Xanthurenic Acid in the Shell Purple Patterns of Crassostrea gigas: First Evidence of an Ommochrome Metabolite in a Mollusk Shell
International audience Ommochromes are one of the least studied groups of natural pigments, frequently confused with melanin and, so far, exclusively found in invertebrates such as cephalopods and butterflies. In this study focused on the purple color of the shells of a mollusk, Crassostrea gigas, t...
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Online Access: | https://hal.umontpellier.fr/hal-03516064 https://doi.org/10.3390/molecules26237263 |
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ftccsdartic:oai:HAL:hal-03516064v1 2023-05-15T15:57:35+02:00 Xanthurenic Acid in the Shell Purple Patterns of Crassostrea gigas: First Evidence of an Ommochrome Metabolite in a Mollusk Shell Bonnard, Michel Boury, Bruno Parrot, Isabelle Institut des Biomolécules Max Mousseron Pôle Chimie Balard (IBMM) Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM) Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM) Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS) 2021-12 https://hal.umontpellier.fr/hal-03516064 https://doi.org/10.3390/molecules26237263 en eng HAL CCSD MDPI info:eu-repo/semantics/altIdentifier/doi/10.3390/molecules26237263 hal-03516064 https://hal.umontpellier.fr/hal-03516064 doi:10.3390/molecules26237263 ISSN: 1420-3049 Molecules https://hal.umontpellier.fr/hal-03516064 Molecules, MDPI, 2021, 26 (23), pp.7263. ⟨10.3390/molecules26237263⟩ [CHIM]Chemical Sciences info:eu-repo/semantics/article Journal articles 2021 ftccsdartic https://doi.org/10.3390/molecules26237263 2022-01-08T23:22:46Z International audience Ommochromes are one of the least studied groups of natural pigments, frequently confused with melanin and, so far, exclusively found in invertebrates such as cephalopods and butterflies. In this study focused on the purple color of the shells of a mollusk, Crassostrea gigas, the first evidence of a metabolite of ommochromes, xanthurenic acid (XA), was obtained by liquid chromatography combined with mass spectrometry (UPLC-MS). In addition to XA and various porphyrins previously identified, a second group of high molecular weight acid-soluble pigments (HMASP) has been identified with physicochemical and structural characteristics similar to those of ommochromes. In addition, fragmentation of HMASP by tandem mass spectrometry (MS/MS) has revealed a substructure common to XA and ommochromes of the ommatin type. Furthermore, the presence of melanins was excluded by the absence of characteristic by-products among the oxidation residues of HMASP. Altogether, these results show that the purple color of the shells of Crassostrea gigas is a complex association of porphyrins and ommochromes of potentially ommatin or ommin type. Article in Journal/Newspaper Crassostrea gigas Archive ouverte HAL (Hyper Article en Ligne, CCSD - Centre pour la Communication Scientifique Directe) Molecules 26 23 7263 |
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Archive ouverte HAL (Hyper Article en Ligne, CCSD - Centre pour la Communication Scientifique Directe) |
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language |
English |
topic |
[CHIM]Chemical Sciences |
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[CHIM]Chemical Sciences Bonnard, Michel Boury, Bruno Parrot, Isabelle Xanthurenic Acid in the Shell Purple Patterns of Crassostrea gigas: First Evidence of an Ommochrome Metabolite in a Mollusk Shell |
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[CHIM]Chemical Sciences |
description |
International audience Ommochromes are one of the least studied groups of natural pigments, frequently confused with melanin and, so far, exclusively found in invertebrates such as cephalopods and butterflies. In this study focused on the purple color of the shells of a mollusk, Crassostrea gigas, the first evidence of a metabolite of ommochromes, xanthurenic acid (XA), was obtained by liquid chromatography combined with mass spectrometry (UPLC-MS). In addition to XA and various porphyrins previously identified, a second group of high molecular weight acid-soluble pigments (HMASP) has been identified with physicochemical and structural characteristics similar to those of ommochromes. In addition, fragmentation of HMASP by tandem mass spectrometry (MS/MS) has revealed a substructure common to XA and ommochromes of the ommatin type. Furthermore, the presence of melanins was excluded by the absence of characteristic by-products among the oxidation residues of HMASP. Altogether, these results show that the purple color of the shells of Crassostrea gigas is a complex association of porphyrins and ommochromes of potentially ommatin or ommin type. |
author2 |
Institut des Biomolécules Max Mousseron Pôle Chimie Balard (IBMM) Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM) Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM) Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS) |
format |
Article in Journal/Newspaper |
author |
Bonnard, Michel Boury, Bruno Parrot, Isabelle |
author_facet |
Bonnard, Michel Boury, Bruno Parrot, Isabelle |
author_sort |
Bonnard, Michel |
title |
Xanthurenic Acid in the Shell Purple Patterns of Crassostrea gigas: First Evidence of an Ommochrome Metabolite in a Mollusk Shell |
title_short |
Xanthurenic Acid in the Shell Purple Patterns of Crassostrea gigas: First Evidence of an Ommochrome Metabolite in a Mollusk Shell |
title_full |
Xanthurenic Acid in the Shell Purple Patterns of Crassostrea gigas: First Evidence of an Ommochrome Metabolite in a Mollusk Shell |
title_fullStr |
Xanthurenic Acid in the Shell Purple Patterns of Crassostrea gigas: First Evidence of an Ommochrome Metabolite in a Mollusk Shell |
title_full_unstemmed |
Xanthurenic Acid in the Shell Purple Patterns of Crassostrea gigas: First Evidence of an Ommochrome Metabolite in a Mollusk Shell |
title_sort |
xanthurenic acid in the shell purple patterns of crassostrea gigas: first evidence of an ommochrome metabolite in a mollusk shell |
publisher |
HAL CCSD |
publishDate |
2021 |
url |
https://hal.umontpellier.fr/hal-03516064 https://doi.org/10.3390/molecules26237263 |
genre |
Crassostrea gigas |
genre_facet |
Crassostrea gigas |
op_source |
ISSN: 1420-3049 Molecules https://hal.umontpellier.fr/hal-03516064 Molecules, MDPI, 2021, 26 (23), pp.7263. ⟨10.3390/molecules26237263⟩ |
op_relation |
info:eu-repo/semantics/altIdentifier/doi/10.3390/molecules26237263 hal-03516064 https://hal.umontpellier.fr/hal-03516064 doi:10.3390/molecules26237263 |
op_doi |
https://doi.org/10.3390/molecules26237263 |
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Molecules |
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26 |
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23 |
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7263 |
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1766393250209333248 |