Synthesis, characterization and functional properties of galactosylated derivatives of chitosan through amide formation
Autor(a) principal: | |
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Data de Publicação: | 2013 |
Outros Autores: | , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/10400.14/34013 |
Resumo: | Low molecular weight chitosan (LMWC) and chitooligosaccharide (COS) derivatives were obtained by the introduction of lactobionic acid (LA) through amide formation, obtaining different complexes COS-LA and LMWC-LA (1-5), with a degree of substitution (DS) between 3 and 16%. The synthesis of these derivatives was monitored by Scanning Electron Microscopy (SEM), Fourier Transform Infrared Spectroscopy (FT-IR), High-Performance Liquid Chromatography-Size Exclusion Chromatography (HPLC-SEC) and proton Nuclear Magnetic Resonance (1H NMR) analyses. Different functional properties, solubility, water binding capacity (WBC) and fat binding capacity (FBC), as well as the antioxidant activity (DPPH radical scavenging activity) of these derivatives were evaluated. Solubility, WBC and FBC increased in all of the chitosan derivatives respect to those of the native LMWC or COS. The most substituted derivative (LMWC-LA1, DS 15%) presented the highest value of solubility (14.4mg/mL) while the highest levels of WBC and FBC were obtained for the derivative with a DS of 3% (LMWC-LA5; 4730% and 7100%, respectively). COS and COS-LA presented the best DPPH scavenging abilities, as shown by their low values of EC50 (1.29 and 3.45mg/mL, respectively). An inverse relationship between the DS of chitosan derivatives and antioxidant activity was observed. LMWC-LA5 (3% DS) was the derivative with the highest DPPH activity, being higher than LMWC in all the concentrations assayed (10.2-14.3% and 6.9-13.7%, respectively). Due to their enhanced functional properties, these chitosan derivatives could be considered as very promising for their future use as additives in the food industry (i.e. to bind fat and cholesterol or avoid hardening of foods). |
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Synthesis, characterization and functional properties of galactosylated derivatives of chitosan through amide formationChitooligosaccharidesChitosanFunctional propertiesGlycosylationLactobionic acidLow molecular weight chitosan (LMWC) and chitooligosaccharide (COS) derivatives were obtained by the introduction of lactobionic acid (LA) through amide formation, obtaining different complexes COS-LA and LMWC-LA (1-5), with a degree of substitution (DS) between 3 and 16%. The synthesis of these derivatives was monitored by Scanning Electron Microscopy (SEM), Fourier Transform Infrared Spectroscopy (FT-IR), High-Performance Liquid Chromatography-Size Exclusion Chromatography (HPLC-SEC) and proton Nuclear Magnetic Resonance (1H NMR) analyses. Different functional properties, solubility, water binding capacity (WBC) and fat binding capacity (FBC), as well as the antioxidant activity (DPPH radical scavenging activity) of these derivatives were evaluated. Solubility, WBC and FBC increased in all of the chitosan derivatives respect to those of the native LMWC or COS. The most substituted derivative (LMWC-LA1, DS 15%) presented the highest value of solubility (14.4mg/mL) while the highest levels of WBC and FBC were obtained for the derivative with a DS of 3% (LMWC-LA5; 4730% and 7100%, respectively). COS and COS-LA presented the best DPPH scavenging abilities, as shown by their low values of EC50 (1.29 and 3.45mg/mL, respectively). An inverse relationship between the DS of chitosan derivatives and antioxidant activity was observed. LMWC-LA5 (3% DS) was the derivative with the highest DPPH activity, being higher than LMWC in all the concentrations assayed (10.2-14.3% and 6.9-13.7%, respectively). Due to their enhanced functional properties, these chitosan derivatives could be considered as very promising for their future use as additives in the food industry (i.e. to bind fat and cholesterol or avoid hardening of foods).Veritati - Repositório Institucional da Universidade Católica PortuguesaMatute, Ana I. RuizCardelle-Cobas, AlejandraGarcía-Bermejo, Ana B.Montilla, AntoniaOlano, AgustinCorzo, Nieves2021-06-27T17:07:41Z2013-122013-12-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10400.14/34013eng0268-005X10.1016/j.foodhyd.2013.03.01684877067473000320614500010info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-07-12T17:39:30Zoai:repositorio.ucp.pt:10400.14/34013Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T18:27:31.838761Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse |
dc.title.none.fl_str_mv |
Synthesis, characterization and functional properties of galactosylated derivatives of chitosan through amide formation |
title |
Synthesis, characterization and functional properties of galactosylated derivatives of chitosan through amide formation |
spellingShingle |
Synthesis, characterization and functional properties of galactosylated derivatives of chitosan through amide formation Matute, Ana I. Ruiz Chitooligosaccharides Chitosan Functional properties Glycosylation Lactobionic acid |
title_short |
Synthesis, characterization and functional properties of galactosylated derivatives of chitosan through amide formation |
title_full |
Synthesis, characterization and functional properties of galactosylated derivatives of chitosan through amide formation |
title_fullStr |
Synthesis, characterization and functional properties of galactosylated derivatives of chitosan through amide formation |
title_full_unstemmed |
Synthesis, characterization and functional properties of galactosylated derivatives of chitosan through amide formation |
title_sort |
Synthesis, characterization and functional properties of galactosylated derivatives of chitosan through amide formation |
author |
Matute, Ana I. Ruiz |
author_facet |
Matute, Ana I. Ruiz Cardelle-Cobas, Alejandra García-Bermejo, Ana B. Montilla, Antonia Olano, Agustin Corzo, Nieves |
author_role |
author |
author2 |
Cardelle-Cobas, Alejandra García-Bermejo, Ana B. Montilla, Antonia Olano, Agustin Corzo, Nieves |
author2_role |
author author author author author |
dc.contributor.none.fl_str_mv |
Veritati - Repositório Institucional da Universidade Católica Portuguesa |
dc.contributor.author.fl_str_mv |
Matute, Ana I. Ruiz Cardelle-Cobas, Alejandra García-Bermejo, Ana B. Montilla, Antonia Olano, Agustin Corzo, Nieves |
dc.subject.por.fl_str_mv |
Chitooligosaccharides Chitosan Functional properties Glycosylation Lactobionic acid |
topic |
Chitooligosaccharides Chitosan Functional properties Glycosylation Lactobionic acid |
description |
Low molecular weight chitosan (LMWC) and chitooligosaccharide (COS) derivatives were obtained by the introduction of lactobionic acid (LA) through amide formation, obtaining different complexes COS-LA and LMWC-LA (1-5), with a degree of substitution (DS) between 3 and 16%. The synthesis of these derivatives was monitored by Scanning Electron Microscopy (SEM), Fourier Transform Infrared Spectroscopy (FT-IR), High-Performance Liquid Chromatography-Size Exclusion Chromatography (HPLC-SEC) and proton Nuclear Magnetic Resonance (1H NMR) analyses. Different functional properties, solubility, water binding capacity (WBC) and fat binding capacity (FBC), as well as the antioxidant activity (DPPH radical scavenging activity) of these derivatives were evaluated. Solubility, WBC and FBC increased in all of the chitosan derivatives respect to those of the native LMWC or COS. The most substituted derivative (LMWC-LA1, DS 15%) presented the highest value of solubility (14.4mg/mL) while the highest levels of WBC and FBC were obtained for the derivative with a DS of 3% (LMWC-LA5; 4730% and 7100%, respectively). COS and COS-LA presented the best DPPH scavenging abilities, as shown by their low values of EC50 (1.29 and 3.45mg/mL, respectively). An inverse relationship between the DS of chitosan derivatives and antioxidant activity was observed. LMWC-LA5 (3% DS) was the derivative with the highest DPPH activity, being higher than LMWC in all the concentrations assayed (10.2-14.3% and 6.9-13.7%, respectively). Due to their enhanced functional properties, these chitosan derivatives could be considered as very promising for their future use as additives in the food industry (i.e. to bind fat and cholesterol or avoid hardening of foods). |
publishDate |
2013 |
dc.date.none.fl_str_mv |
2013-12 2013-12-01T00:00:00Z 2021-06-27T17:07:41Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://hdl.handle.net/10400.14/34013 |
url |
http://hdl.handle.net/10400.14/34013 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
0268-005X 10.1016/j.foodhyd.2013.03.016 84877067473 000320614500010 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.source.none.fl_str_mv |
reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
instname_str |
Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
instacron_str |
RCAAP |
institution |
RCAAP |
reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
collection |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
repository.name.fl_str_mv |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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1799131992701272064 |