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 Mar 27;194:. doi: 10.3390/md19040187.
Show Gene links
Show Anatomy links
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.
Silchenko AS
,
Kalinovsky AI
,
Avilov SA
,
Andrijaschenko PV
,
Popov RS
,
Dmitrenok PS
,
Chingizova EA
,
Kalinin VI
.
???displayArticle.abstract???
Nine new mono-, di-, and trisulfated triterpene penta- and hexaosides, kurilosides A3 (1), D1 (2), G (3), H (4), I (5), I1 (6), J (7), K (8), and K1 (9) and two desulfated derivatives, DS-kuriloside L (10), having a trisaccharide branched chain, and DS-kuriloside M (11), having hexa-nor-lanostane aglycone with a 7(8)-double bond, have been isolated from the Far-Eastern deep-water sea cucumber Thyonidium (=Duasmodactyla) kurilensis (Levin) and their structures were elucidated based on 2D NMR spectroscopy and HR-ESI mass-spectrometry. Five earlier unknown carbohydrate chains and two aglycones (having a 16β,(20S)-dihydroxy-fragment and a 16β-acetoxy,(20S)-hydroxy fragment) were found in these glycosides. All the glycosides 1-9 have a sulfate group at C-6 Glc, attached to C-4 Xyl1, while the positions of the other sulfate groups vary in different groups of kurilosides. The analysis of the structural features of the aglycones and the carbohydrate chains of all the glycosides of T. kurilensis showed their biogenetic relationships. Cytotoxic activities of the compounds 1-9 against mouse neuroblastoma Neuro 2a, normal epithelial JB-6 cells, and erythrocytes were studied. The highest cytotoxicity in the series was demonstrated by trisulfated hexaoside kuriloside H (4), having acetoxy-groups at C(16) and C(20), the latter one obviously compensated the absence of a side chain, essential for the membranolytic action of the glycosides. Kuriloside I1 (6), differing from 4 in the lacking of a terminal glucose residue in the bottom semi-chain, was slightly less active. The compounds 1-3, 5, and 8 did not demonstrate cytotoxic activity due to the presence of hydroxyl groups in their aglycones.
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
Caulier,
When a repellent becomes an attractant: harmful saponins are kairomones attracting the symbiotic Harlequin crab.
2013,
Pubmed
,
Echinobase
Claereboudt,
Triterpenoids in Echinoderms: Fundamental Differences in Diversity and Biosynthetic Pathways.
2019,
Pubmed
,
Echinobase
Cuong,
Cytotoxic triterpene diglycosides from the sea cucumber Stichopus horrens.
2017,
Pubmed
,
Echinobase
Kalinin,
Triterpene glycosides of sea cucumbers (Holothuroidea, Echinodermata) as taxonomic markers.
2015,
Pubmed
,
Echinobase
Kalinin,
Non-holostane aglycones of sea cucumber triterpene glycosides. Structure, biosynthesis, evolution.
2019,
Pubmed
,
Echinobase
Kamyab,
Chemical Defense Mechanisms and Ecological Implications of Indo-Pacific Holothurians.
2020,
Pubmed
,
Echinobase
Kamyab,
Anti-Fouling Effects of Saponin-Containing Crude Extracts from Tropical Indo-Pacific Sea Cucumbers.
2020,
Pubmed
,
Echinobase
Khotimchenko,
Pharmacological Potential of Sea Cucumbers.
2018,
Pubmed
,
Echinobase
Li,
Sea cucumber genome provides insights into saponin biosynthesis and aestivation regulation.
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
Park,
Relationships between chemical structures and functions of triterpene glycosides isolated from sea cucumbers.
2014,
Pubmed
,
Echinobase
Popov,
Metabolite Profiling of Triterpene Glycosides of the Far Eastern Sea Cucumber Eupentacta fraudatrix and Their Distribution in Various Body Components Using LC-ESI QTOF-MS.
2017,
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,
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,
Structure and biological action of cladolosides B1, B2, C, C1, C2 and D, six new triterpene glycosides from the sea cucumber Cladolabes schmeltzii.
2013,
Pubmed
,
Echinobase
Silchenkoa,
Fallaxosides C₁, C₂, D₁ and D₂, Unusual Oligosulfated Triterpene Glycosides from the Sea Cucumber Cucumariafallax (Cucumariidae, Dendrochirotida, Holothurioidea) and Taxonomic Status of this Animal.
2016,
Pubmed
,
Echinobase
Vien,
Triterpene tetraglycosides from the sea cucumber Stichopus horrens.
2018,
Pubmed
,
Echinobase
Zhao,
Saponins from Sea Cucumber and Their Biological Activities.
2018,
Pubmed
,
Echinobase
