%0 Journal Article
%9 ACL : Articles dans des revues avec comité de lecture répertoriées par l'AERES
%A Moriou, C.
%A Lacroix, D.
%A Petek, Sylvain
%A El-Demerdash, A.
%A Trepos, R.
%A Leu, T. M.
%A Florean, C.
%A Diederich, M.
%A Hellio, C.
%A Debitus, Cécile
%A Al-Mourabit, A.
%T Bioactive bromotyrosine derivatives from the Pacific marine sponge Suberea clavata (Pulitzer-Finali, 1982)
%D 2021
%L fdi:010081163
%G ENG
%J Marine Drugs
%K sponge ; Verongiida ; Suberea clavata ; bromotyrosine ; fistularin-3 ; acetylcholinesterase inhibition ; antifouling
%K PACIFIQUE
%K SALOMON ILES
%M ISI:000633826900001
%N 3
%P 143 [22 ]
%R 10.3390/md19030143
%U https://www.documentation.ird.fr/hor/fdi:010081163
%> https://horizon.documentation.ird.fr/exl-doc/pleins_textes/2021-05/010081163.pdf
%V 19
%W Horizon (IRD)
%X 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.
%$ 035