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Chemistry of aged garlic: Diversity of constituents in aged garlic extract and their production mechanisms via the combination of chemical and enzymatic reactions

Raw garlic contains characteristic compounds, such as S-alk(en)ylcysteine sulfoxides, γ-glutamyl-S-alk(en)-ylcysteines and polysaccharides. These compounds undergo various transformation processes during the aging process. Among these compounds, the change of sulfur-containing molecules is diverse a...

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Autores principales: Kodera, Yukihiro, Kurita, Masahiro, Nakamoto, Masato, Matsutomo, Toshiaki
Formato: Online Artículo Texto
Lenguaje:English
Publicado: D.A. Spandidos 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6966121/
https://www.ncbi.nlm.nih.gov/pubmed/32010342
http://dx.doi.org/10.3892/etm.2019.8393
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author Kodera, Yukihiro
Kurita, Masahiro
Nakamoto, Masato
Matsutomo, Toshiaki
author_facet Kodera, Yukihiro
Kurita, Masahiro
Nakamoto, Masato
Matsutomo, Toshiaki
author_sort Kodera, Yukihiro
collection PubMed
description Raw garlic contains characteristic compounds, such as S-alk(en)ylcysteine sulfoxides, γ-glutamyl-S-alk(en)-ylcysteines and polysaccharides. These compounds undergo various transformation processes during the aging process. Among these compounds, the change of sulfur-containing molecules is diverse and time-dependent. Previously, by means of the liquid chromatography (LC)/LC-mass spectrometry (MS) method, a number of unidentified peaks corresponding to candidates of sulfur-containing molecules were detected in the chromatogram of aged garlic extract (AGE), and identified using MS and nuclear magnetic resonance (NMR). The production mechanisms of these compounds were then examined by model reactions and laboratory experiments mimicking the aging process. Three γ-glutamyl tripeptides [γ-glutamyl-γ-glutamyl-S-methylcysteine, γ-glutamyl-γ-gluta-myl-S-allylcysteine (GGSAC), γ-glutamyl-γ-glutamyl-S−1-propenylcysteine], γ-glutamyl-S-allylmercaptocysteine (GSAMC) and cis-S−1-propenylcysteine (cis-S1PC) were isolated and identified. GGSAC was produced from GSAC through the enzymatic reaction catalyzed by γ-glutamyltranspeptidase (GGT), and two other tripeptides could be produced in similar reactions. GSAMC was produced by the reaction between γ-glutamyl dipeptides and allicin. Furthermore, GSAMC was a precursor compound of S-allyl-mercaptocysteine (SAMC), and thus it was produced from GSAMC by GGT. cis-S1PC was produced from trans-S1PC by the isomerization reaction. A number of other compounds were also identified, including Maillard reaction products; however, their production mechanisms have not been elucidated. In this review, we present the changes in characteristic constituents in raw garlic and garlic extract during the aging process and discuss their production mechanisms involving the various chemical and enzymatic reactions.
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spelling pubmed-69661212020-01-31 Chemistry of aged garlic: Diversity of constituents in aged garlic extract and their production mechanisms via the combination of chemical and enzymatic reactions Kodera, Yukihiro Kurita, Masahiro Nakamoto, Masato Matsutomo, Toshiaki Exp Ther Med Review Raw garlic contains characteristic compounds, such as S-alk(en)ylcysteine sulfoxides, γ-glutamyl-S-alk(en)-ylcysteines and polysaccharides. These compounds undergo various transformation processes during the aging process. Among these compounds, the change of sulfur-containing molecules is diverse and time-dependent. Previously, by means of the liquid chromatography (LC)/LC-mass spectrometry (MS) method, a number of unidentified peaks corresponding to candidates of sulfur-containing molecules were detected in the chromatogram of aged garlic extract (AGE), and identified using MS and nuclear magnetic resonance (NMR). The production mechanisms of these compounds were then examined by model reactions and laboratory experiments mimicking the aging process. Three γ-glutamyl tripeptides [γ-glutamyl-γ-glutamyl-S-methylcysteine, γ-glutamyl-γ-gluta-myl-S-allylcysteine (GGSAC), γ-glutamyl-γ-glutamyl-S−1-propenylcysteine], γ-glutamyl-S-allylmercaptocysteine (GSAMC) and cis-S−1-propenylcysteine (cis-S1PC) were isolated and identified. GGSAC was produced from GSAC through the enzymatic reaction catalyzed by γ-glutamyltranspeptidase (GGT), and two other tripeptides could be produced in similar reactions. GSAMC was produced by the reaction between γ-glutamyl dipeptides and allicin. Furthermore, GSAMC was a precursor compound of S-allyl-mercaptocysteine (SAMC), and thus it was produced from GSAMC by GGT. cis-S1PC was produced from trans-S1PC by the isomerization reaction. A number of other compounds were also identified, including Maillard reaction products; however, their production mechanisms have not been elucidated. In this review, we present the changes in characteristic constituents in raw garlic and garlic extract during the aging process and discuss their production mechanisms involving the various chemical and enzymatic reactions. D.A. Spandidos 2020-02 2019-12-27 /pmc/articles/PMC6966121/ /pubmed/32010342 http://dx.doi.org/10.3892/etm.2019.8393 Text en Copyright: © Kodera et al. This is an open access article distributed under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License (https://creativecommons.org/licenses/by-nc-nd/4.0/) , which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.
spellingShingle Review
Kodera, Yukihiro
Kurita, Masahiro
Nakamoto, Masato
Matsutomo, Toshiaki
Chemistry of aged garlic: Diversity of constituents in aged garlic extract and their production mechanisms via the combination of chemical and enzymatic reactions
title Chemistry of aged garlic: Diversity of constituents in aged garlic extract and their production mechanisms via the combination of chemical and enzymatic reactions
title_full Chemistry of aged garlic: Diversity of constituents in aged garlic extract and their production mechanisms via the combination of chemical and enzymatic reactions
title_fullStr Chemistry of aged garlic: Diversity of constituents in aged garlic extract and their production mechanisms via the combination of chemical and enzymatic reactions
title_full_unstemmed Chemistry of aged garlic: Diversity of constituents in aged garlic extract and their production mechanisms via the combination of chemical and enzymatic reactions
title_short Chemistry of aged garlic: Diversity of constituents in aged garlic extract and their production mechanisms via the combination of chemical and enzymatic reactions
title_sort chemistry of aged garlic: diversity of constituents in aged garlic extract and their production mechanisms via the combination of chemical and enzymatic reactions
topic Review
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6966121/
https://www.ncbi.nlm.nih.gov/pubmed/32010342
http://dx.doi.org/10.3892/etm.2019.8393
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