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Article: Inhibition of mutagenic PhIP formation by epigallocatechin gallate via scavenging of phenylacetaldehyde

TitleInhibition of mutagenic PhIP formation by epigallocatechin gallate via scavenging of phenylacetaldehyde
Authors
KeywordsAdducts
Chemical model reactions
Epigallocatechin gallate peracetate
Phenylacetaldehyde
PhIP
Issue Date2009
Citation
Molecular Nutrition And Food Research, 2009, v. 53 n. 6, p. 716-725 How to Cite?
AbstractChemical model investigation showed that both epigallocatechin gallate (EGCG) and its peracetate, which has all the hydroxyl groups acetylated, effectively reduced the formation of 2-amino-1-methyl- 6-phenylimidazo[4,5-b]pyridine (PhIP), the most abundant mutagenic heterocyclic amine found in foods. Mechanistic study was subsequently carried out to characterize the probable inhibitory mechanism involved. GC-MS analysis showed that EGCG in only one-fourth molar quantity of phenylalanine reduced formation of phenylacetaldehyde, a key PhIP intermediate by nearly 90%. Its peracetate also showed similar inhibitory activity. This further supported the existence of an antioxidant-independent mechanism contributing to the inhibition of PhIP formation by EGCG. Subsequent LC-MS analyses of samples from a wide range of model systems consisting of PhIP precursors showed the generation of characteristic analytes with molecular weight corresponding to the sum of EGCG and phenylalanine fragment(s) only in models where phenylalanine and EGCG were simultaneously present. An isotope-labeling study revealed that these analytes all contained fragment(s) of phenylalanine origin. Direct reaction employing phenylacetaldehyde and EGCG further confirmed the capability of EGCG to form adducts with phenylacetaldehyde, thus reducing its availability for PhIP formation. Finally, an investigation of the time course of the generation of postulated adduction products supported EGCG as an effective inhibitor of PhIP formation in prolonged heating processes. © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Persistent Identifierhttp://hdl.handle.net/10722/168391
ISSN
2015 Impact Factor: 4.551
2015 SCImago Journal Rankings: 1.679
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorCheng, KWen_HK
dc.contributor.authorWong, CCen_HK
dc.contributor.authorChao, Jen_HK
dc.contributor.authorLo, Cen_HK
dc.contributor.authorChen, Fen_HK
dc.contributor.authorChu, IKen_HK
dc.contributor.authorChe, CMen_HK
dc.contributor.authorHo, CTen_HK
dc.contributor.authorWang, Men_HK
dc.date.accessioned2012-10-08T03:18:21Z-
dc.date.available2012-10-08T03:18:21Z-
dc.date.issued2009en_HK
dc.identifier.citationMolecular Nutrition And Food Research, 2009, v. 53 n. 6, p. 716-725en_HK
dc.identifier.issn1613-4125en_HK
dc.identifier.urihttp://hdl.handle.net/10722/168391-
dc.description.abstractChemical model investigation showed that both epigallocatechin gallate (EGCG) and its peracetate, which has all the hydroxyl groups acetylated, effectively reduced the formation of 2-amino-1-methyl- 6-phenylimidazo[4,5-b]pyridine (PhIP), the most abundant mutagenic heterocyclic amine found in foods. Mechanistic study was subsequently carried out to characterize the probable inhibitory mechanism involved. GC-MS analysis showed that EGCG in only one-fourth molar quantity of phenylalanine reduced formation of phenylacetaldehyde, a key PhIP intermediate by nearly 90%. Its peracetate also showed similar inhibitory activity. This further supported the existence of an antioxidant-independent mechanism contributing to the inhibition of PhIP formation by EGCG. Subsequent LC-MS analyses of samples from a wide range of model systems consisting of PhIP precursors showed the generation of characteristic analytes with molecular weight corresponding to the sum of EGCG and phenylalanine fragment(s) only in models where phenylalanine and EGCG were simultaneously present. An isotope-labeling study revealed that these analytes all contained fragment(s) of phenylalanine origin. Direct reaction employing phenylacetaldehyde and EGCG further confirmed the capability of EGCG to form adducts with phenylacetaldehyde, thus reducing its availability for PhIP formation. Finally, an investigation of the time course of the generation of postulated adduction products supported EGCG as an effective inhibitor of PhIP formation in prolonged heating processes. © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.en_HK
dc.languageengen_US
dc.relation.ispartofMolecular Nutrition and Food Researchen_HK
dc.subjectAdductsen_HK
dc.subjectChemical model reactionsen_HK
dc.subjectEpigallocatechin gallate peracetateen_HK
dc.subjectPhenylacetaldehydeen_HK
dc.subjectPhIPen_HK
dc.subject.meshAcetaldehyde - Analogs & Derivatives - Metabolismen_US
dc.subject.meshAntimutagenic Agents - Pharmacologyen_US
dc.subject.meshCatechin - Analogs & Derivatives - Pharmacologyen_US
dc.subject.meshImidazoles - Metabolismen_US
dc.subject.meshMutagens - Metabolismen_US
dc.titleInhibition of mutagenic PhIP formation by epigallocatechin gallate via scavenging of phenylacetaldehydeen_HK
dc.typeArticleen_HK
dc.identifier.emailLo, C: clivelo@hkucc.hku.hken_HK
dc.identifier.emailChen, F: sfchen@hku.hken_HK
dc.identifier.emailChu, IK: ivankchu@hku.hken_HK
dc.identifier.emailChe, CM: cmche@hku.hken_HK
dc.identifier.emailWang, M: mfwang@hku.hken_HK
dc.identifier.authorityLo, C=rp00751en_HK
dc.identifier.authorityChen, F=rp00672en_HK
dc.identifier.authorityChu, IK=rp00683en_HK
dc.identifier.authorityChe, CM=rp00670en_HK
dc.identifier.authorityWang, M=rp00800en_HK
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1002/mnfr.200800206en_HK
dc.identifier.pmid19437482-
dc.identifier.scopuseid_2-s2.0-67651009738en_HK
dc.identifier.hkuros163920-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-67651009738&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume53en_HK
dc.identifier.issue6en_HK
dc.identifier.spage716en_HK
dc.identifier.epage725en_HK
dc.identifier.eissn1613-4133-
dc.identifier.isiWOS:000267398200005-
dc.publisher.placeGermanyen_HK
dc.identifier.scopusauthoridCheng, KW=12141247000en_HK
dc.identifier.scopusauthoridWong, CC=35333095100en_HK
dc.identifier.scopusauthoridChao, J=24558959000en_HK
dc.identifier.scopusauthoridLo, C=15737175700en_HK
dc.identifier.scopusauthoridChen, F=7404907980en_HK
dc.identifier.scopusauthoridChu, IK=7103327484en_HK
dc.identifier.scopusauthoridChe, CM=7102442791en_HK
dc.identifier.scopusauthoridHo, CT=7404652573en_HK
dc.identifier.scopusauthoridWang, M=7406691844en_HK

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