Unusual Structures and Cytotoxicities of Chitonoidosides A, A(1), B, C, D, and E, Six Triterpene Glycosides from the Far Eastern Sea Cucumber Psolus chitonoides
Six new triterpene tetra-, penta- and hexaosides, chitonoidosides A (1), A(1) (2), B (3), C (4), D (5), and E (6), containing one or two sulfate groups, have been isolated from the Far-Eastern sea cucumber Psolus chitonoides, collected near Bering Island (Commander Islands) from the depth of 100–150...
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Online Access: | http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8398228/ http://www.ncbi.nlm.nih.gov/pubmed/34436288 https://doi.org/10.3390/md19080449 |
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ftpubmed:oai:pubmedcentral.nih.gov:8398228 2023-05-15T15:42:31+02:00 Unusual Structures and Cytotoxicities of Chitonoidosides A, A(1), B, C, D, and E, Six Triterpene Glycosides from the Far Eastern Sea Cucumber Psolus chitonoides Silchenko, Alexandra S. Kalinovsky, Anatoly I. Avilov, Sergey A. Andrijaschenko, Pelageya V. Popov, Roman S. Dmitrenok, Pavel S. Chingizova, Ekaterina A. Kalinin, Vladimir I. 2021-08-05 http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8398228/ http://www.ncbi.nlm.nih.gov/pubmed/34436288 https://doi.org/10.3390/md19080449 en eng MDPI http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8398228/ http://www.ncbi.nlm.nih.gov/pubmed/34436288 http://dx.doi.org/10.3390/md19080449 © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/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 (https://creativecommons.org/licenses/by/4.0/). CC-BY Mar Drugs Article Text 2021 ftpubmed https://doi.org/10.3390/md19080449 2021-09-05T00:51:41Z Six new triterpene tetra-, penta- and hexaosides, chitonoidosides A (1), A(1) (2), B (3), C (4), D (5), and E (6), containing one or two sulfate groups, have been isolated from the Far-Eastern sea cucumber Psolus chitonoides, collected near Bering Island (Commander Islands) from the depth of 100–150 m. Three of the isolated compounds (1, 3 and 6) are characterized by the unusual aglycone of new type having 18(20)-ether bond and lacking a lactone in contrast with wide spread holostane derivatives. Another unexpected finding is 3-O-methylxylose residue as a terminal unit in the carbohydrate chains of chitonoidosides B (3), C (4), and E (6), which has never been found before in the glycosides from holothurians belonging to the Psolidae family. Moreover, this monosaccharide is sulfated in the compound 4 into unprecedented 3-O-methylxylose 4-O-sulfate residue. Chitonoidoside C (4) is characterized by tetrasaccharide moiety lacking a part of the bottom semi-chain, but having disaccharide fragment attached to C-4 of Xyl1. Such architecture is not common in sea cucumber glycosides. Cytotoxic activities of the compounds 1–5 against mouse and human erythrocytes and human cancer cell lines: adenocarcinoma HeLa, colorectal adenocarcinoma DLD-1, and leukemia promyeloblast HL-60 cells were studied. The cytotoxic effect of chitonoidoside d (5) was the most significant in this series due to the presence of pentasaccharide disulfated sugar chain in combination with holostane aglycone. Surprisingly, the glycosides 1 and 3, comprising the new aglycone without γ-lactone, demonstrated similar activity to the known compounds with holostane aglycones. Chitonoidoside C (4) was less cytotoxic due to the different architecture of the carbohydrate chain compared to the other glycosides and probably due to the presence of a sulfate group at C-4 in 3-O-MeXyl4. Text Bering Island PubMed Central (PMC) Marine Drugs 19 8 449 |
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Article Silchenko, Alexandra S. Kalinovsky, Anatoly I. Avilov, Sergey A. Andrijaschenko, Pelageya V. Popov, Roman S. Dmitrenok, Pavel S. Chingizova, Ekaterina A. Kalinin, Vladimir I. Unusual Structures and Cytotoxicities of Chitonoidosides A, A(1), B, C, D, and E, Six Triterpene Glycosides from the Far Eastern Sea Cucumber Psolus chitonoides |
topic_facet |
Article |
description |
Six new triterpene tetra-, penta- and hexaosides, chitonoidosides A (1), A(1) (2), B (3), C (4), D (5), and E (6), containing one or two sulfate groups, have been isolated from the Far-Eastern sea cucumber Psolus chitonoides, collected near Bering Island (Commander Islands) from the depth of 100–150 m. Three of the isolated compounds (1, 3 and 6) are characterized by the unusual aglycone of new type having 18(20)-ether bond and lacking a lactone in contrast with wide spread holostane derivatives. Another unexpected finding is 3-O-methylxylose residue as a terminal unit in the carbohydrate chains of chitonoidosides B (3), C (4), and E (6), which has never been found before in the glycosides from holothurians belonging to the Psolidae family. Moreover, this monosaccharide is sulfated in the compound 4 into unprecedented 3-O-methylxylose 4-O-sulfate residue. Chitonoidoside C (4) is characterized by tetrasaccharide moiety lacking a part of the bottom semi-chain, but having disaccharide fragment attached to C-4 of Xyl1. Such architecture is not common in sea cucumber glycosides. Cytotoxic activities of the compounds 1–5 against mouse and human erythrocytes and human cancer cell lines: adenocarcinoma HeLa, colorectal adenocarcinoma DLD-1, and leukemia promyeloblast HL-60 cells were studied. The cytotoxic effect of chitonoidoside d (5) was the most significant in this series due to the presence of pentasaccharide disulfated sugar chain in combination with holostane aglycone. Surprisingly, the glycosides 1 and 3, comprising the new aglycone without γ-lactone, demonstrated similar activity to the known compounds with holostane aglycones. Chitonoidoside C (4) was less cytotoxic due to the different architecture of the carbohydrate chain compared to the other glycosides and probably due to the presence of a sulfate group at C-4 in 3-O-MeXyl4. |
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Text |
author |
Silchenko, Alexandra S. Kalinovsky, Anatoly I. Avilov, Sergey A. Andrijaschenko, Pelageya V. Popov, Roman S. Dmitrenok, Pavel S. Chingizova, Ekaterina A. Kalinin, Vladimir I. |
author_facet |
Silchenko, Alexandra S. Kalinovsky, Anatoly I. Avilov, Sergey A. Andrijaschenko, Pelageya V. Popov, Roman S. Dmitrenok, Pavel S. Chingizova, Ekaterina A. Kalinin, Vladimir I. |
author_sort |
Silchenko, Alexandra S. |
title |
Unusual Structures and Cytotoxicities of Chitonoidosides A, A(1), B, C, D, and E, Six Triterpene Glycosides from the Far Eastern Sea Cucumber Psolus chitonoides |
title_short |
Unusual Structures and Cytotoxicities of Chitonoidosides A, A(1), B, C, D, and E, Six Triterpene Glycosides from the Far Eastern Sea Cucumber Psolus chitonoides |
title_full |
Unusual Structures and Cytotoxicities of Chitonoidosides A, A(1), B, C, D, and E, Six Triterpene Glycosides from the Far Eastern Sea Cucumber Psolus chitonoides |
title_fullStr |
Unusual Structures and Cytotoxicities of Chitonoidosides A, A(1), B, C, D, and E, Six Triterpene Glycosides from the Far Eastern Sea Cucumber Psolus chitonoides |
title_full_unstemmed |
Unusual Structures and Cytotoxicities of Chitonoidosides A, A(1), B, C, D, and E, Six Triterpene Glycosides from the Far Eastern Sea Cucumber Psolus chitonoides |
title_sort |
unusual structures and cytotoxicities of chitonoidosides a, a(1), b, c, d, and e, six triterpene glycosides from the far eastern sea cucumber psolus chitonoides |
publisher |
MDPI |
publishDate |
2021 |
url |
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8398228/ http://www.ncbi.nlm.nih.gov/pubmed/34436288 https://doi.org/10.3390/md19080449 |
genre |
Bering Island |
genre_facet |
Bering Island |
op_source |
Mar Drugs |
op_relation |
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8398228/ http://www.ncbi.nlm.nih.gov/pubmed/34436288 http://dx.doi.org/10.3390/md19080449 |
op_rights |
© 2021 by the authors. https://creativecommons.org/licenses/by/4.0/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 (https://creativecommons.org/licenses/by/4.0/). |
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CC-BY |
op_doi |
https://doi.org/10.3390/md19080449 |
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Marine Drugs |
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19 |
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449 |
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