New cytotoxic natural products from the Red Sea sponge Stylissa carteri

Please always quote using this URN: urn:nbn:de:bvb:20-opus-205795
  • Bioactivity-guided isolation supported by LC-HRESIMS metabolic profiling led to the isolation of two new compounds, a ceramide, stylissamide A (1), and a cerebroside, stylissoside A (2), from the methanol extract of the Red Sea sponge Stylissa carteri. Structure elucidation was achieved using spectroscopic techniques, including 1D and 2D NMR and HRMS. The bioactive extract’s metabolomic profiling showed the existence of various secondary metabolites, mainly oleanane-type saponins, phenolic diterpenes, and lupane triterpenes. The in vitroBioactivity-guided isolation supported by LC-HRESIMS metabolic profiling led to the isolation of two new compounds, a ceramide, stylissamide A (1), and a cerebroside, stylissoside A (2), from the methanol extract of the Red Sea sponge Stylissa carteri. Structure elucidation was achieved using spectroscopic techniques, including 1D and 2D NMR and HRMS. The bioactive extract’s metabolomic profiling showed the existence of various secondary metabolites, mainly oleanane-type saponins, phenolic diterpenes, and lupane triterpenes. The in vitro cytotoxic activity of the isolated compounds was tested against two human cancer cell lines, MCF-7 and HepG2. Both compounds, 1 and 2, displayed strong cytotoxicity against the MCF-7 cell line, with IC\(_{50}\) values at 21.1 ± 0.17 µM and 27.5 ± 0.18 µM, respectively. They likewise showed a promising activity against HepG2 with IC\(_{50}\) at 36.8 ± 0.16 µM for 1 and IC\(_{50}\) 30.5 ± 0.23 µM for 2 compared to the standard drug cisplatin. Molecular docking experiments showed that 1 and 2 displayed high affinity to the SET protein and to inhibitor 2 of protein phosphatase 2A (I2PP2A), which could be a possible mechanism for their cytotoxic activity. This paper spreads light on the role of these metabolites in holding fouling organisms away from the outer surface of the sponge, and the potential use of these defensive molecules in the production of novel anticancer agents.show moreshow less

Download full text files

Export metadata

Additional Services

Share in Twitter Search Google Scholar Statistics
Metadaten
Author: Reda F. A. Abdelhameed, Eman S. Habib, Nermeen A. Eltahawy, Hashim A. Hassanean, Amany K. Ibrahim, Anber F. Mohammed, Shaimaa Fayez, Alaa M. Hayallah, Koji Yamada, Fathy A. Behery, Mohammad M. Al-Sanea, Sami I. Alzarea, Gerhard Bringmann, Safwat A. Ahmed, Usama Ramadan Abdelmohsen
URN:urn:nbn:de:bvb:20-opus-205795
Document Type:Journal article
Faculties:Fakultät für Chemie und Pharmazie / Institut für Organische Chemie
Language:English
Parent Title (English):Marine Drugs
ISSN:1660-3397
Year of Completion:2020
Volume:18
Issue:5
Article Number:241
Source:Marine Drugs (2020) 18:5, 241. https://doi.org/10.3390/md18050241
DOI:https://doi.org/10.3390/md18050241
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
6 Technik, Medizin, angewandte Wissenschaften / 61 Medizin und Gesundheit / 615 Pharmakologie, Therapeutik
Tag:LC-HRESIMS; Stylissa carteri; ceramide; cerebroside; cytotoxic activity; docking
Release Date:2022/06/01
Date of first Publication:2020/05/03
Licence (German):License LogoCC BY: Creative-Commons-Lizenz: Namensnennung 4.0 International