Thalassosterol, a New Cytotoxic Aromatase Inhibitor Ergosterol Derivative from the Red Sea Seagrass Thalassodendron ciliatum

Please always quote using this URN: urn:nbn:de:bvb:20-opus-236085
  • Thalassodendron ciliatum (Forssk.) Den Hartog is a seagrass belonging to the plant family Cymodoceaceae with ubiquitous phytoconstituents and important pharmacological potential, including antioxidant, antiviral, and cytotoxic activities. In this work, a new ergosterol derivative named thalassosterol (1) was isolated from the methanolic extract of T. ciliatum growing in the Red Sea, along with two known first-reported sterols, namely ergosterol (2) and stigmasterol (3), using different chromatographic techniques. The structure of the newThalassodendron ciliatum (Forssk.) Den Hartog is a seagrass belonging to the plant family Cymodoceaceae with ubiquitous phytoconstituents and important pharmacological potential, including antioxidant, antiviral, and cytotoxic activities. In this work, a new ergosterol derivative named thalassosterol (1) was isolated from the methanolic extract of T. ciliatum growing in the Red Sea, along with two known first-reported sterols, namely ergosterol (2) and stigmasterol (3), using different chromatographic techniques. The structure of the new compound was established based on 1D and 2D NMR spectroscopy and high-resolution mass spectrometry (HR-MS) and by comparison with the literature data. The new ergosterol derivative showed significant in vitro antiproliferative potential against the human cervical cancer cell line (HeLa) and human breast cancer (MCF-7) cell lines, with IC\(_{50}\) values of 8.12 and 14.24 µM, respectively. In addition, docking studies on the new sterol 1 explained the possible binding interactions with an aromatase enzyme; this inhibition is beneficial in both cervical and breast cancer therapy. A metabolic analysis of the crude extract of T. ciliatum using liquid chromatography combined with high-resolution electrospray ionization mass spectrometry (LC-ESI-HR-MS) revealed the presence of an array of phenolic compounds, sterols and ceramides, as well as di- and triglycerides.show moreshow less

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Author: Reda F. A. Abdelhameed, Eman S. Habib, Marwa S. Goda, John Refaat Fahim, Hashem A. Hassanean, Enas E. Eltamany, Amany K. Ibrahim, Asmaa M. AboulMagd, Shaimaa Fayez, Adel M. Abd El-kader, Tarfah Al-Warhi, Gerhard BringmannORCiD, Safwat A. Ahmed, Usama Ramadan Abdelmohsen
URN:urn:nbn:de:bvb:20-opus-236085
Document Type:Journal article
Faculties:Fakultät für Chemie und Pharmazie / Institut für Organische Chemie
Language:English
Parent Title (English):Marine Drugs
Year of Completion:2020
Volume:18
Issue:7
Article Number:354
Source:Marine Drugs 2020, 18(7), 354; https://doi.org/10.3390/md18070354
DOI:https://doi.org/10.3390/md18070354
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Tag:Thalassodendron ciliatum; cytotoxic activity; docking studies; ergosterol derivative; metabolic analysis; seagrass
Release Date:2021/05/10
Collections:Open-Access-Publikationsfonds / Förderzeitraum 2020
Licence (German):License LogoCC BY: Creative-Commons-Lizenz: Namensnennung 4.0 International