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.
Molecules
2022 Nov 07;2721:. doi: 10.3390/molecules27217655.
Show Gene links
Show Anatomy links
The Isolation, Structure Elucidation and Bioactivity Study of Chilensosides A, A1, B, C, and D, Holostane Triterpene Di-, Tri- and Tetrasulfated Pentaosides from the Sea Cucumber Paracaudina chilensis (Caudinidae, Molpadida).
Silchenko AS
,
Avilov SA
,
Andrijaschenko PV
,
Popov RS
,
Chingizova EA
,
Grebnev BB
,
Rasin AB
,
Kalinin VI
.
???displayArticle.abstract???
Five new triterpene (4,4,14-trimethylsterol) di-, tri- and tetrasulfated pentaosides, chilensosides A (1), A1 (2), B (3), C (4), and D (5) were isolated from the Far-Eastern sea cucumber Paracaudina chilensis. The structures were established on the basis of extensive analysis of 1D and 2D NMR spectra and confirmed by HR-ESI-MS data. The structural variability of the glycosides concerned the pentasaccharide chains. Their architecture was characterized by the upper semi-chain consisting of three sugar units and the bottom semi-chain of two sugars. Carbohydrate chains of compounds 2-5 differed in the quantity and positions of sulfate groups. The interesting structural features of the glycosides were: the presence of two sulfate groups at C-4 and C-6 of the same glucose residue in the upper semi-chain of 1, 2, 4, and 5 and the sulfation at C-3 of terminal glucose residue in the bottom semi-chain of 4 that makes its further elongation impossible. Chilensoside D (5) was the sixth tetrasulfated glycoside found in sea cucumbers. The architecture of the sugar chains of chilensosides A-D (1-5), the positions of sulfation, the quantity of sulfate groups, as well as the aglycone structures, demonstrate their similarity to the glycosides of the representatives of the order Dendrochirotida, confirming the phylogenetic closeness of the orders Molpadida and Dendrochirotida. The cytotoxic activities of the compounds 1-5 against human erythrocytes and some cancer cell lines are presented. Disulfated chilensosides A1 (2) and B (3) and trisulfated chilensoside C (4) showed significant cytotoxic activity against human cancer cells.
Bahrami,
Distribution of Saponins in the Sea Cucumber Holothuria lessoni; the Body Wall Versus the Viscera, and Their Biological Activities.
2018, Pubmed,
Echinobase
Bahrami,
Distribution of Saponins in the Sea Cucumber Holothuria lessoni; the Body Wall Versus the Viscera, and Their Biological Activities.
2018,
Pubmed
,
Echinobase
Bondoc,
Chemical fingerprinting and phylogenetic mapping of saponin congeners from three tropical holothurian sea cucumbers.
2013,
Pubmed
,
Echinobase
Byrne,
Molecular taxonomy, phylogeny and evolution in the family Stichopodidae (Aspidochirotida: Holothuroidea) based on COI and 16S mitochondrial DNA.
2010,
Pubmed
,
Echinobase
Claereboudt,
Triterpenoids in Echinoderms: Fundamental Differences in Diversity and Biosynthetic Pathways.
2019,
Pubmed
,
Echinobase
Elyakov,
Glycosides of marine invertebrates. III. Biosynthesis of stichoposides from acetate.
1975,
Pubmed
Honey-Escandón,
Biological and taxonomic perspective of triterpenoid glycosides of sea cucumbers of the family Holothuriidae (Echinodermata, Holothuroidea).
2015,
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
Kerr,
In vivo and in vitro biosynthesis of saponins in sea cucumbers.
1995,
Pubmed
,
Echinobase
Khotimchenko,
Pharmacological Potential of Sea Cucumbers.
2018,
Pubmed
,
Echinobase
Kim,
Triterpene glycosides from sea cucumbers and their biological activities.
2012,
Pubmed
,
Echinobase
Li,
Sea cucumber genome provides insights into saponin biosynthesis and aestivation regulation.
2018,
Pubmed
,
Echinobase
Makarieva,
Biosynthetic studies of marine lipids. 42. Biosynthesis of steroid and triterpenoid metabolites in the sea cucumber Eupentacta fraudatrix.
1993,
Pubmed
,
Echinobase
Miller,
Molecular phylogeny of extant Holothuroidea (Echinodermata).
2017,
Pubmed
,
Echinobase
Mitu,
Evidence for a Saponin Biosynthesis Pathway in the Body Wall of the Commercially Significant Sea Cucumber Holothuria scabra.
2017,
Pubmed
,
Echinobase
Mondol,
Sea Cucumber Glycosides: Chemical Structures, Producing Species and Important Biological Properties.
2017,
Pubmed
,
Echinobase
Park,
Relationships between chemical structures and functions of triterpene glycosides isolated from sea cucumbers.
2014,
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,
Triterpene glycosides from the sea cucumber Cladolabes schmeltzii. II. Structure and biological action of cladolosides A1-A6 .
2014,
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,
Structures and Biologic Activity of Chitonoidosides I, J, K, K1 and L-Triterpene Di-, Tri- and Tetrasulfated Hexaosides from the Sea Cucumber Psolus chitonoides.
2022,
Pubmed
,
Echinobase
Silchenko,
Unusual Structures and Cytotoxicities of Chitonoidosides A, A1, B, C, D, and E, Six Triterpene Glycosides from the Far Eastern Sea Cucumber Psolus chitonoides.
2021,
Pubmed
,
Echinobase
Silchenko,
Triterpene Glycosides from the Far Eastern Sea Cucumber Psolus chitonoides: Chemical Structures and Cytotoxicities of Chitonoidosides E1, F, G, and H.
2021,
Pubmed
,
Echinobase
Van Dyck,
Localization of secondary metabolites in marine invertebrates: contribution of MALDI MSI for the study of saponins in Cuvierian tubules of H. forskali.
2010,
Pubmed
,
Echinobase
Van Dyck,
The triterpene glycosides of Holothuria forskali: usefulness and efficiency as a chemical defense mechanism against predatory fish.
2011,
Pubmed
,
Echinobase
Van Dyck,
Elucidation of molecular diversity and body distribution of saponins in the sea cucumber Holothuria forskali (Echinodermata) by mass spectrometry.
2009,
Pubmed
,
Echinobase
Van Dyck,
Qualitative and quantitative saponin contents in five sea cucumbers from the Indian ocean.
2010,
Pubmed
,
Echinobase
Zelepuga,
Structure-Activity Relationships of Holothuroid's Triterpene Glycosides and Some In Silico Insights Obtained by Molecular Dynamics Study on the Mechanisms of Their Membranolytic Action.
2021,
Pubmed
,
Echinobase
Zhao,
Saponins from Sea Cucumber and Their Biological Activities.
2018,
Pubmed
,
Echinobase
