an absorption shift of ca. 60 nm even under acidic conditions (pH 3-6). Consequently, the enzymatic hydrolysis of these glycosides was monitored continuously in the acidic to neutral pH range (pH 4-7), the optimum pH for most glycosidases. The absorbance of liberated aglycon increased linearly at 390 nm until 10% consumption of the substrate to enable the initial rate to be determined at once without terminating the reaction. The kinetic parameters for the hydrolysis of 3-nitro-2-pyridyl glycosides were obtained from the slopes of the progress curves and were compared with those obtained from the conventional discontinuous assay using p- and o-nitrophenyl glycosides as substrates. The kinetic parameters indicated that 3-nitro-2-pyridyl glycosides were more activated and specific substrates, but with less affinity to the enzymes than the corresponding nitrophenyl glycosides. Moreover, the absorbance shift by tautomerization should promise further applications to continuous spectrophotometric assays for other enzymes acting under acidic conditions, such as acid proteases and acid phosphatases. (C) 2002 Elsevier Science (USA).

DOI： 10.1006/abio.2001.5558

TMSCl as a mild and effective source of acidic catalysis in Fischer glycosidation and use of propargyl glycoside for anomeric protection Reviewed

M Izumi, K Fukase, S Kusumoto

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 66 ( 1 ) 211 - 214 2002.1

Authorship：Lead author Language：English Publishing type：Research paper (scientific journal) Publisher：TAYLOR & FRANCIS LTD

Practical Fischer glycosidation was effected at room temperature or 60degreesC by using 5 to 10 equiv. of TMSCl. The anomeric propargyl group formed by this method was found to be a versatile new protecting group, being stable in neat TFA but readily cleaved by treatment with Co-2(CO)(8) and TFA in CH2Cl2 via the formation of an alkyne-Co complex.

DOI： 10.1271/bbb.66.211

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