Xanthommatin is Behind the Antioxidant Activity of the Skin of <i>Dosidicus gigas</i>
Marine bioactive compounds have been found in very different sources and exert a very vast array of activities. Squid skin, normally considered a discard, is a source of bioactive compounds such as pigments. Recovering these compounds is a potential means of valorizing seafood byproducts. Until now,...
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MDPI AG
2019-09-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/19/3420 |
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| author | Jesús Enrique Chan-Higuera Hisila del Carmen Santacruz-Ortega Ángel A. Carbonell-Barrachina Armando Burgos-Hernández Rosario Maribel Robles-Sánchez Susana Gabriela Cruz-Ramírez Josafat Marina Ezquerra-Brauer |
| author_facet | Jesús Enrique Chan-Higuera Hisila del Carmen Santacruz-Ortega Ángel A. Carbonell-Barrachina Armando Burgos-Hernández Rosario Maribel Robles-Sánchez Susana Gabriela Cruz-Ramírez Josafat Marina Ezquerra-Brauer |
| author_sort | Jesús Enrique Chan-Higuera |
| collection | DOAJ |
| description | Marine bioactive compounds have been found in very different sources and exert a very vast array of activities. Squid skin, normally considered a discard, is a source of bioactive compounds such as pigments. Recovering these compounds is a potential means of valorizing seafood byproducts. Until now, the structure and molecular properties of the bioactive pigments in jumbo squid skin (JSS) have not been established. In this study, methanol−HCl (1%) pigment extracts from JSS were fractionated by open column chromatography and grouped by thin-layer chromatography in order to isolate antioxidant pigments. Antioxidant activity was determined by the 2,2-diphenyl-1-picrylhydrazyl (DPPH<sup>●</sup>) and 2,2′-azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS<sup>●+</sup>) radical scavenging assays and ferric reducing power (FRAP) assay. Fractions 11−34 were separated and grouped according to flow rate values (F1−F8). Fractions F1, F3, and F7 had the lowest IC<sub>50</sub> against ABTS<sup>●+</sup> per milligram, and fractions F3 and F7 showed the lowest IC<sub>50</sub> in the FRAP assay. Finally, fraction F7 had the highest DPPH<sup>●</sup> scavenging activity. The chemical structure of the F7 fraction was characterized by infrared spectroscopy, <sup>1</sup>H nuclear magnetic resonance, and electrospray ionization−mass spectrometry. One of the compounds identified in the fraction was xanthommatin (11-(3-amino-3-carboxypropanoyl)-1-hydroxy-5-oxo-5H-pyrido[3,2-a]phenoxazine-3-carboxylic acid) and their derivatives (hydro- and dihydroxanthommatin). The results show that JSS pigments contain ommochrome molecules like xanthommatin, to which the antioxidant activity can be attributed. |
| first_indexed | 2024-12-10T16:50:25Z |
| format | Article |
| id | doaj.art-80fa923109624164a8a2d780c60d5451 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-10T16:50:25Z |
| publishDate | 2019-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-80fa923109624164a8a2d780c60d54512022-12-22T01:40:54ZengMDPI AGMolecules1420-30492019-09-012419342010.3390/molecules24193420molecules24193420Xanthommatin is Behind the Antioxidant Activity of the Skin of <i>Dosidicus gigas</i>Jesús Enrique Chan-Higuera0Hisila del Carmen Santacruz-Ortega1Ángel A. Carbonell-Barrachina2Armando Burgos-Hernández3Rosario Maribel Robles-Sánchez4Susana Gabriela Cruz-Ramírez5Josafat Marina Ezquerra-Brauer6Departamento de Investigación y Posgrado en Alimentos; University of Sonora (UNISON), 83000 Hermosillo, Sonora, MexicoDepartamento de Investigación en Polimeros y Materiales, University of Sonora (UNISON), 83000 Hermosillo, Sonora, MexicoDepartment of Agro-Food Technology, Escuela Politécnica Superior de Orihuela, Universidad Miguel Hernández de Elche (UMH), Orihuela, Alicante 03312, SpainDepartamento de Investigación y Posgrado en Alimentos; University of Sonora (UNISON), 83000 Hermosillo, Sonora, MexicoDepartamento de Investigación y Posgrado en Alimentos; University of Sonora (UNISON), 83000 Hermosillo, Sonora, MexicoUnidad Hermosillo, Universidad Estatal de Sonora (UES); 83100 Hermosillo, Sonora, MexicoDepartamento de Investigación y Posgrado en Alimentos; University of Sonora (UNISON), 83000 Hermosillo, Sonora, MexicoMarine bioactive compounds have been found in very different sources and exert a very vast array of activities. Squid skin, normally considered a discard, is a source of bioactive compounds such as pigments. Recovering these compounds is a potential means of valorizing seafood byproducts. Until now, the structure and molecular properties of the bioactive pigments in jumbo squid skin (JSS) have not been established. In this study, methanol−HCl (1%) pigment extracts from JSS were fractionated by open column chromatography and grouped by thin-layer chromatography in order to isolate antioxidant pigments. Antioxidant activity was determined by the 2,2-diphenyl-1-picrylhydrazyl (DPPH<sup>●</sup>) and 2,2′-azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS<sup>●+</sup>) radical scavenging assays and ferric reducing power (FRAP) assay. Fractions 11−34 were separated and grouped according to flow rate values (F1−F8). Fractions F1, F3, and F7 had the lowest IC<sub>50</sub> against ABTS<sup>●+</sup> per milligram, and fractions F3 and F7 showed the lowest IC<sub>50</sub> in the FRAP assay. Finally, fraction F7 had the highest DPPH<sup>●</sup> scavenging activity. The chemical structure of the F7 fraction was characterized by infrared spectroscopy, <sup>1</sup>H nuclear magnetic resonance, and electrospray ionization−mass spectrometry. One of the compounds identified in the fraction was xanthommatin (11-(3-amino-3-carboxypropanoyl)-1-hydroxy-5-oxo-5H-pyrido[3,2-a]phenoxazine-3-carboxylic acid) and their derivatives (hydro- and dihydroxanthommatin). The results show that JSS pigments contain ommochrome molecules like xanthommatin, to which the antioxidant activity can be attributed.https://www.mdpi.com/1420-3049/24/19/3420antioxidant activitychromatographyommochromesspectroscopyxanthommatin |
| spellingShingle | Jesús Enrique Chan-Higuera Hisila del Carmen Santacruz-Ortega Ángel A. Carbonell-Barrachina Armando Burgos-Hernández Rosario Maribel Robles-Sánchez Susana Gabriela Cruz-Ramírez Josafat Marina Ezquerra-Brauer Xanthommatin is Behind the Antioxidant Activity of the Skin of <i>Dosidicus gigas</i> Molecules antioxidant activity chromatography ommochromes spectroscopy xanthommatin |
| title | Xanthommatin is Behind the Antioxidant Activity of the Skin of <i>Dosidicus gigas</i> |
| title_full | Xanthommatin is Behind the Antioxidant Activity of the Skin of <i>Dosidicus gigas</i> |
| title_fullStr | Xanthommatin is Behind the Antioxidant Activity of the Skin of <i>Dosidicus gigas</i> |
| title_full_unstemmed | Xanthommatin is Behind the Antioxidant Activity of the Skin of <i>Dosidicus gigas</i> |
| title_short | Xanthommatin is Behind the Antioxidant Activity of the Skin of <i>Dosidicus gigas</i> |
| title_sort | xanthommatin is behind the antioxidant activity of the skin of i dosidicus gigas i |
| topic | antioxidant activity chromatography ommochromes spectroscopy xanthommatin |
| url | https://www.mdpi.com/1420-3049/24/19/3420 |
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