New Ceramides and Cerebrosides from the Deep-Sea Far Eastern Starfish <i>Ceramaster patagonicus</i>
Three new ceramides (<b>1</b>–<b>3</b>) and three new cerebrosides (<b>4</b>, <b>8</b>, and <b>9</b>), along with three previously known cerebrosides (ophidiocerebrosides C (<b>5</b>), D (<b>6</b>), and CE-3-2 (<b...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-10-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/20/10/641 |
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| author | Timofey V. Malyarenko Viktor M. Zakharenko Alla A. Kicha Alexandra S. Kuzmich Olesya S. Malyarenko Anatoly I. Kalinovsky Roman S. Popov Vasily I. Svetashev Natalia V. Ivanchina |
| author_facet | Timofey V. Malyarenko Viktor M. Zakharenko Alla A. Kicha Alexandra S. Kuzmich Olesya S. Malyarenko Anatoly I. Kalinovsky Roman S. Popov Vasily I. Svetashev Natalia V. Ivanchina |
| author_sort | Timofey V. Malyarenko |
| collection | DOAJ |
| description | Three new ceramides (<b>1</b>–<b>3</b>) and three new cerebrosides (<b>4</b>, <b>8</b>, and <b>9</b>), along with three previously known cerebrosides (ophidiocerebrosides C (<b>5</b>), D (<b>6</b>), and CE-3-2 (<b>7</b>)), were isolated from a deep-sea starfish species, the orange cookie starfish <i>Ceramaster patagonicus</i>. The structures of <b>1</b>−<b>4,</b> <b>8</b>, and <b>9</b> were determined by the NMR and ESIMS techniques and also through chemical transformations. Ceramides <b>1</b>–<b>3</b> contain <i>iso-</i>C<sub>21</sub> or C<sub>23</sub> Δ<sup>9</sup>-phytosphingosine as a long-chain base and have C<sub>16</sub> or C<sub>17</sub> (2<i>R</i>)-2-hydroxy-fatty acids of the normal type. Cerebroside <b>4</b> contains C<sub>22</sub> Δ<sup>9</sup>-sphingosine <i>anteiso-</i>type as a long-chain base and (2<i>R</i>)-2-hydroxyheptadecanoic acid of the normal type, while compounds <b>8</b> and <b>9</b> contain saturated C-17 phytosphingosine <i>anteiso-</i>type as a long-chain base and differ from each other in the length of the polymethylene chain of (2<i>R</i>)-2-hydroxy-fatty acids of the normal type: C<sub>23</sub> in <b>8</b> and C<sub>24</sub> in <b>9</b>. All the new cerebrosides (<b>4</b>, <b>8</b>, and <b>9</b>) have β-D-glucopyranose as a monosaccharide residue. The composition of neutral sphingolipids from <i>C. patagonicus</i> was described for the first time. The investigated compounds <b>1</b>–<b>3</b>, <b>5</b>–<b>7</b>, and <b>9</b> exhibit slight to moderate cytotoxic activity against human cancer cells (HT-29, SK-MEL-28, and MDA-MB-231) and normal embryonic kidney cells HEK293. Compounds <b>2</b>, <b>5</b>, and <b>6</b> at a concentration of 20 µM inhibit colony formation of MDA-MB-231 cells by 68%, 54%, and 68%, respectively. The colony-inhibiting activity of compounds <b>2</b>, <b>5</b>, and <b>6</b> is comparable to the effect of doxorubicin, which reduces the number of colonies by 70% at the same concentration. |
| first_indexed | 2024-03-09T19:54:15Z |
| format | Article |
| id | doaj.art-942ba32ba11e46afa53985dc90084c22 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-09T19:54:15Z |
| publishDate | 2022-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-942ba32ba11e46afa53985dc90084c222023-11-24T01:01:24ZengMDPI AGMarine Drugs1660-33972022-10-01201064110.3390/md20100641New Ceramides and Cerebrosides from the Deep-Sea Far Eastern Starfish <i>Ceramaster patagonicus</i>Timofey V. Malyarenko0Viktor M. Zakharenko1Alla A. Kicha2Alexandra S. Kuzmich3Olesya S. Malyarenko4Anatoly I. Kalinovsky5Roman S. Popov6Vasily I. Svetashev7Natalia V. Ivanchina8G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch, Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch, Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch, Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch, Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch, Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch, Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch, Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, RussiaA.V. Zhirmunsky National Scientific Center of Marine Biology, Far Eastern Branch, Russian Academy of Sciences, ul. Palchevskogo 17, 690041 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch, Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, RussiaThree new ceramides (<b>1</b>–<b>3</b>) and three new cerebrosides (<b>4</b>, <b>8</b>, and <b>9</b>), along with three previously known cerebrosides (ophidiocerebrosides C (<b>5</b>), D (<b>6</b>), and CE-3-2 (<b>7</b>)), were isolated from a deep-sea starfish species, the orange cookie starfish <i>Ceramaster patagonicus</i>. The structures of <b>1</b>−<b>4,</b> <b>8</b>, and <b>9</b> were determined by the NMR and ESIMS techniques and also through chemical transformations. Ceramides <b>1</b>–<b>3</b> contain <i>iso-</i>C<sub>21</sub> or C<sub>23</sub> Δ<sup>9</sup>-phytosphingosine as a long-chain base and have C<sub>16</sub> or C<sub>17</sub> (2<i>R</i>)-2-hydroxy-fatty acids of the normal type. Cerebroside <b>4</b> contains C<sub>22</sub> Δ<sup>9</sup>-sphingosine <i>anteiso-</i>type as a long-chain base and (2<i>R</i>)-2-hydroxyheptadecanoic acid of the normal type, while compounds <b>8</b> and <b>9</b> contain saturated C-17 phytosphingosine <i>anteiso-</i>type as a long-chain base and differ from each other in the length of the polymethylene chain of (2<i>R</i>)-2-hydroxy-fatty acids of the normal type: C<sub>23</sub> in <b>8</b> and C<sub>24</sub> in <b>9</b>. All the new cerebrosides (<b>4</b>, <b>8</b>, and <b>9</b>) have β-D-glucopyranose as a monosaccharide residue. The composition of neutral sphingolipids from <i>C. patagonicus</i> was described for the first time. The investigated compounds <b>1</b>–<b>3</b>, <b>5</b>–<b>7</b>, and <b>9</b> exhibit slight to moderate cytotoxic activity against human cancer cells (HT-29, SK-MEL-28, and MDA-MB-231) and normal embryonic kidney cells HEK293. Compounds <b>2</b>, <b>5</b>, and <b>6</b> at a concentration of 20 µM inhibit colony formation of MDA-MB-231 cells by 68%, 54%, and 68%, respectively. The colony-inhibiting activity of compounds <b>2</b>, <b>5</b>, and <b>6</b> is comparable to the effect of doxorubicin, which reduces the number of colonies by 70% at the same concentration.https://www.mdpi.com/1660-3397/20/10/641ceramidescerebrosidesNMR spectrafatty acidslong-chain basesstarfish |
| spellingShingle | Timofey V. Malyarenko Viktor M. Zakharenko Alla A. Kicha Alexandra S. Kuzmich Olesya S. Malyarenko Anatoly I. Kalinovsky Roman S. Popov Vasily I. Svetashev Natalia V. Ivanchina New Ceramides and Cerebrosides from the Deep-Sea Far Eastern Starfish <i>Ceramaster patagonicus</i> Marine Drugs ceramides cerebrosides NMR spectra fatty acids long-chain bases starfish |
| title | New Ceramides and Cerebrosides from the Deep-Sea Far Eastern Starfish <i>Ceramaster patagonicus</i> |
| title_full | New Ceramides and Cerebrosides from the Deep-Sea Far Eastern Starfish <i>Ceramaster patagonicus</i> |
| title_fullStr | New Ceramides and Cerebrosides from the Deep-Sea Far Eastern Starfish <i>Ceramaster patagonicus</i> |
| title_full_unstemmed | New Ceramides and Cerebrosides from the Deep-Sea Far Eastern Starfish <i>Ceramaster patagonicus</i> |
| title_short | New Ceramides and Cerebrosides from the Deep-Sea Far Eastern Starfish <i>Ceramaster patagonicus</i> |
| title_sort | new ceramides and cerebrosides from the deep sea far eastern starfish i ceramaster patagonicus i |
| topic | ceramides cerebrosides NMR spectra fatty acids long-chain bases starfish |
| url | https://www.mdpi.com/1660-3397/20/10/641 |
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