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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Date
Authors
Pérez, Rebeca
Figueredo, Claudia
Burgos, Viviana
Cabrera-Pardo, Jaime R.
Schmidt, Bernd
Heydenreich, Matthias
Koch, Andreas
Deuis, Jennifer R.
Vetter, Irina
Paz, Cristian
Figueredo, Claudia
Burgos, Viviana
Cabrera-Pardo, Jaime R.
Schmidt, Bernd
Heydenreich, Matthias
Koch, Andreas
Deuis, Jennifer R.
Vetter, Irina
Paz, Cristian
Authors
Date
Datos de publicación:
10.3390/ijms242115504
Keywords
Aristotelia Chilensis - Aristoteline - Hobartine - Indole Alkaloids - Makomakinol - Nav1.8 - Carbon - Nitrogen - Polyphenol - Proton - Quercetin - Terpin Hydrate - Alkaloids - Analgesics - Anti-inflammatory Agents - Hobartine - Indole Alkaloids - Plant Extracts - 3 Formylindole - Alkaloid - Aristoteline - Carbon - Dihydro Beta Ionone - Ethyl Caffeate - Hobartine - Hobartinol - Makomakinol - Natural Product - Nitrogen - Polyphenol - Proton - Quercetin - Sodium Channel Nav1.8 - Terpene - Terpin Hydrate - Unclassified Drug - Voltage Gated Sodium Channel - Analgesic Agent - Antiinflammatory Agent - Indole Alkaloid - Plant Extract - Antinociception - Aristotelia Chilensis - Article - Carbon Nuclear Magnetic Resonance - Chemical Structure - Circular Dichroism - Controlled Study - Diastereoisomer - Electric Potential - Electrophysiology - Heteronuclear Multiple Bond Correlation - Human - Human Cell - Ic50 - Isomer - Nociception - Plant Leaf - Proton Nuclear Magnetic Resonance - Stereoisomerism - Tree - Whole Cell Patch Clamp - Elaeocarpaceae - Alkaloids - Analgesics - Anti-inflammatory Agents - Humans - Indole Alkaloids - Plant Extracts
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Abstract
Aristotelia 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.
Description
Keywords
Aristotelia Chilensis , Aristoteline , Hobartine , Indole Alkaloids , Makomakinol , Nav1.8 , Carbon , Nitrogen , Polyphenol , Proton , Quercetin , Terpin Hydrate , Alkaloids , Analgesics , Anti-inflammatory Agents , Hobartine , Indole Alkaloids , Plant Extracts , 3 Formylindole , Alkaloid , Aristoteline , Carbon , Dihydro Beta Ionone , Ethyl Caffeate , Hobartine , Hobartinol , Makomakinol , Natural Product , Nitrogen , Polyphenol , Proton , Quercetin , Sodium Channel Nav1.8 , Terpene , Terpin Hydrate , Unclassified Drug , Voltage Gated Sodium Channel , Analgesic Agent , Antiinflammatory Agent , Indole Alkaloid , Plant Extract , Antinociception , Aristotelia Chilensis , Article , Carbon Nuclear Magnetic Resonance , Chemical Structure , Circular Dichroism , Controlled Study , Diastereoisomer , Electric Potential , Electrophysiology , Heteronuclear Multiple Bond Correlation , Human , Human Cell , Ic50 , Isomer , Nociception , Plant Leaf , Proton Nuclear Magnetic Resonance , Stereoisomerism , Tree , Whole Cell Patch Clamp , Elaeocarpaceae , Alkaloids , Analgesics , Anti-inflammatory Agents , Humans , Indole Alkaloids , Plant Extracts
Citation
10.3390/ijms242115504