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Structures and Bioactivities of Psolusosides B(1), B(2), J, K, L, M, N, O, P, and Q from the Sea Cucumber Psolus fabricii. The First Finding of Tetrasulfated Marine Low Molecular Weight Metabolites
Ten new di-, tri- and tetrasulfated triterpene glycosides, psolusosides B(1) (1), B(2) (2), J (3), K (4), L (5), M (6), N (7), O (8), P (9), and Q (10), were isolated from the sea cucumber Psolus fabricii collected in the Sea of Okhotsk near the Kurile Islands. Structures of these glycosides were es...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6891663/ https://www.ncbi.nlm.nih.gov/pubmed/31698820 http://dx.doi.org/10.3390/md17110631 |
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author | Silchenko, Alexandra S. Kalinovsky, Anatoly I. Avilov, Sergey A. Kalinin, Vladimir I. Andrijaschenko, Pelageya V. Dmitrenok, Pavel S. Popov, Roman S. Chingizova, Ekaterina A. |
author_facet | Silchenko, Alexandra S. Kalinovsky, Anatoly I. Avilov, Sergey A. Kalinin, Vladimir I. Andrijaschenko, Pelageya V. Dmitrenok, Pavel S. Popov, Roman S. Chingizova, Ekaterina A. |
author_sort | Silchenko, Alexandra S. |
collection | PubMed |
description | Ten new di-, tri- and tetrasulfated triterpene glycosides, psolusosides B(1) (1), B(2) (2), J (3), K (4), L (5), M (6), N (7), O (8), P (9), and Q (10), were isolated from the sea cucumber Psolus fabricii 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 9 and 10 contain four sulfate groups in their carbohydrate moieties, including two sulfates in the same terminal glucose residue. Glycoside 2 has an unusual non-holostane aglycone with 18(16)-lactone and a unique 7,8-epoxy fragment. Cytotoxic activities of compounds 1–10 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 (5), pentaoside, with three sulfate groups at C-6 of two glucose and one 3-O-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 (1, 2, 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. |
format | Online Article Text |
id | pubmed-6891663 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-68916632019-12-12 Structures and Bioactivities of Psolusosides B(1), B(2), J, K, L, M, N, O, P, and Q from the Sea Cucumber Psolus fabricii. The First Finding of Tetrasulfated Marine Low Molecular Weight Metabolites Silchenko, Alexandra S. Kalinovsky, Anatoly I. Avilov, Sergey A. Kalinin, Vladimir I. Andrijaschenko, Pelageya V. Dmitrenok, Pavel S. Popov, Roman S. Chingizova, Ekaterina A. Mar Drugs Article Ten new di-, tri- and tetrasulfated triterpene glycosides, psolusosides B(1) (1), B(2) (2), J (3), K (4), L (5), M (6), N (7), O (8), P (9), and Q (10), were isolated from the sea cucumber Psolus fabricii 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 9 and 10 contain four sulfate groups in their carbohydrate moieties, including two sulfates in the same terminal glucose residue. Glycoside 2 has an unusual non-holostane aglycone with 18(16)-lactone and a unique 7,8-epoxy fragment. Cytotoxic activities of compounds 1–10 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 (5), pentaoside, with three sulfate groups at C-6 of two glucose and one 3-O-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 (1, 2, 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. MDPI 2019-11-06 /pmc/articles/PMC6891663/ /pubmed/31698820 http://dx.doi.org/10.3390/md17110631 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Silchenko, Alexandra S. Kalinovsky, Anatoly I. Avilov, Sergey A. Kalinin, Vladimir I. Andrijaschenko, Pelageya V. Dmitrenok, Pavel S. Popov, Roman S. Chingizova, Ekaterina A. Structures and Bioactivities of Psolusosides B(1), B(2), J, K, L, M, N, O, P, and Q from the Sea Cucumber Psolus fabricii. The First Finding of Tetrasulfated Marine Low Molecular Weight Metabolites |
title | Structures and Bioactivities of Psolusosides B(1), B(2), J, K, L, M, N, O, P, and Q from the Sea Cucumber Psolus fabricii. The First Finding of Tetrasulfated Marine Low Molecular Weight Metabolites |
title_full | Structures and Bioactivities of Psolusosides B(1), B(2), J, K, L, M, N, O, P, and Q from the Sea Cucumber Psolus fabricii. The First Finding of Tetrasulfated Marine Low Molecular Weight Metabolites |
title_fullStr | Structures and Bioactivities of Psolusosides B(1), B(2), J, K, L, M, N, O, P, and Q from the Sea Cucumber Psolus fabricii. The First Finding of Tetrasulfated Marine Low Molecular Weight Metabolites |
title_full_unstemmed | Structures and Bioactivities of Psolusosides B(1), B(2), J, K, L, M, N, O, P, and Q from the Sea Cucumber Psolus fabricii. The First Finding of Tetrasulfated Marine Low Molecular Weight Metabolites |
title_short | Structures and Bioactivities of Psolusosides B(1), B(2), J, K, L, M, N, O, P, and Q from the Sea Cucumber Psolus fabricii. The First Finding of Tetrasulfated Marine Low Molecular Weight Metabolites |
title_sort | structures and bioactivities of psolusosides b(1), b(2), j, k, l, m, n, o, p, and q from the sea cucumber psolus fabricii. the first finding of tetrasulfated marine low molecular weight metabolites |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6891663/ https://www.ncbi.nlm.nih.gov/pubmed/31698820 http://dx.doi.org/10.3390/md17110631 |
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