Abstract
As part of our ongoing interest to identify bioactive chemical entities from marine invertebrates, the Red Sea specimen of the Verongid sponge Aplysinella species was studied. Repeated chromatographic fractionation of the methanolic extract of the sponge and HPLC purification of the cytotoxic fractions led to the isolation and the identification of two new compounds, psammaplysin Z and 19-hydroxypsammaplysin Z (1 and 2), together with the previously reported psammaplysins A (3) and E (4). The structural determination of 1–4 was supported by interpretation of their NMR and high-resolution mass spectra. Psammaplysins A and E displayed cytotoxic activity against MBA-MB-231 and HeLa cell lines with IC50 values down to 0.29 µM. On the other hand, psammaplysin Z and 19-hydroxypsammaplysin Z were moderately cytotoxic, indicating the importance of the terminal amine and 2-(methylene)cyclopent-4-ene-1,3-dione moieties in 3 and 4 for potent cytotoxic activity.
Highlights
Marine invertebrates are considered as an excellent source of biologically active biomolecules.Marine sponges, phylum Porifera, represent an attractive subject for chemists and pharmacologists, who target marine-derived biomolecules
Members of the order Verongiida are characterized by production of brominated compounds that are biosynthesized from bromotyrosine [1]
As a part of our ongoing work on the Red Sea Verongiid sponges [15], we investigated the cytotoxic extracts of the sponge Aplysinella species
Summary
Marine invertebrates are considered as an excellent source of biologically active biomolecules.Marine sponges, phylum Porifera, represent an attractive subject for chemists and pharmacologists, who target marine-derived biomolecules. Members of the order Verongiida are characterized by production of brominated compounds that are biosynthesized from bromotyrosine [1]. Compounds possessing the rare dibrominated 1,6-dioxa-2-azaspiro[4.6]undeca-2,7,9-triene moiety (spirooxepinisoxazoline) are derived from bromotyrosine and are named psammaplysins [2,3,4,5,6,7,8,9,10], ceratinamides [9,11] and ceratinadins [12]. Compounds with the spirooxepinisoxazoline moiety were reported mainly from members of the Verongiida [2,3,4,5,6,7,8,9,10,12] with only two representatives from the order Dictyoceratida [11,13]. Psammaplysins’ backbone consists of two dibrominated subunits, 8,10-dibromo-4-hydroxy-9-methoxy-1,6-dioxa-2-azaspiro[4.6]undeca-2,7,9-triene-3-carboxylic acid (subunit A) and 3-(4-(2-aminoethyl)-2,6-dibromophenoxy)propan-1-amine subunit (subunit B, moloka’iamine) [14], connected together through an amidic linkage between the carboxylic moiety
Sign-in/Register to view highlights & summary Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
