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Antiacetylcholinesterase activity and docking studies with chlorogenic acid, cynarin and arzanol from Helichrysum stoechas (Lamiaceae)

2017-11Journal article Restricted access
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dc.contributor.authorSilva, Leticia
dc.contributor.authorRodrigues, Ana M.
dc.contributor.authorCiriani, Marina
dc.contributor.authorFale, Pedro Luís Vieira
dc.contributor.authorTeixeira, Vítor
dc.contributor.authorMadeira, Paulo
dc.contributor.authorMachuqueiro, Miguel
dc.contributor.authorPacheco, Rita
dc.contributor.authorFlorêncio, Maria Helena
dc.contributor.authorAscensão, Lia
dc.contributor.authorSerralheiro, Maria Luisa
dc.date.accessioned2019-03-18T12:51:19Z
dc.date.available2019-03-18T12:51:19Z
dc.date.issued2017-11
dc.description.abstractThis work was aimed at the study of the chemical composition in phenolic compounds responsible for the high antiacetylcholinesterase activity of aqueous extracts (decoctions) from Helichrysum stoechas aerial parts. Chlorogenic acid, cynarin, and arzanol were the main components of decoctions, detected by high-performance liquid chromatography with diode-array detection and liquid chromatography-mass spectrometry/mass spectrometry. Flowers and stems/leaves extracts inhibited antiacetylcholinesterase with IC50 values of 260.7 and 654.8 mu g/mL, respectively. The biological activity of these extracts was maintained after in vitro gastrointestinal digestion, indicating that the active compounds present in the extracts were not enzymatically modified by the gastrointestinal system used to simulate the digestion. Molecular docking studies with the main components were carried out in order to obtain information, at the molecular level, as to how these compounds access the enzyme's active site. The docking study showed for the first time that chlorogenic acid, cynarin, and arzanol fit nicely in the antiacetylcholinesterase active site channel, blocking all access to the catalytic triad. This explained the high inhibitory activity determined during in vitro experiments.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationSILVA, Leticia; [et al] – Antiacetylcholinesterase activity and docking studies with chlorogenic acid, cynarin and arzanol from Helichrysum stoechas (Lamiaceae). Medicinal Chemistry Research. ISSN 1054-2523. Vol. 26, N.º 11 (2017), pp. 2942-2950pt_PT
dc.identifier.doi10.1007/s00044-017-1994-7pt_PT
dc.identifier.issn1054-2523
dc.identifier.issn1554-8120
dc.identifier.urihttp://hdl.handle.net/10400.21/9729
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherSpringerpt_PT
dc.relationPEst-UID/AMB/50017/2013 - FCTpt_PT
dc.relation.publisherversionhttps://link.springer.com/content/pdf/10.1007%2Fs00044-017-1994-7.pdfpt_PT
dc.subjectAcetylcholinesterase inhibitionpt_PT
dc.subjectDocking studiespt_PT
dc.subjectChlorogenic acidpt_PT
dc.subjectCynarinpt_PT
dc.subjectArzanolpt_PT
dc.titleAntiacetylcholinesterase activity and docking studies with chlorogenic acid, cynarin and arzanol from Helichrysum stoechas (Lamiaceae)pt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/3599-PPCDT/PEst-OE%2FQUI%2FUI0612%2F2013/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/5876/UID%2FMulti%2F00612%2F2013/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/3599-PPCDT/PTDC%2FQUI-BIQ%2F113477%2F2009/PT
oaire.citation.endPage2950pt_PT
oaire.citation.issue11pt_PT
oaire.citation.startPage2942pt_PT
oaire.citation.titleMedicinal Chemistry Researchpt_PT
oaire.citation.volume26pt_PT
oaire.fundingStream3599-PPCDT
oaire.fundingStream5876
oaire.fundingStream3599-PPCDT
person.familyNameRodrigues
person.familyNameMachuqueiro
person.familyNamePacheco
person.familyNameFlorêncio
person.familyNameAscensão
person.familyNameSerralheiro
person.givenNameAna M.
person.givenNameMiguel
person.givenNameRita
person.givenNameMaria Helena
person.givenNameLia
person.givenNameMaria Luisa
person.identifier1433605
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person.identifier.ciencia-idA110-D994-4AA1
person.identifier.ciencia-idD416-CB5B-AC3D
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person.identifier.orcid0000-0003-3257-9777
person.identifier.orcid0000-0001-6923-8744
person.identifier.orcid0000-0001-5192-3006
person.identifier.orcid0000-0001-5319-9058
person.identifier.orcid0000-0001-7439-5912
person.identifier.orcid0000-0001-7541-9613
person.identifier.ridC-8012-2011
person.identifier.ridC-3062-2012
person.identifier.ridB-5404-2011
person.identifier.ridA-2685-2014
person.identifier.ridE-3407-2012
person.identifier.scopus-author-id56589402100
person.identifier.scopus-author-id57221975472
person.identifier.scopus-author-id8853708300
person.identifier.scopus-author-id6701856949
person.identifier.scopus-author-id6506279352
person.identifier.scopus-author-id6602688573
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsclosedAccesspt_PT
rcaap.typearticlept_PT
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