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Improvement of Mass Spectrometry of Biologically Active Natural Products.

Research Project

Project/Area Number 62300009
Research Category

Grant-in-Aid for Co-operative Research (A)

Allocation TypeSingle-year Grants
Research Field 広領域
Research InstitutionAichi University of Education

Principal Investigator

NAKATA Hisao  Department of Chemistry, Aichi University of Education (professor), 教育学部, 教授 (90023952)

Co-Investigator(Kenkyū-buntansha) YAMAMOTO Masao  Faculty of Science, Nara Women's University (Professor), 理学部, 教授 (80028159)
GOTO Toshio  Faculty of Agriculture, Nagoya University (Professor), 農学部, 教授 (20023369)
TSUGE Shin  Faculty of Engineering, Nagoya University (Professor), 工学部, 教授 (60023157)
OHASHI Mamoru  Department of Materials Science, The University of Electro-Communications (Profe, 電気通信学部, 教授 (70015535)
NAMBARA Toshio  Faculty of Pharmacy, Tohoku University (Professor), 薬学部, 教授 (30004534)
Project Period (FY) 1987 – 1988
Project Status Completed (Fiscal Year 1988)
Budget Amount *help
¥5,500,000 (Direct Cost: ¥5,500,000)
Fiscal Year 1988: ¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 1987: ¥4,000,000 (Direct Cost: ¥4,000,000)
KeywordsBiologically active natural products / Mass spectrometry / In-beam EI / Desorption CI / HPLC / MS / Liquid ionization / SIMS / FAB / MS / 液体イオン化法 / スフィンゴ脂質 / CI法 / アミノ配糖抗生物質 / マイコトキシンの分析 / デソープションCI / FABマススペクトル / セレブロシド / アントシアニン類
Research Abstract

The Aim of this project is to improve the possible information available from mass spectra of biologically active natural products. 1. Derivatization - Two new derivatization methods, pentafluorobenzylation and diethylhydrogensilylation, were found to be useful for certain types of hydroxylated natural products. 2. Sample Introduction - A new vacuum nebulizing interface for direct combination of liquid chromatography amd mass spectrometer was developed. 3. Ionization - Various ionization methods were examined including in-beam EI, negative CI, desorption CI, FD, liquid ionization, SIMS, and FAB. 4. Improvement of Mass Spectrometer - A relatively large mass spectrometer (total ion flight path 7.4 m) was built which showed resolution of ca. 10,000 for routine measurements. 5. MS/MS - AN EBEB four secter tandem mass spectrometer was successfully applied to stereochemical problems of a suger-containing natural product. 6. Theoretical Approach - The factors for bond cleavege of ionic organic species were clarified on the basis of molecular orbital calculations. 7. Applications - Several biologically active natural products were investigated by mass spectrometry: cerbrosides from guinea pig harderian glands, human and bovine galactocerebrosides, abscisic acid-conjugated metabolites from plants, anthocyanins from Zebrina Pendula and from Ipomoea Tricolor, aminoglucoside antibiotics, depside from lichen micobiont, and fungal spore germination self-inhibitors.

Report

(3 results)
  • 1988 Annual Research Report   Final Research Report Summary
  • 1987 Annual Research Report
  • Research Products

    (76 results)

All Other

All Publications (76 results)

  • [Publications] Hisao Nakata: Organic Mass Spectrometry. 22. 23-29 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Junichi Goto: Jouranal of Chromatography. 388. 379-387 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kozo Matsumoto: Mass Spectroscopy. 35. 15-22 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kozo Matsumoto: Mass Spectroscop. 35. 240-247 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Yoshiko Niki,et al.: Organic Mass Spectrometry. 22. 157-161 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Yasuo Shida,et al.: Bulletin of the Chemical Society of Japan. 60. 1881-1886 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] 辻本和雄: 質量分析. 35. 232-239 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Hisao Nakata: Proceedings of the Second Japan-China Joint Symposium on Mass Spectrometry(Edited by H.Matsuda and Liang Xiao-tian). 233-236 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Maohito Takeda,et al.: Agricultural and Biological Chemistry. 51. 2351-2357 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Tamio Ueno: Pesticide Science and Biotechnology(Proceedings of 6th IUPAC Congress of Pesticide:Chemistry)(Edited by R.Greenhalgh and T.R.Roberts). 89-96 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Tamio Ueno: Proceedings of the Second Japan-China Joint Symposium on Mass Spectrometry(Edited by H.Matsuda and Liang Xiao-tian),Bando. 261-264 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Etsuko Yasugi,et al: Journal of Biochemistry. 102. 1477-1482 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Eiichi Idaka,et al: Tetrahedron Letters. 28. 1901-1904 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Nobuo Hamada,et al: Agricultural and Biological Chemistry. 51. 1705-1706 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Tadao Kondo,et al.: Tetrahedron Letters. 28. 2273-2276 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Masao Yamamoto,et al.: Proceedings of the Second Japan-China Joint Symposium on Mass Spectrometry (Edited by H.Matsuda and liang Xiao-tian). 1987. (61-64)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Junichi Goto,et al.: Journal of Chromatography. 452. 119-129 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kiichiro Otsuka,et al.: Analytical Sciences. 4. 467-472 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] 矢部利江、ほか・: Ear Research Japan. 19. 313-316 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] 藤岡裕二、ほか・: 分析化学. 37. 17-24 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Fumio Okuyama,et al.: International Journal of Mass Spectrometry and Ion Processes. 82. 55-60 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Etsuko Yasugi,et al.: Journal of Biochemistry. 103. 889-893 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Masao Yamamoto,et al.: Advances in Mass Spectrometry. 11. (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Katsuyoshi Masuda,et al.: Organic Mass Spectrometry. 24. 74-75 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Hisao Nakata, et al.: "Diethylhydrogensilyl Cyclic Diethylsilylene Derivatives in Gas Chromatography / Mass Spectrometry of Hydroxylated Steroids. III Fragmentations of 5 -Pregnane-17,20,21-triol DErivatives." Organic Mass Spectrometry. 22. 23-29 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Junichi Goto, et al.: "Trace Analysis of Bile Acids by Gas Chromatography / Mass Spectrometry with Negative Ion Chemical Ionization Detection." Journal of Chromatography. 388. 379-387 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kozo Matsumoto, et al.: "Analysis of Non-ionic Surface Active Agents by Supercritical Fluid Chromatography / Mass Spenctrometry." Mass Spectroscopy (Japan). 35. 15-22 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kozo Matsumoto, et al.: "On-line Liquid Chromatography / Double Focussing Mass Spectrometry with a Newly Improved Vacuum Nebulizing Interface." Mass Spectroscopy (Japan). 35. 240-247 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Yoshiko Niki, et al.: "Discrmination of Isomers by Liquid Ionization Mass Spectrometry with Techniques of Collisional Activation and Adduct Ion Formation." Organic Mass Spectrometry. 22. 157-161 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Yasuo Shida, et al.: "In-beam EIMS and Molecular SIMS of Quaternary Ammonium Chlorides of Benzylamine Dericatives." Bulletin of the Chemical Society of Japan. 60. 1881-1886 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kazuo Tsujimoto, et al.: "In-beam EI Mass Spectrometry of Monosaccharids --- Appearance of Peaks above the Protonated Molecular Peak originated from Fragmentation of the Protonated Dimer." Mass Spectroscopy (Japan). 35. 232-239 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Hisao Nakata.: "Secondary Ion Mass Spectrometry of Simple Bifunctional Organic Compounds. An Evidence for a Mechanism of Proton Transter Ionization." Proceedings of the Second Japan-China Joint Symposium on Mass Spectrometry. 233-236 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Naohito Takeda, et al.: "Characterization of a New Abscisic Acid-conjugated Metabolite in Crude Plant Extract by Desorption Chemical Ionization and Secondaey Ion Mass Spectrometry." Agricultural and Biological Chemistry. 51. 2351-2357 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Tamio Ueno, et al.: "Chemistry and Biological Function of Host-specific Phytotoxins." Pesticide Science and Biotechnology (Proceesings of 6th IUPAC Congress of Prsticide:Chemistry). 89-96 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Tamio Ueno, et al.: "Struture Determination of Fungal Spore Gemination Self-Inhibitors by Mass Spectrometry." Proceedings of the Second Japan-China Joint Symposium on Mass Spectrometry, Bando Press.261-264 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Etsuko Yasugi, et al.: "Branched Long Chain Bases in Cerebrosides of the Guinea Pig Harderian Gland." Journal of Biochemistry. 102. 1477-1482 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Eiichi Idaka, et al.: "Structue of Zebrinin A Novel Acylated Anthocyanin isolated from Zebrina Pendula." Tetrahedron Letters. 28. 1901-1904 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Nobuo Hamada, et al.: "Depside from an Isolated Lichen Mycobiont." Agrucultural and Biological Chemistry. 51. 1705-1706 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Takao Kondo, et al.: "Structure Determination of Heavenly Blue Anthocyanin, A Complex Monomeric Anthocyanin from the Morning Glory Ipomoea Tr icolor, by means of the Negative NOE Method." Tetrahedron Letters. 28. 2273-2276 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Masao Yamamoto, et al.: "Fragmentation of Lower Alkylsilanes appeared in their EI Mass Spectra." Proceedings of the Second Japan-China Joint Symposium on Mass Spectrometry (Edited by H.Matsuda and Liang Xiao-tian) Bando Press.61-64 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Junichi Goto, et al.: "Studied on Steroids. CCXXXVIII. Determination of Bile Acids in Liver Tissue by Gas Chromatography - Mass Spectrometry with Negative Ion Chemical Ionization Detection." Journal of Chromatography. 452. 119-129 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Kiichiro Otsuka, et al.: "An Interface for Liquid Chromatograph / Liquid Ionization Mass Spectrometer." Analytical Sciences. 4. 467-472 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Rie Yabe, et al.: "Analysis of Middle Ear Effusions by Liquid Ionization Mass Sectrometry." Ear Research Japan. 19. 313-316 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Yuji Fujioka, et al.: "Analysis of Coal Tar Pitches by Liquid Ionization Mass Spectrometry." Bunsrki Kagaku. 37. 17-24 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Fumio Okuyama, et al.: "Field Desorption of Sodium Acetate studied by Combined Optical Microscopy and Mass Spectrometry." International Journal of Mass Spectrometry amd Ion Pocesses. 82. 55-60 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Etsuko Yasugi, et al.: "Identififcation of 10-Methylsphinganine in Cerebrosides of the Guinaea Pig Harderian Gland." Journal of Biochemistry. 103. 889-893 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Itsuo Katakuse, et al.: "Ultra-high-mass Spectra of CsI Clusters and Evidence for the Existence of Stable Neutral Cubic-like Structures with an Even Number of Atoms." Rapid Communications in Mass Spectrometry. 2. 191-194 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Masao Yamamoto, et al.: "Fragmentation of the Several Alkylsilane Compounds in EIMS." Advances in Mass Spectrometry. 11. (1989)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Katsuyoshi Masuda, et al.: "Identification of Food Dyes by TLC/SIMS with a Condensation Technique." Organic Mass Spectrometry. 24. 74-75 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Junichi Goto,et al.: Journal of Chromatography. 452. 119-129 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Kozo Matsumoto,et al.: Mass Spectroscopy(Japan). 35. 240-247 (1987)

    • Related Report
      1988 Annual Research Report
  • [Publications] Fumino Okuyama,et al.: International Journal of Mass Spectrometry and Ion Processes. 82. 55-60 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Kiichiro Otsuka,et al.: Analytical Sciences. 4. 467-472 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] 谷部利江 他: Ear Research Japan. 19. 313-316 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] 藤岡裕二 他: 分析化学. 37. 17-24 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Yoshiko Niki,et al.: Organic Mass Spectrometry. 22. 157-161 (1987)

    • Related Report
      1988 Annual Research Report
  • [Publications] Yasuo Shida,et al.: Bulletin of the Chemical Society of Japan. 60. 1881-1886 (1987)

    • Related Report
      1988 Annual Research Report
  • [Publications] Katsuyoshi Masuda,et al.: Organic Mass Spectrometry. 24. 74-75 (1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] Naohito Takeda,et al.: Agricultural and Biological Chemistry. 51. 2351-2357 (1987)

    • Related Report
      1988 Annual Research Report
  • [Publications] Nobuo Hamada,et al.: Agricultural and Biological Chemistry. 51. 1705-1706 (1987)

    • Related Report
      1988 Annual Research Report
  • [Publications] Etsuko Yasugi,et al.: Journal of Biochemistry. 103. 889-893 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Hisao Nakata: Organic Mass Spectrometry. 22. 23-29 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] Junichi Goto: Journal of Chromatography. 388. (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] Fumio Okuyama: International Journal of Mass Spectrometry and Ion Processes. 82. 55-60 (1988)

    • Related Report
      1987 Annual Research Report
  • [Publications] 辻本和雄: 質量分析. 35. 232-239 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] Yasuo Shida: Bulletin of The Chemical Society of Japan. 60. 1881-1886 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] Kozo Matsumoto: Mass Spectroscopy. 35. 15-22 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] Hisao Nakata;H.Matsuda;Liang Xiao-tian Ed.: Proceeding of the Second Japan Symposium on Mass Spectrometry. 233-236 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] Tamio Ueno;R.Greenhalgh;T.R.Roberts Ed.: Pesticide Science and Biotechnology(Proceeding of 6th IUPAC Congress of Pesticide:Chemistry). 89-96 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] Kozo Matsumoto: Mass Spectrometry. 35. 240-247 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] Naohito Takeda: Agricultural and Biological Chemistry. 51. 2351-2357 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] Etsuko Yasugi: Journal of Biochemistry. 102. 1477-1482 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] Eiichi Idaka: Tetrahedron Letters. 28. 1901-1904 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] Tadao Kondo: Tetrahedron Letters. 28. 2273-2276 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] Tmmio Ueno;H.Matsuda;Liang Xiao-tian Ed.: Proceedings of the Second Japan-China Joint Symposium on Mass Spectrometry.261-264 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] Masao Yamamoto;H.Matsuda;Liang Xiao-tian Ed.: Proceedings of the Second Japan-China Joint Symposium on Mass Spectrometry.61-64 (1987)

    • Related Report
      1987 Annual Research Report

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Published: 1987-04-01   Modified: 2016-04-21  

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