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Article: Inhibitory mechanism of naringenin against carcinogenic acrylamide formation and nonenzymatic browning in maillard model reactions

TitleInhibitory mechanism of naringenin against carcinogenic acrylamide formation and nonenzymatic browning in maillard model reactions
Authors
Issue Date2009
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/crt
Citation
Chemical Research In Toxicology, 2009, v. 22 n. 8, p. 1483-1489 How to Cite?
AbstractChemical model reactions were carried out to investigate the effect of a citrus flavonoid, naringenin, on the formation of acrylamide under mild heating conditions. Results showed that naringenin significantly and dose dependently inhibited the formation of acrylamide (20-50% relative to the control), although not in a linear manner. Moreover, the presence of naringenin in acrylamide-producing models effectively reduced the extent of browning. Careful comparison of the HPLC chromatograms of samples from the chemical model reactions revealed that naringenin likely reacted with Maillard intermediates, giving rise to new derivatives. Subsequent LC-MS analyses suggested that the proposed derivatives have a predicted molecular mass of 341 Da. Eventually, two derivatives were purified and characterized with LC-MS/MS and NMR spectroscopy as 8-C-(E-propenamide)naringenin and 6-C-(E-propenamide)naringenin, respectively. In other words, naringenin, a rather weak antioxidant, strongly inhibited acrylamide formation probably by directly reacting with acrylamide precursors, thus diverting them from the pathways that lead to acrylamide formation. © 2009 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/157555
ISSN
2015 Impact Factor: 3.025
2015 SCImago Journal Rankings: 1.323
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorCheng, KWen_HK
dc.contributor.authorZeng, Xen_HK
dc.contributor.authorTang, YSen_HK
dc.contributor.authorWu, JJen_HK
dc.contributor.authorLiu, Zen_HK
dc.contributor.authorSze, KHen_HK
dc.contributor.authorChu, IKen_HK
dc.contributor.authorChen, Fen_HK
dc.contributor.authorWang, Men_HK
dc.date.accessioned2012-08-08T08:51:13Z-
dc.date.available2012-08-08T08:51:13Z-
dc.date.issued2009en_HK
dc.identifier.citationChemical Research In Toxicology, 2009, v. 22 n. 8, p. 1483-1489en_HK
dc.identifier.issn0893-228Xen_HK
dc.identifier.urihttp://hdl.handle.net/10722/157555-
dc.description.abstractChemical model reactions were carried out to investigate the effect of a citrus flavonoid, naringenin, on the formation of acrylamide under mild heating conditions. Results showed that naringenin significantly and dose dependently inhibited the formation of acrylamide (20-50% relative to the control), although not in a linear manner. Moreover, the presence of naringenin in acrylamide-producing models effectively reduced the extent of browning. Careful comparison of the HPLC chromatograms of samples from the chemical model reactions revealed that naringenin likely reacted with Maillard intermediates, giving rise to new derivatives. Subsequent LC-MS analyses suggested that the proposed derivatives have a predicted molecular mass of 341 Da. Eventually, two derivatives were purified and characterized with LC-MS/MS and NMR spectroscopy as 8-C-(E-propenamide)naringenin and 6-C-(E-propenamide)naringenin, respectively. In other words, naringenin, a rather weak antioxidant, strongly inhibited acrylamide formation probably by directly reacting with acrylamide precursors, thus diverting them from the pathways that lead to acrylamide formation. © 2009 American Chemical Society.en_HK
dc.languageengen_US
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/crten_HK
dc.relation.ispartofChemical Research in Toxicologyen_HK
dc.subject.meshAcrylamide - Chemical Synthesis - Metabolismen_US
dc.subject.meshAnimalsen_US
dc.subject.meshAntioxidants - Pharmacologyen_US
dc.subject.meshCarcinogens - Metabolismen_US
dc.subject.meshChromatography, High Pressure Liquiden_US
dc.subject.meshDrug Interactionsen_US
dc.subject.meshFlavanones - Chemistry - Pharmacology - Therapeutic Useen_US
dc.subject.meshFood Contamination - Prevention & Controlen_US
dc.subject.meshFood Handlingen_US
dc.subject.meshHot Temperatureen_US
dc.subject.meshHumansen_US
dc.subject.meshMaillard Reaction - Drug Effectsen_US
dc.subject.meshModels, Chemicalen_US
dc.subject.meshMolecular Structureen_US
dc.subject.meshMutagensen_US
dc.titleInhibitory mechanism of naringenin against carcinogenic acrylamide formation and nonenzymatic browning in maillard model reactionsen_HK
dc.typeArticleen_HK
dc.identifier.emailSze, KH: khsze@hku.hken_HK
dc.identifier.emailChu, IK: ivankchu@hku.hken_HK
dc.identifier.emailChen, F: sfchen@hku.hken_HK
dc.identifier.emailWang, M: mfwang@hku.hken_HK
dc.identifier.authoritySze, KH=rp00785en_HK
dc.identifier.authorityChu, IK=rp00683en_HK
dc.identifier.authorityChen, F=rp00672en_HK
dc.identifier.authorityWang, M=rp00800en_HK
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1021/tx9001644en_HK
dc.identifier.pmid19639978-
dc.identifier.scopuseid_2-s2.0-68949119708en_HK
dc.identifier.hkuros163922-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-68949119708&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume22en_HK
dc.identifier.issue8en_HK
dc.identifier.spage1483en_HK
dc.identifier.epage1489en_HK
dc.identifier.isiWOS:000269044200013-
dc.publisher.placeUnited Statesen_HK
dc.identifier.scopusauthoridCheng, KW=12141247000en_HK
dc.identifier.scopusauthoridZeng, X=35760592200en_HK
dc.identifier.scopusauthoridYun, ST=35079764100en_HK
dc.identifier.scopusauthoridWu, JJ=8298828200en_HK
dc.identifier.scopusauthoridLiu, Z=20434031900en_HK
dc.identifier.scopusauthoridSze, KH=7006735061en_HK
dc.identifier.scopusauthoridChu, IK=7103327484en_HK
dc.identifier.scopusauthoridChen, F=7404907980en_HK
dc.identifier.scopusauthoridWang, M=7406691844en_HK

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