4.7 Article

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

期刊

MARINE DRUGS
卷 19, 期 3, 页码 -

出版社

MDPI
DOI: 10.3390/md19030143

关键词

sponge; Verongiida; Suberea clavata; bromotyrosine; fistularin-3; acetylcholinesterase inhibition; antifouling

资金

  1. CNRS
  2. IRD
  3. AFD [CZZ 3012.01 T]

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Chemical investigation of the South-Pacific marine sponge led to the isolation of new bromotyrosine metabolites along with known congeners. Detailed configuration determination and absolute configurations of the compounds were achieved using various techniques. Additionally, evaluation of biological activities such as acetylcholinesterase inhibition and antifouling activities were conducted.
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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