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

Type Article
Date 2021-03
Language English
Author(s) Moriou Céline1, Lacroix Damien1, Petek SylvainORCID2, El-Demerdash AmrORCID1, Trepos RozennORCID2, Leu Tinihauarii Mareva3, Florean Cristina4, Diederich MarcORCID5, Hellio ClaireORCID2, Debitus Cecile2, Al-Mourabit Ali1
Affiliation(s) 1 : CNRS, Institut de Chimie des Substances Naturelles, Université Paris-Saclay, F-91190 Gif-sur-Yvette, France
2 : IRD, CNRS, Ifremer, LEMAR, Univ Brest, F-29280 Plouzane, France
3 : IRD, Ifremer, ILM, EIO, Univ de la Polynésie française, F-98713 Papeete, French Polynesia
4 : Laboratoire de Biologie Moléculaire et Cellulaire du Cancer, Hôpital Kirchberg, 9, rue Edward Steichen, L-2540 Luxembourg, Luxembourg
5 : Department of Pharmacy, Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 08826, Korea
Source Marine Drugs (1660-3397) (MDPI AG), 2021-03 , Vol. 19 , N. 3 , P. 143 (22p.)
DOI 10.3390/md19030143
Keyword(s) sponge, Verongiida, Suberea clavata, bromotyrosine, fistularin-3, acetylcholinesterase inhibition, antifouling
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.

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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 (2021). Bioactive Bromotyrosine Derivatives from the Pacific Marine Sponge Suberea clavata (Pulitzer-Finali, 1982). Marine Drugs, 19(3), 143 (22p.). Publisher's official version : https://doi.org/10.3390/md19030143 , Open Access version : https://archimer.ifremer.fr/doc/00684/79581/