Thalassosterol, a New Cytotoxic Aromatase Inhibitor Ergosterol Derivative from the Red Sea Seagrass <i>Thalassodendron ciliatum</i>
<i>Thalassodendron ciliatum</i> (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...
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MDPI AG
2020-07-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/18/7/354 |
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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 Bringmann Safwat A. Ahmed Usama Ramadan Abdelmohsen |
| author_facet | 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 Bringmann Safwat A. Ahmed Usama Ramadan Abdelmohsen |
| author_sort | Reda F. A. Abdelhameed |
| collection | DOAJ |
| description | <i>Thalassodendron ciliatum</i> (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 (<b>1</b>) was isolated from the methanolic extract of <i>T. ciliatum</i> growing in the Red Sea, along with two known first-reported sterols, namely ergosterol (<b>2</b>) and stigmasterol (<b>3</b>), 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<sub>50</sub> values of 8.12 and 14.24 µM, respectively. In addition, docking studies on the new sterol <b>1</b> 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 <i>T. ciliatum</i> 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. |
| first_indexed | 2024-03-10T18:36:37Z |
| format | Article |
| id | doaj.art-80fd95c2ea5f44c8a5e93873682c05e2 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-10T18:36:37Z |
| publishDate | 2020-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-80fd95c2ea5f44c8a5e93873682c05e22023-11-20T06:09:50ZengMDPI AGMarine Drugs1660-33972020-07-0118735410.3390/md18070354Thalassosterol, a New Cytotoxic Aromatase Inhibitor Ergosterol Derivative from the Red Sea Seagrass <i>Thalassodendron ciliatum</i>Reda F. A. Abdelhameed0Eman S. Habib1Marwa S. Goda2John Refaat Fahim3Hashem A. Hassanean4Enas E. Eltamany5Amany K. Ibrahim6Asmaa M. AboulMagd7Shaimaa Fayez8Adel M. Abd El-kader9Tarfah Al-Warhi10Gerhard Bringmann11Safwat A. Ahmed12Usama Ramadan Abdelmohsen13Department of Pharmacognosy, Faculty of Pharmacy, Suez Canal University, Ismailia 41522, EgyptDepartment of Pharmacognosy, Faculty of Pharmacy, Suez Canal University, Ismailia 41522, EgyptDepartment of Pharmacognosy, Faculty of Pharmacy, Suez Canal University, Ismailia 41522, EgyptDepartment of Pharmacognosy, Faculty of Pharmacy, Minia University, Minia 61519, EgyptDepartment of Pharmacognosy, Faculty of Pharmacy, Suez Canal University, Ismailia 41522, EgyptDepartment of Pharmacognosy, Faculty of Pharmacy, Suez Canal University, Ismailia 41522, EgyptDepartment of Pharmacognosy, Faculty of Pharmacy, Suez Canal University, Ismailia 41522, EgyptPharmaceutical Chemistry Department, Faculty of Pharmacy, Nahda University, BeniSuef 62513, EgyptInstitute of Organic Chemistry, University of Würzburg, Am Hubland, 97074 Würzburg, GermanyDepartment of Pharmacognosy, Faculty of Pharmacy, Deraya University, New Minia 61111, EgyptDepartment of Chemistry, College of Science, Princess Nourah bint Abdulrahman University, Riyadh 13414, Saudi ArabiaInstitute of Organic Chemistry, University of Würzburg, Am Hubland, 97074 Würzburg, GermanyDepartment of Pharmacognosy, Faculty of Pharmacy, Suez Canal University, Ismailia 41522, EgyptDepartment of Pharmacognosy, Faculty of Pharmacy, Minia University, Minia 61519, Egypt<i>Thalassodendron ciliatum</i> (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 (<b>1</b>) was isolated from the methanolic extract of <i>T. ciliatum</i> growing in the Red Sea, along with two known first-reported sterols, namely ergosterol (<b>2</b>) and stigmasterol (<b>3</b>), 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<sub>50</sub> values of 8.12 and 14.24 µM, respectively. In addition, docking studies on the new sterol <b>1</b> 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 <i>T. ciliatum</i> 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.https://www.mdpi.com/1660-3397/18/7/354cytotoxic activityergosterol derivativemetabolic analysisdocking studiesseagrass<i>Thalassodendron ciliatum</i> |
| spellingShingle | 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 Bringmann Safwat A. Ahmed Usama Ramadan Abdelmohsen Thalassosterol, a New Cytotoxic Aromatase Inhibitor Ergosterol Derivative from the Red Sea Seagrass <i>Thalassodendron ciliatum</i> Marine Drugs cytotoxic activity ergosterol derivative metabolic analysis docking studies seagrass <i>Thalassodendron ciliatum</i> |
| title | Thalassosterol, a New Cytotoxic Aromatase Inhibitor Ergosterol Derivative from the Red Sea Seagrass <i>Thalassodendron ciliatum</i> |
| title_full | Thalassosterol, a New Cytotoxic Aromatase Inhibitor Ergosterol Derivative from the Red Sea Seagrass <i>Thalassodendron ciliatum</i> |
| title_fullStr | Thalassosterol, a New Cytotoxic Aromatase Inhibitor Ergosterol Derivative from the Red Sea Seagrass <i>Thalassodendron ciliatum</i> |
| title_full_unstemmed | Thalassosterol, a New Cytotoxic Aromatase Inhibitor Ergosterol Derivative from the Red Sea Seagrass <i>Thalassodendron ciliatum</i> |
| title_short | Thalassosterol, a New Cytotoxic Aromatase Inhibitor Ergosterol Derivative from the Red Sea Seagrass <i>Thalassodendron ciliatum</i> |
| title_sort | thalassosterol a new cytotoxic aromatase inhibitor ergosterol derivative from the red sea seagrass i thalassodendron ciliatum i |
| topic | cytotoxic activity ergosterol derivative metabolic analysis docking studies seagrass <i>Thalassodendron ciliatum</i> |
| url | https://www.mdpi.com/1660-3397/18/7/354 |
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