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Potential of fascaplysin and palauolide from Fascaplysinopsis cf reticulata to reduce the risk of bacterial infection in fish farming ArchiMer
Mai, Tepoerau; Toullec, Jordan; Van Wynsberge, Simon; Besson, Marc; Soulet, Stephanie; Petek, Sylvain; Aliotti, Emmanuelle; Ekins, Merrick; Hall, Kathryn; Erpenbeck, Dirk; Lecchini, David; Beniddir, Mehdi A.; Saulnier, Denis; Debitus, Cecile.
Marine natural products isolated from the sponge Fascaplysinopsis cf reticulata, in French Polynesia, were investigated as an alternative to antibiotics to control pathogens in aquaculture. The overuse of antibiotics in aquaculture is largely considered to be an environmental pollution, because it supports the transfer of antibiotic resistance genes within the aquatic environment. One environmentally friendly alternative to antibiotics is the use of quorum sensing inhibitors (QSIs). Quorum sensing (QS) is a regulatory mechanism in bacteria which control virulence factors through the secretion of autoinducers (AIs), such as acyl-homoserine lactone (AHL) in gram-negative bacteria. Vibrio harveyi QS is controlled through three parallel pathways: HAI-1, AI-2,...
Tipo: Text Palavras-chave: Porifera; Marine natural products; Quorum sensing inhibitors; Antibiotic; Fascaplysinopsis cf reticulata.
Ano: 2019 URL: https://archimer.ifremer.fr/doc/00598/71052/69366.pdf
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Quorum Sensing Inhibitory and Antifouling Activities of New Bromotyrosine Metabolites from the Polynesian Sponge Pseudoceratina n. sp. ArchiMer
Tintillier, Florent; Moriou, Céline; Petek, Sylvain; Fauchon, Marilyne; Hellio, Claire; Saulnier, Denis; Ekins, Merrick; Hooper, John N. A.; Al-mourabit, Ali; Debitus, Cecile.
Four new brominated tyrosine metabolites, aplyzanzines C–F (1–4), were isolated from the French Polynesian sponge Pseudoceratina n. sp., along with the two known 2-aminoimidazolic derivatives, purealidin A (5) and 6, previously isolated, respectively, from the sponges Psammaplysilla purpurea and Verongula sp. Their structures were assigned based on the interpretation of their NMR and HRMS data. The compounds exhibited quorum sensing inhibition (QSi) and antifouling activities against several strains of bacteria and microalgae. To our knowledge, the QSi activity of this type of bromotyrosine metabolite is described here for the first time.
Tipo: Text Palavras-chave: Sponge; Pseudoceratina; Quorum sensing inhibitory activity; Antifouling; Verongiida; Bromotyrosine.
Ano: 2020 URL: https://archimer.ifremer.fr/doc/00630/74200/73825.pdf
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New Sulfur-Containing Polyarsenicals from the New Caledonian Sponge Echinochalina bargibanti ArchiMer
Tahtinen, Petri; Guella, Graziano; Saielli, Giacomo; Debitus, Cecile; Hnawia, Edouard; Mancini, Ines.
Arsenicin A (C3H6As4O3) was isolated from the New Caledonian poecilosclerid sponge Echinochalina bargibanti, and described as the first natural organic polyarsenic compound. Further bioguided fractionation of the extracts of this sponge led us to isolate the first sulfur-containing organic polyarsenicals ever found in Nature. These metabolites, called arsenicin B and arsenicin C, are built on a noradamantane-type framework that is characterized by an unusual As-As bonding. Extensive NMR measurements, in combination with mass spectra, enabled the assignment of the structure for arsenicin B (C3H6As4S2) as 2. The scarcity of arsenicin C and its intrinsic chemical instability only allowed the collection of partial spectral data, which prevented the full...
Tipo: Text Palavras-chave: Antibacterial; Arsenical; Calculated NMR spectrum; Density functional theory; Natural products; NMR spectroscopy; Structure elucidation; Sulfur metabolite.
Ano: 2018 URL: https://archimer.ifremer.fr/doc/00469/58051/72242.pdf
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Bioactive Indole Derivatives from the South Pacific Marine Sponges Rhopaloeides odorabile and Hyrtios sp. ArchiMer
Longeon, Arlette; Copp, Brent R.; Quevrain, Elodie; Roue, Melanie; Kientz, Betty; Cresteil, Thierry; Petek, Sylvain; Debitus, Cecile; Bourguet-kondracki, Marie-lise.
Indole derivatives including bromoindoles have been isolated from the South Pacific marine sponges Rhopaloeides odorabile and Hyrtios sp. Their structures were established through analysis of mass spectra and 1D and 2D NMR spectroscopic data. Their potential inhibitory phospholipase A(2) (PLA(2)), antioxidant and cytotoxic activities were evaluated. The new derivative 5,6-dibromo-L-hypaphorine (9) isolated from Hyrtios sp. revealed a weak bee venom PLA2 inhibition (IC50 0.2 mM) and a significant antioxidant activity with an Oxygen Radical Absorbance Capacity (ORAC) value of 0.22. The sesquiterpene aureol (4), also isolated from Hyrtios sp., showed the most potent antioxidant activity with an ORAC value of 0.29.
Tipo: Text Palavras-chave: Indole derivatives; Bromoindoles; Marine sponge; Rhopaloeides odorabile; Hyrtios sp.; PLA(2) inhibitor; Antioxidant; Cytotoxic.
Ano: 2011 URL: https://archimer.ifremer.fr/doc/00214/32485/30975.pdf
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Marine Natural Occurring 2,5-Diketopiperazines: Isolation, Synthesis and Optical Properties ArchiMer
Laville, Remi; Thanh Binh Nguyen,; Moriou, Celine; Petek, Sylvain; Debitus, Cecile; Al-mourabit, Ali.
Seven 2,5-diketopiperazines (DKPs) were isolated from the Fijian marine sponge Acanthella cavernosa. NMR and circular dichroism (CD) comparison with synthetic L-L DKPs allowed us to determine unambiguously the L-L absolute configuration of the natural DKPs. This work initiated the setting up of an optical properties database of natural DKPs, including specific rotation and CD.
Tipo: Text Palavras-chave: Diketopiperazine; Sponge; Marine Metabolite; Circular Dichroism.
Ano: 2015 URL: https://archimer.ifremer.fr/doc/00667/77944/82136.pdf
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Swinholide J, a Potent Cytotoxin from the Marine Sponge Theonella swinhoei ArchiMer
De Marino, Simona; Festa, Carmen; D'Auria, Maria Valeria; Cresteil, Thierry; Debitus, Cecile; Zampella, Angela.
In our ongoing search for new pharmacologically active leads from Solomon organisms, we have examined the sponge Theonella swinhoei. Herein we report the isolation and structure elucidation of swinholide A (1) and one new macrolide, swinholide J (2). Swinholide J is an unprecedented asymmetric 44-membered dilactone with an epoxide functionality in half of the molecule. The structural determination was based on extensive interpretation of high-field NMR spectra and HRESIMS data. Swinholide J displayed potent in vitro cytotoxicity against KB cells (human nasopharynx cancer) with an IC(50) value of 6 nM.
Tipo: Text Palavras-chave: Marine cytotoxin; Swinholide J; Theonella swinhoei.
Ano: 2011 URL: https://archimer.ifremer.fr/doc/00214/32484/30974.pdf
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Synergistic AML Cell Death Induction by Marine Cytotoxin (+)-1(R), 6(S), 1'(R), 6'(S), 11(R), 17(S)-Fistularin-3 and Bcl-2 Inhibitor Venetoclax ArchiMer
Florean, Cristina; Kim, Kyung Rok; Schnekenburger, Michael; Kim, Hyun-jung; Moriou, Celine; Debitus, Cecile; Dicato, Mario; Al-mourabit, Ali; Han, Byung Woo; Diederich, Marc.
Treatment of acute myeloid leukemia (AML) patients is still hindered by resistance and relapse, resulting in an overall poor survival rate. Recently, combining specific B-cell lymphoma (Bcl)-2 inhibitors with compounds downregulating myeloid cell leukemia (Mcl)-1 has been proposed as a new effective strategy to eradicate resistant AML cells. We show here that 1(R), 6(S), 1'(R), 6'(S), 11(R), 17(S)-fistularin-3, a bromotyrosine compound of the fistularin family, isolated from the marine sponge Suberea clavata, synergizes with Bcl-2 inhibitor ABT-199 to efficiently kill Mcl-1/Bcl-2-positive AML cell lines, associated with Mcl-1 downregulation and endoplasmic reticulum stress induction. The absolute configuration of carbons 11 and 17 of the fistularin-3...
Tipo: Text Palavras-chave: Acute myeloid leukemia; ABT-199; Mcl-1; Bromotyrosine; (+)-11(R); 17(S)-fistularin-3; Configuration; Anticancer drug combination.
Ano: 2018 URL: https://archimer.ifremer.fr/doc/00476/58783/62419.pdf
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Bioactive Bromotyrosine-Derived Alkaloids from the Polynesian Sponge Suberea ianthelliformis ArchiMer
El-demerdash, Amr; Moriou, Celine; Toullec, Jordan; Besson, Marc; Soulet, Stephanie; Schmitt, Nelly; Petek, Sylvain; Lecchini, David; Debitus, Cecile; Al-mourabit, Ali.
Herein, we describe the isolation and spectroscopic identification of eight new tetrabrominated tyrosine alkaloids 2–9 from the Polynesian sponge Suberea ianthelliformis, along with known major compound psammaplysene D (1), N,N-dimethyldibromotyramine, 5-hydroxy xanthenuric acid, and xanthenuric acid. Cytotoxicity and acetylcholinesterase inhibition activities were evaluated for some of the isolated metabolites. They exhibited moderate antiproliferative activity against KB cancer cell lines, but psammaplysene D (1) displayed substantial cytotoxicity as well as acetylcholinesterase inhibition with IC50 values of 0.7 μM and 1.3 μM, respectively.
Tipo: Text Palavras-chave: Brominated tyrosine alkaloids; Suberea ianthelliformis; Cytotoxicity; Acetylcholinesterase inhibition.
Ano: 2018 URL: https://archimer.ifremer.fr/doc/00439/55076/56506.pdf
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Sporochartines A-E, A New Family of Natural Products from the Marine Fungus Hypoxylon monticulosum Isolated from a Sphaerocladina Sponge ArchiMer
Leman-loubiere, Charlotte; Le Goff, Geraldine; Debitus, Cecile; Ouazzani, Jamal.
Four new sporochartines B-E were isolated from the marine fungus Hypoxylon monticulosurn CLL-205, isolated from a sponge belonging to the Sphaerocladina order and collected in Tahiti coast. Sporochartine A (1), the first representative of this family was previously isolated from the same fungus. The structures of sporochartines B-E were elucidated using 1D and 2D NMR, HRMS and IR data. Their configurations were established according to ROE correlations and comparison with the absolute configuration of sporochartine A (1) previously obtained from X-ray analysis. Sporochartines A-D (2-4) may be derived from endo Diels-Alderase type catalysis and sporochartine E (5) from an exo Diels-Alderase catalysis. The spatial conformation of sporochartines drastically...
Tipo: Text Palavras-chave: Hypoxylon; Sphaerocladina; Sporothriolide; Sporochartines; Cytotoxic compounds.
Ano: 2017 URL: https://archimer.ifremer.fr/doc/00602/71415/69899.pdf
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Bioactive Bromotyrosine Derivatives from the Pacific Marine Sponge Suberea clavata (Pulitzer-Finali, 1982) ArchiMer
Moriou, Céline; Lacroix, Damien; Petek, Sylvain; El-demerdash, Amr; Trepos, Rozenn; Leu, Tinihauarii Mareva; Florean, Cristina; Diederich, Marc; Hellio, Claire; Debitus, Cecile; Al-mourabit, Ali.
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...
Tipo: Text Palavras-chave: Sponge; Verongiida; Suberea clavata; Bromotyrosine; Fistularin-3; Acetylcholinesterase inhibition; Antifouling.
Ano: 2021 URL: https://archimer.ifremer.fr/doc/00684/79581/82258.pdf
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