title: Suppression of the tert-butylhydroquinone toxicity by its grafting onto chitosan and further cross-linking to agavin toward a novel antioxidant and prebiotic material.
abstract: The enzyme-mediated grafting of tert-butylhydroquinone (TBHQ) onto chitosan and further crosslinking to agave inulin (agavin) has been successfully achieved in a mild and non-toxic two-step route. The resulting products were characterized by nuclear magnetic resonance (NMR) and Infra-red spectroscopies to assess the molecular structure. The study of acute oral toxicity in mice revealed no adverse short-term effects of consumption in the synthesized materials with non-toxicity evidence until 2000 mg/kg through an oral acute administration. Importantly, this study proves that the compound maintains the radical scavenging capacity of the phenolic antioxidant upon ferric-reducing antioxidant power (FRAP) and oxygen radical absorbance capacity (ORAC) assays with a measured half-maximal inhibitory concentration (IC50) for the best case of 1.54 g/L based on inhibition of 2,2'-azino-bis(3-ethylbenzothiazoline)-6-sulfonic acid diammonium salt (ABTS). Additionally, the novel compound presented high prebiotic activities as ascertained in the presence of lactic acid bacteria (LAB).
authors.affiliation: Facultad de Química, Departamento de Alimentos y Biotecnología, Universidad Nacional Autónoma de México, Ciudad Universitaria, México D.F. 04510, Mexico.
authors.forename: Miguel A
authors.initials: MA
authors.lastname: Hernández-Valdepeña
authors.affiliation: Facultad de Química, Departamento de Biología, Universidad Nacional Autónoma de México, Ciudad Universitaria, México D.F. 04510, Mexico.
authors.forename: José
authors.initials: J
authors.lastname: Pedraza-Chaverri
authors.affiliation: Unidad de Investigación Preclínica (UNIPREC), Universidad Nacional Autónoma de México, Ciudad Universitaria, México D.F. 04510, Mexico.
authors.forename: Isabel
authors.initials: I
authors.lastname: Gracia-Mora
authors.affiliation: Departamento de Ecología de Agentes Patógenos, Hospital General "Dr. Manuel Gea González", Tlalpan, Mexico.
authors.forename: Rigoberto
authors.initials: R
authors.lastname: Hernández-Castro
authors.affiliation: Unidad de Investigación Preclínica (UNIPREC), Universidad Nacional Autónoma de México, Ciudad Universitaria, México D.F. 04510, Mexico.
authors.forename: Francisco
authors.initials: F
authors.lastname: Sánchez-Bartez
authors.affiliation: Instituto de Biología, Universidad Nacional Autónoma de México, Ciudad Universitaria, México D.F. 04510, Mexico.
authors.forename: Jorge
authors.initials: J
authors.lastname: Nieto-Sotelo
authors.affiliation: Facultad de Química, Departamento de Alimentos y Biotecnología, Universidad Nacional Autónoma de México, Ciudad Universitaria, México D.F. 04510, Mexico.
authors.forename: Carmina
authors.initials: C
authors.lastname: Montiel
authors.affiliation: Universidad Autónoma Metropolitana, Biotechnology Department, Laboratory of Biopolymers and Pilot Plant of Bioprocessing of Agro-Industrial and Food By-Products, 09340 Mexico City, Mexico.
authors.forename: Keiko
authors.initials: K
authors.lastname: Shirai
authors.affiliation: Facultad de Química, Departamento de Alimentos y Biotecnología, Universidad Nacional Autónoma de México, Ciudad Universitaria, México D.F. 04510, Mexico. Electronic address: mgimeno@unam.mx.
authors.forename: Miquel
authors.initials: M
authors.lastname: Gimeno
mesh_terms: D027882:Agave / Q000737:chemistry; D000818:Animals; D000975:Antioxidants / Q000737:chemistry*; D048271:Chitosan / Q000737:chemistry*; D006873:Hydroquinones / Q000737:chemistry*; D007444:Inulin / Q000737:chemistry*; D051379:Mice; D056692:Prebiotics / Q000032:analysis*
chemical_list: D000975:Antioxidants; D006873:Hydroquinones; D056692:Prebiotics; D007444:Inulin; D048271:Chitosan; C018855:2-tert-butylhydroquinone
keywords: Agavin; Antioxidant; Chitosan; TBHQ