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The contribution of phenolic acids to the anti-inflammatory activity of mushrooms: screening in phenolic extracts, individual parent molecules and synthesized glucuronated and methylated derivatives

2015Journal article Restricted access
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dc.contributor.authorTaofiq, Oludemi
dc.contributor.authorCalhelha, Ricardo C.
dc.contributor.authorHeleno, Sandrina A.
dc.contributor.authorBarros, Lillian
dc.contributor.authorMartins, Anabela
dc.contributor.authorSantos-Buelga, Celestino
dc.contributor.authorQueiroz, Maria João R.P.
dc.contributor.authorFerreira, Isabel C.F.R.
dc.date.accessioned2015-11-30T15:29:25Z
dc.date.available2015-11-30T15:29:25Z
dc.date.issued2015
dc.description.abstractIn the present study, the ethanolic extracts of fourteen edible mushrooms were investigated for their anti-inflammatory potential in LPS (lipopolysaccharide) activated RAW 264.7 macrophages. Furthermore the extracts were chemically characterized in terms of phenolic acids and related compounds. The identified molecules (p-hydroxybenzoic, p-coumaric and cinnamic acids) and their glucuronated and methylated derivatives obtained by chemical synthesis were also evaluated for the same bioactivity, in order to establish structure-activity relationships and to comprehend the effects of in vivo metabolism reactions in the activity of the compounds. The extracts of Pleurotus ostreatus, Macrolepiota procera, Boletus impolitus and Agaricus bisporus revealed the strongest anti-inflammatory potential (EC50 values 96 ± 1 to 190 ± 6 µg/mL, and also the highest concentration of cinnamic acid (656 to 156 µg/g), which was also the individual compound with the highest anti-inflammatory activity. The derivatives of p-coumaric acid revealed the strongest properties, specially the derivative methylated in the carboxylic group (CoA-M1) that exhibited similar activity to the one showed by dexamethaxone used as anti-inflammatory standard; by contrast, the derivatives of p-hydroxybenzoic revealed the lowest inhibition of NO production. All in all, whereas the conjugation reactions change the chemical structure of phenolic acids and may increase or decrease their activity, the glucuronated and methylated derivatives of the studied compounds are still displaying anti-inflammatory activity.pt_PT
dc.description.sponsorshipThe authors are grateful to Fundação para a Ciência e a Tecnologia (FCT, Portugal) and FEDER-COMPETE/QREN/EU for the financial support through the research projects PEst-OE/AGR/UI0690/2011 and PEst-C/QUI/UI0686/2011. S.A. Heleno (BD/70304/2010) and R.C. Calhelha (BPD/68344/2010) also thank FCT, POPH-QREN and FSE. C. Santos-Buelga is also thankful to the Spanish MINECO for financial support through the project BFU2012-35228.pt_PT
dc.identifier.citationAyodele, Oludemi Taofiq; Calhelha, Ricardo C.; Heleno, Sandrina A.; Barros, Lillian; Martins, Anabela; Santos-Buelga, Celestino; Queiroz, Maria João R.P..; Ferreira, Isabel C.F.R. (2015). The contribution of phenolic acids to the anti-inflammatory activity of mushrooms: screening in phenolic extracts, individual parent molecules and synthesized glucuronated and methylated derivatives. Food Research International. ISSN 0963-9969. 76:3, p. 821–827pt_PT
dc.identifier.doi10.1016/j.foodres.2015.07.044pt_PT
dc.identifier.issn0963-9969
dc.identifier.urihttp://hdl.handle.net/10198/12458
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherElsevierpt_PT
dc.relationBFU2012-35228pt_PT
dc.relationIMPORTANT HUMAN METABOLITES OF PHENOLIC ACIDS FROM DIET WITH WILD EDIBLE MUSHROOMS: CHEMICAL SYNTHESIS AND STUDIES OF THEIR ANTIOXIDANT AND ANTITUMOR PROPERTIES
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/pt_PT
dc.subjectEdible mushroomspt_PT
dc.subjectPhenolic acidspt_PT
dc.subjectGlucuronated and methylated derivativespt_PT
dc.subjectAnti-inflammatorypt_PT
dc.subjectNitric oxide productionpt_PT
dc.subjectHPLC-PDApt_PT
dc.titleThe contribution of phenolic acids to the anti-inflammatory activity of mushrooms: screening in phenolic extracts, individual parent molecules and synthesized glucuronated and methylated derivativespt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleIMPORTANT HUMAN METABOLITES OF PHENOLIC ACIDS FROM DIET WITH WILD EDIBLE MUSHROOMS: CHEMICAL SYNTHESIS AND STUDIES OF THEIR ANTIOXIDANT AND ANTITUMOR PROPERTIES
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/5876/PEst-OE%2FAGR%2FUI0690%2F2014/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/3599-PPCDT/Incentivo%2FQUI%2FUI0686%2F2014/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT//SFRH%2FBD%2F70304%2F2010/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/SFRH/SFRH%2FBPD%2F68344%2F2010/PT
oaire.citation.endPage827pt_PT
oaire.citation.startPage821pt_PT
oaire.citation.titleFood Research Internationalpt_PT
oaire.citation.volume76pt_PT
oaire.fundingStream5876
oaire.fundingStream3599-PPCDT
oaire.fundingStreamSFRH
person.familyNameCalhelha
person.familyNameHeleno
person.familyNameBarros
person.familyNameMartins
person.familyNameFerreira
person.givenNameRicardo C.
person.givenNameSandrina A.
person.givenNameLillian
person.givenNameAnabela
person.givenNameIsabel C.F.R.
person.identifier469085
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person.identifier.ciencia-id9418-CF95-9919
person.identifier.orcid0000-0002-6801-4578
person.identifier.orcid0000-0001-7224-1098
person.identifier.orcid0000-0002-9050-5189
person.identifier.orcid0000-0001-6218-4413
person.identifier.orcid0000-0003-4910-4882
person.identifier.ridJ-2172-2014
person.identifier.ridL-5951-2014
person.identifier.ridJ-3600-2013
person.identifier.ridG-5488-2013
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person.identifier.scopus-author-id6507978333
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person.identifier.scopus-author-id35236343600
person.identifier.scopus-author-id7203013518
person.identifier.scopus-author-id36868826600
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.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
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsopenAccesspt_PT
rcaap.typearticlept_PT
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