Structures and Bioactivities of Psolusosides B<sub>1</sub>, B<sub>2</sub>, J, K, L, M, N, O, P, and Q from the Sea Cucumber <i>Psolus fabricii</i>. The First Finding of Tetrasulfated Marine Low Molecular Weight Metabolites
Ten new di-, tri- and tetrasulfated triterpene glycosides, psolusosides B<sub>1</sub> (<b>1</b>), B<sub>2</sub> (<b>2</b>), J (<b>3</b>), K (<b>4</b>), L (<b>5</b>), M (<b>6</b>), N (<b>7</b>)...
| Main Authors: | , , , , , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2019-11-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/17/11/631 |
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| author | Alexandra S. Silchenko Anatoly I. Kalinovsky Sergey A. Avilov Vladimir I. Kalinin Pelageya V. Andrijaschenko Pavel S. Dmitrenok Roman S. Popov Ekaterina A. Chingizova |
| author_facet | Alexandra S. Silchenko Anatoly I. Kalinovsky Sergey A. Avilov Vladimir I. Kalinin Pelageya V. Andrijaschenko Pavel S. Dmitrenok Roman S. Popov Ekaterina A. Chingizova |
| author_sort | Alexandra S. Silchenko |
| collection | DOAJ |
| description | Ten new di-, tri- and tetrasulfated triterpene glycosides, psolusosides B<sub>1</sub> (<b>1</b>), B<sub>2</sub> (<b>2</b>), J (<b>3</b>), K (<b>4</b>), L (<b>5</b>), M (<b>6</b>), N (<b>7</b>), O (<b>8</b>), P (<b>9</b>), and Q (<b>10</b>), were isolated from the sea cucumber <i>Psolus fabricii </i>collected in the Sea of Okhotsk near the Kurile Islands. Structures of these glycosides were established by two-dimensional (2D) NMR spectroscopy and HR-ESI mass-spectrometry. It is particularly interesting that highly polar compounds <b>9</b> and <b>10</b> contain four sulfate groups in their carbohydrate moieties, including two sulfates in the same terminal glucose residue. Glycoside <b>2</b> has an unusual non-holostane aglycone with 18(16)-lactone and a unique 7,8-epoxy fragment. Cytotoxic activities of compounds <b>1</b>−<b>10</b> against several mouse cell lines such as Ehrlich ascites carcinoma cells, neuroblastoma Neuro 2A, normal epithelial JB-6 cells, and erythrocytes were quite different depending both on structural peculiarities of these glycosides and the type of cells subjected to their actions. Psolusoside L (<b>5</b>), pentaoside, with three sulfate groups at C-6 of two glucose and one 3-<i>O</i>-methylglucose residue and holostane aglycone, is the most active compound in the series. The presence of a sulfate group at C-2 of the terminal glucose residue attached to C-4 of the first (xylose) residue significantly decreases activities of the corresponding glycosides. Psolusosides of group B (<b>1</b>, <b>2</b><b>,</b><b> </b>and known psolusoside B) are inactive in all tests due to the presence of non-holostane aglycones and tetrasaccharide-branched sugar chains sulfated by C-2 of Glc4. |
| first_indexed | 2024-04-11T13:58:29Z |
| format | Article |
| id | doaj.art-c192e389c76f44439e5d1005d0d75f85 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-04-11T13:58:29Z |
| publishDate | 2019-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-c192e389c76f44439e5d1005d0d75f852022-12-22T04:20:12ZengMDPI AGMarine Drugs1660-33972019-11-01171163110.3390/md17110631md17110631Structures and Bioactivities of Psolusosides B<sub>1</sub>, B<sub>2</sub>, J, K, L, M, N, O, P, and Q from the Sea Cucumber <i>Psolus fabricii</i>. The First Finding of Tetrasulfated Marine Low Molecular Weight MetabolitesAlexandra S. Silchenko0Anatoly I. Kalinovsky1Sergey A. Avilov2Vladimir I. Kalinin3Pelageya V. Andrijaschenko4Pavel S. Dmitrenok5Roman S. Popov6Ekaterina A. Chingizova7G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, 690022 Vladivostok, RussiaTen new di-, tri- and tetrasulfated triterpene glycosides, psolusosides B<sub>1</sub> (<b>1</b>), B<sub>2</sub> (<b>2</b>), J (<b>3</b>), K (<b>4</b>), L (<b>5</b>), M (<b>6</b>), N (<b>7</b>), O (<b>8</b>), P (<b>9</b>), and Q (<b>10</b>), were isolated from the sea cucumber <i>Psolus fabricii </i>collected in the Sea of Okhotsk near the Kurile Islands. Structures of these glycosides were established by two-dimensional (2D) NMR spectroscopy and HR-ESI mass-spectrometry. It is particularly interesting that highly polar compounds <b>9</b> and <b>10</b> contain four sulfate groups in their carbohydrate moieties, including two sulfates in the same terminal glucose residue. Glycoside <b>2</b> has an unusual non-holostane aglycone with 18(16)-lactone and a unique 7,8-epoxy fragment. Cytotoxic activities of compounds <b>1</b>−<b>10</b> against several mouse cell lines such as Ehrlich ascites carcinoma cells, neuroblastoma Neuro 2A, normal epithelial JB-6 cells, and erythrocytes were quite different depending both on structural peculiarities of these glycosides and the type of cells subjected to their actions. Psolusoside L (<b>5</b>), pentaoside, with three sulfate groups at C-6 of two glucose and one 3-<i>O</i>-methylglucose residue and holostane aglycone, is the most active compound in the series. The presence of a sulfate group at C-2 of the terminal glucose residue attached to C-4 of the first (xylose) residue significantly decreases activities of the corresponding glycosides. Psolusosides of group B (<b>1</b>, <b>2</b><b>,</b><b> </b>and known psolusoside B) are inactive in all tests due to the presence of non-holostane aglycones and tetrasaccharide-branched sugar chains sulfated by C-2 of Glc4.https://www.mdpi.com/1660-3397/17/11/631psolus fabriciitriterpene glycosidespsolusosidessea cucumbercytotoxic activity |
| spellingShingle | Alexandra S. Silchenko Anatoly I. Kalinovsky Sergey A. Avilov Vladimir I. Kalinin Pelageya V. Andrijaschenko Pavel S. Dmitrenok Roman S. Popov Ekaterina A. Chingizova Structures and Bioactivities of Psolusosides B<sub>1</sub>, B<sub>2</sub>, J, K, L, M, N, O, P, and Q from the Sea Cucumber <i>Psolus fabricii</i>. The First Finding of Tetrasulfated Marine Low Molecular Weight Metabolites Marine Drugs psolus fabricii triterpene glycosides psolusosides sea cucumber cytotoxic activity |
| title | Structures and Bioactivities of Psolusosides B<sub>1</sub>, B<sub>2</sub>, J, K, L, M, N, O, P, and Q from the Sea Cucumber <i>Psolus fabricii</i>. The First Finding of Tetrasulfated Marine Low Molecular Weight Metabolites |
| title_full | Structures and Bioactivities of Psolusosides B<sub>1</sub>, B<sub>2</sub>, J, K, L, M, N, O, P, and Q from the Sea Cucumber <i>Psolus fabricii</i>. The First Finding of Tetrasulfated Marine Low Molecular Weight Metabolites |
| title_fullStr | Structures and Bioactivities of Psolusosides B<sub>1</sub>, B<sub>2</sub>, J, K, L, M, N, O, P, and Q from the Sea Cucumber <i>Psolus fabricii</i>. The First Finding of Tetrasulfated Marine Low Molecular Weight Metabolites |
| title_full_unstemmed | Structures and Bioactivities of Psolusosides B<sub>1</sub>, B<sub>2</sub>, J, K, L, M, N, O, P, and Q from the Sea Cucumber <i>Psolus fabricii</i>. The First Finding of Tetrasulfated Marine Low Molecular Weight Metabolites |
| title_short | Structures and Bioactivities of Psolusosides B<sub>1</sub>, B<sub>2</sub>, J, K, L, M, N, O, P, and Q from the Sea Cucumber <i>Psolus fabricii</i>. The First Finding of Tetrasulfated Marine Low Molecular Weight Metabolites |
| title_sort | structures and bioactivities of psolusosides b sub 1 sub b sub 2 sub j k l m n o p and q from the sea cucumber i psolus fabricii i the first finding of tetrasulfated marine low molecular weight metabolites |
| topic | psolus fabricii triterpene glycosides psolusosides sea cucumber cytotoxic activity |
| url | https://www.mdpi.com/1660-3397/17/11/631 |
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