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1. Glycoglycerolipids From Sargassum vulgare as Potential Antifouling Agents

Author

Erwan Plouguerné, Lauro M. de Souza, Guilherme L. Sassaki, Claire Hellio, Rozenn Trepos, Bernardo A. P. da Gama, Renato Crespo Pereira, and Eliana Barreto-Bergter

Subjects
Sargassum vulgare, glycoglycerolipids, antifouling, microfouling, macroalgae, Science, General. Including nature conservation, geographical distribution, QH1-199.5
Abstract

Unraveling new environmentally friendly antifouling (AF) agents is one of the major quests currently facing marine biotechnology. Marine macroalgae represent a rich source of new compounds with promising biological properties, including AF activity, but most of the macroalgal compounds studied to date are terpenoids or polyphenolics. The aim of this work was to investigate the possible AF role played by a usually neglected class of marine natural products: glycolipids (monogalactosyldiacylglycerols – MGDG, digalactosyldiacylglycerols – DGDG and sulfoquinovosyldiacylglycerols – SQDG) isolated from the Phaeophyceae Sargassum vulgare collected along the coast of south-eastern Brazil. Among the 18 extracts, fractions and sub-fractions tested, 3 sub-fractions demonstrated particularly promising AF activity toward the growth inhibition of marine bacteria and microalgae: F3III117, F4II70a, and F4II70b. The main compounds present in these fractions were identified as MGDG, DGDG, and SQDG, respectively. These results highlight the potential of glycoglycerolipids from S. vulgare as new promising antifouling agents.

Published
2020
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2. Bioactive Bromotyrosine Derivatives from the Pacific Marine Sponge Suberea clavata (Pulitzer-Finali, 1982)

Author

Céline Moriou, Damien Lacroix, Sylvain Petek, Amr El-Demerdash, Rozenn Trepos, Tinihauarii Mareva Leu, Cristina Florean, Marc Diederich, Claire Hellio, Cécile Debitus, and Ali Al-Mourabit

Subjects
sponge, Verongiida, Suberea clavata, bromotyrosine, fistularin-3, acetylcholinesterase inhibition, Biology (General), QH301-705.5
Abstract

Chemical investigation of the South-Pacific marine sponge Suberea clavata led to the isolation of eight new bromotyrosine metabolites named subereins 1–8 (2–9) along with twelve known co-isolated congeners. The detailed configuration determination of the first representative major compound of this family 11-epi-fistularin-3 (11R,17S) (1) is described. Their chemical characterization was achieved by HRMS and integrated 1D and 2D NMR (nuclear magnetic resonance) spectroscopic studies and extensive comparison with literature data. For the first time, a complete assignment of the absolute configurations for stereogenic centers C-11/17 of the known members (11R,17S) 11-epi-fistularin-3 (1) and 17-deoxyfistularin-3 (10) was determined by a combination of chemical modifications, Mosher’s technology, and ECD spectroscopy. Consequently, the absolute configurations of all our new isolated compounds 2–9 were determined by the combination of NMR, Mosher’s method, ECD comparison, and chemical modifications. Interestingly, compounds 2–7 were obtained by chemical transformation of the major compound 11-epi-fistularin-3 (1). Evaluation for acetylcholinesterase inhibition (AChE), DNA methyltransferase 1 (DNMT1) modulating activity and antifouling activities using marine bacterial strains are also presented.

Published
2021
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3. From Ecology to Biotechnology, Study of the Defense Strategies of Algae and Halophytes (from Trapani Saltworks, NW Sicily) with a Focus on Antioxidants and Antimicrobial Properties

Author

Concetta Maria Messina, Giuseppe Renda, Vincenzo Alessandro Laudicella, Rozenn Trepos, Marilyne Fauchon, Claire Hellio, and Andrea Santulli

Subjects
polyphenols, defenses, anti-oxidants, antifouling, anti-microbial, Cystoseira foeniculacea, Halocnemum strobilaceum, Biology (General), QH301-705.5, Chemistry, QD1-999
Abstract

This study aimed at the characterization of the antioxidant power of polyphenol extracts (PE) obtained from the algae Cystoseira foeniculacea (CYS) (Phaeophyta) and from the halophyte Halocnemum strobilaceum (HAL), growing in the solar saltworks of western Sicily (Italy), and at the evaluation of their anti-microfouling properties, in order to correlate these activities to defense strategies in extreme environmental conditions. The antioxidant properties were assessed in the PE based on the total antioxidant activity test and the reducing power test; the anti-microfouling properties of the two PE were evaluated by measuring the growth inhibition of marine fish and shellfish pathogen bacteria as well as marine surface fouling bacteria and microalgae exposed to the fractions. Similar polyphenol content (CYS 5.88 ± 0.75 and HAL 6.03 ± 0.25 mg gallic acid equivalents (GAE) g−1 dried weight, DW) and similar reducing power percentage (93.91 ± 4.34 and 90.03 ± 6.19) were recorded for both species, even if they exhibited a different total antioxidant power (measured by the percentage of inhibition of the radical 2,2 diphenyl-1-picrylhydrazyl DPPH), with CYS (79.30) more active than HAL (59.90). Both PE showed anti-microfouling properties, being inhibitors of adhesion and growth of marine fish and shellfish pathogen bacteria (V. aestuarianus, V. carchariae, V. harveyi, P. elyakovii, H. aquamarina) and fouling bacteria (V. natriegens, V. proteolyticus, P. iirgensii, R. litoralis) with minimum inhibitory concentrations comparable to the commercial antifouling products used as a positive control (SEA-NINE™ 211N). Only CYS was a significant inhibitor of the microalgae strains tested, being able to reduce E. gayraliae and C. closterium growth (MIC 10 µg·mL−1) and the adhesion of all three strains tested (E. gayraliae, C. closterium and P. purpureum), suggesting its promise for use as an antifouling (AF) product.

Published
2019
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4. Bioactive Bromotyrosine Derivatives from the Pacific Marine Sponge Suberea clavata (Pulitzer-Finali, 1982)

Author

Cristina Florean, Marc Diederich, Tinihauarii Mareva Leu, Ali Al-Mourabit, Cécile Debitus, Céline Moriou, Sylvain Petek, Damien Lacroix, Rozenn Trepos, Amr El-Demerdash, Claire Hellio, Institut de Chimie des Substances Naturelles (ICSN), Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), University of Sheffield [Sheffield], Ecosystèmes Insulaires Océaniens (UMR 241) (EIO), Université de la Polynésie Française (UPF)-Institut Louis Malardé [Papeete] (ILM), Institut de Recherche pour le Développement (IRD)-Institut de Recherche pour le Développement (IRD)-Institut Français de Recherche pour l'Exploitation de la Mer (IFREMER), Laboratoire des Sciences de l'Environnement Marin (LEMAR) (LEMAR), Institut de Recherche pour le Développement (IRD)-Institut Français de Recherche pour l'Exploitation de la Mer (IFREMER)-Université de Brest (UBO)-Institut Universitaire Européen de la Mer (IUEM), Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Hôpital Kirchberg, Hôpital Kirchberg [Luxembourg], Seoul National University [Seoul] (SNU), Institut de Recherche pour le Développement (IRD)-Institut Français de Recherche pour l'Exploitation de la Mer (IFREMER)-Université de la Polynésie Française (UPF)-Institut Louis Malardé [Papeete] (ILM), Institut de Recherche pour le Développement (IRD), and Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)

Subjects
DNA (Cytosine-5-)-Methyltransferase 1, Chemical transformation, Magnetic Resonance Spectroscopy, Biofouling, Stereochemistry, [SDV]Life Sciences [q-bio], Pharmaceutical Science, 01 natural sciences, acetylcholinesterase inhibition, Article, Stereocenter, sponge, 03 medical and health sciences, Drug Discovery, Animals, [CHIM]Chemical Sciences, 14. Life underwater, Suberea clavata, Pharmacology, Toxicology and Pharmaceutics (miscellaneous), Verongiida, lcsh:QH301-705.5, 030304 developmental biology, 0303 health sciences, Pacific Ocean, biology, 010405 organic chemistry, Chemistry, antifouling, biology.organism_classification, Porifera, 0104 chemical sciences, fistularin-3, Sponge, lcsh:Biology (General), bromotyrosine, Tyrosine, Fistularin 3, Cholinesterase Inhibitors, Two-dimensional nuclear magnetic resonance spectroscopy
Abstract

Chemical investigation of the South-Pacific marine sponge Suberea clavata led to the isolation of eight new bromotyrosine metabolites named subereins 1–8 (2–9) along with twelve known co-isolated congeners. The detailed configuration determination of the first representative major compound of this family 11-epi-fistularin-3 (11R,17S) (1) is described. Their chemical characterization was achieved by HRMS and integrated 1D and 2D NMR (nuclear magnetic resonance) spectroscopic studies and extensive comparison with literature data. For the first time, a complete assignment of the absolute configurations for stereogenic centers C-11/17 of the known members (11R,17S) 11-epi-fistularin-3 (1) and 17-deoxyfistularin-3 (10) was determined by a combination of chemical modifications, Mosher’s technology, and ECD spectroscopy. Consequently, the absolute configurations of all our new isolated compounds 2–9 were determined by the combination of NMR, Mosher’s method, ECD comparison, and chemical modifications. Interestingly, compounds 2–7 were obtained by chemical transformation of the major compound 11-epi-fistularin-3 (1). Evaluation for acetylcholinesterase inhibition (AChE), DNA methyltransferase 1 (DNMT1) modulating activity and antifouling activities using marine bacterial strains are also presented.

Published
2021

5. Reduction of potential ennoblement of stainless steel in natural seawater by an ecofriendly biopolymer

Author

Benoit Lescop, Maher Abboud, Marilyne Fauchon, Stéphane Rioual, L. Abi Nassif, Dominique Thierry, Wehbeh Farah, Claire Hellio, Erwan Diler, Rozenn Trepos, Laboratoire des sciences et techniques de l'information, de la communication et de la connaissance (Lab-STICC), École Nationale d'Ingénieurs de Brest (ENIB)-Université de Bretagne Sud (UBS)-Université de Brest (UBO)-École Nationale Supérieure de Techniques Avancées Bretagne (ENSTA Bretagne)-Institut Mines-Télécom [Paris] (IMT)-Centre National de la Recherche Scientifique (CNRS)-Université Bretagne Loire (UBL)-IMT Atlantique (IMT Atlantique), Institut Mines-Télécom [Paris] (IMT), Université Saint-Joseph de Beyrouth (USJ), Lab-STICC_UBO_MOM_DIM, Institut Brestois du Numérique et des Mathématiques (IBNM), Université de Brest (UBO)-Université de Brest (UBO)-Laboratoire des sciences et techniques de l'information, de la communication et de la connaissance (Lab-STICC), Institut Mines-Télécom [Paris] (IMT)-École Nationale d'Ingénieurs de Brest (ENIB)-Université de Bretagne Sud (UBS)-École Nationale Supérieure de Techniques Avancées Bretagne (ENSTA Bretagne)-Institut Mines-Télécom [Paris] (IMT)-Centre National de la Recherche Scientifique (CNRS)-Université Bretagne Loire (UBL)-IMT Atlantique (IMT Atlantique), Laboratoire des Sciences de l'Environnement Marin (LEMAR) (LEMAR), Institut de Recherche pour le Développement (IRD)-Institut Français de Recherche pour l'Exploitation de la Mer (IFREMER)-Université de Brest (UBO)-Institut Universitaire Européen de la Mer (IUEM), Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Institut de la Corrosion, École Nationale d'Ingénieurs de Brest (ENIB)-Université de Bretagne Sud (UBS)-Université de Brest (UBO)-École Nationale Supérieure de Techniques Avancées Bretagne (ENSTA Bretagne)-Institut Mines-Télécom [Paris] (IMT)-Centre National de la Recherche Scientifique (CNRS)-Université Bretagne Loire (UBL)-IMT Atlantique Bretagne-Pays de la Loire (IMT Atlantique), Institut Mines-Télécom [Paris] (IMT)-École Nationale d'Ingénieurs de Brest (ENIB)-Université de Bretagne Sud (UBS)-École Nationale Supérieure de Techniques Avancées Bretagne (ENSTA Bretagne)-Institut Mines-Télécom [Paris] (IMT)-Centre National de la Recherche Scientifique (CNRS)-Université Bretagne Loire (UBL)-IMT Atlantique Bretagne-Pays de la Loire (IMT Atlantique), and Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Biopolymer, 02 engineering and technology, 010501 environmental sciences, engineering.material, 01 natural sciences, Chemical Engineering (miscellaneous), Waste Management and Disposal, 0105 earth and related environmental sciences, Chemistry, Process Chemistry and Technology, Ennoblement, Biofilm, Acl, fungi, Alginate, technology, industry, and agriculture, biochemical phenomena, metabolism, and nutrition, 021001 nanoscience & nanotechnology, Pollution, Chemical engineering, Steel, engineering, [PHYS.COND.CM-MS]Physics [physics]/Condensed Matter [cond-mat]/Materials Science [cond-mat.mtrl-sci], Seawater, Antimicrobial, [SDE.BE]Environmental Sciences/Biodiversity and Ecology, 0210 nano-technology
Abstract

International audience; The effect of biofilm formation on passive stainless steel in seawater environments is of primary importance since it leads to potential ennoblement of surfaces and subsequently to localized corrosion such as pitting and crevice corrosion. This study aims at developing an ecofriendly alginate biopolymer containing both non-toxic calcium and a limited amount of biocidal zinc ions which inhibits this effect. For this purpose, calcium alginate containing less than 1 % of zinc ions localized in the vicinity of the steel surface in natural and renewed seawater is demonstrated to reduce significantly the ennoblement process of steel. After 1 month of immersion, a mass loss of only 4 % of the active material is observed authorizing thereby long-term protection of steel in real environment.

Published
2020

6. Design and Biological Evaluation of Antifouling Dihydrostilbene Oxime Hybrids

Author

Claire Hellio, Lindon W. K. Moodie, Gunnar Cervin, Henrik Pavia, Christophe Labriere, Rozenn Trepos, Johan Svenson, Department of Chemistry [Tromsø], University of Tromsø (UiT), Department of Marine Sciences [Gothenburg], University of Gothenburg (GU), Laboratoire des Sciences de l'Environnement Marin (LEMAR) (LEMAR), Institut de Recherche pour le Développement (IRD)-Institut Français de Recherche pour l'Exploitation de la Mer (IFREMER)-Université de Brest (UBO)-Institut Universitaire Européen de la Mer (IUEM), Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), RISE Bioscience and Materials/Chemistry and Materials, RISE Research Institutes of Sweden, and Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)

Subjects
0301 basic medicine, Biofouling, Oceanografi, hydrologi och vattenresurser, 01 natural sciences, Applied Microbiology and Biotechnology, Oxime, Oceanography, Hydrology and Water Resources, chemistry.chemical_compound, biodimar, Naturvetenskap, inhibitors, Oximes, Stilbenes, Microalgae, Organic chemistry, Moiety, metabolites, Biological evaluation, helicobacter-pylori urease, natural-products, Environmental biotechnology, VDP::Matematikk og Naturvitenskap: 400::Kjemi: 440, Larva, Original Article, Natural Sciences, Batatasin, surfaces, Biology, Microbiology, 03 medical and health sciences, Environmental Biotechnology, Animals, Miljöbioteknik, marine sponges, Dihydrostilbene, synthetic analogs, VDP::Mathematics and natural science: 400::Chemistry: 440, Bacteria, 010405 organic chemistry, ACL, Thoracica, Antifouling, Ianthelline, Hybrid, agents, 0104 chemical sciences, Mikrobiologi, 030104 developmental biology, chemistry, derivatives, potent, [SDE.BE]Environmental Sciences/Biodiversity and Ecology
Abstract

By combining the recently reported repelling natural dihydrostilbene scaffold with an oxime moiety found in many marine antifoulants, a library of nine antifouling hybrid compounds was developed and biologically evaluated. The prepared compounds were shown to display a low antifouling effect against marine bacteria but a high potency against the attachment and growth of microalgae down to MIC values of 0.01 μg/mL for the most potent hybrid. The mode of action can be characterized as repelling via a reversible non-toxic biostatic mechanism. Barnacle cyprid larval settlement was also inhibited at low μg/mL concentrations with low levels or no toxicity observed. Several of the prepared compounds performed better than many reported antifouling marine natural products. While several of the prepared compounds are highly active as antifoulants, no apparent synergy is observed by incorporating the oxime functionality into the dihydrostilbene scaffold. This observation is discussed in light of recently reported literature data on related marine natural antifoulants and antifouling hybrids as a potentially general strategy for generation of improved antifoulants. Electronic supplementary material The online version of this article (10.1007/s10126-018-9802-z) contains supplementary material, which is available to authorized users.

Published
2018

7. Prevention of Marine Biofouling Using the Natural Allelopathic Compound Batatasin-III and Synthetic Analogues

Author

Rigmor Reiersen, Bente Lindgård, Kari Anne Bråthen, Henrik Pavia, Claire Hellio, Rozenn Trepos, Johan Svenson, Patrick L. Cahill, Lindon W. K. Moodie, Gunnar Cervin, Department of Chemistry [Tromsø], University of Tromsø (UiT), Laboratoire des Sciences de l'Environnement Marin (LEMAR) (LEMAR), Institut de Recherche pour le Développement (IRD)-Institut Français de Recherche pour l'Exploitation de la Mer (IFREMER)-Université de Brest (UBO)-Institut Universitaire Européen de la Mer (IUEM), Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Department of Marine Sciences [Gothenburg], University of Gothenburg (GU), SP Technical Research Institute of Sweden, Institut Universitaire Européen de la Mer (IUEM), Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Institut Français de Recherche pour l'Exploitation de la Mer (IFREMER)-Centre National de la Recherche Scientifique (CNRS)-Université de Brest (UBO), and Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)

Subjects
antifouling activity, 0301 basic medicine, Aquatic Organisms, Biofouling, ved/biology.organism_classification_rank.species, Blue green algae, Pharmaceutical Science, Marine Biology, coatings, Biology, Analytical Chemistry, 03 medical and health sciences, inhibitors, Stilbenes, Drug Discovery, Terrestrial plant, VDP::Mathematics and natural science: 400::Zoology and botany: 480, Animals, blue-green-algae, Allelopathy, Volume concentration, Pharmacology, Marine biology, Biological Products, Molecular Structure, ved/biology, ACL, Thoracica, Organic Chemistry, herbivores, 030104 developmental biology, aquaculture, Complementary and alternative medicine, 13. Climate action, bacterial attachment, empetrum-hermaphroditum, Environmental chemistry, derivatives, Molecular Medicine, [SDE.BE]Environmental Sciences/Biodiversity and Ecology, environment, Batatasin-III, VDP::Matematikk og Naturvitenskap: 400::Zoologiske og botaniske fag: 480
Abstract

This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Natural Products, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.jnatprod.7b00129. The current study reports the first comprehensive evaluation of a class of allelopathic terrestrial natural products as antifoulants in a marine setting. To investigate the antifouling potential of the natural dihydrostilbene scaffold, a library of 22 synthetic dihydrostilbenes with varying substitution patterns, many of which occur naturally in terrestrial plants, were prepared and assessed for their antifouling capacity. The compounds were evaluated in an extensive screen against 16 fouling marine organisms. The dihydrostilbene scaffold was shown to possess powerful general antifouling effects against both marine microfoulers and macrofoulers with inhibitory activities at low concentrations. The species of microalgae examined displayed a particular sensitivity toward the evaluated compounds at low ng/mL concentrations. It was shown that several of the natural and synthetic compounds exerted their repelling activities via nontoxic and reversible mechanisms. The activities of the most active compounds such as 3,5-dimethoxybibenzyl (5), 3,4-dimethoxybibenzyl (9), and 3-hydroxy-3′,4,5′-trimethoxybibenzyl (20) were comparable to the commercial antifouling booster biocide Sea-nine, which was employed as a positive control. The investigation of terrestrial allelopathic natural products to counter marine fouling represents a novel strategy for the design of “green” antifouling technologies, and these compounds offer a potential alternative to traditional biocidal antifoulants.

Published
2017

8. Probing the Structure–Activity Relationship of the Natural Antifouling Agent Polygodial against both Micro- and Macrofoulers by Semisynthetic Modification

Author

Henrik Pavia, Rozenn Trepos, Lesley Larsen, Johan Svenson, Lindon W. K. Moodie, Gunnar Cervin, David S. Larsen, Patrick L. Cahill, Claire Hellio, Department of Chemistry [Tromsø], University of Tromsø (UiT), Laboratoire des Sciences de l'Environnement Marin (LEMAR) (LEMAR), Institut Universitaire Européen de la Mer (IUEM), Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Institut Français de Recherche pour l'Exploitation de la Mer (IFREMER)-Centre National de la Recherche Scientifique (CNRS)-Université de Brest (UBO), Department of Marine Sciences [Gothenburg], University of Gothenburg (GU), University of Otago [Dunedin, Nouvelle-Zélande], SP Technical Research Institute of Sweden, Institut de Recherche pour le Développement (IRD)-Institut Français de Recherche pour l'Exploitation de la Mer (IFREMER)-Université de Brest (UBO)-Institut Universitaire Européen de la Mer (IUEM), and Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)

Subjects
0301 basic medicine, Biofouling, Ciona savignyi, Polygodial, Pharmaceutical Science, panorama, Sesquiterpene, antifeedant activity, Analytical Chemistry, Structure-Activity Relationship, antimicrobial peptides, 03 medical and health sciences, chemistry.chemical_compound, Drug Discovery, Animals, Structure–activity relationship, Urochordata, 14. Life underwater, barnacle balanus-improvisus, ciona-intestinalis, Polycyclic Sesquiterpenes, synthetic analogs, Pharmacology, Bacteria, Molecular Structure, biology, Chemistry, ACL, Thoracica, Organic Chemistry, nordrimane compounds, Chemical basis, biology.organism_classification, Combinatorial chemistry, Semisynthesis, 030104 developmental biology, Complementary and alternative medicine, Larva, bacterial attachment, saccharomyces-cerevisiae, Molecular Medicine, resistant cancer-cells, drimane sesquiterpenoids, [SDE.BE]Environmental Sciences/Biodiversity and Ecology, Sesquiterpenes
Abstract

WOS:000395046900033; International audience; The current study represents the first comprehensive investigation into the general antifouling activities of the natural drimane sesquiterpene polygodial. Previous studies have highlighted a high antifouling effect toward macrofoulers, such as ascidians, tubeworms, and mussels, but no reports about the general antifouling effect of polygodial have been communicated before. To probe the structural and chemical basis for antifouling activity, a library of 11 polygodial analogues was prepared by semisynthesis. The library was designed to yield derivatives with ranging polarities and the ability to engage in both covalent and noncovalent interactions, while still remaining within the drimane sesquiterpene scaffold. The prepared compounds were screened against 14 relevant marine micro- and macrofouling species. Several of the polygodial analogues displayed inhibitory activities at sub-microgram/mL concentrations. These antifouling effects were most pronounced against the macrofouling ascidian Ciona savignyi and the barnacle Balanus improvisus, with inhibitory activities observed for selected compounds comparable or superior to several commercial antifouling products. The inhibitory activity against the microfouling bacteria and microalgae was reversible and significantly less pronounced than for the macrofoulers. This study illustrates that the macro- and microfoulers are targeted by the compounds via different mechanisms.

Published
2017

9. Marine bacterial inhibitors from the sponge-derived fungus Aspergillus sp

Author

Abdessamad Debbab, Wenhan Lin, Barbara Schulz, Yaming Zhou, Claire Pile, Amal H. Aly, Claire Hellio, Peter Proksch, Rozenn Trepos, and Victor Wray

Subjects
Aspergillus, Sponge-derived fungi, biology, Chemistry, Stereochemistry, Alkaloid, Organic Chemistry, Tryptophan, Fungus, biology.organism_classification, Biochemistry, Sponge, Marine bacteriophage, Marine natural products, Drug Discovery, Tethya aurantium, Antibacterial activity, Biology
Abstract

Chromatographic separation of a crude extract obtained from the fungus Aspergillus sp., isolated from the Mediterranean sponge Tethya aurantium , yielded a new tryptophan derived alkaloid, 3-((1-hydroxy-3-(2-methylbut-3-en-2-yl)-2-oxoindolin-3-yl)methyl)-1-methyl-3,4-dihydrobenzo[ e ][1,4]diazepine-2,5-dione ( 1 ), and a new meroterpenoid, austalide R ( 2 ), together with three known compounds ( 3 – 5 ). The structures of the new compounds were unambiguously elucidated on the basis of extensive one and two-dimensional NMR ( 1 H, 13 C, COSY, HMBC, and ROESY) and mass spectral analysis. Interestingly, the compounds exhibited antibacterial activity when tested against a panel of marine bacteria, with 1 selectively inhibiting Vibrio species and 2 showing a broad spectrum of activity. In contrast, no significant activity was observed against terrestrial bacterial strains and the murine cancer cell line L5178Y.

Published
2014

10. Protocol for Assessing Antifouling Activities of Macroalgal Extracts

Author

Claire, Hellio, Rozenn, Trepos, R Noemí, Aguila-Ramírez, and Claudia J, Hernández-Guerrero

Subjects
Biological Products, Ulva, Anti-Infective Agents, Bacteria, Biofouling, Mytilus edulis, Microalgae, Animals, Biological Assay, Microbial Sensitivity Tests, Seaweed, Bacterial Adhesion
Abstract

The development of novel environmentally friendly antifouling (AF) solutions is a very active field in fundamental and applied research. An attractive option in producing such material resides in biomimetic studies: living organisms have evolved well-adapted structures and materials over geological times through natural selection. In this chapter, we explain the experimental procedure to be followed for the preparation of macroalgal extracts and to assess their AF efficiency towards key species. All bioassays described here have the advantage of being fast, reliable, and standardized.

Published
2015

11. Protocol for assessing antifouling activities of macroalgal extracts

Author

Rozenn Trepos, Claudia J. Hernández-Guerrero, R. Noemí Aguila-Ramírez, Claire Hellio, Laboratoire des Sciences de l'Environnement Marin (LEMAR) (LEMAR), Institut de Recherche pour le Développement (IRD)-Institut Français de Recherche pour l'Exploitation de la Mer (IFREMER)-Université de Brest (UBO)-Institut Universitaire Européen de la Mer (IUEM), Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), University of Portsmouth, Centre for Environment, Fisheries and Aquaculture Science [Weymouth] (CEFAS), Stengel Dagmar B., Connan Solène, European Project: 314697,EC:FP7:TPT,FP7-SST-2012-RTD-1,LEAF(2012), and Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Bacteria, Marine extracts, OS, Antifouling, Environmentally friendly, Biofouling, Macroalgae, Microalgae, Environmental science, Mussels, Bioassay, Biochemical engineering, [SDE.BE]Environmental Sciences/Biodiversity and Ecology, Barnacles
Abstract

International audience; The development of novel environmentally friendly antifouling (AF) solutions is a very active field in fundamental and applied research. An attractive option in producing such material resides in biomimetic studies: living organisms have evolved well-adapted structures and materials over geological times through natural selection. In this chapter, we explain the experimental procedure to be followed for the preparation of macroalgal extracts and to assess their AF efficiency towards key species. All bioassays described here have the advantage of being fast, reliable, and standardized.

Published
2015

12. Evaluation of cationic micropeptides derived from the innate immune system as inhibitors of marine biofouling

Author

Claire Hellio, Claire Pile, Rozenn Trepos, Henrik Pavia, Johan Svenson, Gunnar Cervin, University of Portsmouth, University of Gothenburg (GU), Laboratoire des Sciences de l'Environnement Marin (LEMAR) (LEMAR), Institut de Recherche pour le Développement (IRD)-Institut Français de Recherche pour l'Exploitation de la Mer (IFREMER)-Université de Brest (UBO)-Institut Universitaire Européen de la Mer (IUEM), Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), and University of Tromsø (UiT)

Subjects
Aquatic Organisms, nontoxic, Biofouling, Microorganism, fouling-release, release coatings, Aquatic Science, Biology, Applied Microbiology and Biotechnology, Balanus, Bacterial Adhesion, Microbiology, bovine lactoferrin, 03 medical and health sciences, Marine bacteriophage, Anti-Infective Agents, Peptide Library, amphiphilic, Microalgae, analogs, innate defence, Animals, barnacle balanus-improvisus, 030304 developmental biology, Water Science and Technology, 0303 health sciences, Innate immune system, Fouling, Bacteria, 030306 microbiology, antifouling, ACL, Thoracica, antibacterial peptides, Biofilm, natural-products, stability, Antimicrobial, biology.organism_classification, Immunity, Innate, Lactoferrin, antifouling compounds, synthetic antimicrobial peptidomimetics, Biofilms, peptides, [SDE.BE]Environmental Sciences/Biodiversity and Ecology
Abstract

WOS:000356074000007; A series of 13 short synthetic amphiphilic cationic micropeptides, derived from the antimicrobial iron-binding innate defence protein lactoferrin, have been evaluated for their capacity to inhibit the marine fouling process. The whole biofouling process was studied and microfouling organisms such as marine bacteria and microalgae were included as well as the macrofouling barnacle Balanus improvisus. In total 19 different marine fouling organisms (18 microfoulers and one macrofouler) were included and both the adhesion and growth of the microfoulers were investigated. It was shown that the majority of the peptides inhibited barnacle cyprid settlement via a reversible nontoxic mechanism, with IC50 values as low as 0.5 mu g ml(-1). Six peptides inhibited adhesion and growth of microorganisms. Two of these were particularly active against the microfoulers with MIC-values ranging between 0.01 and 1 mu g ml(-1), which is comparable with the commercial reference antifoulant SeaNine.

Published
2015

13. The Bromotyrosine Derivative Ianthelline Isolated from the Arctic Marine Sponge Stryphnus fortis Inhibits Marine Micro- and Macrobiofouling

Author

Jeanette Hammer Andersen, Espen Hansen, Henrik Pavia, Claire Hellio, Julie Petitbois, Rozenn Trepos, Johan Svenson, Tor Haug, Kine Østnes Hanssen, Gunnar Cervin, The Arctic University of Norway (UiT), University of Gothenburg (GU), School of Biological Sciences, University of Portsmouth, Marbio, University of Tromsø (UiT), Laboratoire des Sciences de l'Environnement Marin (LEMAR) (LEMAR), Institut de Recherche pour le Développement (IRD)-Institut Français de Recherche pour l'Exploitation de la Mer (IFREMER)-Université de Brest (UBO)-Institut Universitaire Européen de la Mer (IUEM), Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), and Research Council of Norway Centre for Marine Chemical Ecology at the University of Gothenburg

Subjects
Biofouling, Mytilus edulis, [SDV]Life Sciences [q-bio], Marine natural product, Sponge metabolite, Microbial Sensitivity Tests, medicine.disease_cause, Applied Microbiology and Biotechnology, Balanus, Microbiology, Minimum inhibitory concentration, Marine bacteriophage, medicine, Microalgae, Animals, 14. Life underwater, Biology, biology, Bacteria, Molecular Structure, Arctic Regions, Monophenol Monooxygenase, ACL, Thoracica, Imidazoles, Adhesiveness, Pathogenic bacteria, Ianthelline, Antifouling, biology.organism_classification, Mytilus, Porifera, Sponge, Bromotyrosine, [SDE]Environmental Sciences, Tyrosine, [SDE.BE]Environmental Sciences/Biodiversity and Ecology, Blue mussel
Abstract

International audience; The inhibition of marine biofouling by the bromotyrosine derivative ianthelline, isolated from the Arctic marine sponge Stryphnus fortis, is described. All major stages of the fouling process are investigated. The effect of ianthelline on adhesion and growth of marine bacteria and microalgae is tested to investigate its influence on the initial microfouling process comparing with the known marine antifoulant barettin as a reference. Macrofouling is studied via barnacle (Balanus improvisus) settlement assays and blue mussel (Mytilus edulis) phenoloxidase inhibition. Ianthelline is shown to inhibit both marine micro-and macrofoulers with a pronounced effect on marine bacteria (minimum inhibitory concentration (MIC) values 0.1-10 mu g/mL) and barnacle larval settlement (IC50= 3.0 mu g/mL). Moderate effects are recorded on M. edulis (IC50= 45.2 mu g/mL) and microalgae, where growth is more affected than surface adhesion. The effect of ianthelline is also investigated against human pathogenic bacteria. Ianthelline displayed low micromolar MIC values against several bacterial strains, both Gram positive and Gram negative, down to 2.5 mu g/mL. In summary, the effect of ianthelline on 20 different representative marine antifouling organisms and seven human pathogenic bacterial strains is presented.

Published
2014

14. ChemInform Abstract: Marine Bacterial Inhibitors from the Sponge-Derived Fungus Aspergillus sp

Author

Wenhan Lin, Victor Wray, Claire Pile, Abdessamad Debbab, Rozenn Trepos, Claire Hellio, Barbara Schulz, Yaming Zhou, Amal H. Aly, and Peter Proksch

Subjects
Aspergillus, Sponge, Marine bacteriophage, biology, Stereochemistry, Chemistry, Alkaloid, Tryptophan, General Medicine, Fungus, Tethya aurantium, biology.organism_classification, Antibacterial activity
Abstract

Chromatographic separation of a crude extract obtained from the fungus Aspergillus sp., isolated from the Mediterranean sponge Tethya aurantium , yielded a new tryptophan derived alkaloid, 3-((1-hydroxy-3-(2-methylbut-3-en-2-yl)-2-oxoindolin-3-yl)methyl)-1-methyl-3,4-dihydrobenzo[ e ][1,4]diazepine-2,5-dione ( 1 ), and a new meroterpenoid, austalide R ( 2 ), together with three known compounds ( 3 – 5 ). The structures of the new compounds were unambiguously elucidated on the basis of extensive one and two-dimensional NMR ( 1 H, 13 C, COSY, HMBC, and ROESY) and mass spectral analysis. Interestingly, the compounds exhibited antibacterial activity when tested against a panel of marine bacteria, with 1 selectively inhibiting Vibrio species and 2 showing a broad spectrum of activity. In contrast, no significant activity was observed against terrestrial bacterial strains and the murine cancer cell line L5178Y.

Published
2014

15. Antifouling compounds from the sub-arctic ascidian Synoicum pulmonaria: synoxazolidinones A and C, pulmonarins A and B, and synthetic analogues

Author

Wenche Stensen, Tor Haug, Claire Hellio, Gunnar Cervin, Rozenn Trepos, Henrik Pavia, Johan Svenson, Klara Stensvåg, John-Sigurd Svendsen, University of Portsmouth, University of Gothenburg (GU), Laboratoire des Sciences de l'Environnement Marin (LEMAR) (LEMAR), Institut de Recherche pour le Développement (IRD)-Institut Français de Recherche pour l'Exploitation de la Mer (IFREMER)-Université de Brest (UBO)-Institut Universitaire Européen de la Mer (IUEM), Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), and The Arctic University of Norway (UiT)

Subjects
Stereochemistry, Biofouling, [SDV]Life Sciences [q-bio], ved/biology.organism_classification_rank.species, Pharmaceutical Science, Marine Biology, Guanidines, Balanus, Analytical Chemistry, Synoxazolidinone C, Sub arctic, FUTURE, Drug Discovery, Botany, Animals, Urochordata, Lower activity, Guanidine, Oxazolidinones, Pharmacology, COATINGS, ENVIRONMENT, biology, Low toxicity, Molecular Structure, ved/biology, AQUACULTURE, SPONGE GEODIA-BARRETTI, ACL, Organic Chemistry, Thoracica, biology.organism_classification, 4-OXAZOLIDINONES, BARNACLE BALANUS-IMPROVISUS, Synoicum pulmonaria, MARINE NATURAL-PRODUCTS, Complementary and alternative medicine, SECONDARY METABOLITES, ALKALOIDS, Mic values, Larva, Molecular Medicine, [SDE.BE]Environmental Sciences/Biodiversity and Ecology, Bromobenzenes
Abstract

International audience; The current study describes the antifouling properties of four members belonging to the recently discovered synoxazolidinone and pulmonarin families, isolated from the sub-Arctic sessile ascidian Synoicum pulmonaria collected off the Norwegian coast. Four simplified synthetic analogues were also prepared and included in the study. Several of the studied compounds displayed MIC values in the micro-nanomolar range against 16 relevant marine species involved in both the micro- and macrofouling process. Settlement studies on Balanus improvisus cyprids indicated a deterrent effect and a low toxicity for selected compounds. The two synoxazolidinones displayed broad activity and are shown to be among the most active natural antifouling bromotyrosine derivatives described. Synoxazolidinone C displayed selected antifouling properties comparable to the commercial antifouling product Sea-Nine-211. The pulmonarins prevented the growth of several bacterial strains at nanomolar concentrations but displayed a lower activity toward microalgae and no effect on barnacles. The linear and cyclic synthetic peptidic mimics also displayed potent antifouling activities mainly directed against bacterial adhesion and growth.

Published
2014

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

Author

Pierre-Eric Campos, Emmanuel Pichon, Céline Moriou, Patricia Clerc, Rozenn Trépos, Michel Frederich, Nicole De Voogd, Claire Hellio, Anne Gauvin-Bialecki, and Ali Al-Mourabit

Subjects
Fascaplysinopsis reticulata, marine sponge, tryptamine alkaloids, antimalarial activity, antimicrobial activity, Biology (General), QH301-705.5
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.

Published
2019
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17. New Antimalarial and Antimicrobial Tryptamine Derivatives from the Marine Sponge Fascaplysinopsis reticulata

Author

Emmanuel Pichon, Rozenn Trepos, Nicole J. de Voogd, Ali Al-Mourabit, Patricia Clerc, Michel Frederich, Claire Hellio, Anne Gauvin-Bialecki, Céline Moriou, Pierre-Eric Campos, Laboratoire de Chimie des Substances Naturelles et des Sciences des Aliments (LCSNSA), Université de La Réunion (UR), Institut de Chimie des Substances Naturelles (ICSN), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire des Sciences de l'Environnement Marin (LEMAR) (LEMAR), Institut de Recherche pour le Développement (IRD)-Institut Français de Recherche pour l'Exploitation de la Mer (IFREMER)-Université de Brest (UBO)-Institut Universitaire Européen de la Mer (IUEM), Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Université de Liège, Naturalis Biodiversity Center [Leiden], ANR-11-EBIM-0006,POMARE,Invertébrés benthiques de Polynésie, Martinique et Réunion : interactions et évaluation de la chimiodiversité pour un usage durable de la biodiversité(2011), European Project: 634674,H2020,H2020-BG-2014-2,TASCMAR(2015), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Institut national des sciences de l'Univers (INSU - CNRS)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS), Institut de Recherche pour le Développement (IRD)-Institut Universitaire Européen de la Mer (IUEM), Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Université de Brest (UBO)-Institut Français de Recherche pour l'Exploitation de la Mer (IFREMER)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS), Laboratory of Pharmacognosy, Université de Liège-Natural and Synthetic Drugs Research Center, and This project was supported by the Regional Council of Reunion Island and the ANR 2011-EBIM-006-01 (ERA-NET Netbiome project POMARE). This publication was also made possible by TASCMAR project which is funded by the European Union under grant agreement number 634674.

Subjects
Tryptamine, Fascaplysinopsis reticulata, Stereochemistry, [SDV]Life Sciences [q-bio], Plasmodium falciparum, Pharmaceutical Science, Marine Biology, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, 01 natural sciences, antimalarial activity, Article, 03 medical and health sciences, chemistry.chemical_compound, Minimum inhibitory concentration, Antimalarials, Inhibitory Concentration 50, Alkaloids, Anti-Infective Agents, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Drug Discovery, [CHIM]Chemical Sciences, Animals, lcsh:QH301-705.5, Pharmacology, Toxicology and Pharmaceutics (miscellaneous), 030304 developmental biology, Vibrio, 0303 health sciences, antimicrobial activity, biology, 010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, ACL, Tryptophan, biology.organism_classification, Antimicrobial, Tryptamines, 0104 chemical sciences, 3. Good health, Porifera, Sponge, lcsh:Biology (General), chemistry, [SDE.BE]Environmental Sciences/Biodiversity and Ecology, Two-dimensional nuclear magnetic resonance spectroscopy, tryptamine alkaloids, marine sponge
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&prime, bis-(debromo)-gelliusine F (1), 6-bromo-8,1&prime, dihydro-isoplysin A (2) and 5,6-dibromo-8,1&prime, 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&prime, demethyl-3&prime, N-methylaplysinopsin (6) and (Z)-6-bromo-2&prime, 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 &micro, g/mL, respectively, towards Vibrio natrigens, and (5), with MIC values of 1 &micro, g/mL towards Vibrio carchariae. In addition the known 8-oxo-tryptamine (4) and the mixture of the (E)-6-bromo-2&prime, N-methylaplysinopsin (7) showed moderate antiplasmodial activity against Plasmodium falciparum with IC50 values of 8.8 and 8.0 &micro, g/mL, respectively.

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