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| 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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| 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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| Campos, Pierre-eric; Pichon, Emmanuel; Moriou, Céline; Clerc, Patricia; Trépos, Rozenn; Frederich, Michel; De Voogd, Nicole; Hellio, Claire; Gauvin-bialecki, Anne; Al-mourabit, Ali. |
| 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... |
| Tipo: Text |
Palavras-chave: Fascaplysinopsis reticulata; Marine sponge; Tryptamine alkaloids; Antimalarial activity; Antimicrobial activity. |
| Ano: 2019 |
URL: https://archimer.ifremer.fr/doc/00485/59664/62722.pdf |
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| 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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| 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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