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中村光裕

徳島大学

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Jグローバル
KAKEN
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2024年12月20日更新

職名: 講師
電話: 088-656-7246
電子メール: nakamura.mitsuhiro@tokushima-u.ac.jp
学歴: 2002/3: 名古屋大学大学院生命農学研究科博士課程修了
学位: 農学博士 (名古屋大学) (2002年3月)
職歴・経歴: 2010/4: 徳島大学講師, 大学院ソシオ・アーツ・アンド・サイエンス研究部 (-2016.3.)
2016/4: 徳島大学講師, 大学院理工学研究部 (-2017.3.)
2017/4: 徳島大学講師, 大学院社会産業理工学研究部

専門分野・研究分野: 化学 (Chemistry)
天然物化学 (Natural Products Chemistry)
生物有機化学 (Bioorganic Chemistry)

研究者総覧で最新データを確認する

2024年12月20日更新

専門分野・研究分野: 化学 (Chemistry)
天然物化学 (Natural Products Chemistry)
生物有機化学 (Bioorganic Chemistry)
担当経験のある授業科目: STEM演習 (学部)
化学基礎実験 (学部)
化学実験1 (学部)
化学実験2 (学部)
卒業研究 (学部)
基礎化学実験 (共通教育)
応用理数セミナー (学部)
技術英語基礎2 (学部)
有機機器分析 (学部)
有機機能性物質化学特論 (大学院)
物質化学特論 (大学院)
理工学特別実習 (大学院)
生物有機化学 (学部)
自然科学特別研究 (大学院)
自然科学特別輪講 (大学院)
雑誌講読 (学部)
指導経験: 4人 (学士)

研究者総覧で最新データを確認する

2024年12月20日更新

専門分野・研究分野: 化学 (Chemistry)
天然物化学 (Natural Products Chemistry)
生物有機化学 (Bioorganic Chemistry)

研究テーマ: 機能性天然物質の探索と高機能化 (機能性物質, 生物発光基質, 硫酸化)

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論文

Satoshi Inouye, Kazuo Matsuda and Mitsuhiro Nakamura :
Enzymatic sulfation of coelenterazine by human cytosolic aryl sulfotransferase SULT1A1: identification of coelenterazine C2-benzyl monosulfate by LC/ESI-TOF-MS,
Biochemical and Biophysical Research Communications, Vol.665, 133-140, 2023.

(要約): Coelenterazine (CTZ) is known as a light-emitting source for the bioluminescence reaction in marine organisms. CTZ has two phenolic hydroxy groups at the C2-benzyl and C6-phenyl positions, and a keto-enol type hydroxy group at the C3-position in the core structure of imidazopyrazinone (= 3,7-dihydroimidazopyrazin-3-one). These hydroxy groups in CTZ could be sulfated by sulfotransferase(s), and the sulfates of Watasenia luciferin (CTZ disulfate at the C2- and C6-positions) and Renilla pre-luciferin (CTZ 3-enol sulfate) have been identified in marine organisms. To characterize the sulfation process of CTZ, human cytosolic aryl sulfotransferase SULT1A1 (SUTase) was used as a model enzyme. The sulfated products catalyzed by SUTase with 3'-phosphoadenosine 5'-phosphosulfate (PAPS) were analyzed by LC/ESI-TOF-MS. The product was the monosulfate of CTZ and identified as the C2-benzyl sulfate of CTZ (CTZ C2-benzyl monosulfate), but CTZ disulfate, CTZ 3-enol sulfate, and CTZ C6-phenyl monosulfate were not detected. The non-enzymatic oxidation products of dehydrocoelenterazine (dCTZ, dehydrogenated derivative of CTZ), coelenteramide (CTMD), and coelenteramine (CTM) from CTZ were also identified as their monosulfates.
(キーワード): Humans / Arylsulfotransferase / Imidazoles / Sulfotransferases / Luciferins / Sulfates
(出版サイトへのリンク): ● Publication site (DOI): 10.1016/j.bbrc.2023.05.007
(文献検索サイトへのリンク): ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 37163933; ● Summary page in Scopus @ Elsevier: 2-s2.0-85156174973

(DOI: 10.1016/j.bbrc.2023.05.007, PubMed: 37163933, Elsevier: Scopus) Satoshi Inouye, Mitsuhiro Nakamura and Takamitsu Hosoya :
Formation of Coelenteramine from 2-Peroxycoelenterazine in the Ca2+-Binding Photoprotein Aequorin,
Photochemistry and Photobiology, Vol.98, No.5, 1068-1076, 2022.

(要約): Aequorin consists of apoprotein (apoAequorin) and (S)-2-peroxycoelenterazine (CTZ-OOH) and is considered to be a transient-state complex of an enzyme (apoAequorin) and a substrate (coelenterazine and molecular oxygen) in the enzymatic reaction. The degradation process of CTZ-OOH in aequorin was characterized under various conditions of protein denaturation. By acid treatment, the major product from CTZ-OOH was coelenteramine (CTM), but not coelenteramide (CTMD), and no significant luminescence was observed. The counterparts of CTM from CTZ-OOH were identified as 4-hydroxyphenylpyruvic acid (4HPPA) and 4-hydroxyphenylacetic acid (4HPAA) by liquid chromatography/electrospray ionization-time-of-flight mass spectrometry (LC/ESI-TOF-MS). In the luminescence reaction of aequorin with Ca , similar amounts of 4HPPA and 4HPAA were detected, indicating that CTM is formed by two pathways from CTZ-OOH through dioxetanone anion and not by hydrolysis from CTMD.
(出版サイトへのリンク): ● Publication site (DOI): 10.1111/php.13590
(文献検索サイトへのリンク): ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 34971002; ● Search Scopus @ Elsevier (PMID): 34971002; ● Search Scopus @ Elsevier (DOI): 10.1111/php.13590

(DOI: 10.1111/php.13590, PubMed: 34971002) Satoshi Inouye, Mitsuhiro Nakamura and Takamitsu Hosoya :
Enzymatic conversion of dehydrocoelenterazine to coelenterazine using FMN-bound flavin reductase of NAD(P)H:FMN oxidoreductase,
Biochemical and Biophysical Research Communications, Vol.587, 24-28, 2022.

(要約): Coelenterazine (CTZ) is known as luciferin (a substrate) for the luminescence reaction with luciferase (an enzyme) in marine organisms and is unstable in aqueous solutions. The dehydrogenated form of CTZ (dehydrocoelenterazine, dCTZ) is stable and thought to be a storage form of CTZ and a recycling intermediate from the condensation reaction of coelenteramine and 4-hydroxyphenylpyruvic acid to CTZ. In this study, the enzymatic conversion of dCTZ to CTZ was successfully achieved using NAD(P)H:FMN oxidoreductase from the bioluminescent bacterium Vibrio fischeri ATCC 7744 (FRase) in the presence of NADH (the FRase-NADH reaction). CTZ reduced from dCTZ in the FRase-NADH reaction was identified by HPLC and LC/ESI-TOF-MS analyses. Thus, dCTZ can be enzymatically converted to CTZ in vitro. Furthermore, the concentration of dCTZ could be determined by the luminescence activity using the CTZ-utilizing luciferases (Gaussia luciferase or Renilla luciferase) coupled with the FRase-NADH reaction.
(出版サイトへのリンク): ● Publication site (DOI): 10.1016/j.bbrc.2021.11.089
(文献検索サイトへのリンク): ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 34864391; ● Summary page in Scopus @ Elsevier: 2-s2.0-85120360598

(DOI: 10.1016/j.bbrc.2021.11.089, PubMed: 34864391, Elsevier: Scopus) Inouye Satoshi, Mitsuhiro Nakamura, Taguchi Jumpei and Hosoya Takamitsu :
Identification of a novel oxidation product from yellow fluorophore in the complex of apoPholasin and dehydrocoelenterazine,
Bioorganic & Medicinal Chemistry Letters, 127435, 2020.

(要約): The complex of the recombinant fusion protein of apoPholasin and glutathione S-transferase (GST-apoPholasin) with non-fluorescent dehydrocoelenterazine (dCTZ) (GST-apoPholasin/dCTZ complex) shows yellow fluorescence at 539 nm by excitation at 430 nm. The GST-apoPholasin/dCTZ complex with a fluorophore (dCTZ*) has considerably weak luminescence activity, converting slowly to a blue fluorescence protein with the emission peak at 430 nm. The main oxidation products from dCTZ* for blue fluorescence were identified as coelenteramine (CTM) and an unreported pyrazine derivative, 3-benzyl-5-(4-hydroxyphenyl)pyrazin-2(1H)-one (CTO) that was confirmed by chemical synthesis.
(出版サイトへのリンク): ● Publication site (DOI): 10.1016/j.bmcl.2020.127435
(文献検索サイトへのリンク): ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 32717370; ● Search Scopus @ Elsevier (PMID): 32717370; ● Search Scopus @ Elsevier (DOI): 10.1016/j.bmcl.2020.127435

(DOI: 10.1016/j.bmcl.2020.127435, PubMed: 32717370) Mitsuhiro Nakamura, Kazuo Matsuda, Takashi Morikawa, Kohsuke Ishizuka and Satoshi Inouye :
Efficient conversion to Cypridina luciferin from Cypridina luciferyl sulfate, coupled with enzymatic sulfation of acetic acid.,
Biochemical and Biophysical Research Communications, Vol.529, No.3, 678-684, 2020.

(要約): In Cypridina (Vargula) hilgendorfii, Cypridina luciferin is converted from Cypridina luciferyl sulfate by a sulfotransferase with adenosine 3', 5'-diphosphate (PAP), and is used for the luminescence reaction of Cypridina luciferase. We found that the luminescence activity of crude extracts of C. hilgendorfii was significantly stimulated by the addition of acetic acid. This stimulation may be explained by an efficient supply of PAP from 3'-phosphoadenosine 5'-phosphosulfate (PAPS) catalyzed by a sulfotransferase. Thus, acetic acid acts as a sulfate acceptor from PAPS, followed by forming acetyl sulfate and PAP. The structure of acetyl sulfate was identified using mass spectrometry and it spontaneously decomposed to acetic acid and free sulfate ion in aqueous solutions. This enzymatic conversion from Cypridina luciferyl sulfate to Cypridina luciferin could be coupled with acetic acid and PAPS by a sulfotransferase.
(出版サイトへのリンク): ● Publication site (DOI): 10.1016/j.bbrc.2020.05.167
(文献検索サイトへのリンク): ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 32736692; ● Summary page in Scopus @ Elsevier: 2-s2.0-85088150307

(DOI: 10.1016/j.bbrc.2020.05.167, PubMed: 32736692, Elsevier: Scopus) Satoshi Inouye, Yuiko Miura-Sahara, Rie Iimori, Yuki Sakata, Yuki Hazama, Suguru Yoshida, Mitsuhiro Nakamura and Takamitsu Hosoya :
A novel yellow fluorescent protein of recombinant apoPholasin with dehydrocoelenterazine,
Biochemical and Biophysical Research Communications, Vol.526, No.2, 404-409, 2020.

(要約): Pholasin is classified as a photoprotein and comprises apoPholasin (an apoprotein of pholasin) and an unknown prosthetic group as the light-emitting source. The luminescence reaction of pholasin is triggered by reactive oxygen species. Recombinant apoPholasin was recently expressed as a fusion protein of glutathione S-transferase (GST-apoPholasin) and purified from E. coli cells. By incubating non-fluorescent dehydrocoelenterazine (dCTZ, dehydrogenated form of CTZ) with GST-apoPholasin, the complex of GST-apoPholasin and dCTZ (GST-apoPholasin/dCTZ complex) was formed immediately and showed bright yellow fluorescence (λ = 539 nm, excited at 430 nm). Unexpectedly, the fluorescent chromophore of the GST-apoPholasin/dCTZ complex was identified as non-fluorescent dCTZ. The luminescence intensity of the GST-apoPholasin/dCTZ complex was increased in a catalase-HO system, but not in sodium hypochlorite.
(出版サイトへのリンク): ● Publication site (DOI): 10.1016/j.bbrc.2020.03.085
(文献検索サイトへのリンク): ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 32223929; ● Summary page in Scopus @ Elsevier: 2-s2.0-85082430542

(DOI: 10.1016/j.bbrc.2020.03.085, PubMed: 32223929, Elsevier: Scopus) Satoshi Inouye, Yuiko Sahara-Miura, Mitsuhiro Nakamura and Takamitsu Hosoya :
Expression, purification, and characterization of recombinant apoPholasin,
Protein Expression and Purification, 105615, 2020.

(要約): Pholasin is a reactive oxygen-sensitive photoprotein that consists of an apoprotein (apoPholasin) and an unknown chromophore. The preferred human codon-optimized apoPholasin gene was transiently expressed in mammalian cells and apoPholasin was detected using an anti-recombinant apoPholasin antibody. For the first time, we found that apoPholasin secreted into the culture medium could catalyze the oxidation of coelenterazine (CTZ, a luciferin) to produce continuous luminescence. The fusion protein of apoPholasin and glutathione S-transferase (GST-apoPholasin) was successfully expressed as a soluble form in bacterial cells using the cold induction system. The purified GST-apoPholasin also had luminescence activity with CTZ, showing the bioluminescence emission peak at 461 nm, and the resultant product showed purple blue fluorescence under 365 nm light. Unexpectedly, the main oxidation product of CTZ was identified as coelenteramine (CTM), not coelenteramide (CTMD).
(出版サイトへのリンク): ● Publication site (DOI): 10.1016/j.pep.2020.105615
(文献検索サイトへのリンク): ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 32114101; ● Search Scopus @ Elsevier (PMID): 32114101; ● Search Scopus @ Elsevier (DOI): 10.1016/j.pep.2020.105615

(DOI: 10.1016/j.pep.2020.105615, PubMed: 32114101) Mitsuhiro Nakamura, Kazuo Matsuda, Misaki Nakamura, Kyohei Yamashita, Tomoko Suzuki and Satoshi Inouye :
Enzymatic conversion of Cypridina luciferyl sulfate to Cypridina luciferin with coenzyme A as a sulfate acceptor in Cypridina (Vargula) hilgendorfii,
Photochemistry and Photobiology, Vol.95, No.6, 1376-1386, 2019.

(要約): In the luminous ostracod Cypridina (presently Vargula) hilgendorfii, Cypridina luciferyl sulfate (3-enol sulfate of Cypridina luciferin) is converted to Cypridina luciferin by a sulfotransferase with 3'-phosphoadenosine-5'-phosphate (PAP) as a sulfate acceptor. The resultant Cypridina luciferin is used for the luciferase-luciferin reaction of Cypridina to emit blue light. The luminescence stimulation with major organic cofactors was examined using the crude extracts of Cypridina specimens, and we found that the addition of coenzyme A (CoA) to the crude extracts significantly stimulated luminescence intensity. Further, the light-emitting source in the crude extracts stimulated with CoA was identified as Cypridina luciferyl sulfate, and we demonstrated that CoA could act as a sulfate acceptor from Cypridina luciferyl sulfate. In addition, the sulfate group of Cypridina luciferyl sulfate was also transferred to adenosine 5'-monophosphate (5'-AMP) and adenosine 3'-monophosphate (3'-AMP) by a sulfotransferase. The sulfated products corresponding to CoA, 5'-AMP, and 3'-AMP were identified using mass spectrometry. This is the first report that CoA can act as a sulfate acceptor in a sulfotransferase reaction. This article is protected by copyright. All rights reserved.
(キーワード): luciferyl sulfate / sulfotransferase / PAP / luciferase / coenzyme A
(徳島大学機関リポジトリ): ● Metadata: 117348
(出版サイトへのリンク): ● Publication site (DOI): 10.1111/php.13137
(文献検索サイトへのリンク): ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 31230356; ● Search Scopus @ Elsevier (PMID): 31230356; ● Search Scopus @ Elsevier (DOI): 10.1111/php.13137

(徳島大学機関リポジトリ: 117348, DOI: 10.1111/php.13137, PubMed: 31230356) So Masaki, Isao Kii, Yuto Sumida, Tomoe Kato-Sumida, Yasushi Ogawa, Nobutoshi Ito, Mitsuhiro Nakamura, Rie Sonamoto, Naoyuki Kataoka, Takamitsu Hosoya and Masatoshi Hagiwara :
Design and synthesis of a potent inhibitor of class 1 DYRK kinases as a suppressor of adipogenesis.,
Bioorganic & Medicinal Chemistry, Vol.23, No.15, 4434-4441, 2015.

(要約): Dysregulation of dual-specificity tyrosine-phosphorylation-regulated kinase 1A (DYRK1A) has been demonstrated in several pathological conditions, including Alzheimer's disease and cancer progression. It has been recently reported that a gain of function-mutation in the human DYRK1B gene exacerbates metabolic syndrome by enhancing obesity. In the previous study, we developed an inhibitor of DYRK family kinases (INDY) and demonstrated that INDY suppresses the pathological phenotypes induced by overexpression of DYRK1A or DYRK1B in cellular and animal models. In this study, we designed and synthesized a novel inhibitor of DYRK family kinases based on the crystal structure of the DYRK1A/INDY complex by replacing the phenol group of INDY with dibenzofuran to produce a derivative, named BINDY. This compound exhibited potent and selective inhibitory activity toward DYRK family kinases in an in vitro assay. Furthermore, treatment of 3T3-L1 pre-adipocytes with BINDY hampered adipogenesis by suppressing gene expression of the critical transcription factors PPARγ and C/EBPα. This study indicates the possibility of BINDY as a potential drug for metabolic syndrome.
(キーワード): 3T3-L1 Cells / Adipogenesis / Animals / Benzofurans / Benzothiazoles / Binding Sites / CCAAT-Enhancer-Binding Protein-alpha / Drug Design / Humans / Mice / Molecular Docking Simulation / PPAR gamma / Protein Kinase Inhibitors / Protein Structure, Tertiary / Protein-Serine-Threonine Kinases / Protein-Tyrosine Kinases
(出版サイトへのリンク): ● Publication site (DOI): 10.1016/j.bmc.2015.06.018
(文献検索サイトへのリンク): ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 26145823; ● Summary page in Scopus @ Elsevier: 2-s2.0-84937818438

(DOI: 10.1016/j.bmc.2015.06.018, PubMed: 26145823, Elsevier: Scopus) Mitsuhiro Nakamura, Tomoko Suzuki, Norihiro Ishizaka, Jun-ichi Sato and Satoshi Inouye :
Identification of 3-enol sulfate of Cypridina luciferin, Cypridina luciferyl sulfate, in the sea-firefly Cypridina (Vargula) hilgendorfii,
Tetrahedron, Vol.70, No.12, 2161-2168, 2014.

(出版サイトへのリンク): ● Publication site (DOI): 10.1016/j.tet.2014.01.075
(文献検索サイトへのリンク): ● Summary page in Scopus @ Elsevier: 2-s2.0-84896707880

(DOI: 10.1016/j.tet.2014.01.075, Elsevier: Scopus) Iwano Satoshi, Obata Rika, Miura Chihiro, Kiyama Masahiro, Hama Kazutoshi, Mitsuhiro Nakamura, Amano Yoshiharu, Kojima Satoshi, Hirano Takashi, Maki Shojiro and Niwa Haruki :
Development of simple firefly luciferin analogs emitting blue, green, red, and near-infrared biological window light,
Tetrahedron, Vol.69, No.19, 3847-3856, 2013.

(出版サイトへのリンク): ● Publication site (DOI): 10.1016/j.tet.2013.03.050
(文献検索サイトへのリンク): ● Summary page in Scopus @ Elsevier: 2-s2.0-84875935248

(DOI: 10.1016/j.tet.2013.03.050, Elsevier: Scopus) Toshiya Masuda, Inouchi Tomoko, Aya Fujimoto, Shingai Yoshimi, Inai Miyuki, Mitsuhiro Nakamura and Shoji Imai :
Radical Scavenging Activity of Spring Mountain Herbs in the Shikoku Mountain Area and Identification of Antiradical Constituents by Simple HPLC Detection and LC-MS Methods,
Bioscience, Biotechnology, and Biochemistry, Vol.76, No.4, 705-711, 2012.

(要約): The functionality of spring mountain herbs, which were collected in the Kajigamori mountain area of Shikoku area in Japan, was investigated in the course of our studies for utilizing local plant resources. The radical scavenging activity of the extracts from seventeen herbs was measured. Among these herbs, two extracts from Polystichym ovato-paleaceum (Japanese name: Tsuyanashiinode) and Sambucus racemosa subsp. sieboldiana (Japanese name: Niwatoko) showed potent DPPH radical scavenging activity. The material evidence for the potent activity of the extracts was studied by a combination of our developed method for detecting antiradical compounds, LC-MS/MS, and enzymatic hydrolysis.
(キーワード): Biphenyl Compounds / Caffeic Acids / Chromatography, Liquid / Free Radical Scavengers / Free Radicals / Japan / Kaempferols / Natural Springs / Picrates / Plant Components, Aerial / Plant Extracts / Plant Roots / Plants, Medicinal / Polystichum / Quercetin / Sambucus / Tandem Mass Spectrometry
(出版サイトへのリンク): ● Publication site (DOI): 10.1271/bbb.110837
(文献検索サイトへのリンク): ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 22484936; ● Search Scopus @ Elsevier (PMID): 22484936; ● Search Scopus @ Elsevier (DOI): 10.1271/bbb.110837

(DOI: 10.1271/bbb.110837, PubMed: 22484936) Yoshiyasu Ichikawa, Ken Okumura, Yasunori Matsuda, Tomoyuki Hasegawa, Mitsuhiro Nakamura, Aya Fujimoto, Toshiya Masuda, Ken Nakano and Hiyoshizo Kotsuki :
Synthesis of manzacidin A and C: efficient construction of quarternary carbon stereocenters bearing nitrogen substituents,
Organic & Biomolecular Chemistry, Vol.10, No.3, 614-622, 2012.

(要約): An efficient synthetic method for stereoselective construction of asymmetric quaternary carbon stereocenters, bearing nitrogen in the form of Boc-protected allyl amines, has been developed. This methodology is employed in the synthesis of marine alkaloids, manzacidin A and C.
(キーワード): Carbon / Chemistry Techniques, Synthetic / Nitrogen / Pyrimidines / Pyrroles / Stereoisomerism
(出版サイトへのリンク): ● Publication site (DOI): 10.1039/c1ob06559a
(文献検索サイトへのリンク): ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 22113586; ● Search Scopus @ Elsevier (PMID): 22113586; ● Search Scopus @ Elsevier (DOI): 10.1039/c1ob06559a

(DOI: 10.1039/c1ob06559a, PubMed: 22113586) Yoshimi Shingai, Aya Fujimoto, Mitsuhiro Nakamura and Toshiya Masuda :
Structure and function of the oxidation products of polyphenols and identification of potent lipoxygenase inhibitors from fe-catalyzed oxidation of resveratrol.,
Journal of Agricultural and Food Chemistry, Vol.59, No.15, 8180-8186, 2011.

(要約): Polyphenols have recently attracted much attention as potent antioxidants and related bioactive substances. These potent antioxidative polyphenols are very oxidizable due to their chemical properties, and their oxidation products must accumulate in the oxidizing foods when they are contained as the active ingredients. In this investigation, 30 polyphenols and related phenolics were oxidized with oxygen in the presence of a catalytic amount of Fe ions. Piceatannol, catechin, epicatechin, hydroxytyrosol, carnosol, and carnosic acid were oxidized very quickly. Sinapic acid, caffeic acid, chlorogenic acid, rosmarinic acid, gallic acid, propyl gallate, α-tocopherol, quercetin, and nordihydroguaiaretic acid were moderately oxidized. Protocatechuic acid, syringic acid, taxifolin, resveratrol, gentisic acid, secoisolariciresinol, and ellagic acid were oxidized for 19-20 days; however, their oxidation was very slow and did not complete. The other phenolics were not oxidized. The obtained oxidation products were next subjected to a lipoxygenase inhibition assay and the results compared to those of the corresponding phenols. Very interestingly, the oxidation product from resveratrol showed a high inhibitory activity, whereas resveratrol itself had no activity and its oxidation efficiency was low. To clarify the inhibition principle of the oxidation product, an LC-MS analysis was carried out on the oxidation product. The analytical results showed that they are the oligomeric and degraded compounds of resveratrol. Among them, the structures of three dimeric compounds were successfully identified, and their activity data clarified that the closed ring dimers were potent lipoxygenase inhibitors, whereas the opened ring dimer was not. It should be noted that resveratrol had almost no lipoxygenase inhibitory activity, contrary to some researchers' findings.
(出版サイトへのリンク): ● Publication site (DOI): 10.1021/jf202561p
(文献検索サイトへのリンク): ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 21726087; ● Search Scopus @ Elsevier (PMID): 21726087; ● Search Scopus @ Elsevier (DOI): 10.1021/jf202561p

(DOI: 10.1021/jf202561p, PubMed: 21726087) Yoshiyasu Ichikawa, Yasunori Matsuda, Ken Okumura, Mitsuhiro Nakamura, Toshiya Masuda, Hiyoshizo Kotsuki and Keiji Nakano :
Asymmetric synthesis of (+)-geranyllinaloisocyanide: assignment of absolute stereochemistry.,
Organic Letters, Vol.13, No.10, 2520-2523, 2011.

(要約): The first nonracemic synthesis of (+)-geranyllinaloisocyanide, starting with (-)-lactic acid methyl ester, has been accomplished by exploiting a [3.3] sigmatropic rearrangement of allyl cyanate. The synthesis enables assignment of the S configuration of the C(3) isocyano substituted, quaternary stereogenic center in natural geranyllinaloisocyanide.
(出版サイトへのリンク): ● Publication site (DOI): 10.1021/ol200308m
(文献検索サイトへのリンク): ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 21491897; ● Search Scopus @ Elsevier (PMID): 21491897; ● Search Scopus @ Elsevier (DOI): 10.1021/ol200308m

(DOI: 10.1021/ol200308m, PubMed: 21491897) Aya Fujimoto, Yoshimi Shingai, Mitsuhiro Nakamura, Tomomi Maekawa, Yoshiaki Sone and Toshiya Masuda :
A novel ring-expanded product with enhanced tyrosinase inhibitory activity from classical Fe-catalyzed oxidation of rosmarinic acid, a potent antioxidative Lamiaceae polyphenol,
Bioorganic & Medicinal Chemistry Letters, Vol.20, No.24, 7393-7396, 2010.

(要約): The iron-ion catalyzed oxidation of the ethanol solution of rosmarinic acid, a potent antioxidant polyphenol of Lamiaceae (Labiatae) plants, afforded a highly tyrosinase-inhibitory active product. The structure of the active product in the oxidation product mixture was determined using extensive NMR spectroscopy to have a novel oxygen-containing seven-membered ring system. The formation mechanism of the unique ring structure from the catechol part of the rosmarinic acid was proposed.
(キーワード): Antioxidants / Catalysis / Catechols / Cinnamates / Depsides / Enzyme Inhibitors / Flavonoids / Iron / Lamiaceae / Magnetic Resonance Spectroscopy / Molecular Conformation / Monophenol Monooxygenase / Oxidation-Reduction / Phenols / Polyphenols
(出版サイトへのリンク): ● Publication site (DOI): 10.1016/j.bmcl.2010.10.040
(文献検索サイトへのリンク): ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 21041086; ● Search Scopus @ Elsevier (PMID): 21041086; ● Search Scopus @ Elsevier (DOI): 10.1016/j.bmcl.2010.10.040

(DOI: 10.1016/j.bmcl.2010.10.040, PubMed: 21041086) Toshiya Masuda, Yoshimi Shingai, Aya Fujimoto, Mitsuhiro Nakamura, Yasuo Oyama, Tomomi Maekawa and Yoshiaki Sone :
Identification of cytotoxic dimers in oxidation product from sesamol, a potent antioxidant of sesame oil,
Journal of Agricultural and Food Chemistry, Vol.58, No.20, 10880-10885, 2010.

(出版サイトへのリンク): ● Publication site (DOI): 10.1021/jf103015j
(文献検索サイトへのリンク): ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 20925385; ● Search Scopus @ Elsevier (PMID): 20925385; ● Search Scopus @ Elsevier (DOI): 10.1021/jf103015j

(DOI: 10.1021/jf103015j, PubMed: 20925385) Yexi Chen, Yuki Yamaguchi, Yuta Tsugeno, Junichi Yamamoto, Tomoko Yamada, Mitsuhiro Nakamura, Koji Hisatake and Hiroshi Handa :
DSIF, the Paf1 complex, and Tat-SF1 have nonredundant, cooperative roles in RNA polymerase II elongation,
Genes & Development, Vol.23, No.23, 2765-2777, 2009.

(要約): Transcription elongation factor DSIF/Spt4-Spt5 is capable of promoting and inhibiting RNA polymerase II elongation and is involved in the expression of various genes. While it has been known for many years that DSIF inhibits elongation in collaboration with the negative elongation factor NELF, how DSIF promotes elongation is largely unknown. Here, an activity-based biochemical approach was taken to understand the mechanism of elongation activation by DSIF. We show that the Paf1 complex (Paf1C) and Tat-SF1, two factors implicated previously in elongation control, collaborate with DSIF to facilitate efficient elongation. In human cells, these factors are recruited to the FOS gene in a temporally coordinated manner and contribute to its high-level expression. We also show that elongation activation by these factors depends on P-TEFb-mediated phosphorylation of the Spt5 C-terminal region. A clear conclusion emerging from this study is that a set of elongation factors plays nonredundant, cooperative roles in elongation. This study also shows unambiguously that Paf1C, which is generally thought to have chromatin-related functions, is involve directlyd in elongation control.
(キーワード): Gene Expression Regulation, Enzymologic / Genes, fos / HeLa Cells / Humans / Mutation / Nuclear Proteins / RNA Polymerase II / Transcription Factors
(出版サイトへのリンク): ● Publication site (DOI): 10.1101/gad.1834709
(文献検索サイトへのリンク): ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 19952111; ● Search Scopus @ Elsevier (PMID): 19952111; ● Search Scopus @ Elsevier (DOI): 10.1101/gad.1834709

(DOI: 10.1101/gad.1834709, PubMed: 19952111) Yoko Ohashi, Masayuki Kubota, Hiroshi Hatase, Mitsuhiro Nakamura, Takashi Hirano, Haruki Niwa and Yoshitaka Nagai :
Distinction of Sialyl Anomers on ESI- and FAB-MS/MS: Stereo-Specific Fragmentations,
Journal of the American Society for Mass Spectrometry, Vol.20, No.3, 394-397, 2009.

(出版サイトへのリンク): ● Publication site (DOI): 10.1016/j.jasms.2008.10.020
(文献検索サイトへのリンク): ● Search Scopus @ Elsevier (DOI): 10.1016/j.jasms.2008.10.020

(DOI: 10.1016/j.jasms.2008.10.020) Jinsuk Kang, Matthew Gemberling, Mitsuhiro Nakamura, FrankG. Whitby, Hiroshi Handa, WilliamG. Fairbrother and Dean Tantin :
A general mechanism for transcription regulation by Oct1 and Oct4 in response to genotoxic and oxidative stress,
Genes & Development, Vol.23, No.2, 208-222, 2009.

(要約): Oct1 and Oct4 are homologous transcription factors with similar DNA-binding specificities. Here we show that Oct1 is dynamically phosphorylated in vivo following exposure of cells to oxidative and genotoxic stress. We further show that stress regulates the selectivity of both proteins for specific DNA sequences. Mutation of conserved phosphorylation target DNA-binding domain residues in Oct1, and Oct4 confirms their role in regulating binding selectivity. Using chromatin immunoprecipitation, we show that association of Oct4 and Oct1 with a distinct group of in vivo targets is inducible by stress, and that Oct1 is essential for a normal post-stress transcriptional response. Finally, using an unbiased Oct1 target screen we identify a large number of genes targeted by Oct1 specifically under conditions of stress, and show that several of these inducible Oct1 targets are also inducibly bound by Oct4 in embryonic stem cells following stress exposure.
(キーワード): Amino Acid Sequence / Animals / DNA Damage / Dimerization / Gene Expression Regulation / HeLa Cells / Humans / Inverted Repeat Sequences / Mice / Models, Molecular / Molecular Sequence Data / Mutation / Octamer Transcription Factor-1 / Octamer Transcription Factor-3 / Oxidative Stress / Phosphorylation / Protein Binding / Protein Structure, Tertiary
(出版サイトへのリンク): ● Publication site (DOI): 10.1101/gad.1750709
(文献検索サイトへのリンク): ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 19171782; ● Search Scopus @ Elsevier (PMID): 19171782; ● Search Scopus @ Elsevier (DOI): 10.1101/gad.1750709

(DOI: 10.1101/gad.1750709, PubMed: 19171782) Masafumi Suzuki, Shoichiro Furukawa, Chikanori Kuramori, Chika Sawa, Yasuaki Kabe, Mitsuhiro Nakamura, Jun-ichi Sawada, Yuki Yamaguchi, Satoshi Sakamoto, Satoshi Inouye and Hiroshi Handa :
Development of a chemical screening system using aqueorin-fused protein,
Biochemical and Biophysical Research Communications, Vol.368, No.3, 600-605, 2008.

(要約): We developed a unique screening system that consists of combination of high photo-sensitivity of photoprotein aequorin (AQ) and our developed high-performance affinity purification system. In the present study, we demonstrated to detect the specific interaction between methotrexate (MTX) and its target dihydrofolate reductase (DHFR) fused with AQ. We succeeded to prepare highly purified AQ-fused DHFR, which showed high sensitive light emission. To test the screening system, we prepared the complex of MTX-immobilized magnetic nanobeads and AQ-fused DHFR. Bound AQ-fused DHFR with the beads was specifically released by addition of MTX. Thus, this methodology enables us to search a novel chemical that binds to target proteins without complicated processes. Furthermore, thank to the highly sensitive luminescence intensity of AQ, this methodology would be performed in very small scale with high responsibility, leading to development of high throughput screening systems.
(キーワード): Aequorin / Drug Delivery Systems / Immunomagnetic Separation / Luminescent Measurements / Methotrexate / Protein Binding / Protein Interaction Mapping / Sensitivity and Specificity / Tetrahydrofolate Dehydrogenase
(出版サイトへのリンク): ● Publication site (DOI): 10.1016/j.bbrc.2008.01.107
(文献検索サイトへのリンク): ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 18243129; ● Search Scopus @ Elsevier (PMID): 18243129; ● Search Scopus @ Elsevier (DOI): 10.1016/j.bbrc.2008.01.107

(DOI: 10.1016/j.bbrc.2008.01.107, PubMed: 18243129) Kazuki Niwa, Mitsuhiro Nakamura and Yoshihiro Ohmiya :
Stereoisomeric bio-inversion key to biosynthesis of firefly D-luciferin,
FEBS Letters, Vol.580, No.22, 5283-5287, 2006.

(要約): The chirality of the luciferin substrate is critical to the luciferin-luciferase reaction producing bioluminescence. In firefly, the biosynthetic pathway of D-luciferin is still unclear, although it can be synthesized in vitro from D-cysteine. Here, we show that the firefly produces both D- and L-luciferin, and that the amount of active D-luciferin increases gradually with maturation stage. Studies of firefly body extracts indicate the possible conversion of L-cysteine via L-luciferin into D-luciferin, suggesting that the biosynthesis is enzymatically regulated by stereoisomeric bio-inversion of L-luciferin. We conclude that the selection of chirality in living organisms is not as rigid as previously thought.
(キーワード): Animals / Fireflies / Firefly Luciferin / Stereoisomerism
(出版サイトへのリンク): ● Publication site (DOI): 10.1016/j.febslet.2006.08.073
(文献検索サイトへのリンク): ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 16979628; ● Search Scopus @ Elsevier (PMID): 16979628; ● Search Scopus @ Elsevier (DOI): 10.1016/j.febslet.2006.08.073

(DOI: 10.1016/j.febslet.2006.08.073, PubMed: 16979628) Mitsuhiro Nakamura, Kazuki Niwa, Shojiro Maki, Takashi Hirano, Yoshihiro Ohmiya and Haruki Niwa :
Construction of a new firefly bioluminescence system using L-luciferin as substrate,
Tetrahedron Letters, Vol.47, No.7, 1197-1200, 2006.

(出版サイトへのリンク): ● Publication site (DOI): 10.1016/j.tetlet.2005.12.033
(文献検索サイトへのリンク): ● Search Scopus @ Elsevier (DOI): 10.1016/j.tetlet.2005.12.033

(DOI: 10.1016/j.tetlet.2005.12.033) Mitsuhiro Nakamura, Takahiko Kakuda, Jianhua Qi, Masayuki Hirata, Tomoaki Shintani, Yukio Yoshioka, Tetsuji Okamoto, Yuichi Oba, Hideshi Nakamura and Makoto Ojika :
Novel relationship beween the antifungal activity and cytotoxicity of marine-derived methabolite xestoquinone and its family,
Bioscience, Biotechnology, and Biochemistry, Vol.69, No.9, 1749-1752, 2005.

(要約): Xestoquinone and related metabolites (the xestoquinone family) occur in marine sponges and are known to show a variety of biological activities. In this study, the first comprehensive evaluation of antifungal activity was performed for xestoquinone and nine natural and unnatural analogues in comparison with their cytotoxicity. The cytotoxicity against two human squamous cell carcinoma cell lines, A431 and Nakata, indicated that the terminal quinone structure of the polycyclic molecules was important (xestoquinone, etc.) and that the presence of a ketone group at C-3 of the opposite terminus dramatically diminished the activity (halenaquinone, etc.). In contrast, a ketone group at C-3 enhanced the antifungal activity against the plant pathogen, Phytophthora capsici, regardless of the presence of a quinone moiety. The cytotoxicity and antifungal activity of the xestoquinone family were negatively correlated with each other.
(キーワード): Animals / Antifungal Agents / Antineoplastic Agents / Cell Line, Tumor / Drug Screening Assays, Antitumor / Humans / Microbial Sensitivity Tests / Phytophthora / Quinones / Structure-Activity Relationship / Xestospongia
(出版サイトへのリンク): ● Publication site (DOI): 10.1271/bbb.69.1749
(文献検索サイトへのリンク): ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 16195594; ● Search Scopus @ Elsevier (PMID): 16195594; ● Search Scopus @ Elsevier (DOI): 10.1271/bbb.69.1749

(DOI: 10.1271/bbb.69.1749, PubMed: 16195594) Mitsuhiro Nakamura, Shojiro Maki, Yoshiharu Amano, Yutaka Ohkita, Kazuki Niwa, Takashi Hirano, Yoshihiro Ohmiya and Haruki Niwa :
Firefly luciferase exhibits bimodal action depending on the luciferin chirality,
Biochemical and Biophysical Research Communications, Vol.331, No.2, 471-475, 2005.

(要約): Firefly luciferase is able to convert L-luciferin into luciferyl-CoA even under ordinary aerobic luciferin-luciferase reaction conditions. The luciferase is able to recognize strictly the chirality of the luciferin structure, serving as the acyl-CoA synthetase for L-luciferin, whereas d-luciferin is used for the bioluminescence reaction. D-Luciferin inhibits the luciferyl-CoA synthetase activity of L-luciferin, whereas L-luciferin retards the bioluminescence reaction of D-luciferin, meaning that both enzyme activities are prevented by the enantiomer of its own substrate.
(キーワード): Acyl Coenzyme A / Animals / Chromatography, High Pressure Liquid / Coenzyme A / Firefly Luciferin / Luciferases, Firefly / Luminescence / Luminescent Proteins / Molecular Structure / Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization / Stereoisomerism / Substrate Specificity
(出版サイトへのリンク): ● Publication site (DOI): 10.1016/j.bbrc.2005.03.202
(文献検索サイトへのリンク): ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 15850783; ● Search Scopus @ Elsevier (PMID): 15850783; ● Search Scopus @ Elsevier (DOI): 10.1016/j.bbrc.2005.03.202

(DOI: 10.1016/j.bbrc.2005.03.202, PubMed: 15850783) Yoko Ohashi, Hiroshi Hatase, Mitsuhiro Nakamura, Takashi Hirano, Shojiro Maki and Haruki Niwa :
Characterization of [1-13C]-specifically labeled amino acids using ESIMS/MS in the selected reaction monitoring mode mode.,
Journal of the Mass Spectrometry Society of Japan, Vol.53, No.6, 309-314, 2005.

(要約): ESIMS/MS was employed for the analyses of 1-13CO-labeled amino acids. Conventionally, in order to estimate the 13C-content, the intensity of molecule-related ion of the sample has been compared against the natural compound. However, this method is incompetent for specifying the position of the 13C-labeling, hence is unable to distinguish the specifically 1-13C-labeled compound from otherwise-(generally or non-specifically) labeled amino acids. With the intention of distinguishing 1-13CO-labeled amino acids from generally labeled and non-labeled molecules we utilized ESIMS/MS in the selected reaction monitoring mode, choosing the protonated molecules as the precursor ion and specifying the product ion generated by a 47 u- (instead of 46 u-) elimination from the precursor ion for the labeled samples. By this new method, characterization of solely 1-13CO-labeled amino acids has been successfully conducted, enabling their distinction from otherwise-labeled compounds.
(キーワード): [1-^<13>C]-Amino acids / ESIMS / MS / Selected reaction monitoring (SRM) / Phenylalanine / Methionine
(出版サイトへのリンク): ● Publication site (DOI): 10.5702/massspec.53.309
(文献検索サイトへのリンク): ● CiNii @ 国立情報学研究所 (CRID): 1390282681469082496; ● Search Scopus @ Elsevier (DOI): 10.5702/massspec.53.309

(DOI: 10.5702/massspec.53.309, CiNii: 1390282681469082496) Mitsuhiro Nakamura, Masashi Mamino, Mizuki Masaki, Shojiro Maki, Ryo Matsui, Satoshi Kojima, Takashi Hirano, Yoshihiro Ohmiya and Haruki Niwa :
Bioluminescence activity of Latia luciferin analogues: Replacement of the 2,6,6-trimethylcyclohexene ring onto the methyl-substituted phenyl groups,
Tetrahedron Letters, Vol.46, No.1, 53-56, 2005.

(出版サイトへのリンク): ● Publication site (DOI): 10.1016/j.tetlet.2004.11.043
(文献検索サイトへのリンク): ● Search Scopus @ Elsevier (DOI): 10.1016/j.tetlet.2004.11.043

(DOI: 10.1016/j.tetlet.2004.11.043) Mitsuhiro Nakamura, Yukisato Ishida, Toshiyuki Kohno, Kazuki Sato, Yuichi Oba and Hideshi Nakamura :
Effects of modification at the fifth residue of mu-conotoxin GIIIA with bulky tags on the electrically stimulated contraction of the rat diaphragm,
The Journal of Peptide Research, Vol.64, 110-117, 2004.

(要約): Mu-conotoxin GIIIA, a peptide toxin from the cone snail, blocks muscle-type sodium channels. Thr-5 of mu-conotoxin GIIIA, located on the opposite side of the active site in the globular molecule, was replaced by Cys to which the bulky tags were attached. The tagged mu-conotoxin GIIIA derivatives, except for the phospholipid-tagged one, exerted the biological activity with a potency slightly weaker than natural mu-conotoxin GIIIA. When the biotinylated tags of various lengths were added, the presence of avidin suppressed the action of the biotinylated toxins of <4 nm, but not with 5 nm. The bulky biotinylated tags are useful as a caliper to measure the depth of receptor sites in the channels.
(キーワード): Amino Acid Sequence / Amino Acid Substitution / Animals / Avidin / Biotin / Circular Dichroism / Conotoxins / Diaphragm / Electric Stimulation / Male / Models, Biological / Molecular Sequence Data / Muscle Contraction / Rats / Rats, Wistar / Structure-Activity Relationship
(出版サイトへのリンク): ● Publication site (DOI): 10.1111/j.1399-3011.2004.00175.x
(文献検索サイトへのリンク): ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 15317501; ● Search Scopus @ Elsevier (PMID): 15317501; ● Search Scopus @ Elsevier (DOI): 10.1111/j.1399-3011.2004.00175.x

(DOI: 10.1111/j.1399-3011.2004.00175.x, PubMed: 15317501) Mitsuhiro Nakamura, Mizuki Masaki, Shojiro Maki, Ryo Matsui, Minako Hieda, Masashi Mamino, Takashi Hirano, Yoshihiro Ohmiya and Haruki Niwa :
Synthesis of Latia luciferin benzoate analogues and their bioluminescent activity,
Tetrahedron Letters, Vol.45, 2203-2205, 2004.

(出版サイトへのリンク): ● Publication site (DOI): 10.1016/j.tetlet.2004.01.027
(文献検索サイトへのリンク): ● Search Scopus @ Elsevier (DOI): 10.1016/j.tetlet.2004.01.027

(DOI: 10.1016/j.tetlet.2004.01.027) Mitsuhiro Nakamura, Takahiko Kakuda, Yuichi Oba, Makoto Ojika and Hideshi Nakamura :
Synthesis of Biotinylated Xestoquinone That Retains Inhibitory Activity Against Ca2+ ATPase of Skeletal Muscle Myosin,
Bioorganic & Medicinal Chemistry, Vol.11, 3077-3082, 2003.

(要約): Xestoquinone isolated from a marine sponge binds to skeletal muscle myosin and inhibits its Ca(2+) ATPase activity. In this study, we first examined xestoquinone and its analogues to assess the relationships between structure and myosin Ca(2+) ATPase inhibitory activity. On the basis of the resultant data, we then designed a biotinylated xestoquinone analogue. Xestoquinone and its analogues were derived from extracts of the marine sponge Xestospongia sapra. Four xestoquinone analogues with a quinone structure significantly inhibited Ca(2+) ATPase activity. In contrast, four xestoquinone analogues in which the quinone structure was converted to a quinol dimethyl ether did not inhibit Ca(2+) ATPase activity. This suggests that the quinone moiety is essential for inhibitory activity. Then, we synthesized a biotinylated xestoquinone in which a biotin tag was introduced to a site far from the quinone moiety, and this molecule exhibited stronger inhibitory activity than that of xestoquinone. This biotinylated xestoquinone could be useful as a probe in studies of the xestoquinone-myosin binding mode.
(キーワード): Animals / Binding Sites / Biotinylation / Calcium-Transporting ATPases / Enzyme Inhibitors / Hydroquinones / Models, Chemical / Quinones / Skeletal Muscle Myosins / Structure-Activity Relationship
(出版サイトへのリンク): ● Publication site (DOI): 10.1016/S0968-0896(03)00276-1
(文献検索サイトへのリンク): ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 12818670; ● Search Scopus @ Elsevier (PMID): 12818670; ● Search Scopus @ Elsevier (DOI): 10.1016/S0968-0896(03)00276-1

(DOI: 10.1016/S0968-0896(03)00276-1, PubMed: 12818670) Chieko Nakada, Kenneth Ritchie, Yuichi Oba, Mitsuhiro Nakamura, Yoko Hotta, Ryota Iino, RinshiS. Kasai, Kazuhiko Yamaguchi, Satoshi Sakamoto, Takahiro Fujiwara and Akihiro Kusumi :
Accumulation of anchored proteins forms membrane diffusion barriers during neuronal polarization,
Nature Cell Biology, Vol.5, No.7, 626-632, 2003.

(要約): The formation and maintenance of polarized distributions of membrane proteins in the cell membrane are key to the function of polarized cells. In polarized neurons, various membrane proteins are localized to the somatodendritic domain or the axon. Neurons control polarized delivery of membrane proteins to each domain, and in addition, they must also block diffusional mixing of proteins between these domains. However, the presence of a diffusion barrier in the cell membrane of the axonal initial segment (IS), which separates these two domains, has been controversial: it is difficult to conceive barrier mechanisms by which an even diffusion of phospholipids could be blocked. Here, by observing the dynamics of individual phospholipid molecules in the plasma membrane of developing hippocampal neurons in culture, we found that their diffusion was blocked in the IS membrane. We also found that the diffusion barrier is formed in neurons 7-10 days after birth through the accumulation of various transmembrane proteins that are anchored to the dense actin-based membrane skeleton meshes being formed under the IS membrane. We conclude that various membrane proteins anchored to the dense membrane skeleton function as rows of pickets, which even stop the overall diffusion of phospholipids, and may represent a universal mechanism for formation of diffusion barriers in the cell membrane.
(キーワード): Actin Cytoskeleton / Aging / Animals / Animals, Newborn / Axons / CHO Cells / Cell Differentiation / Cell Membrane / Cell Polarity / Cricetinae / Dendrites / Diffusion / Hippocampus / Membrane Lipids / Membrane Proteins / Phospholipids / Rats / Rats, Wistar
(出版サイトへのリンク): ● Publication site (DOI): 10.1038/ncb1009
(文献検索サイトへのリンク): ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 12819789; ● Search Scopus @ Elsevier (PMID): 12819789; ● Search Scopus @ Elsevier (DOI): 10.1038/ncb1009

(DOI: 10.1038/ncb1009, PubMed: 12819789) Satoshi Inouye and Mitsuhiro Nakamura :
Identification of biotinylated lysine residues in the photoprotein aequorin by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry peptide mapping after lysine-specific endopeptidase digestion,
Analytical Biochemistry: Methods in the Biological Sciences, Vol.316, No.2, 216-222, 2003.

(要約): A method for identifying modified lysine residues in a protein, using lysine-specific endopeptidase treatment followed by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF-MS) peptide mapping, is described. As a model protein, the photoprotein aequorin was chosen and the N-hydroxysuccinimide ester of biotin was employed to chemically modify the lysine residues. After digestion with lysine-specific endopeptidase, the biotinylated residues of an amino terminus and five potential lysine residues were identified by MALDI-TOF-MS without any other separation procedure.
(キーワード): Aequorin / Amino Acid Sequence / Biotin / Endopeptidases / Lysine / Molecular Sequence Data / Peptide Fragments / Peptide Mapping / Spectrometry, Mass, Electrospray Ionization / Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
(出版サイトへのリンク): ● Publication site (DOI): 10.1016/S0003-2697(03)00055-1
(文献検索サイトへのリンク): ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 12711343; ● Search Scopus @ Elsevier (PMID): 12711343; ● Search Scopus @ Elsevier (DOI): 10.1016/S0003-2697(03)00055-1

(DOI: 10.1016/S0003-2697(03)00055-1, PubMed: 12711343) Atsunori Furuhata, Mitsuhiro Nakamura, Toshihiko Osawa and Koji Uchida :
Thiolation of protein-bound carcinogenic aldehyde: An electrophilic acrolein-lysine adduct that covalently binds to thiols,
The Journal of Biological Chemistry, Vol.277, No.31, 27919-27926, 2002.

(要約): Acrolein, a representative carcinogenic aldehyde that could be ubiquitously generated in biological systems under oxidative stress, shows facile reactivity with the epsilon-amino group of lysine to form N(epsilon)-(3-formyl-3,4-dehydropiperidino)lysine (FDP-lysine) as the major product (Uchida, K., Kanematsu, M., Morimitsu, Y., Osawa, T., Noguchi, N., and Niki, E. (1998) J. Biol. Chem. 273, 16058-16066). In the present study, we determined the electrophilic potential of FDP-lysine and established a novel mechanism of protein thiolation in which the FDP-lysine generated in the acrolein-modified protein reacts with sulfhydryl groups to form thioether adducts. When a sulfhydryl enzyme, glyceraldehyde-3-phosphate dehydrogenase, was incubated with acrolein-modified bovine serum albumin in sodium phosphate buffer (pH 7.2) at 37 degrees C, a significant loss of sulfhydryl groups, which was accompanied by the loss of enzyme activity and the formation of high molecular mass protein species (>200 kDa), was observed. The FDP-lysine adduct generated in the acrolein-modified protein was suggested to represent a thiol-reactive electrophile based on the following observations. (i) N(alpha)-acetyl-FDP-lysine, prepared from the reaction of N(alpha)-acetyl lysine with acrolein, was covalently bound to glyceraldehyde-3-phosphate dehydrogenase. (ii) The FDP-lysine derivative reacted with glutathione to form a GSH conjugate. (iii) The acrolein-modified bovine serum albumin significantly reacted with GSH to form a glutathiolated protein. Furthermore, the observation that the glutathiolated acrolein-modified protein showed decreased immunoreactivity with an anti-FDP-lysine monoclonal antibody suggested that the FDP-lysine residues in the acrolein-modified protein served as the binding site of GSH. These data suggest that thiolation of the protein-bound acrolein may be involved in redox alteration under oxidative stress, whereby oxidative stress generates the increased production of acrolein and its protein adducts that further potentiate oxidative stress via the depletion of GSH in the cells.
(キーワード): Acrolein / Animals / Carcinogens / Cattle / Electrochemistry / Glyceraldehyde-3-Phosphate Dehydrogenases / Kinetics / Lysine / Molecular Weight / Oxidative Stress / Protein Binding / Serum Albumin, Bovine
(出版サイトへのリンク): ● Publication site (DOI): 10.1074/jbc.M202794200
(文献検索サイトへのリンク): ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 12032148; ● Search Scopus @ Elsevier (PMID): 12032148; ● Search Scopus @ Elsevier (DOI): 10.1074/jbc.M202794200

(DOI: 10.1074/jbc.M202794200, PubMed: 12032148) Mitsuhiro Nakamura, Yuichi Oba, Tatsuya Mori, Kazuki Sato, Yukisato Ishida, Tsukasa Matsuda and Hideshi Nakamura :
Generation of Polyclonal Antibody against mu-Conotoxin GIIIA Using an Immunogen of [Cys5]mu-Conotoxin GIIIA Site-Specifically Conjugated with Bovine Serum Albumin,
Biochemical and Biophysical Research Communications, Vol.290, No.3, 1037-1041, 2002.

(要約): mu-Conotoxin GIIIA, one of the strong peptide toxins in the cone shell, preferentially blocks the skeletal muscle-type sodium channels in vertebrates. The toxicity of mu-conotoxin GIIIA is nearly equal to that of tetrodotoxin. The generation of an antibody for the native toxins is analytically useful, but practically difficult due to its high toxicity to animals. In this study, we generated the polyclonal antibody for mu-conotoxin GIIIA using a specific conjugation method in which the immunogen was detoxified while retaining the active-site structure for the sodium channels. ELISA analysis showed that the generated antibody recognized the native toxin folded with three disulfide bridges, but not the linear one. Furthermore, the physiologically active mutants of GIIIA were recognized while the inactive mutants were not, suggesting that the newly generated antibody can selectively recognize the physiologically active toxins. These methods for generating an antibody against peptide toxins will be applicable to other peptide toxins.
(キーワード): Amino Acid Sequence / Animals / Antibodies / Binding, Competitive / Cattle / Conotoxins / Cysteine / Enzyme-Linked Immunosorbent Assay / Lethal Dose 50 / Mice / Molecular Sequence Data / Muscle Contraction / Mutation / Rats / Sequence Homology, Amino Acid / Serum Albumin, Bovine
(出版サイトへのリンク): ● Publication site (DOI): 10.1006/bbrc.2001.6276
(文献検索サイトへのリンク): ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 11798179; ● Search Scopus @ Elsevier (PMID): 11798179; ● Search Scopus @ Elsevier (DOI): 10.1006/bbrc.2001.6276

(DOI: 10.1006/bbrc.2001.6276, PubMed: 11798179) Mitsuhiro Nakamura, Yukari Niwa, Yukisato Ishida, Toshiyuki Kohno, Kazuki Sato, Yuichi Oba and Hideshi Nakamura :
Modification of Arg-13 of mu-conotoxin GIIIA with piperidinyl-Arg analogs and the relation to the inhibition of sodium channels,
FEBS Letters, Vol.503, No.1, 107-110, 2001.

(要約): mu-Conotoxin GIIIA, a peptide toxin isolated from the marine snail Conus geographus, preferentially blocks skeletal muscle sodium channels in vertebrates. In this study, analogs of mu-conotoxin GIIIA in which essential Arg-13 was replaced with arginine analogs consisting of a piperidyl framework to regulate length and direction of the side chain were synthesized. Synthesized analogs exhibited similar CD and NMR spectra to that of GIIIA, suggesting a three-dimensional structure identical to that of the native toxin. The biological activities of piperidyl analogs were decreased or lost despite the small change in the side chain of Arg-13. The investigated structure-activity relationships in inhibiting electrically stimulated muscle contraction suggest that the guanidinium group at amino acid position 13 interacts best when spaced with three to four carbons and placed in a vertical direction from the peptide loop. Thus, the position of the guanidinium group at Arg-13 of GIIIA must be located in a certain range for its strong interaction with the channel protein.
(キーワード): Amino Acid Sequence / Animals / Arginine / Circular Dichroism / Conotoxins / Male / Molecular Sequence Data / Muscle Contraction / Nuclear Magnetic Resonance, Biomolecular / Piperidines / Rats / Rats, Wistar / Sodium Channel Blockers
(出版サイトへのリンク): ● Publication site (DOI): 10.1016/S0014-5793(01)02714-4
(文献検索サイトへのリンク): ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 11513864; ● Summary page in Scopus @ Elsevier: 2-s2.0-0035839122

(DOI: 10.1016/S0014-5793(01)02714-4, PubMed: 11513864, Elsevier: Scopus) Mitsuhiro Nakamura, Yukisato Ishida, Toshiyuki Kohno, Kazuki Sato and Hideshi Nakamura :
Synthesis of [Cys5]mu-conotoxin GIIIA and its derivatives as a probe of Na+ channel analysis,
Biochemical and Biophysical Research Communications, Vol.283, 374-378, 2001.

(要約): The residue of Thr-5 in mu-conotoxin GIIIA (GIIIA), a receptor site I sodium channel blocker, was replaced with Cys. The synthesized [Cys(5)]GIIIA had a similar 3D structure to the native GIIIA, revealed by CD and NMR. [Cys(5)]GIIIA and its tagged peptides inhibited the electrically stimulated contraction of the rat diaphragm with relatively comparable potency to that of GIIIA. Since the contractile response to electrical stimuli is caused by the activation of sodium channels, [Cys(5)]GIIIA could be a prototype for synthesizing useful tools for the analysis of sodium channels. Thus, [Cys(5)]GIIIA could be a prototype for synthesizing useful tools for the analysis of sodium channels.
(キーワード): Amino Acid Sequence / Animals / Circular Dichroism / Conotoxins / In Vitro Techniques / Magnetic Resonance Spectroscopy / Male / Molecular Probes / Molecular Sequence Data / Muscle Contraction / Rats / Rats, Wistar / Sodium Channels / Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
(出版サイトへのリンク): ● Publication site (DOI): 10.1006/bbrc.2001.4800
(文献検索サイトへのリンク): ● PubMed @ National Institutes of Health, US National Library of Medicine (PMID): 11327711; ● Summary page in Scopus @ Elsevier: 2-s2.0-0034811219

(DOI: 10.1006/bbrc.2001.4800, PubMed: 11327711, Elsevier: Scopus)

MISC

Mitsuhiro Nakamura, Yuichi Oba, Kazuki Sato, Yukisato Ishida, Tsukasa Matsuda and Hideshi Nakamura :
Generation of polyclonal antibody against peptide toxin mu-conotoxin GIIIA and their characterizations,
Peptide Science 2001 (Aoyagi, H. Ed.), 385-386, 2002. Mitsuhiro Nakamura, Yukari Niwa, Yukisato Ishida, Toshiyuki Kohno, Kazuki Sato, Yuichi Oba and Hideshi Nakamura :
Modification to Arg-13 of mu-conotoxin GIIIA with piperidinyl-Arg analogs and their evaluations,
Peptide Science 2001 (Aoyagi, H. Ed.), 203-204, 2002. Mitsuhiro Nakamura, Yukisato Ishida, Toshiyuki Kohno, Kazuki Sato and Hideshi Nakamura :
Syntheses and activity of mu-conotoxin analogs with a modified amino acid,
Peptide Science 2000 (Shioiri, T. Ed.), Vol.283, 85-88, 2001.

総説・解説

中村光裕, 井上敏 :
コエンザイムA を硫酸基受容体とした硫酸化ウミホタルルシフェリンからウミホタルルシフェリンへの変換,
硫酸と工業, No.12, 153-160, 2021年12月.

(文献検索サイトへのリンク): ● CiNii @ 国立情報学研究所 (CRID): 1521417756222415232

(CiNii: 1521417756222415232) 畠山士, 西尾広介, 中村光裕, 坂本聡, 加部泰明, 和田忠士, 半田宏 :
アフィニティ精製用担体としての高分子微粒子,
高分子論文集, Vol.64, No.1, 9-20, 2007年1月.

(出版サイトへのリンク): ● Publication site (DOI): 10.1295/koron.64.9
(文献検索サイトへのリンク): ● Summary page in Scopus @ Elsevier: 2-s2.0-33847027206

(DOI: 10.1295/koron.64.9, Elsevier: Scopus) Yoshihiro Ohmiya, Satoshi Kojima, Mitsuhiro Nakamura and Haruki Niwa :
Bioluminescence in the Limpet-Like Snail, Latia neritoides,
Bulletin of the Chemical Society of Japan, Vol.78, No.7, 1197-1205, Jul. 2005.

(出版サイトへのリンク): ● Publication site (DOI): 10.1246/bcsj.78.1197
(文献検索サイトへのリンク): ● CiNii @ 国立情報学研究所 (CRID): 1522262180536833280; ● Search Scopus @ Elsevier (DOI): 10.1246/bcsj.78.1197

(DOI: 10.1246/bcsj.78.1197, CiNii: 1522262180536833280) 中村光裕 :
イモ貝由来の毒，μ-コノトキシンの科学,
化学と工業, Vol.57, No.2, 123-126, 2004年2月.

講演・発表

Aya Fujimoto, Yoshimi Shingai, Mitsuhiro Nakamura, Tomomi Maekawa, Sone Yoshiaki and Toshiya Masuda :
POLYPHENOL OXIDATION, STRUCTURE AND FUNCTION OF THE PRODUCT I.TYROSINASE INHIBITORY OXIDATION PRODUCTS FROM ROSMARINIC ACID,
International Conference of Food Factor 2011, Taipei, Nov. 2011. Yoshimi Shingai, Aya Fujimoto, Mitsuhiro Nakamura and Toshiya Masuda :
Polyphenol Oxidation,Structure and Function of the Product II.LC-MS Investigation of Lipoxygenase Inhibitory Products of Resveratrol Oxidation,
International Conference of Food Factor 2011, Taipei, Nov. 2011. 吉田愛菜, 中村光裕, 田井章博 :
高感度かつハイスループットなアスコルビン酸定量法,
日本農芸化学会2022年度中四国支部大会(第63回講演会), 2022年9月. 中村光裕, 松田和生, 森川貴史, 石塚幸扶, 井上敏 :
酢酸の硫酸化反応と共役したCypridina luciferyl sulfateからCypridina luciferinへの酵素的変換,
第62回天然有機化合物討論会, 2020年9月. 中村光裕, 松田和生, 中村美沙樹, 山下喬平, 鈴木智子, 小笠原正道, 井上敏 :
アデニン誘導体のCypridina luciferyl sulfateの硫酸基受容体としての機能性,
2019年日本化学会中国四国支部大会, 2019年11月. 中村光裕, 松田和生, 中村美沙樹, 山下喬平, 鈴木智子, 井上敏 :
アデニン誘導体を硫酸基受容体としたCypridina luciferyl sulfateからCypridina luciferinへの酵素的変換,
第61回天然有機化合物討論会, 2019年9月. 中村光裕, 中原舞, 松田和生 :
セルロースを用いたチオール化合物の精製法の開発,
2017年日本化学会中国四国支部大会鳥取大会, 2017年11月. 中村光裕 :
ホタル発光系を利用したL-ルシフェリンからホタルD-ルシフェリンの生成,
2013年日本化学会中国四国支部大会, 2013年11月. 中村光裕 :
ホタル発光系を利用したL-ルシフェリンからホタルD-ルシフェリンの生成,
日本農芸化学会中四国支部第14回若手シンポジウム, 2012年10月. 藤本彩, 稲井美由紀, 中村光裕, 増田俊哉 :
チオール物質存在下でのカフェ酸，ジヒドロカフェ酸の酸化・抗酸化反応,
日本農芸化学会2012年度大会, 2012年3月. 新開愛美, 藤本彩, 中村光裕, 増田俊哉 :
ポリフェノール酸化物の機能-α‐グルコシダーゼ，キサンチンオキシダーゼ阻害能と活性物質-,
日本農芸化学会中四国支部第32回講演会, 2012年1月. 新開愛美, 藤本彩, 小山保夫, 中村光裕, 前川智美, 曽根良昭, 増田俊哉 :
ゴマ抗酸化フェノール・セサモール酸化物の構造と細胞毒性,
第53回天然有機化合物討論会講演要旨集, 277-282, 2011年9月. 中村光裕 :
ホタル発光系を利用したL-ルシフェリンからホタルD-ルシフェリンの生成,
第27回若手化学者のための化学道場(高知2011), 2011年9月. 新開愛美, 藤本彩, 中村光裕, 増田俊哉 :
ポリフェノール酸化物のリポキシゲナーゼ阻害活性-レスベラトロール酸化物の解析について-,
日本農芸化学会2011年度大会, 2011年3月.

(要約): ポリフェノール酸化物の機能として，リポキシゲナーゼ阻害活性をスクリーニングし，レスベラトロール酸化物に強い活性を発見したことを発表

藤本彩, 新開愛美, 中村光裕, 増田俊哉 :
ロスマリン酸の酸化により生成した特異な7員環物質の化学的性質[抗酸化フェノール物質の酸化生成物の構造と機能Ⅵ],
日本農芸化学会2011年度大会, 2011年3月.

(要約): 強いチロシナーゼ阻害活性を有するロスマリン酸酸化物の特異な構造とその活性への寄与を発表

藤本彩, 新開愛美, 中村光裕, 増田俊哉 :
抗酸化反応物に基づいたシソ科ハーブポリフェノールの抗酸化機構の解析,
第52回天然有機化合物討論会講演要旨集, 475-480, 2010年9月. 新開愛美, 藤本彩, 中村光裕, 増田俊哉, 小山保夫 :
ペルオキシ結合を有する特異なセサモール酸化ダイマーの構造ー酸化生成物の構造と機能IV,
日本農芸化学会中四国支部第28回講演会, 62, 2010年9月.

研究会・報告書: 田井章博, 吉田愛菜, 中村光裕, 古賀武尊 :
アスコルビン酸の高感度ハイスループット定量法,
第169回ビタミンC研究委員会, 2023年6月.

特許: 近江谷克裕, 丹羽一樹, 丹羽治樹, 中村光裕, 龍福正行 : 天然型L-システインまたはその誘導体を用いたホタル発光基質の生合成システム及び本システムを含んだ発光基質溶液, 特願PCT/JP2005/23847 (2005年12月), 特開WO/2006/070775 (2006年7月), 特許第WO/2006/070775号 (2006年7月). 近江谷克裕, 丹羽一樹, 丹羽治樹, 中村光裕, 龍福正行 : 天然型L-システインまたはその誘導体を用いたホタル発光基質の生合成システム及び本システムを含んだ発光基質溶液, 特願2004-379971 (2004年12月), 特開2006-180825 (2006年7月), 特許第2006-180825号 (2006年7月). 中村英士, 大場裕一, 中村光裕 : 受容体認識部位が保存された生理活性物質の誘導体及びその使用方法, 特願2001-66198 (2001年3月), 特開2001-322999 (2001年11月), 特許第2001-322999号 (2001年11月).
作品: 研究者総覧に該当データはありませんでした。
補助金・競争的資金: イミダゾピラジノン骨格を有する生物発光基質の硫酸化とその機能性 (研究課題/領域番号: 21K05414 )
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専門分野・研究分野: 化学 (Chemistry)
天然物化学 (Natural Products Chemistry)
生物有機化学 (Bioorganic Chemistry)
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受賞: 2004年3月, 若い世代の特別講演会講演者 (社団法人日本化学会)
2009年6月, 第20回落合記念賞 (埼玉医科大学)
2014年9月, 2014年度前期共通教育賞 (徳島大学)
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Jグローバル最終確認日: 2024/12/21 01:01
氏名（漢字）: 中村光裕
氏名（フリガナ）: ナカムラミツヒロ
氏名（英字）: Nakamura Mitsuhiro
所属機関: 徳島大学講師

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researchmap最終確認日: 2024/12/22 01:45
氏名（漢字）: 中村光裕
氏名（フリガナ）: ナカムラミツヒロ
氏名（英字）: Nakamura Mitsuhiro
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研究者番号: 50392056

所属（現在）: 2024/4/1 : 徳島大学, 大学院社会産業理工学研究部(理工学域), 講師

所属（過去の研究課題 情報に基づく）*注記: 2021/4/1 – 2022/4/1 : 徳島大学, 大学院社会産業理工学研究部(理工学域), 講師

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研究創発を活性化する有機化合物ライブラリーの構築

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