Bioactive Steroids from the Red Sea Soft Coral <i>Sinularia polydactyla</i>
Six new (<b>1</b>, <b>2</b>, <b>6</b>, <b>8</b>, <b>13,</b> and <b>20</b>) and twenty previously isolated (<b>3</b>–<b>5</b>, <b>7</b>, <b>9</b>–<b>12</b>, <b>14&...
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| Format: | Article |
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MDPI AG
2020-12-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/18/12/632 |
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| author | Mohamed A. Tammam Lucie Rárová Marie Kvasnicová Gabriel Gonzalez Ahmed M. Emam Aldoushy Mahdy Miroslav Strnad Efstathia Ioannou Vassilios Roussis |
| author_facet | Mohamed A. Tammam Lucie Rárová Marie Kvasnicová Gabriel Gonzalez Ahmed M. Emam Aldoushy Mahdy Miroslav Strnad Efstathia Ioannou Vassilios Roussis |
| author_sort | Mohamed A. Tammam |
| collection | DOAJ |
| description | Six new (<b>1</b>, <b>2</b>, <b>6</b>, <b>8</b>, <b>13,</b> and <b>20</b>) and twenty previously isolated (<b>3</b>–<b>5</b>, <b>7</b>, <b>9</b>–<b>12</b>, <b>14</b>–<b>19</b>, and <b>21</b>–<b>26</b>) steroids featuring thirteen different carbocycle motifs were isolated from the organic extract of the soft coral <i>Sinularia polydactyla</i> collected from the Hurghada reef in the Red Sea. The structures and the relative configurations of the isolated natural products have been determined based on extensive analysis of their NMR and MS data. The cytotoxic, anti-inflammatory, anti-angiogenic, and neuroprotective activity of compounds <b>3</b>–<b>7</b>, <b>9</b>–<b>12</b>, <b>14</b>–<b>20</b>, and <b>22</b>–<b>26</b>, as well as their effect on androgen receptor-regulated transcription was evaluated in vitro in human tumor and non-cancerous cells. Steroids <b>22</b> and <b>23</b> showed significant cytotoxicity in the low micromolar range against the HeLa and MCF7 cancer cell lines, while migration of endothelial cells was inhibited by compounds <b>11</b>, <b>12</b>, <b>22,</b> and <b>23</b> at 20 µM. The results of the androgen receptor (AR) reporter assay showed that compound <b>11</b> exhibited the strongest inhibition of AR at 10 µM, while it is noteworthy that steroids <b>10</b>, <b>16,</b> and <b>20</b> displayed increased inhibition of AR with decreasing concentrations. Additionally, compounds <b>11</b> and <b>23</b> showed neuroprotective activity on neuron-like SH-SY5Y cells. |
| first_indexed | 2024-03-10T14:09:38Z |
| format | Article |
| id | doaj.art-502c5988787d4ac1af682ef9c9cfe69d |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-10T14:09:38Z |
| publishDate | 2020-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-502c5988787d4ac1af682ef9c9cfe69d2023-11-21T00:16:44ZengMDPI AGMarine Drugs1660-33972020-12-01181263210.3390/md18120632Bioactive Steroids from the Red Sea Soft Coral <i>Sinularia polydactyla</i>Mohamed A. Tammam0Lucie Rárová1Marie Kvasnicová2Gabriel Gonzalez3Ahmed M. Emam4Aldoushy Mahdy5Miroslav Strnad6Efstathia Ioannou7Vassilios Roussis8Section of Pharmacognosy and Chemistry of Natural Products, Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis Zografou, 15771 Athens, GreeceLaboratory of Growth Regulators, Institute of Experimental Botany, The Czech Academy of Sciences, Faculty of Science, Palacký University, Šlechtitelů 27, CZ-78371 Olomouc, Czech RepublicLaboratory of Growth Regulators, Institute of Experimental Botany, The Czech Academy of Sciences, Faculty of Science, Palacký University, Šlechtitelů 27, CZ-78371 Olomouc, Czech RepublicLaboratory of Growth Regulators, Institute of Experimental Botany, The Czech Academy of Sciences, Faculty of Science, Palacký University, Šlechtitelů 27, CZ-78371 Olomouc, Czech RepublicDepartment of Biochemistry, Faculty of Agriculture, Fayoum University, Fayoum 63514, EgyptDepartment of Zoology, Faculty of Science, Al-Azhar University (Assiut Branch), Assiut 71524, EgyptLaboratory of Growth Regulators, Institute of Experimental Botany, The Czech Academy of Sciences, Faculty of Science, Palacký University, Šlechtitelů 27, CZ-78371 Olomouc, Czech RepublicSection of Pharmacognosy and Chemistry of Natural Products, Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis Zografou, 15771 Athens, GreeceSection of Pharmacognosy and Chemistry of Natural Products, Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis Zografou, 15771 Athens, GreeceSix new (<b>1</b>, <b>2</b>, <b>6</b>, <b>8</b>, <b>13,</b> and <b>20</b>) and twenty previously isolated (<b>3</b>–<b>5</b>, <b>7</b>, <b>9</b>–<b>12</b>, <b>14</b>–<b>19</b>, and <b>21</b>–<b>26</b>) steroids featuring thirteen different carbocycle motifs were isolated from the organic extract of the soft coral <i>Sinularia polydactyla</i> collected from the Hurghada reef in the Red Sea. The structures and the relative configurations of the isolated natural products have been determined based on extensive analysis of their NMR and MS data. The cytotoxic, anti-inflammatory, anti-angiogenic, and neuroprotective activity of compounds <b>3</b>–<b>7</b>, <b>9</b>–<b>12</b>, <b>14</b>–<b>20</b>, and <b>22</b>–<b>26</b>, as well as their effect on androgen receptor-regulated transcription was evaluated in vitro in human tumor and non-cancerous cells. Steroids <b>22</b> and <b>23</b> showed significant cytotoxicity in the low micromolar range against the HeLa and MCF7 cancer cell lines, while migration of endothelial cells was inhibited by compounds <b>11</b>, <b>12</b>, <b>22,</b> and <b>23</b> at 20 µM. The results of the androgen receptor (AR) reporter assay showed that compound <b>11</b> exhibited the strongest inhibition of AR at 10 µM, while it is noteworthy that steroids <b>10</b>, <b>16,</b> and <b>20</b> displayed increased inhibition of AR with decreasing concentrations. Additionally, compounds <b>11</b> and <b>23</b> showed neuroprotective activity on neuron-like SH-SY5Y cells.https://www.mdpi.com/1660-3397/18/12/632<i>Sinularia polydactyla</i>soft coralsteroidscytotoxicanti-inflammatoryneuroprotective |
| spellingShingle | Mohamed A. Tammam Lucie Rárová Marie Kvasnicová Gabriel Gonzalez Ahmed M. Emam Aldoushy Mahdy Miroslav Strnad Efstathia Ioannou Vassilios Roussis Bioactive Steroids from the Red Sea Soft Coral <i>Sinularia polydactyla</i> Marine Drugs <i>Sinularia polydactyla</i> soft coral steroids cytotoxic anti-inflammatory neuroprotective |
| title | Bioactive Steroids from the Red Sea Soft Coral <i>Sinularia polydactyla</i> |
| title_full | Bioactive Steroids from the Red Sea Soft Coral <i>Sinularia polydactyla</i> |
| title_fullStr | Bioactive Steroids from the Red Sea Soft Coral <i>Sinularia polydactyla</i> |
| title_full_unstemmed | Bioactive Steroids from the Red Sea Soft Coral <i>Sinularia polydactyla</i> |
| title_short | Bioactive Steroids from the Red Sea Soft Coral <i>Sinularia polydactyla</i> |
| title_sort | bioactive steroids from the red sea soft coral i sinularia polydactyla i |
| topic | <i>Sinularia polydactyla</i> soft coral steroids cytotoxic anti-inflammatory neuroprotective |
| url | https://www.mdpi.com/1660-3397/18/12/632 |
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