Development of an analysis method for 4-Deoxy-L-erythro-5-hexoseulose uronic acid by LC/ESI/MS with selected ion monitoring

Toshiyuki Shibata, Reona Fujii, Hideo Miyake, Reiji Tanaka, Tetsushi Mori, Mami Takahashi, Toshiyuki Takagi, Hiroyuki Yoshikawa, Kouichi Kuroda, Mitsuyoshi Ueda

    Research output: Contribution to journalArticle

    1 Citation (Scopus)

    Abstract

    This study describes a simple and rapid analytical quantitative method for measuring 4-deoxy-L-erythro-5-hexoseulose uronic acid (DEH) using liquid chromatography-electrospray ionization-mass spectrometry (LC/ESI/MS). For a chromatographic condition, Shodex IC NI-424 column (4.6 mm i.d. x 100 mm, 5 μm) for anion analysis and an isocratic elution of 40 mM ammonium formate buffer including 0.1% formic acid (pH 3.75) at a flow rate of 0.5 mL/min was used. The column temperature was set to 40°C. In the analysis of DEH produced by exo-type alginate lyase (AlyFRB) from Falsirhodobacter sp. alg1, a peak was detected with a retention time of 3.207 min. The prepared calibration curves for DEH analysis using the selected ion monitoring (SIM) mode of a mass spectrometer revealed a good linear relationship (correlation factor: 0.9998) within the test range (0.1-100 μg/mL). The limits of detection (S/N = 3) and quantification (S/N = 10) for DEH in SIM analysis were 0.008 and 0.027 μg/mL, respectively. Using the developed condition of LC/ESI/MS analysis, separation and detection of alginate unsaturated oligosaccharides were also tested. In an analysis time of about 13 min, this method was able to separate and detect an alginate unsaturated disaccharide, a trisaccharide, and a tetrasaccaride produced by poly(β-D-mannuronate) lyase, respectively. The analysis method established in this study will contribute to the quantitative and qualitative analysis of DEH, and the activity measurement of exo-type alginate lyase.

    Original languageEnglish
    Pages (from-to)941-944
    Number of pages4
    JournalNatural Product Communications
    Volume12
    Issue number6
    Publication statusPublished - 2017

    Fingerprint

    formic acid
    Uronic Acids
    uronic acids
    Electrospray Ionization Mass Spectrometry
    alginates
    Liquid Chromatography
    liquid chromatography
    quantitative analysis
    Ions
    ions
    trisaccharides
    formates
    monitoring
    lyases
    disaccharides
    qualitative analysis
    spectrometers
    oligosaccharides
    anions
    analytical methods

    Keywords

    • 4-Deoxy-L-erythro-5-hexoseulose uronic acid
    • Alginate
    • Exo-type alginate lyase
    • Falsirhodobacter sp. alg1
    • Liquid chromatography-electrospray ionization-mass spectrometry

    ASJC Scopus subject areas

    • Medicine(all)
    • Pharmacology
    • Plant Science
    • Drug Discovery
    • Complementary and alternative medicine

    Cite this

    Shibata, T., Fujii, R., Miyake, H., Tanaka, R., Mori, T., Takahashi, M., ... Ueda, M. (2017). Development of an analysis method for 4-Deoxy-L-erythro-5-hexoseulose uronic acid by LC/ESI/MS with selected ion monitoring. Natural Product Communications, 12(6), 941-944.

    Development of an analysis method for 4-Deoxy-L-erythro-5-hexoseulose uronic acid by LC/ESI/MS with selected ion monitoring. / Shibata, Toshiyuki; Fujii, Reona; Miyake, Hideo; Tanaka, Reiji; Mori, Tetsushi; Takahashi, Mami; Takagi, Toshiyuki; Yoshikawa, Hiroyuki; Kuroda, Kouichi; Ueda, Mitsuyoshi.

    In: Natural Product Communications, Vol. 12, No. 6, 2017, p. 941-944.

    Research output: Contribution to journalArticle

    Shibata, T, Fujii, R, Miyake, H, Tanaka, R, Mori, T, Takahashi, M, Takagi, T, Yoshikawa, H, Kuroda, K & Ueda, M 2017, 'Development of an analysis method for 4-Deoxy-L-erythro-5-hexoseulose uronic acid by LC/ESI/MS with selected ion monitoring', Natural Product Communications, vol. 12, no. 6, pp. 941-944.
    Shibata, Toshiyuki ; Fujii, Reona ; Miyake, Hideo ; Tanaka, Reiji ; Mori, Tetsushi ; Takahashi, Mami ; Takagi, Toshiyuki ; Yoshikawa, Hiroyuki ; Kuroda, Kouichi ; Ueda, Mitsuyoshi. / Development of an analysis method for 4-Deoxy-L-erythro-5-hexoseulose uronic acid by LC/ESI/MS with selected ion monitoring. In: Natural Product Communications. 2017 ; Vol. 12, No. 6. pp. 941-944.
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    AU - Shibata, Toshiyuki

    AU - Fujii, Reona

    AU - Miyake, Hideo

    AU - Tanaka, Reiji

    AU - Mori, Tetsushi

    AU - Takahashi, Mami

    AU - Takagi, Toshiyuki

    AU - Yoshikawa, Hiroyuki

    AU - Kuroda, Kouichi

    AU - Ueda, Mitsuyoshi

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    AB - This study describes a simple and rapid analytical quantitative method for measuring 4-deoxy-L-erythro-5-hexoseulose uronic acid (DEH) using liquid chromatography-electrospray ionization-mass spectrometry (LC/ESI/MS). For a chromatographic condition, Shodex IC NI-424 column (4.6 mm i.d. x 100 mm, 5 μm) for anion analysis and an isocratic elution of 40 mM ammonium formate buffer including 0.1% formic acid (pH 3.75) at a flow rate of 0.5 mL/min was used. The column temperature was set to 40°C. In the analysis of DEH produced by exo-type alginate lyase (AlyFRB) from Falsirhodobacter sp. alg1, a peak was detected with a retention time of 3.207 min. The prepared calibration curves for DEH analysis using the selected ion monitoring (SIM) mode of a mass spectrometer revealed a good linear relationship (correlation factor: 0.9998) within the test range (0.1-100 μg/mL). The limits of detection (S/N = 3) and quantification (S/N = 10) for DEH in SIM analysis were 0.008 and 0.027 μg/mL, respectively. Using the developed condition of LC/ESI/MS analysis, separation and detection of alginate unsaturated oligosaccharides were also tested. In an analysis time of about 13 min, this method was able to separate and detect an alginate unsaturated disaccharide, a trisaccharide, and a tetrasaccaride produced by poly(β-D-mannuronate) lyase, respectively. The analysis method established in this study will contribute to the quantitative and qualitative analysis of DEH, and the activity measurement of exo-type alginate lyase.

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    KW - Falsirhodobacter sp. alg1

    KW - Liquid chromatography-electrospray ionization-mass spectrometry

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