Natural Compounds Purified from the Leaves of <i>Aristotelia chilensis</i>: Makomakinol, a New Alkaloid and the Effect of Aristoteline and Hobartine on Na<sub>V</sub> Channels

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datacite.alternateIdentifier.citationINTERNATIONAL JOURNAL OF MOLECULAR SCIENCES,Vol.24,2023
datacite.alternateIdentifier.doi10.3390/ijms242115504
datacite.creatorPerez, 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.subject.englishindole alkaloids
datacite.subject.englishmakomakinol
datacite.subject.englisharistoteline
datacite.subject.englishhobartine
datacite.subject.englishAristotelia chilensis
datacite.subject.englishNa(V)1.8
datacite.titleNatural Compounds Purified from the Leaves of <i>Aristotelia chilensis</i>: Makomakinol, a New Alkaloid and the Effect of Aristoteline and Hobartine on Na<sub>V</sub> Channels
dc.date.accessioned2024-05-27T18:27:51Z
dc.date.available2024-05-27T18:27:51Z
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-beta-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(V)1.8, a key Na-V isoform involved in nociception, using automated whole-cell patch-clamp electrophysiology. Aristoteline and hobartine both inhibited Nav1.8 with an IC50 of 68 +/- 3 mu M and 54 +/- 1 mu M, 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-V channels may contribute to the reported analgesic properties of Aristotelia chilensis used by the Mapuche people.
dc.identifier.urihttps://repositoriodigital.uct.cl/handle/10925/5875
dc.language.isoen
dc.publisherMDPI
dc.sourceINTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
oaire.resourceTypeArticle
uct.indizacionSCI
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