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. 2018 Apr 27;16(5):146.
doi: 10.3390/md16050146.

Bioactive Bromotyrosine-Derived Alkaloids from the Polynesian Sponge Suberea ianthelliformis

Amr El-Demerdash  1   2 , Céline Moriou  3 , Jordan Toullec  4 , Marc Besson  5   6 , Stéphanie Soulet  7 , Nelly Schmitt  8 , Sylvain Petek  9 , David Lecchini  10 , Cécile Debitus  11 , Ali Al-Mourabit  12
Affiliations

Bioactive Bromotyrosine-Derived Alkaloids from the Polynesian Sponge Suberea ianthelliformis

Amr El-Demerdash et al. Mar Drugs. .

Abstract

Herein, we describe the isolation and spectroscopic identification of eight new tetrabrominated tyrosine alkaloids 2⁻9 from the Polynesian sponge Suberea ianthelliformis, along with known major compound psammaplysene D (1), N,N-dimethyldibromotyramine, 5-hydroxy xanthenuric acid, and xanthenuric acid. Cytotoxicity and acetylcholinesterase inhibition activities were evaluated for some of the isolated metabolites. They exhibited moderate antiproliferative activity against KB cancer cell lines, but psammaplysene D (1) displayed substantial cytotoxicity as well as acetylcholinesterase inhibition with IC50 values of 0.7 μM and 1.3 μM, respectively.

Keywords: Suberea ianthelliformis; acetylcholinesterase inhibition; brominated tyrosine alkaloids; cytotoxicity.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structures of isolated compounds 1–12.
Figure 2
Figure 2
COSY and key HMBC correlations for psammaplysenes F (2) and G (3).
Figure 3
Figure 3
COSY and key HMBC correlations for psammaplysenes H (4) and I (5).
Figure 4
Figure 4
COSY and key HMBC correlations for anomoians C (6) and D (7).
Figure 5
Figure 5
COSY and key HMBC correlations for anomoians E (8) and F (9).
Figure 6
Figure 6
Number of bites on coral pieces per A. triostegus recruit and per hour. Error bars represent standard deviation of the mean (N = 6). ** p < 0.01.
Figure 7
Figure 7
(a) AChE activity, U·mg−1, after 1 h exposure to 100 µg/mL of Psammalysene D (1). Boxplot distribution was made with 5 fish (N = 5). * p < 0.05; (b) AChE activity, U·mg−1, after 72 h exposure to 5 µg/mL of crude extract. Boxplot distribution was made with 5 fish (N = 5).
Figure 7
Figure 7
(a) AChE activity, U·mg−1, after 1 h exposure to 100 µg/mL of Psammalysene D (1). Boxplot distribution was made with 5 fish (N = 5). * p < 0.05; (b) AChE activity, U·mg−1, after 72 h exposure to 5 µg/mL of crude extract. Boxplot distribution was made with 5 fish (N = 5).
See this image and copyright information in PMC

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