Xanthommatin is behind the antioxidant activity of the skin of dosidicus gigas

Jesús Enrique Chan-Higuera; Hisila Del Carmen Santacruz-Ortega; Angel A. Carbonell-Barrachina; Armando Burgos-Hernández; Rosario Maribel Robles-Sánchez; Susana Gabriela Cruz-Ramírez; Josafat Marina Ezquerra-Brauer

doi:10.3390/molecules24193420

Xanthommatin is behind the antioxidant activity of the skin of dosidicus gigas

Jesús Enrique Chan-Higuera, Hisila Del Carmen Santacruz-Ortega, Angel A. Carbonell-Barrachina, Armando Burgos-Hernández, Rosario Maribel Robles-Sánchez, Susana Gabriela Cruz-Ramírez, Josafat Marina Ezquerra-Brauer^*

^*Corresponding author for this work

Departamento de Investigación y Posgrado en Alimentos

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

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•) and 2,20-azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS•+) 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 IC₅₀ against ABTS•+ per milligram, and fractions F3 and F7 showed the lowest IC₅₀ in the FRAP assay. Finally, fraction F7 had the highest DPPH• scavenging activity. The chemical structure of the F7 fraction was characterized by infrared spectroscopy, ¹H 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.

Original language	English
Article number	3420
Journal	Molecules
Volume	24
Issue number	19
DOIs	https://doi.org/10.3390/molecules24193420
State	Published - 20 Sep 2019

Bibliographical note

Funding Information:
Funding: This research was funded by Consejo Nacional de Ciencia y Tecnología (CONACyT-Mexico), grant number 2174 and the author, J.E.C.H., acknowledges doctoral fellowship from CONACyT.

Publisher Copyright:
© 2019 by the authors.

Keywords

Antioxidant activity
Chromatography
Ommochromes
Spectroscopy
Xanthommatin

Access to Document

10.3390/molecules24193420

Cite this

@article{4e765639af20412fb0040c37b0c60f1c,

title = "Xanthommatin is behind the antioxidant activity of the skin of dosidicus gigas",

abstract = "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•) and 2,20-azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS•+) 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 IC50 against ABTS•+ per milligram, and fractions F3 and F7 showed the lowest IC50 in the FRAP assay. Finally, fraction F7 had the highest DPPH• scavenging activity. The chemical structure of the F7 fraction was characterized by infrared spectroscopy, 1H 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.",

keywords = "Antioxidant activity, Chromatography, Ommochromes, Spectroscopy, Xanthommatin",

author = "Chan-Higuera, {Jes{\'u}s Enrique} and Santacruz-Ortega, {Hisila Del Carmen} and Carbonell-Barrachina, {Angel A.} and Armando Burgos-Hern{\'a}ndez and Robles-S{\'a}nchez, {Rosario Maribel} and Cruz-Ram{\'i}rez, {Susana Gabriela} and Ezquerra-Brauer, {Josafat Marina}",

note = "Publisher Copyright: {\textcopyright} 2019 by the authors.",

year = "2019",

month = sep,

day = "20",

doi = "10.3390/molecules24193420",

language = "Ingl{\'e}s",

volume = "24",

journal = "Molecules",

issn = "1420-3049",

publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

number = "19",

}

TY - JOUR

T1 - Xanthommatin is behind the antioxidant activity of the skin of dosidicus gigas

AU - Chan-Higuera, Jesús Enrique

AU - Santacruz-Ortega, Hisila Del Carmen

AU - Carbonell-Barrachina, Angel A.

AU - Burgos-Hernández, Armando

AU - Robles-Sánchez, Rosario Maribel

AU - Cruz-Ramírez, Susana Gabriela

AU - Ezquerra-Brauer, Josafat Marina

PY - 2019/9/20

Y1 - 2019/9/20

N2 - 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•) and 2,20-azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS•+) 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 IC50 against ABTS•+ per milligram, and fractions F3 and F7 showed the lowest IC50 in the FRAP assay. Finally, fraction F7 had the highest DPPH• scavenging activity. The chemical structure of the F7 fraction was characterized by infrared spectroscopy, 1H 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.

AB - 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•) and 2,20-azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS•+) 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 IC50 against ABTS•+ per milligram, and fractions F3 and F7 showed the lowest IC50 in the FRAP assay. Finally, fraction F7 had the highest DPPH• scavenging activity. The chemical structure of the F7 fraction was characterized by infrared spectroscopy, 1H 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.

KW - Antioxidant activity

KW - Chromatography

KW - Ommochromes

KW - Spectroscopy

KW - Xanthommatin

UR - http://www.scopus.com/inward/record.url?scp=85072555514&partnerID=8YFLogxK

U2 - 10.3390/molecules24193420

DO - 10.3390/molecules24193420

M3 - Artículo

C2 - 31547094

AN - SCOPUS:85072555514

SN - 1420-3049

VL - 24

JO - Molecules

JF - Molecules

IS - 19

M1 - 3420

ER -

Xanthommatin is behind the antioxidant activity of the skin of dosidicus gigas

Abstract

Bibliographical note

Keywords

Access to Document

Other files and links

Fingerprint

Cite this