Click
here to close Hello! We notice that
you are using Internet Explorer, which is not supported by Echinobase
and may cause the site to display incorrectly. We suggest using a
current version of Chrome,
FireFox,
or Safari.
Mar Drugs
2021 Aug 05;198:. doi: 10.3390/md19080449.
Show Gene links
Show Anatomy links
Unusual Structures and Cytotoxicities of Chitonoidosides A, A1, B, C, D, and E, Six Triterpene Glycosides from the Far Eastern Sea Cucumber Psolus chitonoides.
Silchenko AS
,
Kalinovsky AI
,
Avilov SA
,
Andrijaschenko PV
,
Popov RS
,
Dmitrenok PS
,
Chingizova EA
,
Kalinin VI
.
???displayArticle.abstract???
Six new triterpene tetra-, penta- and hexaosides, chitonoidosides A (1), A1 (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.
Aminin,
Glycosides from edible sea cucumbers stimulate macrophages via purinergic receptors.
2016, Pubmed,
Echinobase
Aminin,
Glycosides from edible sea cucumbers stimulate macrophages via purinergic receptors.
2016,
Pubmed
,
Echinobase
Avilov,
Triterpene glycosides from the far eastern sea cucumber Pentamera calcigera II: disulfated glycosides.
2000,
Pubmed
,
Echinobase
Avilov,
Triterpene glycosides from the Far-Eastern sea cucumber Pentamera calcigera. 1. Monosulfated glycosides and cytotoxicity of their unsulfated derivatives.
2000,
Pubmed
,
Echinobase
Careaga,
Patagonicosides B and C, two antifungal sulfated triterpene glycosides from the sea cucumber Psolus patagonicus.
2011,
Pubmed
,
Echinobase
Dyshlovoy,
The marine triterpene glycoside frondoside A induces p53-independent apoptosis and inhibits autophagy in urothelial carcinoma cells.
2017,
Pubmed
,
Echinobase
Kalinin,
Non-holostane aglycones of sea cucumber triterpene glycosides. Structure, biosynthesis, evolution.
2019,
Pubmed
,
Echinobase
Kalinin,
Structure of eximisoside A, a novel triterpene glycoside from the Far-Eastern sea cucumber psolus eximius.
1997,
Pubmed
,
Echinobase
Khotimchenko,
Pharmacological Potential of Sea Cucumbers.
2018,
Pubmed
,
Echinobase
Maltsev,
Triterpene glycosides from sea cucumber Stichopus japonicus Selenka.
1984,
Pubmed
,
Echinobase
Menchinskaya,
Modulation of Doxorubicin Intracellular Accumulation and Anticancer Activity by Triterpene Glycoside Cucumarioside A2-2.
2019,
Pubmed
,
Echinobase
Silchenko,
Structures and Bioactivities of Psolusosides B1, B2, 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.
2019,
Pubmed
,
Echinobase
Silchenko,
Triterpene Glycosides from the Far Eastern Sea Cucumber Thyonidium (=Duasmodactyla) kurilensis (Levin): The Structures, Cytotoxicities, and Biogenesis of Kurilosides A3, D1, G, H, I, I1, J, K, and K1.
2021,
Pubmed
,
Echinobase
Silchenko,
Triterpene glycosides from the deep-water North-Pacific sea cucumber Synallactes nozawai Mitsukuri.
2002,
Pubmed
,
Echinobase
Silchenko,
Structures and Bioactivities of Six New Triterpene Glycosides, Psolusosides E, F, G, H, H1, and I and the Corrected Structure of Psolusoside B from the Sea Cucumber Psolus fabricii.
2019,
Pubmed
,
Echinobase
Silchenko,
Kurilosides A1, A2, C1, D, E and F-Triterpene Glycosides from the Far Eastern Sea Cucumber Thyonidium (= Duasmodactyla) kurilensis (Levin): Structures with Unusual Non-Holostane Aglycones and Cytotoxicities.
2020,
Pubmed
,
Echinobase
Silchenko,
Cladolosides I1, I2, J1, K1, K2 and L1, monosulfated triterpene glycosides with new carbohydrate chains from the sea cucumber Cladolabes schmeltzii.
2017,
Pubmed
,
Echinobase
Zhao,
Saponins from Sea Cucumber and Their Biological Activities.
2018,
Pubmed
,
Echinobase
