Degree of polymerization of 5,6-dihydroxyindole-derived eumelanin from chemical degradation study

Hidekazu Okuda, Kyoji Yoshino, Kazumasa Wakamatsu, Shosuke Ito, Takayuki Sota

    研究成果: Article

    12 引用 (Scopus)

    抄録

    Summary: Eumelanin is a brown-black pigment comprising 5,6-dihydroxyindole (DHI) and its 2-carboxy derivative (DHICA), but the detailed structure of eumelanin is unclear. Chemical degradation is a powerful tool for analyzing melanin. H2O2 oxidation degradation of eumelanin affords pyrrole-2,3,5-tricarboxylic acid (PTCA) and pyrrole-2,3-dicarboxylic acid (PDCA). The ratio of PDCA to PTCA provides information about the eumelanin structure. In this article, we propose simple equations on the basis of previous experimental results on dimer yields for evaluating the yields of PTCA and PDCA from any DHI oligomers. Assuming the chemical disorder model of DHI-melanin, we solve an equation where a theoretical expression for the ratio of PDCA to PTCA is set to the corresponding experimental value to obtain a plausible Poisson distribution of DHI oligomers. The results demonstrate that the main contributors to DHI-melanin are tetramers and pentamers as shown by the mass spectrometry.

    元の言語English
    ページ(範囲)664-667
    ページ数4
    ジャーナルPigment Cell and Melanoma Research
    27
    発行部数4
    DOI
    出版物ステータスPublished - 2014

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    Polymerization
    Degradation
    Oligomers
    Poisson Distribution
    Chemical Models
    Poisson distribution
    Melanins
    Pigments
    Dimers
    Mass spectrometry
    Mass Spectrometry
    Derivatives
    Oxidation
    pyrrole-2,3-dicarboxylic acid
    eumelanin
    5,6-dihydroxyindole
    pyrrole-2,3,5-tricarboxylic acid
    dihydroxyindole-melanin

    ASJC Scopus subject areas

    • Dermatology
    • Oncology
    • Biochemistry, Genetics and Molecular Biology(all)

    これを引用

    Degree of polymerization of 5,6-dihydroxyindole-derived eumelanin from chemical degradation study. / Okuda, Hidekazu; Yoshino, Kyoji; Wakamatsu, Kazumasa; Ito, Shosuke; Sota, Takayuki.

    :: Pigment Cell and Melanoma Research, 巻 27, 番号 4, 2014, p. 664-667.

    研究成果: Article

    Okuda, Hidekazu ; Yoshino, Kyoji ; Wakamatsu, Kazumasa ; Ito, Shosuke ; Sota, Takayuki. / Degree of polymerization of 5,6-dihydroxyindole-derived eumelanin from chemical degradation study. :: Pigment Cell and Melanoma Research. 2014 ; 巻 27, 番号 4. pp. 664-667.
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    AU - Yoshino, Kyoji

    AU - Wakamatsu, Kazumasa

    AU - Ito, Shosuke

    AU - Sota, Takayuki

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    N2 - Summary: Eumelanin is a brown-black pigment comprising 5,6-dihydroxyindole (DHI) and its 2-carboxy derivative (DHICA), but the detailed structure of eumelanin is unclear. Chemical degradation is a powerful tool for analyzing melanin. H2O2 oxidation degradation of eumelanin affords pyrrole-2,3,5-tricarboxylic acid (PTCA) and pyrrole-2,3-dicarboxylic acid (PDCA). The ratio of PDCA to PTCA provides information about the eumelanin structure. In this article, we propose simple equations on the basis of previous experimental results on dimer yields for evaluating the yields of PTCA and PDCA from any DHI oligomers. Assuming the chemical disorder model of DHI-melanin, we solve an equation where a theoretical expression for the ratio of PDCA to PTCA is set to the corresponding experimental value to obtain a plausible Poisson distribution of DHI oligomers. The results demonstrate that the main contributors to DHI-melanin are tetramers and pentamers as shown by the mass spectrometry.

    AB - Summary: Eumelanin is a brown-black pigment comprising 5,6-dihydroxyindole (DHI) and its 2-carboxy derivative (DHICA), but the detailed structure of eumelanin is unclear. Chemical degradation is a powerful tool for analyzing melanin. H2O2 oxidation degradation of eumelanin affords pyrrole-2,3,5-tricarboxylic acid (PTCA) and pyrrole-2,3-dicarboxylic acid (PDCA). The ratio of PDCA to PTCA provides information about the eumelanin structure. In this article, we propose simple equations on the basis of previous experimental results on dimer yields for evaluating the yields of PTCA and PDCA from any DHI oligomers. Assuming the chemical disorder model of DHI-melanin, we solve an equation where a theoretical expression for the ratio of PDCA to PTCA is set to the corresponding experimental value to obtain a plausible Poisson distribution of DHI oligomers. The results demonstrate that the main contributors to DHI-melanin are tetramers and pentamers as shown by the mass spectrometry.

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    KW - Eumelanin

    KW - Hydrogen peroxide oxidation

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