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 dept...
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MDPI AG
2021
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Online Access: | https://doi.org/10.3390/md19080449 https://doaj.org/article/0d4781bde71c4b7db2271dcdc5f3e2d1 |
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ftdoajarticles:oai:doaj.org/article:0d4781bde71c4b7db2271dcdc5f3e2d1 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 Alexandra S. Silchenko Anatoly I. Kalinovsky Sergey A. Avilov Pelageya V. Andrijaschenko Roman S. Popov Pavel S. Dmitrenok Ekaterina A. Chingizova Vladimir I. Kalinin 2021-08-01T00:00:00Z https://doi.org/10.3390/md19080449 https://doaj.org/article/0d4781bde71c4b7db2271dcdc5f3e2d1 EN eng MDPI AG https://www.mdpi.com/1660-3397/19/8/449 https://doaj.org/toc/1660-3397 doi:10.3390/md19080449 1660-3397 https://doaj.org/article/0d4781bde71c4b7db2271dcdc5f3e2d1 Marine Drugs, Vol 19, Iss 449, p 449 (2021) Psolus chitonoides triterpene glycosides chitonoidosides sea cucumber cytotoxic activity Biology (General) QH301-705.5 article 2021 ftdoajarticles https://doi.org/10.3390/md19080449 2022-12-30T21:09:56Z 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. Article in Journal/Newspaper Bering Island Directory of Open Access Journals: DOAJ Articles Marine Drugs 19 8 449 |
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Open Polar |
collection |
Directory of Open Access Journals: DOAJ Articles |
op_collection_id |
ftdoajarticles |
language |
English |
topic |
Psolus chitonoides triterpene glycosides chitonoidosides sea cucumber cytotoxic activity Biology (General) QH301-705.5 |
spellingShingle |
Psolus chitonoides triterpene glycosides chitonoidosides sea cucumber cytotoxic activity Biology (General) QH301-705.5 Alexandra S. Silchenko Anatoly I. Kalinovsky Sergey A. Avilov Pelageya V. Andrijaschenko Roman S. Popov Pavel S. Dmitrenok Ekaterina A. Chingizova Vladimir I. Kalinin 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 |
Psolus chitonoides triterpene glycosides chitonoidosides sea cucumber cytotoxic activity Biology (General) QH301-705.5 |
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. |
format |
Article in Journal/Newspaper |
author |
Alexandra S. Silchenko Anatoly I. Kalinovsky Sergey A. Avilov Pelageya V. Andrijaschenko Roman S. Popov Pavel S. Dmitrenok Ekaterina A. Chingizova Vladimir I. Kalinin |
author_facet |
Alexandra S. Silchenko Anatoly I. Kalinovsky Sergey A. Avilov Pelageya V. Andrijaschenko Roman S. Popov Pavel S. Dmitrenok Ekaterina A. Chingizova Vladimir I. Kalinin |
author_sort |
Alexandra S. Silchenko |
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 AG |
publishDate |
2021 |
url |
https://doi.org/10.3390/md19080449 https://doaj.org/article/0d4781bde71c4b7db2271dcdc5f3e2d1 |
genre |
Bering Island |
genre_facet |
Bering Island |
op_source |
Marine Drugs, Vol 19, Iss 449, p 449 (2021) |
op_relation |
https://www.mdpi.com/1660-3397/19/8/449 https://doaj.org/toc/1660-3397 doi:10.3390/md19080449 1660-3397 https://doaj.org/article/0d4781bde71c4b7db2271dcdc5f3e2d1 |
op_doi |
https://doi.org/10.3390/md19080449 |
container_title |
Marine Drugs |
container_volume |
19 |
container_issue |
8 |
container_start_page |
449 |
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1766376246434856960 |