Next Article in Journal
Hydrophilic Glycoproteins of an Edible Green Alga Capsosiphon fulvescens Prevent Aging-Induced Spatial Memory Impairment by Suppressing GSK-3β-Mediated ER Stress in Dorsal Hippocampus
Previous Article in Journal
Anti-Diabetic Activity of 2,3,6-Tribromo-4,5-Dihydroxybenzyl Derivatives from Symphyocladia latiuscula through PTP1B Downregulation and α-Glucosidase Inhibition
Previous Article in Special Issue
Bioactive Bromotyrosine-Derived Alkaloids from the Polynesian Sponge Suberea ianthelliformis
Article Menu
Issue 3 (March) cover image

Export Article

Open AccessArticle
Mar. Drugs 2019, 17(3), 167; https://doi.org/10.3390/md17030167

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

1
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
3
Laboratoire des Sciences de l’Environnement MARin (LEMAR), Université de Brest, CNRS, IRD, Ifremer, LEMAR, F-29280 Plouzane, France
4
Laboratory of Pharmacognosy, Center for Interdisciplinary Research on Medicines, CIRM, University of Liège B36, 4000 Liège, Belgium
5
Naturalis Biodiversity Center, Darwinweg 2, 2333 CR Leiden, The Netherlands
*
Author to whom correspondence should be addressed.
Received: 22 February 2019 / Revised: 6 March 2019 / Accepted: 12 March 2019 / Published: 15 March 2019
(This article belongs to the Collection TASCMAR)
  |  
PDF [728 KB, uploaded 15 March 2019]
  |     |  

Abstract

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
Figures

Graphical abstract

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

Supplementary material

SciFeed

Share & Cite This Article

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.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Mar. Drugs EISSN 1660-3397 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top