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Article: Natural polyphenols as direct trapping agents of lipid peroxidation-derived acrolein and 4-hydroxy-trans-2-nonenal

TitleNatural polyphenols as direct trapping agents of lipid peroxidation-derived acrolein and 4-hydroxy-trans-2-nonenal
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. 10, p. 1721-1727 How to Cite?
AbstractAcrolein (ACR) and 4-hydroxy-trans-2-nonenal (HNE) are two cytotoxic lipid-derived α,β-unsaturated aldehydes which have been implicated as causative agents in the development of carbonyl stress-associated pathologies. In this study, 21 natural polyphenols were screened to identify effective scavenging agents of ACR and/or HNE in simulated physiological conditions. It was found that flavan-3-ols, theaflavins, cyanomaclurin, and dihydrochalcones effectively trapped ACR and HNE by working as sacrificial nucleophiles. The most effective one was phloretin, which quenched up to 99.6% ACR in 90 min and 90.1% HNE in 24 h. Subsequent LC-MS/MS analysis showed that these effective polyphenols formed adducts with ACR and HNE. A major adduct formed from phloretin and ACR was purified, and its structure was characterized by LC-MS and NMR spectroscopy as diACR-conjugated phloretin. The chemical nature of interactions between ACR and polyphenols was proposed as the Michael addition reaction of phloretin to the C=C double bond of ACR, followed by the formation of hemiacetal between the hydroxyl group in the A ring of phloretin and the C=O carbonyl group in ACR, thus yielding more stable products. Findings of the present study highlighted certain classes of polyphenols as promising sequestering agents of α,β-unsaturated aldehydes to inhibit or restrain carbonyl stress-associated diseases. © 2009 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/69904
ISSN
2015 Impact Factor: 3.025
2015 SCImago Journal Rankings: 1.323
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorZhu, Qen_HK
dc.contributor.authorZheng, ZPen_HK
dc.contributor.authorCheng, KWen_HK
dc.contributor.authorWu, JJen_HK
dc.contributor.authorZhang, Sen_HK
dc.contributor.authorYun, STen_HK
dc.contributor.authorSze, KHen_HK
dc.contributor.authorChen, Jen_HK
dc.contributor.authorChen, Fen_HK
dc.contributor.authorWang, Men_HK
dc.date.accessioned2010-09-06T06:17:54Z-
dc.date.available2010-09-06T06:17:54Z-
dc.date.issued2009en_HK
dc.identifier.citationChemical Research In Toxicology, 2009, v. 22 n. 10, p. 1721-1727en_HK
dc.identifier.issn0893-228Xen_HK
dc.identifier.urihttp://hdl.handle.net/10722/69904-
dc.description.abstractAcrolein (ACR) and 4-hydroxy-trans-2-nonenal (HNE) are two cytotoxic lipid-derived α,β-unsaturated aldehydes which have been implicated as causative agents in the development of carbonyl stress-associated pathologies. In this study, 21 natural polyphenols were screened to identify effective scavenging agents of ACR and/or HNE in simulated physiological conditions. It was found that flavan-3-ols, theaflavins, cyanomaclurin, and dihydrochalcones effectively trapped ACR and HNE by working as sacrificial nucleophiles. The most effective one was phloretin, which quenched up to 99.6% ACR in 90 min and 90.1% HNE in 24 h. Subsequent LC-MS/MS analysis showed that these effective polyphenols formed adducts with ACR and HNE. A major adduct formed from phloretin and ACR was purified, and its structure was characterized by LC-MS and NMR spectroscopy as diACR-conjugated phloretin. The chemical nature of interactions between ACR and polyphenols was proposed as the Michael addition reaction of phloretin to the C=C double bond of ACR, followed by the formation of hemiacetal between the hydroxyl group in the A ring of phloretin and the C=O carbonyl group in ACR, thus yielding more stable products. Findings of the present study highlighted certain classes of polyphenols as promising sequestering agents of α,β-unsaturated aldehydes to inhibit or restrain carbonyl stress-associated diseases. © 2009 American Chemical Society.en_HK
dc.languageengen_HK
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.meshAcrolein - chemistry - toxicity-
dc.subject.meshAldehydes - chemistry - toxicity-
dc.subject.meshCross-Linking Reagents - chemistry - toxicity-
dc.subject.meshFlavonoids - chemistry-
dc.subject.meshLipid Peroxidation-
dc.titleNatural polyphenols as direct trapping agents of lipid peroxidation-derived acrolein and 4-hydroxy-trans-2-nonenalen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0893-228X&volume=22&issue=10&spage=1721&epage=1727&date=2009&atitle=Natural+Polyphenols+as+Direct+Trapping+Agents+of+Lipid+Peroxidation-derived+Acrolein+and+4-Hydroxy-trans-2-nonenalen_HK
dc.identifier.emailSze, KH: khsze@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.authorityChen, F=rp00672en_HK
dc.identifier.authorityWang, M=rp00800en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/tx900221sen_HK
dc.identifier.pmid19743801en_HK
dc.identifier.scopuseid_2-s2.0-70350248021en_HK
dc.identifier.hkuros169740en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-70350248021&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume22en_HK
dc.identifier.issue10en_HK
dc.identifier.spage1721en_HK
dc.identifier.epage1727en_HK
dc.identifier.isiWOS:000270810200009-
dc.publisher.placeUnited Statesen_HK
dc.identifier.scopusauthoridZhu, Q=54909442800en_HK
dc.identifier.scopusauthoridZheng, ZP=8451746600en_HK
dc.identifier.scopusauthoridCheng, KW=12141247000en_HK
dc.identifier.scopusauthoridWu, JJ=8298828200en_HK
dc.identifier.scopusauthoridZhang, S=35228266900en_HK
dc.identifier.scopusauthoridYun, ST=35079764100en_HK
dc.identifier.scopusauthoridSze, KH=7006735061en_HK
dc.identifier.scopusauthoridChen, J=35291294100en_HK
dc.identifier.scopusauthoridChen, F=7404907980en_HK
dc.identifier.scopusauthoridWang, M=7406691844en_HK

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