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Open AccessArticle

Cytotoxic Psammaplysin Analogues from the Verongid Red Sea Sponge Aplysinella Species

by Lamiaa A. Shaala 1,2,3,* and Diaa T. A. Youssef 4,5,*
1
Natural Products Unit, King Fahd Medical Research Center, King Abdulaziz University, Jeddah 21589, Saudi Arabia
2
Department of Medical Laboratory Technology, Faculty of Applied Medical Sciences, King Abdulaziz University, Jeddah 21589, Saudi Arabia
3
Suez Canal University Hospital, Suez Canal University, Ismailia 41522, Egypt
4
Department of Natural Products, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Saudi Arabia
5
Department of Pharmacognosy, Faculty of Pharmacy, Suez Canal University, Ismailia 41522, Egypt
*
Authors to whom correspondence should be addressed.
Biomolecules 2019, 9(12), 841; https://doi.org/10.3390/biom9120841
Received: 6 November 2019 / Revised: 4 December 2019 / Accepted: 6 December 2019 / Published: 8 December 2019
(This article belongs to the Special Issue Marine-Derived Biomolecules)
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 14 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. View Full-Text
Keywords: Order Verongiida; Red Sea sponges; Aplysinella species; bromotyrosine-derived metabolites; psammaplysin A; psammaplysin E; psammaplysin Z and 19-hydroxypsammaplysin Z; cytotoxicity; human cancer cell lines Order Verongiida; Red Sea sponges; Aplysinella species; bromotyrosine-derived metabolites; psammaplysin A; psammaplysin E; psammaplysin Z and 19-hydroxypsammaplysin Z; cytotoxicity; human cancer cell lines
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Shaala, L.A.; Youssef, D.T.A. Cytotoxic Psammaplysin Analogues from the Verongid Red Sea Sponge Aplysinella Species. Biomolecules 2019, 9, 841.

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