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Isolation and Identification of Three γ-Glutamyl Tripeptides and Their Putative Production Mechanism in Aged Garlic Extract

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    Isolation and Identification of Three γ-Glutamyl Tripeptides and Their Putative Production Mechanism in Aged Garlic Extract
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    • Masashi Nakamoto
      Masashi Nakamoto
      Healthcare Research and Development Division, Wakunaga Pharmaceutical Co., Ltd., 1624 Shimokotachi, Koda-cho, Akitakata-shi, Hiroshima 739-1195, Japan
      More by Masashi Nakamoto
    • Takuto Fujii
      Takuto Fujii
      Central Research Institute, Wakunaga Pharmaceutical Co., Ltd., 1624 Shimokotachi, Koda-cho, Akitakata-shi, Hiroshima 739-1195, Japan
      More by Takuto Fujii
    • Toshiaki Matsutomo
      Toshiaki Matsutomo
      Central Research Institute, Wakunaga Pharmaceutical Co., Ltd., 1624 Shimokotachi, Koda-cho, Akitakata-shi, Hiroshima 739-1195, Japan
      More by Toshiaki Matsutomo
    • Yukihiro Kodera*
      Yukihiro Kodera
      Central Research Institute, Wakunaga Pharmaceutical Co., Ltd., 1624 Shimokotachi, Koda-cho, Akitakata-shi, Hiroshima 739-1195, Japan
      *E-mail: [email protected]. Phone: +81 826 45 2331. Fax: +81 826 45 4351.
      More by Yukihiro Kodera
      Orcidhttp://orcid.org/0000-0003-0538-0105
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    Journal of Agricultural and Food Chemistry

    Cite this: J. Agric. Food Chem. 2018, 66, 11, 2891–2899
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.jafc.7b05480
    Published March 2, 2018
    Copyright © 2018 American Chemical Society
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    Abstract

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    We analyzed aged garlic extract (AGE) to understand its complex sulfur chemistry using post-column high-performance liquid chromatography with an iodoplatinate reagent and liquid chromatography high resolution mass spectrometry (LC–MS). We observed unidentified peaks of putative sulfur compounds. Three compounds were isolated and identified as γ-glutamyl-γ-glutamyl-S-methylcysteine, γ-glutamyl-γ-glutamyl-S-allylcysteine (GGSAC) and γ-glutamyl-γ-glutamyl-S-1-propenyl-cysteine (GGS1PC) by nuclear magnetic resonance and LC–MS analysis based on comparisons with chemically synthesized reference compounds. GGSAC and GGS1PC were novel compounds. Trace amounts of these compounds were detected in raw garlic, but the contents of these compounds increased during the aging process. Production of these compounds was inhibited using a γ-glutamyl transpeptidase (GGT) inhibitor in the model reaction mixtures. These findings suggest that γ-glutamyl tripeptides in AGE are produced by GGT during the aging process.

    Copyright © 2018 American Chemical Society

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    Cited By

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    This article is cited by 22 publications.

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    Journal of Agricultural and Food Chemistry

    Cite this: J. Agric. Food Chem. 2018, 66, 11, 2891–2899
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.jafc.7b05480
    Published March 2, 2018
    Copyright © 2018 American Chemical Society
    Request reuse permissions

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