Phytoceramides from the Marine Sponge <i>Monanchora clathrata</i>: Structural Analysis and Cytoprotective Effects
In our research on sphingolipids from marine invertebrates, a mixture of phytoceramides was isolated from the sponge <i>Monanchora clathrata</i> (Western Australia). Total ceramide, ceramide molecular species (obtained by RP-HPLC, high-performance liquid chromatography on reversed-phase...
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| Format: | Article |
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MDPI AG
2023-04-01
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| Series: | Biomolecules |
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| Online Access: | https://www.mdpi.com/2218-273X/13/4/677 |
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| author | Elena A. Santalova Alexandra S. Kuzmich Ekaterina A. Chingizova Ekaterina S. Menchinskaya Evgeny A. Pislyagin Pavel S. Dmitrenok |
| author_facet | Elena A. Santalova Alexandra S. Kuzmich Ekaterina A. Chingizova Ekaterina S. Menchinskaya Evgeny A. Pislyagin Pavel S. Dmitrenok |
| author_sort | Elena A. Santalova |
| collection | DOAJ |
| description | In our research on sphingolipids from marine invertebrates, a mixture of phytoceramides was isolated from the sponge <i>Monanchora clathrata</i> (Western Australia). Total ceramide, ceramide molecular species (obtained by RP-HPLC, high-performance liquid chromatography on reversed-phase column) and their sphingoid/fatty acid components were analyzed by NMR (nuclear magnetic resonance) spectroscopy and mass spectrometry. Sixteen new (<b>1b</b>, <b>3a</b>, <b>3c</b>, <b>3d</b>, <b>3f</b>, <b>3g</b>, <b>5c</b>, <b>5d</b>, <b>5f</b>, <b>5g</b>, <b>6b</b>–<b>g</b>) and twelve known (<b>2b</b>, <b>2e</b>, <b>2f</b>, <b>3b</b>, <b>3e</b>, <b>4a</b>–<b>c</b>, <b>4e</b>, <b>4f</b>, <b>5b</b>, <b>5e</b>) compounds were shown to contain phytosphingosine-type backbones <i>i</i>-t17:0 (<b>1</b>), <i>n</i>-t17:0 (<b>2</b>), <i>i</i>-t18:0 (<b>3</b>), <i>n</i>-t18:0 (<b>4</b>), <i>i</i>-t19:0 (<b>5</b>), or <i>ai</i>-t19:0 (<b>6</b>), <i>N</i>-acylated with saturated (2<i>R</i>)-2-hydroxy C<sub>21</sub> (<b>a</b>), C<sub>22</sub> (<b>b</b>), C<sub>23</sub> (<b>c</b>), <i>i-</i>C<sub>23</sub> (<b>d</b>), C<sub>24</sub> (<b>e</b>), C<sub>25</sub> (<b>f</b>), or C<sub>26</sub> (<b>g</b>) acids. The used combination of the instrumental and chemical methods permitted the more detailed investigation of the sponge ceramides than previously reported. It was found that the cytotoxic effect of crambescidin 359 (alkaloid from <i>M. clathrata</i>) and cisplatin decreased after pre-incubation of MDA-MB-231 and HL-60 cells with the investigated phytoceramides. In an in vitro paraquat model of Parkinson’s disease, the phytoceramides decreased the neurodegenerative effect and ROS (reactive oxygen species) formation induced by paraquat in neuroblastoma cells. In general, the preliminary treatment (for 24 or 48 h) of the cells with the phytoceramides of <i>M. clathrata</i> was necessary for their cytoprotective functions, otherwise the additive damaging effect of these sphingolipids and cytotoxic compounds (crambescidin 359, cisplatin or paraquat) was observed. |
| first_indexed | 2024-03-11T05:12:03Z |
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| institution | Directory Open Access Journal |
| issn | 2218-273X |
| language | English |
| last_indexed | 2024-03-11T05:12:03Z |
| publishDate | 2023-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Biomolecules |
| spelling | doaj.art-77e4b743acfe41a08d5e81089b3b165a2023-11-17T18:29:46ZengMDPI AGBiomolecules2218-273X2023-04-0113467710.3390/biom13040677Phytoceramides from the Marine Sponge <i>Monanchora clathrata</i>: Structural Analysis and Cytoprotective EffectsElena A. Santalova0Alexandra S. Kuzmich1Ekaterina A. Chingizova2Ekaterina S. Menchinskaya3Evgeny A. Pislyagin4Pavel S. Dmitrenok5G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, RussiaIn our research on sphingolipids from marine invertebrates, a mixture of phytoceramides was isolated from the sponge <i>Monanchora clathrata</i> (Western Australia). Total ceramide, ceramide molecular species (obtained by RP-HPLC, high-performance liquid chromatography on reversed-phase column) and their sphingoid/fatty acid components were analyzed by NMR (nuclear magnetic resonance) spectroscopy and mass spectrometry. Sixteen new (<b>1b</b>, <b>3a</b>, <b>3c</b>, <b>3d</b>, <b>3f</b>, <b>3g</b>, <b>5c</b>, <b>5d</b>, <b>5f</b>, <b>5g</b>, <b>6b</b>–<b>g</b>) and twelve known (<b>2b</b>, <b>2e</b>, <b>2f</b>, <b>3b</b>, <b>3e</b>, <b>4a</b>–<b>c</b>, <b>4e</b>, <b>4f</b>, <b>5b</b>, <b>5e</b>) compounds were shown to contain phytosphingosine-type backbones <i>i</i>-t17:0 (<b>1</b>), <i>n</i>-t17:0 (<b>2</b>), <i>i</i>-t18:0 (<b>3</b>), <i>n</i>-t18:0 (<b>4</b>), <i>i</i>-t19:0 (<b>5</b>), or <i>ai</i>-t19:0 (<b>6</b>), <i>N</i>-acylated with saturated (2<i>R</i>)-2-hydroxy C<sub>21</sub> (<b>a</b>), C<sub>22</sub> (<b>b</b>), C<sub>23</sub> (<b>c</b>), <i>i-</i>C<sub>23</sub> (<b>d</b>), C<sub>24</sub> (<b>e</b>), C<sub>25</sub> (<b>f</b>), or C<sub>26</sub> (<b>g</b>) acids. The used combination of the instrumental and chemical methods permitted the more detailed investigation of the sponge ceramides than previously reported. It was found that the cytotoxic effect of crambescidin 359 (alkaloid from <i>M. clathrata</i>) and cisplatin decreased after pre-incubation of MDA-MB-231 and HL-60 cells with the investigated phytoceramides. In an in vitro paraquat model of Parkinson’s disease, the phytoceramides decreased the neurodegenerative effect and ROS (reactive oxygen species) formation induced by paraquat in neuroblastoma cells. In general, the preliminary treatment (for 24 or 48 h) of the cells with the phytoceramides of <i>M. clathrata</i> was necessary for their cytoprotective functions, otherwise the additive damaging effect of these sphingolipids and cytotoxic compounds (crambescidin 359, cisplatin or paraquat) was observed.https://www.mdpi.com/2218-273X/13/4/677phytoceramidesstructural analysisNMRESI-MSsponge<i>Monanchora clathrata</i> |
| spellingShingle | Elena A. Santalova Alexandra S. Kuzmich Ekaterina A. Chingizova Ekaterina S. Menchinskaya Evgeny A. Pislyagin Pavel S. Dmitrenok Phytoceramides from the Marine Sponge <i>Monanchora clathrata</i>: Structural Analysis and Cytoprotective Effects Biomolecules phytoceramides structural analysis NMR ESI-MS sponge <i>Monanchora clathrata</i> |
| title | Phytoceramides from the Marine Sponge <i>Monanchora clathrata</i>: Structural Analysis and Cytoprotective Effects |
| title_full | Phytoceramides from the Marine Sponge <i>Monanchora clathrata</i>: Structural Analysis and Cytoprotective Effects |
| title_fullStr | Phytoceramides from the Marine Sponge <i>Monanchora clathrata</i>: Structural Analysis and Cytoprotective Effects |
| title_full_unstemmed | Phytoceramides from the Marine Sponge <i>Monanchora clathrata</i>: Structural Analysis and Cytoprotective Effects |
| title_short | Phytoceramides from the Marine Sponge <i>Monanchora clathrata</i>: Structural Analysis and Cytoprotective Effects |
| title_sort | phytoceramides from the marine sponge i monanchora clathrata i structural analysis and cytoprotective effects |
| topic | phytoceramides structural analysis NMR ESI-MS sponge <i>Monanchora clathrata</i> |
| url | https://www.mdpi.com/2218-273X/13/4/677 |
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