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Antileishmanial activity of meroditerpenoids from the macroalgae Cystoseira baccata

2017-03Journal article Open access
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dc.contributor.authorSousa, Carolina Bruno de
dc.contributor.authorGangadhar, Katkam N.
dc.contributor.authorMorais, Thiago R.
dc.contributor.authorConserva, Geanne A. A.
dc.contributor.authorVizetto-Duarte, C
dc.contributor.authorPereira, H.
dc.contributor.authorLaurenti, Marcia D.
dc.contributor.authorCampino, Lenea
dc.contributor.authorLevy, Debora
dc.contributor.authorUemi, Miriam
dc.contributor.authorBarreira, Luísa
dc.contributor.authorCustódio, L.
dc.contributor.authorPassero, Luiz Felipe D.
dc.contributor.authorLago, Joao Henrique G.
dc.contributor.authorVarela, João
dc.date.accessioned2019-11-20T15:07:45Z
dc.date.available2019-11-20T15:07:45Z
dc.date.issued2017-03
dc.description.abstractThe development of novel drugs for the treatment of leishmaniases continues to be crucial to overcome the severe impacts of these diseases on human and animal health. Several bioactivities have been described in extracts from macroalgae belonging to the Cystoseira genus. However, none of the studies has reported the chemical compounds responsible for the antileishmanial activity observed upon incubation of the parasite with the aforementioned extracts. Thus, this work aimed to isolate and characterize the molecules present in a hexane extract of Cystoseira baccata that was found to be bioactive against Leishmania infantum in a previous screening effort. A bioactivity-guided fractionation of the C. baccata extract was carried out and the inhibitory potential of the isolated compounds was evaluated via the MIT assay against promastigotes and murine macrophages as well as direct counting against intracellular amastigotes. Moreover, the promastigote ultrastructure, DNA fragmentation and changes in the mitochondrial potential were assessed to unravel their mechanism of action. In this process, two antileishmanial meroditerpenoids, (3R)- and (3S)-tetraprenyltoluquinol (1a/1b) and (3R)- and (3S)-tetraprenyltoluquinone (2a/2b), were isolated. Compounds 1 and 2 inhibited the growth of the L. infantum promastigotes (IC50 = 44.9 +/- 4.3 and 94.4 +/- 10.1 mu M, respectively), inducing cytoplasmic vacuolization and the presence of coiled multilamellar structures in mitochondria as well as an intense disruption of the mitochondrial membrane potential. Compound 1 decreased the intracellular infection index (IC50 = 25.0 +/- 4.1 mu M), while compound 2 eliminated 50% of the intracellular amastigotes at a concentration > 88.0 mu M. This work identified compound 2 as a novel metabolite and compound 1 as a biochemical isolated from Cystoseira algae displaying antileishmanial activity. Compound 1 can thus be an interesting scaffold for the development of novel chemotherapeutic molecules for canine and human visceral leishmaniases studies. This work reinforces the evidence of the marine environment as source of novel molecules. (C) 2017 Elsevier Inc. All rights reserved.
dc.description.sponsorshipPortuguese FCT CCMAR/Multi/04326/2013
dc.description.sponsorshipFAPESP [2013/16297-2, 2015/11936-2]
dc.description.sponsorshipCNPq [470853/2012-3]
dc.description.sponsorshipFCT doctoral grants [ SFRH/BD/105541/2014 ]
dc.description.sponsorshipFCT Investigator Programme [IF/00049/2012]
dc.description.versioninfo:eu-repo/semantics/publishedVersion
dc.identifier.doi10.1016/j.exppara.2017.01.002
dc.identifier.issn0014-4894
dc.identifier.issn1090-2449
dc.identifier.urihttp://hdl.handle.net/10400.1/13197
dc.language.isoeng
dc.peerreviewedyes
dc.publisherAcademic Press
dc.relationMarine photosynthetic organisms of the Algarve coast with biomedical applications
dc.relationMARINE ALGAE EXTRACTS AS A SOURCE OF NATURAL ANTILEISHMANIAL COMPOUNDS
dc.relationBiomedical properties of Cystoseira species: insights into nutra- and pharmaceutical applications
dc.relationTECHNOLOGICAL IMPROVEMENTS OF BIODIESEL PRODUCTION USING OILS SYNTHESIZED BY MICROALGAE
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.subjectMarine brown-algae
dc.subjectVisceral leishmaniasis
dc.subjectCytotoxic activity
dc.subjectIn-vitro
dc.subjectDeath
dc.subjectPromastigotes
dc.subjectAmazonensis
dc.subjectApoptosis
dc.subjectInfection
dc.subjectAutophagy
dc.titleAntileishmanial activity of meroditerpenoids from the macroalgae Cystoseira baccata
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleMarine photosynthetic organisms of the Algarve coast with biomedical applications
oaire.awardTitleMARINE ALGAE EXTRACTS AS A SOURCE OF NATURAL ANTILEISHMANIAL COMPOUNDS
oaire.awardTitleBiomedical properties of Cystoseira species: insights into nutra- and pharmaceutical applications
oaire.awardTitleTECHNOLOGICAL IMPROVEMENTS OF BIODIESEL PRODUCTION USING OILS SYNTHESIZED BY MICROALGAE
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/3599-PPCDT/PTDC%2FMAR%2F103957%2F2008/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT//SFRH%2FBD%2F78062%2F2011/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT//SFRH%2FBD%2F81425%2F2011/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT//SFRH%2FBPD%2F81882%2F2011/PT
oaire.citation.endPage9
oaire.citation.startPage1
oaire.citation.titleExperimental Parasitology
oaire.citation.volume174
oaire.fundingStream3599-PPCDT
person.familyNameBruno de Sousa
person.familyNameVizetto-Duarte
person.familyNamePereira
person.familyNameCampino
person.familyNameBarreira
person.familyNameCustódio
person.familyNameVarela
person.givenNameCarolina
person.givenNameCatarina
person.givenNameHugo
person.givenNameLenea
person.givenNameLuísa
person.givenNameLuísa
person.givenNameJoão
person.identifier282781
person.identifier.ciencia-id0714-2E19-7817
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person.identifier.orcid0000-0002-4077-855X
person.identifier.orcid0000-0003-4338-7703
person.identifier.orcid0000-0003-3101-693X
person.identifier.ridJ-9538-2015
person.identifier.ridE-9360-2015
person.identifier.ridM-6101-2013
person.identifier.ridM-4223-2013
person.identifier.scopus-author-id56835726000
person.identifier.scopus-author-id54080259900
person.identifier.scopus-author-id6603808132
person.identifier.scopus-author-id15831018900
person.identifier.scopus-author-id55741416000
project.funder.identifierhttp://doi.org/10.13039/501100001871
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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.rightsopenAccess
rcaap.typearticle
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