Moriou C., Lacroix D., Petek Sylvain, El-Demerdash A., Trepos R., Leu T. M., Florean C., Diederich M., Hellio C., Debitus Cécile, Al-Mourabit A. (2021). Bioactive bromotyrosine derivatives from the Pacific marine sponge Suberea clavata (Pulitzer-Finali, 1982). Marine Drugs, 19 (3), 143 [22 p.].
Titre du document
Bioactive bromotyrosine derivatives from the Pacific marine sponge Suberea clavata (Pulitzer-Finali, 1982)
Année de publication
2021
Auteurs
Moriou C., Lacroix D., Petek Sylvain, El-Demerdash A., Trepos R., Leu T. M., Florean C., Diederich M., Hellio C., Debitus Cécile, Al-Mourabit A.
Source
Marine Drugs, 2021,
19 (3), 143 [22 p.]
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.
Plan de classement
Substances naturelles [035]
Description Géographique
PACIFIQUE
Localisation
Fonds IRD [F B010081163]
Identifiant IRD
fdi:010081163
