Structures and Bioactivities of Six New Triterpene Glycosides, Psolusosides E, F, G, H, H<sub>1</sub>, and I and the Corrected Structure of Psolusoside B from the Sea Cucumber <i>Psolus fabricii</i>
Seven sulfated triterpene glycosides, psolusosides B (<b>1</b>), E (<b>2</b>), F (<b>3</b>), G (<b>4</b>), H (<b>5</b>), H<sub>1</sub> (<b>6</b>), and I (<b>7</b>), along with earlier known psolusoside A...
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| Format: | Article |
| Language: | English |
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MDPI AG
2019-06-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/17/6/358 |
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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 Svetlana P. Ermakova Olesya S. Malyarenko |
| 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 Svetlana P. Ermakova Olesya S. Malyarenko |
| author_sort | Alexandra S. Silchenko |
| collection | DOAJ |
| description | Seven sulfated triterpene glycosides, psolusosides B (<b>1</b>), E (<b>2</b>), F (<b>3</b>), G (<b>4</b>), H (<b>5</b>), H<sub>1</sub> (<b>6</b>), and I (<b>7</b>), along with earlier known psolusoside A and colochiroside D have been isolated from the sea cucumber <i>Psolus fabricii</i> collected in the Sea of Okhotsk. Herein, the structure of psolusoside B (<b>1</b>), elucidated by us in 1989 as a monosulfated tetraoside, has been revised with application of modern NMR and particularly MS data and proved to be a disulfated tetraoside. The structures of other glycosides were elucidated by 2D NMR spectroscopy and HR-ESI mass-spectrometry. Psolusosides E (<b>2</b>), F (<b>3</b>), and G (<b>4</b>) contain holostane aglycones identical to each other and differ in their sugar compositions and the quantity and position of sulfate groups in linear tetrasaccharide carbohydrate moieties. Psolusosides H (<b>5</b>) and H<sub>1</sub> (<b>6</b>) are characterized by an unusual sulfated trisaccharide carbohydrate moiety with the glucose as the second sugar unit. Psolusoside I (<b>7</b>) has an unprecedented branched tetrasaccharide disulfated carbohydrate moiety with the xylose unit in the second position of the chain. The cytotoxic activities of the compounds <b>2</b>−<b>7</b> against several mouse cell lines—ascite form of Ehrlich carcinoma, neuroblastoma Neuro 2A, normal epithelial JB-6 cells, and erythrocytes—were quite different, at that hemolytic effects of the tested compounds were higher than their cytotoxicity against other cells, especially against the ascites of Ehrlich carcinoma. Interestingly, psolusoside G (<b>4</b>) was not cytotoxic against normal JB-6 cells but demonstrated high activity against Neuro 2A cells. The cytotoxic activity against human colorectal adenocarcinoma HT-29 cells and the influence on the colony formation and growth of HT-29 cells of compounds <b>1</b>−<b>3</b>, <b>5</b>−<b>7</b> and psolusoside A was checked. The highest inhibitory activities were demonstrated by psolusosides E (<b>2</b>) and F (<b>3</b>). |
| first_indexed | 2024-04-13T08:53:52Z |
| format | Article |
| id | doaj.art-f2effd91516b4777a2df1878057a51eb |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-04-13T08:53:52Z |
| publishDate | 2019-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-f2effd91516b4777a2df1878057a51eb2022-12-22T02:53:23ZengMDPI AGMarine Drugs1660-33972019-06-0117635810.3390/md17060358md17060358Structures and Bioactivities of Six New Triterpene Glycosides, Psolusosides E, F, G, H, H<sub>1</sub>, and I and the Corrected Structure of Psolusoside B from the Sea Cucumber <i>Psolus fabricii</i>Alexandra S. Silchenko0Anatoly I. Kalinovsky1Sergey A. Avilov2Vladimir I. Kalinin3Pelageya V. Andrijaschenko4Pavel S. Dmitrenok5Roman S. Popov6Ekaterina A. Chingizova7Svetlana P. Ermakova8Olesya S. Malyarenko9G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, Vladivostok 690022, RussiaSeven sulfated triterpene glycosides, psolusosides B (<b>1</b>), E (<b>2</b>), F (<b>3</b>), G (<b>4</b>), H (<b>5</b>), H<sub>1</sub> (<b>6</b>), and I (<b>7</b>), along with earlier known psolusoside A and colochiroside D have been isolated from the sea cucumber <i>Psolus fabricii</i> collected in the Sea of Okhotsk. Herein, the structure of psolusoside B (<b>1</b>), elucidated by us in 1989 as a monosulfated tetraoside, has been revised with application of modern NMR and particularly MS data and proved to be a disulfated tetraoside. The structures of other glycosides were elucidated by 2D NMR spectroscopy and HR-ESI mass-spectrometry. Psolusosides E (<b>2</b>), F (<b>3</b>), and G (<b>4</b>) contain holostane aglycones identical to each other and differ in their sugar compositions and the quantity and position of sulfate groups in linear tetrasaccharide carbohydrate moieties. Psolusosides H (<b>5</b>) and H<sub>1</sub> (<b>6</b>) are characterized by an unusual sulfated trisaccharide carbohydrate moiety with the glucose as the second sugar unit. Psolusoside I (<b>7</b>) has an unprecedented branched tetrasaccharide disulfated carbohydrate moiety with the xylose unit in the second position of the chain. The cytotoxic activities of the compounds <b>2</b>−<b>7</b> against several mouse cell lines—ascite form of Ehrlich carcinoma, neuroblastoma Neuro 2A, normal epithelial JB-6 cells, and erythrocytes—were quite different, at that hemolytic effects of the tested compounds were higher than their cytotoxicity against other cells, especially against the ascites of Ehrlich carcinoma. Interestingly, psolusoside G (<b>4</b>) was not cytotoxic against normal JB-6 cells but demonstrated high activity against Neuro 2A cells. The cytotoxic activity against human colorectal adenocarcinoma HT-29 cells and the influence on the colony formation and growth of HT-29 cells of compounds <b>1</b>−<b>3</b>, <b>5</b>−<b>7</b> and psolusoside A was checked. The highest inhibitory activities were demonstrated by psolusosides E (<b>2</b>) and F (<b>3</b>).https://www.mdpi.com/1660-3397/17/6/358<i>Psolus fabricii</i>triterpene 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 Svetlana P. Ermakova Olesya S. Malyarenko Structures and Bioactivities of Six New Triterpene Glycosides, Psolusosides E, F, G, H, H<sub>1</sub>, and I and the Corrected Structure of Psolusoside B from the Sea Cucumber <i>Psolus fabricii</i> Marine Drugs <i>Psolus fabricii</i> triterpene glycosides psolusosides sea cucumber cytotoxic activity |
| title | Structures and Bioactivities of Six New Triterpene Glycosides, Psolusosides E, F, G, H, H<sub>1</sub>, and I and the Corrected Structure of Psolusoside B from the Sea Cucumber <i>Psolus fabricii</i> |
| title_full | Structures and Bioactivities of Six New Triterpene Glycosides, Psolusosides E, F, G, H, H<sub>1</sub>, and I and the Corrected Structure of Psolusoside B from the Sea Cucumber <i>Psolus fabricii</i> |
| title_fullStr | Structures and Bioactivities of Six New Triterpene Glycosides, Psolusosides E, F, G, H, H<sub>1</sub>, and I and the Corrected Structure of Psolusoside B from the Sea Cucumber <i>Psolus fabricii</i> |
| title_full_unstemmed | Structures and Bioactivities of Six New Triterpene Glycosides, Psolusosides E, F, G, H, H<sub>1</sub>, and I and the Corrected Structure of Psolusoside B from the Sea Cucumber <i>Psolus fabricii</i> |
| title_short | Structures and Bioactivities of Six New Triterpene Glycosides, Psolusosides E, F, G, H, H<sub>1</sub>, and I and the Corrected Structure of Psolusoside B from the Sea Cucumber <i>Psolus fabricii</i> |
| title_sort | structures and bioactivities of six new triterpene glycosides psolusosides e f g h h sub 1 sub and i and the corrected structure of psolusoside b from the sea cucumber i psolus fabricii i |
| topic | <i>Psolus fabricii</i> triterpene glycosides psolusosides sea cucumber cytotoxic activity |
| url | https://www.mdpi.com/1660-3397/17/6/358 |
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