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Open AccessArticle

New Antimalarial and Antimicrobial Tryptamine Derivatives from the Marine Sponge Fascaplysinopsis reticulata

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Laboratoire de Chimie des Substances Naturelles et des Sciences des Aliments, Faculté des Sciences et Technologies, Université de La Réunion, 15 Avenue René Cassin, CS 92003, 97744 Saint-Denis CEDEX 9, La Réunion, France
2
Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Univ. Paris-Sud, Université Paris-Saclay, 1, av. de la Terrasse, 91198 Gif-sur-Yvette, France
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Laboratoire des Sciences de l’Environnement MARin (LEMAR), Université de Brest, CNRS, IRD, Ifremer, LEMAR, F-29280 Plouzane, France
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Laboratory of Pharmacognosy, Center for Interdisciplinary Research on Medicines, CIRM, University of Liège B36, 4000 Liège, Belgium
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Naturalis Biodiversity Center, Darwinweg 2, 2333 CR Leiden, The Netherlands
*
Author to whom correspondence should be addressed.
Mar. Drugs 2019, 17(3), 167; https://doi.org/10.3390/md17030167
Received: 22 February 2019 / Revised: 6 March 2019 / Accepted: 12 March 2019 / Published: 15 March 2019
(This article belongs to the Collection TASCMAR)
Chemical study of the CH2Cl2-MeOH (1:1) extract of the sponge Fascaplysinopsis reticulata collected in Mayotte highlighted three new tryptophan derived alkaloids, 6,6′-bis-(debromo)-gelliusine F (1), 6-bromo-8,1′-dihydro-isoplysin A (2) and 5,6-dibromo-8,1′-dihydro-isoplysin A (3), along with the synthetically known 8-oxo-tryptamine (4) and the three known molecules from the same family, tryptamine (5), (E)-6-bromo-2′-demethyl-3′-N-methylaplysinopsin (6) and (Z)-6-bromo-2′-demethyl-3′-N-methylaplysinopsin (7). Their structures were elucidated by 1D and 2D NMR spectra and HRESIMS data. All compounds were evaluated for their antimicrobial and their antiplasmodial activities. Regarding antimicrobial activities, the best compounds are (2) and (3), with minimum inhibitory concentration (MIC) of 0.01 and 1 µg/mL, respectively, towards Vibrio natrigens, and (5), with MIC values of 1 µg/mL towards Vibrio carchariae. In addition the known 8-oxo-tryptamine (4) and the mixture of the (E)-6-bromo-2′-demethyl-3′-N-methylaplysinopsin (6) and (Z)-6-bromo-2′-demethyl-3′-N-methylaplysinopsin (7) showed moderate antiplasmodial activity against Plasmodium falciparum with IC50 values of 8.8 and 8.0 µg/mL, respectively. View Full-Text
Keywords: Fascaplysinopsis reticulata; marine sponge; tryptamine alkaloids; antimalarial activity; antimicrobial activity Fascaplysinopsis reticulata; marine sponge; tryptamine alkaloids; antimalarial activity; antimicrobial activity
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MDPI and ACS Style

Campos, P.-E.; Pichon, E.; Moriou, C.; Clerc, P.; Trépos, R.; Frederich, M.; De Voogd, N.; Hellio, C.; Gauvin-Bialecki, A.; Al-Mourabit, A. New Antimalarial and Antimicrobial Tryptamine Derivatives from the Marine Sponge Fascaplysinopsis reticulata. Mar. Drugs 2019, 17, 167.

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