Bioactive Bromotyrosine Derivatives from the Pacific Marine Sponge <i>Suberea clavata</i> (Pulitzer-Finali, 1982)
Céline Moriou,
Damien Lacroix,
Sylvain Petek,
Amr El-Demerdash,
Rozenn Trepos,
Tinihauarii Mareva Leu,
Cristina Florean,
Marc Diederich,
Claire Hellio,
Cécile Debitus,
Ali Al-Mourabit
Affiliations
Céline Moriou
CNRS, Institut de Chimie des Substances Naturelles, Université Paris-Saclay, F-91190 Gif-sur-Yvette, France
Damien Lacroix
CNRS, Institut de Chimie des Substances Naturelles, Université Paris-Saclay, F-91190 Gif-sur-Yvette, France
Sylvain Petek
IRD, CNRS, Ifremer, LEMAR, Univ Brest, F-29280 Plouzane, France
Amr El-Demerdash
CNRS, Institut de Chimie des Substances Naturelles, Université Paris-Saclay, F-91190 Gif-sur-Yvette, France
Rozenn Trepos
IRD, CNRS, Ifremer, LEMAR, Univ Brest, F-29280 Plouzane, France
Tinihauarii Mareva Leu
IRD, Ifremer, ILM, EIO, Univ de la Polynésie française, F-98713 Papeete, French Polynesia
Cristina Florean
Laboratoire de Biologie Moléculaire et Cellulaire du Cancer, Hôpital Kirchberg, 9, rue Edward Steichen, L-2540 Luxembourg, Luxembourg
Marc Diederich
Department of Pharmacy, Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 08826, Korea
Claire Hellio
IRD, CNRS, Ifremer, LEMAR, Univ Brest, F-29280 Plouzane, France
Cécile Debitus
IRD, CNRS, Ifremer, LEMAR, Univ Brest, F-29280 Plouzane, France
Ali Al-Mourabit
CNRS, Institut de Chimie des Substances Naturelles, Université Paris-Saclay, F-91190 Gif-sur-Yvette, France
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.