Natural Compounds Purified from the Leaves of Aristotelia chilensis: Makomakinol, a New Alkaloid and the Effect of Aristoteline and Hobartine on NaV Channels

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datacite.alternateIdentifier.citationInternational Journal of Molecular Sciences, 24 (21), 2023
datacite.alternateIdentifier.doi10.3390/ijms242115504
datacite.alternateIdentifier.issn1422-0067
datacite.creatorPérez, Rebeca
datacite.creatorFigueredo, Claudia
datacite.creatorBurgos, Viviana
datacite.creatorCabrera-Pardo, Jaime R.
datacite.creatorSchmidt, Bernd
datacite.creatorHeydenreich, Matthias
datacite.creatorKoch, Andreas
datacite.creatorDeuis, Jennifer R.
datacite.creatorVetter, Irina
datacite.creatorPaz, Cristian
datacite.date2023
datacite.rightsAcceso abierto
datacite.subjectAristotelia Chilensis
datacite.subjectAristoteline
datacite.subjectHobartine
datacite.subjectIndole Alkaloids
datacite.subjectMakomakinol
datacite.subjectNav1.8
datacite.subjectCarbon
datacite.subjectNitrogen
datacite.subjectPolyphenol
datacite.subjectProton
datacite.subjectQuercetin
datacite.subjectTerpin Hydrate
datacite.subjectAlkaloids
datacite.subjectAnalgesics
datacite.subjectAnti-inflammatory Agents
datacite.subjectHobartine
datacite.subjectIndole Alkaloids
datacite.subjectPlant Extracts
datacite.subject3 Formylindole
datacite.subjectAlkaloid
datacite.subjectAristoteline
datacite.subjectCarbon
datacite.subjectDihydro Beta Ionone
datacite.subjectEthyl Caffeate
datacite.subjectHobartine
datacite.subjectHobartinol
datacite.subjectMakomakinol
datacite.subjectNatural Product
datacite.subjectNitrogen
datacite.subjectPolyphenol
datacite.subjectProton
datacite.subjectQuercetin
datacite.subjectSodium Channel Nav1.8
datacite.subjectTerpene
datacite.subjectTerpin Hydrate
datacite.subjectUnclassified Drug
datacite.subjectVoltage Gated Sodium Channel
datacite.subjectAnalgesic Agent
datacite.subjectAntiinflammatory Agent
datacite.subjectIndole Alkaloid
datacite.subjectPlant Extract
datacite.subjectAntinociception
datacite.subjectAristotelia Chilensis
datacite.subjectArticle
datacite.subjectCarbon Nuclear Magnetic Resonance
datacite.subjectChemical Structure
datacite.subjectCircular Dichroism
datacite.subjectControlled Study
datacite.subjectDiastereoisomer
datacite.subjectElectric Potential
datacite.subjectElectrophysiology
datacite.subjectHeteronuclear Multiple Bond Correlation
datacite.subjectHuman
datacite.subjectHuman Cell
datacite.subjectIc50
datacite.subjectIsomer
datacite.subjectNociception
datacite.subjectPlant Leaf
datacite.subjectProton Nuclear Magnetic Resonance
datacite.subjectStereoisomerism
datacite.subjectTree
datacite.subjectWhole Cell Patch Clamp
datacite.subjectElaeocarpaceae
datacite.subjectAlkaloids
datacite.subjectAnalgesics
datacite.subjectAnti-inflammatory Agents
datacite.subjectHumans
datacite.subjectIndole Alkaloids
datacite.subjectPlant Extracts
datacite.titleNatural Compounds Purified from the Leaves of Aristotelia chilensis: Makomakinol, a New Alkaloid and the Effect of Aristoteline and Hobartine on NaV Channels
dc.description.abstractAristotelia chilensis or maqui is a tree native to Chile used in the folk medicine of the Mapuche people as an anti-inflammatory agent for the treatment of digestive ailments, fever, and skin lesions. Maqui fruits are black berries which are considered a superfruit with notable potential health benefits, promoted to be an antioxidant, cardioprotective, and anti-inflammatory. Maqui leaves contain non-iridoid monoterpene indole alkaloids which have previously been shown to act on nicotinic acetylcholine receptors, potassium channels, and calcium channels. Here, we isolated a new alkaloid from maqui leaves, now called makomakinol, together with the known alkaloids aristoteline, hobartine, and 3-formylindole. Moreover, the polyphenols quercetine, ethyl caffeate, and the terpenes, dihydro-?-ionone and terpin hydrate, were also obtained. In light of the reported analgesic and anti-nociceptive properties of A. chilensis, in particular a crude mixture of alkaloids containing aristoteline and hobartinol (PMID 21585384), we therefore evaluated the activity of aristoteline and hobartine on Na<inf>V</inf>1.8, a key Na<inf>V</inf> isoform involved in nociception, using automated whole-cell patch-clamp electrophysiology. Aristoteline and hobartine both inhibited Nav1.8 with an IC<inf>50</inf> of 68 ± 3 µM and 54 ± 1 µM, respectively. Hobartine caused a hyperpolarizing shift of the voltage-dependence of the activation, whereas aristoteline did not change the voltage-dependence of the activation or inactivation. The inhibitory activity of these alkaloids on Na<inf>V</inf> channels may contribute to the reported analgesic properties of Aristotelia chilensis used by the Mapuche people. © 2023 Elsevier B.V., All rights reserved.
dc.description.ia_keywordaristoteline, hobartine, chilensis, maqui, alkaloids, channels, aristotelia
dc.formatPDF
dc.identifier.issn1661-6596
dc.identifier.urihttps://repositoriodigital.uct.cl/handle/10925/5875
dc.language.isoen
dc.publisherMultidisciplinary Digital Publishing Institute (MDPI)
dc.relationinstname: ANID
dc.relationreponame: Repositorio Digital RI2.0
dc.rights.driverinfo:eu-repo/semantics/openAccess
dc.sourceInternational Journal of Molecular Sciences
dc.subject.ia_odsODS 3: Salud y bienestar
dc.subject.ia_oecd1nCiencias Médicas y de la Salud
dc.subject.ia_oecd2nMedicina Clínica
dc.subject.ia_oecd3nMedicina Clínica
dc.type.driverinfo:eu-repo/semantics/article
dc.type.driverhttp://purl.org/coar/resource_type/c_2df8fbb1
dc.type.openaireinfo:eu-repo/semantics/publishedVersion
dspace.entity.typePublication
oaire.citationEdition2023
oaire.citationIssue21
oaire.citationTitleInternational Journal of Molecular Sciences
oaire.citationVolume24
oaire.fundingReferenceCONICYT-FAPESP 201808426-0
oaire.fundingReferenceANID FONDECYT 1220831 (Regular)
oaire.fundingReferenceANID Fondequip EQM220161
oaire.fundingReferenceARC DE210100422
oaire.fundingReferenceNHMRC Australia APP1162503
oaire.licenseConditionObra bajo licencia Creative Commons Atribución 4.0 Internacional
oaire.licenseCondition.urihttps://creativecommons.org/licenses/by/4.0/
oaire.resourceTypeArtículo
oaire.resourceType.enArticle
uct.catalogadorjvu
uct.comunidadRecursos Naturalesen_US
uct.departamentoDepartamento de Ciencias Biológicas y Químicas
uct.facultadFacultad de Recursos Naturales
uct.indizacionScience Citation Index Expanded - SCIE
uct.indizacionScopus
uct.indizacionPubMed Central (PMC)
uct.indizacionChemical Abstracts Service (CAS)
uct.indizacionMEDLINE
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