New Conjugates of Polyhydroxysteroids with Long-Chain Fatty Acids from the Deep-Water Far Eastern Starfish <i>Ceramaster patagonicus</i> and Their Anticancer Activity
Four new conjugates, esters of polyhydroxysteroids with long-chain fatty acids (<b>1</b>–<b>4</b>), were isolated from the deep-water Far Eastern starfish <i>Ceramaster patagonicus.</i> The structures of <b>1</b>–<b>4</b> were established b...
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| Format: | Article |
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MDPI AG
2020-05-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/18/5/260 |
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| author | Timofey V. Malyarenko Alla A. Kicha Olesya S. Malyarenko Viktor M. Zakharenko Ivan P. Kotlyarov Anatoly I. Kalinovsky Roman S. Popov Vasily I. Svetashev Natalia V. Ivanchina |
| author_facet | Timofey V. Malyarenko Alla A. Kicha Olesya S. Malyarenko Viktor M. Zakharenko Ivan P. Kotlyarov Anatoly I. Kalinovsky Roman S. Popov Vasily I. Svetashev Natalia V. Ivanchina |
| author_sort | Timofey V. Malyarenko |
| collection | DOAJ |
| description | Four new conjugates, esters of polyhydroxysteroids with long-chain fatty acids (<b>1</b>–<b>4</b>), were isolated from the deep-water Far Eastern starfish <i>Ceramaster patagonicus.</i> The structures of <b>1</b>–<b>4</b> were established by NMR and ESIMS techniques as well as chemical transformations. Unusual compounds <b>1</b>–<b>4</b> contain the same 5α-cholestane-3β,6β,15α,16β,26-pentahydroxysteroidal moiety and differ from each other in the fatty acid units: 5′<i>Z</i>,11′<i>Z</i>-octadecadienoic (<b>1</b>), 11′<i>Z</i>-octadecenoic (<b>2</b>), 5′<i>Z</i>,11′<i>Z</i>-eicosadienoic (<b>3</b>), and 7′<i>Z</i>-eicosenoic (<b>4</b>) acids. Previously, only one such steroid conjugate with a fatty acid was known from starfish. After 72 h of cell incubation, using MTS assay it was found that the concentrations of compounds <b>1</b>, <b>2</b>, and <b>3</b> that caused 50% inhibition of growth (IC<sub>50</sub>) of JB6 Cl41 cells were 81, 40, and 79 µM, respectively; for MDA-MB-231 cells, IC<sub>50</sub> of compounds <b>1</b>, <b>2</b>, and <b>3</b> were 74, 33, and 73 µM, respectively; for HCT 116 cells, IC<sub>50</sub> of compounds <b>1</b>, <b>2</b>, and <b>3</b> were 73, 31, and 71 µM, respectively. Compound <b>4</b> was non-toxic against tested cell lines even in three days of treatment. Compound <b>2</b> (20 µM) suppressed colony formation and migration of MDA-MB-231 and HCT 116 cells. |
| first_indexed | 2024-03-10T19:48:11Z |
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| id | doaj.art-f252ecaa25504c768638f00d12b23ee0 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-10T19:48:11Z |
| publishDate | 2020-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-f252ecaa25504c768638f00d12b23ee02023-11-20T00:38:09ZengMDPI AGMarine Drugs1660-33972020-05-0118526010.3390/md18050260New Conjugates of Polyhydroxysteroids with Long-Chain Fatty Acids from the Deep-Water Far Eastern Starfish <i>Ceramaster patagonicus</i> and Their Anticancer ActivityTimofey V. Malyarenko0Alla A. Kicha1Olesya S. Malyarenko2Viktor M. Zakharenko3Ivan P. Kotlyarov4Anatoly I. Kalinovsky5Roman S. Popov6Vasily I. Svetashev7Natalia V. Ivanchina8G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, Vladivostok 690022, RussiaDepartment of Bioorganic Chemistry and Biotechnology, School of Natural Sciences, Far Eastern Federal University, Sukhanova Str. 8, Vladivostok 690000, RussiaDepartment of Bioorganic Chemistry and Biotechnology, School of Natural Sciences, Far Eastern Federal University, Sukhanova Str. 8, Vladivostok 690000, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, Vladivostok 690022, RussiaA.V. Zhirmunsky National Scientific Center of Marine Biology, Far Eastern Branch of the Russian Academy of Sciences, 17 Palchevsky St., Vladivostok 690041, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, Vladivostok 690022, RussiaFour new conjugates, esters of polyhydroxysteroids with long-chain fatty acids (<b>1</b>–<b>4</b>), were isolated from the deep-water Far Eastern starfish <i>Ceramaster patagonicus.</i> The structures of <b>1</b>–<b>4</b> were established by NMR and ESIMS techniques as well as chemical transformations. Unusual compounds <b>1</b>–<b>4</b> contain the same 5α-cholestane-3β,6β,15α,16β,26-pentahydroxysteroidal moiety and differ from each other in the fatty acid units: 5′<i>Z</i>,11′<i>Z</i>-octadecadienoic (<b>1</b>), 11′<i>Z</i>-octadecenoic (<b>2</b>), 5′<i>Z</i>,11′<i>Z</i>-eicosadienoic (<b>3</b>), and 7′<i>Z</i>-eicosenoic (<b>4</b>) acids. Previously, only one such steroid conjugate with a fatty acid was known from starfish. After 72 h of cell incubation, using MTS assay it was found that the concentrations of compounds <b>1</b>, <b>2</b>, and <b>3</b> that caused 50% inhibition of growth (IC<sub>50</sub>) of JB6 Cl41 cells were 81, 40, and 79 µM, respectively; for MDA-MB-231 cells, IC<sub>50</sub> of compounds <b>1</b>, <b>2</b>, and <b>3</b> were 74, 33, and 73 µM, respectively; for HCT 116 cells, IC<sub>50</sub> of compounds <b>1</b>, <b>2</b>, and <b>3</b> were 73, 31, and 71 µM, respectively. Compound <b>4</b> was non-toxic against tested cell lines even in three days of treatment. Compound <b>2</b> (20 µM) suppressed colony formation and migration of MDA-MB-231 and HCT 116 cells.https://www.mdpi.com/1660-3397/18/5/260polyhydroxysteroidal estersNMR spectrafatty acidsstarfish<i>Ceramaster patagonicus</i>cytostatic activity |
| spellingShingle | Timofey V. Malyarenko Alla A. Kicha Olesya S. Malyarenko Viktor M. Zakharenko Ivan P. Kotlyarov Anatoly I. Kalinovsky Roman S. Popov Vasily I. Svetashev Natalia V. Ivanchina New Conjugates of Polyhydroxysteroids with Long-Chain Fatty Acids from the Deep-Water Far Eastern Starfish <i>Ceramaster patagonicus</i> and Their Anticancer Activity Marine Drugs polyhydroxysteroidal esters NMR spectra fatty acids starfish <i>Ceramaster patagonicus</i> cytostatic activity |
| title | New Conjugates of Polyhydroxysteroids with Long-Chain Fatty Acids from the Deep-Water Far Eastern Starfish <i>Ceramaster patagonicus</i> and Their Anticancer Activity |
| title_full | New Conjugates of Polyhydroxysteroids with Long-Chain Fatty Acids from the Deep-Water Far Eastern Starfish <i>Ceramaster patagonicus</i> and Their Anticancer Activity |
| title_fullStr | New Conjugates of Polyhydroxysteroids with Long-Chain Fatty Acids from the Deep-Water Far Eastern Starfish <i>Ceramaster patagonicus</i> and Their Anticancer Activity |
| title_full_unstemmed | New Conjugates of Polyhydroxysteroids with Long-Chain Fatty Acids from the Deep-Water Far Eastern Starfish <i>Ceramaster patagonicus</i> and Their Anticancer Activity |
| title_short | New Conjugates of Polyhydroxysteroids with Long-Chain Fatty Acids from the Deep-Water Far Eastern Starfish <i>Ceramaster patagonicus</i> and Their Anticancer Activity |
| title_sort | new conjugates of polyhydroxysteroids with long chain fatty acids from the deep water far eastern starfish i ceramaster patagonicus i and their anticancer activity |
| topic | polyhydroxysteroidal esters NMR spectra fatty acids starfish <i>Ceramaster patagonicus</i> cytostatic activity |
| url | https://www.mdpi.com/1660-3397/18/5/260 |
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