Triterpene Glycosides from the Far Eastern Sea Cucumber Psolus chitonoides : Chemical Structures and Cytotoxicities of Chitonoidosides E 1 , F, G, and H
Four new triterpene disulfated glycosides, chitonoidosides E 1 ( 1 ), F ( 2 ), G ( 3 ), and H ( 4 ), were isolated from the Far-Eastern sea cucumber Psolus chitonoides and collected near Bering Island (Commander Islands) at depths of 100–150 m. Among them there are two hexaosides ( 1 and 3 ), differ...
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MDPI AG
2021
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ftdoajarticles:oai:doaj.org/article:7f92866902d74e16b3a8980617a7961c 2023-05-15T15:42:31+02:00 Triterpene Glycosides from the Far Eastern Sea Cucumber Psolus chitonoides : Chemical Structures and Cytotoxicities of Chitonoidosides E 1 , F, G, and H Alexandra S. Silchenko Anatoly I. Kalinovsky Sergey A. Avilov Pelageya V. Andrijaschenko Roman S. Popov Ekaterina A. Chingizova Vladimir I. Kalinin Pavel S. Dmitrenok 2021-12-01T00:00:00Z https://doi.org/10.3390/md19120696 https://doaj.org/article/7f92866902d74e16b3a8980617a7961c EN eng MDPI AG https://www.mdpi.com/1660-3397/19/12/696 https://doaj.org/toc/1660-3397 doi:10.3390/md19120696 1660-3397 https://doaj.org/article/7f92866902d74e16b3a8980617a7961c Marine Drugs, Vol 19, Iss 696, p 696 (2021) Psolus chitonoides triterpene glycosides chitonoidosides sea cucumber cytotoxic activity Biology (General) QH301-705.5 article 2021 ftdoajarticles https://doi.org/10.3390/md19120696 2022-12-30T19:57:12Z Four new triterpene disulfated glycosides, chitonoidosides E 1 ( 1 ), F ( 2 ), G ( 3 ), and H ( 4 ), were isolated from the Far-Eastern sea cucumber Psolus chitonoides and collected near Bering Island (Commander Islands) at depths of 100–150 m. Among them there are two hexaosides ( 1 and 3 ), differing from each other by the terminal (sixth) sugar residue, one pentaoside ( 4 ) and one tetraoside ( 2 ), characterized by a glycoside architecture of oligosaccharide chains with shortened bottom semi-chains, which is uncommon for sea cucumbers. Some additional distinctive structural features inherent in 1 – 4 were also found: the aglycone of a recently discovered new type, with 18(20)-ether bond and lacking a lactone in chitonoidoside G ( 3 ), glycoside 3- O -methylxylose residue in chitonoidoside E 1 ( 1 ), which is rarely detected in sea cucumbers, and sulfated by uncommon position 4 terminal 3- O -methylglucose in chitonoidosides F ( 2 ) and H ( 4 ). The hemolytic activities of compounds 1 – 4 and chitonoidoside E against human erythrocytes and their cytotoxic action against the human cancer cell lines, adenocarcinoma HeLa, colorectal adenocarcinoma DLD-1, and monocytes THP-1, were studied. The glycoside with hexasaccharide chains ( 1 , 3 and chitonoidoside E) were the most active against erythrocytes. A similar tendency was observed for the cytotoxicity against adenocarcinoma HeLa cells, but the demonstrated effects were moderate. The monocyte THP-1 cell line and erythrocytes were comparably sensitive to the action of the glycosides, but the activity of chitonoidosides E and E 1 ( 1 ) significantly differed from that of 3 in relation to THP-1 cells. A tetraoside with a shortened bottom semi-chain, chitonoidoside F ( 2 ), displayed the weakest membranolytic effect in the series. Article in Journal/Newspaper Bering Island Directory of Open Access Journals: DOAJ Articles Marine Drugs 19 12 696 |
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Open Polar |
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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 Ekaterina A. Chingizova Vladimir I. Kalinin Pavel S. Dmitrenok Triterpene Glycosides from the Far Eastern Sea Cucumber Psolus chitonoides : Chemical Structures and Cytotoxicities of Chitonoidosides E 1 , F, G, and H |
topic_facet |
Psolus chitonoides triterpene glycosides chitonoidosides sea cucumber cytotoxic activity Biology (General) QH301-705.5 |
description |
Four new triterpene disulfated glycosides, chitonoidosides E 1 ( 1 ), F ( 2 ), G ( 3 ), and H ( 4 ), were isolated from the Far-Eastern sea cucumber Psolus chitonoides and collected near Bering Island (Commander Islands) at depths of 100–150 m. Among them there are two hexaosides ( 1 and 3 ), differing from each other by the terminal (sixth) sugar residue, one pentaoside ( 4 ) and one tetraoside ( 2 ), characterized by a glycoside architecture of oligosaccharide chains with shortened bottom semi-chains, which is uncommon for sea cucumbers. Some additional distinctive structural features inherent in 1 – 4 were also found: the aglycone of a recently discovered new type, with 18(20)-ether bond and lacking a lactone in chitonoidoside G ( 3 ), glycoside 3- O -methylxylose residue in chitonoidoside E 1 ( 1 ), which is rarely detected in sea cucumbers, and sulfated by uncommon position 4 terminal 3- O -methylglucose in chitonoidosides F ( 2 ) and H ( 4 ). The hemolytic activities of compounds 1 – 4 and chitonoidoside E against human erythrocytes and their cytotoxic action against the human cancer cell lines, adenocarcinoma HeLa, colorectal adenocarcinoma DLD-1, and monocytes THP-1, were studied. The glycoside with hexasaccharide chains ( 1 , 3 and chitonoidoside E) were the most active against erythrocytes. A similar tendency was observed for the cytotoxicity against adenocarcinoma HeLa cells, but the demonstrated effects were moderate. The monocyte THP-1 cell line and erythrocytes were comparably sensitive to the action of the glycosides, but the activity of chitonoidosides E and E 1 ( 1 ) significantly differed from that of 3 in relation to THP-1 cells. A tetraoside with a shortened bottom semi-chain, chitonoidoside F ( 2 ), displayed the weakest membranolytic effect in the series. |
format |
Article in Journal/Newspaper |
author |
Alexandra S. Silchenko Anatoly I. Kalinovsky Sergey A. Avilov Pelageya V. Andrijaschenko Roman S. Popov Ekaterina A. Chingizova Vladimir I. Kalinin Pavel S. Dmitrenok |
author_facet |
Alexandra S. Silchenko Anatoly I. Kalinovsky Sergey A. Avilov Pelageya V. Andrijaschenko Roman S. Popov Ekaterina A. Chingizova Vladimir I. Kalinin Pavel S. Dmitrenok |
author_sort |
Alexandra S. Silchenko |
title |
Triterpene Glycosides from the Far Eastern Sea Cucumber Psolus chitonoides : Chemical Structures and Cytotoxicities of Chitonoidosides E 1 , F, G, and H |
title_short |
Triterpene Glycosides from the Far Eastern Sea Cucumber Psolus chitonoides : Chemical Structures and Cytotoxicities of Chitonoidosides E 1 , F, G, and H |
title_full |
Triterpene Glycosides from the Far Eastern Sea Cucumber Psolus chitonoides : Chemical Structures and Cytotoxicities of Chitonoidosides E 1 , F, G, and H |
title_fullStr |
Triterpene Glycosides from the Far Eastern Sea Cucumber Psolus chitonoides : Chemical Structures and Cytotoxicities of Chitonoidosides E 1 , F, G, and H |
title_full_unstemmed |
Triterpene Glycosides from the Far Eastern Sea Cucumber Psolus chitonoides : Chemical Structures and Cytotoxicities of Chitonoidosides E 1 , F, G, and H |
title_sort |
triterpene glycosides from the far eastern sea cucumber psolus chitonoides : chemical structures and cytotoxicities of chitonoidosides e 1 , f, g, and h |
publisher |
MDPI AG |
publishDate |
2021 |
url |
https://doi.org/10.3390/md19120696 https://doaj.org/article/7f92866902d74e16b3a8980617a7961c |
genre |
Bering Island |
genre_facet |
Bering Island |
op_source |
Marine Drugs, Vol 19, Iss 696, p 696 (2021) |
op_relation |
https://www.mdpi.com/1660-3397/19/12/696 https://doaj.org/toc/1660-3397 doi:10.3390/md19120696 1660-3397 https://doaj.org/article/7f92866902d74e16b3a8980617a7961c |
op_doi |
https://doi.org/10.3390/md19120696 |
container_title |
Marine Drugs |
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19 |
container_issue |
12 |
container_start_page |
696 |
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1766376245834022912 |