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Article

Potent Antifungal Properties of Dimeric Acylphloroglucinols from Hypericum mexicanum and Mechanism of Action of a Highly Active 3′Prenyl Uliginosin B

1
Research and Innovation Centre, Fondazione Edmund Mach, 38010 San Michele all’Adige (TN), Italy
2
Department of Plant Systematics, BayCEER, University of Bayreuth, 95447 Bayreuth, Germany
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Departamento de Ciencias Biológicas, Universidad de los Andes, Bogotá 111711, Colombia
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Jardín Botánico de Cartagena “Guillermo Piñeres”, Turbaco, Bolívar 131007, Colombia
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Department of Physics, University of Trento, 38123 Trento, Italy
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Department of Cellular, Computational and Integrative Biology, CIBIO, University of Trento, 38122 Trento, Italy
*
Authors to whom correspondence should be addressed.
These authors contributed equally to this work.
Metabolites 2020, 10(11), 459; https://doi.org/10.3390/metabo10110459
Received: 3 October 2020 / Revised: 8 November 2020 / Accepted: 10 November 2020 / Published: 13 November 2020
(This article belongs to the Section Plant Science)
The success of antifungal therapies is often hindered by the limited number of available drugs. To close the gap in the antifungal pipeline, the search of novel leads is of primary importance, and here the exploration of neglected plants has great promise for the discovery of new principles. Through bioassay-guided isolation, uliginosin B and five new dimeric acylphloroglucinols (uliginosins C-D, and 3′prenyl uliginosins B-D), besides cembrenoids, have been isolated from the lipophilic extract of Hypericum mexicanum. Their structures were elucidated by a combination of Liquid Chromatography - Mass Spectrometry LC-MS and Nuclear Magnetic Resonance (NMR) measurements. The compounds showed strong anti-Candida activity, also against fluconazole-resistant strains, with fungal growth inhibition properties at concentrations ranging from 3 to 32 µM, and reduced or absent cytotoxicity against human cell lines. A chemogenomic screen of 3′prenyl uliginosin B revealed target genes that are important for cell cycle regulation and cytoskeleton assembly in fungi. Taken together, our study suggests dimeric acylphloroglucinols as potential candidates for the development of alternative antifungal therapies. View Full-Text
Keywords: Hypericum; bioactive compounds; antifungal activity; acylphloroglucinols; structural annotation; nuclear magnetic resonance spectroscopy; mass spectrometry; cytotoxicity; mechanism of action Hypericum; bioactive compounds; antifungal activity; acylphloroglucinols; structural annotation; nuclear magnetic resonance spectroscopy; mass spectrometry; cytotoxicity; mechanism of action
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MDPI and ACS Style

Tocci, N.; Weil, T.; Perenzoni, D.; Moretto, M.; Nürk, N.; Madriñán, S.; Ferrazza, R.; Guella, G.; Mattivi, F. Potent Antifungal Properties of Dimeric Acylphloroglucinols from Hypericum mexicanum and Mechanism of Action of a Highly Active 3′Prenyl Uliginosin B. Metabolites 2020, 10, 459. https://doi.org/10.3390/metabo10110459

AMA Style

Tocci N, Weil T, Perenzoni D, Moretto M, Nürk N, Madriñán S, Ferrazza R, Guella G, Mattivi F. Potent Antifungal Properties of Dimeric Acylphloroglucinols from Hypericum mexicanum and Mechanism of Action of a Highly Active 3′Prenyl Uliginosin B. Metabolites. 2020; 10(11):459. https://doi.org/10.3390/metabo10110459

Chicago/Turabian Style

Tocci, Noemi, Tobias Weil, Daniele Perenzoni, Marco Moretto, Nicolai Nürk, Santiago Madriñán, Ruggero Ferrazza, Graziano Guella, and Fulvio Mattivi. 2020. "Potent Antifungal Properties of Dimeric Acylphloroglucinols from Hypericum mexicanum and Mechanism of Action of a Highly Active 3′Prenyl Uliginosin B" Metabolites 10, no. 11: 459. https://doi.org/10.3390/metabo10110459

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