scholarly journals 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

Marine Drugs ◽  
2019 ◽  
Vol 17 (6) ◽  
pp. 358 ◽  
Author(s):  
Alexandra S. Silchenko ◽  
Anatoly I. Kalinovsky ◽  
Sergey A. Avilov ◽  
Vladimir I. Kalinin ◽  
Pelageya V. Andrijaschenko ◽  
...  
Keyword(s):  
Sea Cucumber ◽  
2D Nmr ◽  
Mouse Cell ◽  
Triterpene Glycosides ◽  
Carbohydrate Moiety ◽  
Ehrlich Carcinoma ◽  
Cytotoxic Activities ◽  
2D Nmr Spectroscopy ◽  
Sugar Unit ◽  
Ht 29

Seven sulfated triterpene glycosides, psolusosides B (1), E (2), F (3), G (4), H (5), H1 (6), and I (7), along with earlier known psolusoside A and colochiroside D have been isolated from the sea cucumber Psolus fabricii collected in the Sea of Okhotsk. Herein, the structure of psolusoside B (1), elucidated by us in 1989 as a monosulfated tetraoside, has been revised with application of modern NMR and particularly MS data and proved to be a disulfated tetraoside. The structures of other glycosides were elucidated by 2D NMR spectroscopy and HR-ESI mass-spectrometry. Psolusosides E (2), F (3), and G (4) contain holostane aglycones identical to each other and differ in their sugar compositions and the quantity and position of sulfate groups in linear tetrasaccharide carbohydrate moieties. Psolusosides H (5) and H1 (6) are characterized by an unusual sulfated trisaccharide carbohydrate moiety with the glucose as the second sugar unit. Psolusoside I (7) has an unprecedented branched tetrasaccharide disulfated carbohydrate moiety with the xylose unit in the second position of the chain. The cytotoxic activities of the compounds 2–7 against several mouse cell lines—ascite form of Ehrlich carcinoma, neuroblastoma Neuro 2A, normal epithelial JB-6 cells, and erythrocytes—were quite different, at that hemolytic effects of the tested compounds were higher than their cytotoxicity against other cells, especially against the ascites of Ehrlich carcinoma. Interestingly, psolusoside G (4) was not cytotoxic against normal JB-6 cells but demonstrated high activity against Neuro 2A cells. The cytotoxic activity against human colorectal adenocarcinoma HT-29 cells and the influence on the colony formation and growth of HT-29 cells of compounds 1–3, 5–7 and psolusoside A was checked. The highest inhibitory activities were demonstrated by psolusosides E (2) and F (3).

scholarly journals Triterpene Glycosides from the Sea Cucumber Eupentacta fraudatrix. Structure and Biological Activity of Cucumariosides B1 and B2, Two New Minor Non-Sulfated Unprecedented Triosides

2012 ◽  
Vol 7 (9) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Alexandra S. Silchenko ◽  
Anatoly I. Kalinovsky ◽  
Sergey A. Avilov ◽  
Pelageya V. Andryjaschenko ◽  
Pavel S. Dmitrenok ◽  
...  
Keyword(s):  
Hemolytic Activity ◽  
Sea Cucumber ◽  
2D Nmr ◽  
Triterpene Glycosides ◽  
Ehrlich Carcinoma ◽  
Cytotoxic Activities ◽  
Cytotoxic Action ◽  
2D Nmr Spectroscopy ◽  
Spleen Lymphocytes ◽  
Eupentacta Fraudatrix

Two new minor triterpene glycosides, cucumariosides B1 (1) and B2 (2) have been isolated from the Far Eastern sea cucumber Eupentacta fraudatrix. Structures of the glycosides were elucidated by 2D NMR spectroscopy and MS. Glycosides 1 and 2 belong to the cucumariosides B group and have unprecedented trisaccharide carbohydrate moieties without sulfate groups. Glycosides 1 and 2 differ from each other in side chain structures in the aglycone moieties. These minor substances are probably intermediate metabolites in the biosynthesis of triterpene pentaosides. Cytotoxic activities of glycosides 1 and 2 against mouse spleen lymphocytes and the cells of the ascite form of mouse Ehrlich carcinoma were studied, along with hemolytic activity against mouse erythrocytes and antifungal activity. Cucumarioside B1 (1) was not active in any of the tests, while cucumarioside B2 (2) demonstrated moderate hemolytic activity and low cytotoxic action against Ehrlich carcinoma cells.

scholarly journals Triterpene Glycosides from the Sea Cucumber Eupentacta Fraudatrix. Structure and Biological Action of Cucumariosides I1, I3, I4, Three New Minor Disulfated Pentaosides

2013 ◽  
Vol 8 (8) ◽  
pp. 1934578X1300800 ◽  
Author(s):  
Alexandra S. Silchenko ◽  
Anatoly I. Kalinovsky ◽  
Sergey A. Avilov ◽  
Pelageya V. Andryjaschenko ◽  
Pavel S. Dmitrenok ◽  
...  
Keyword(s):  
Double Bond ◽  
Sea Cucumber ◽  
2D Nmr ◽  
Triterpene Glycosides ◽  
Side Chain ◽  
Ehrlich Carcinoma ◽  
Cytotoxic Activities ◽  
Moderate Activity ◽  
2D Nmr Spectroscopy ◽  
Eupentacta Fraudatrix

Three new minor triterpene glycosides, cucumariosides I1 (1), I3 (2) and I4 (3) have been isolated from the Far Eastern sea cucumber Eupentacta fraudatrix. Structures of the glycosides were elucidated by 2D NMR spectroscopy and MS. Glycosides 1–3 belong to the group of cucumariosides I, having branched pentasaccharide carbohydrate moieties with two sulfate groups and possessing 3- O-methyl-D-xylose as a terminal monosaccharide unit that is a characteristic feature of all the glycosides isolated from E. fraudatrix. Glycosides 1 and 2 differ from each other by the side chain structures in the holostane aglycone moieties, while cucumarioside I4 (3) has a 23,24,25,26,27-pentanorlanostane aglycone with an 18(16)-lactone. Cytotoxic activities of glycosides 1–3 against mouse spleen lymphocytes and ascite form of mouse Ehrlich carcinoma cells, along with hemolytic activity against mouse erythrocytes and antifungal activity were studied. Glycoside 1, having an aglycone side chain with a 24(25)-double bond, possesses moderate activity in all the tests, while glycoside 2, having 23(24)-double bond and 25-hydroxy group in the side chain, and glycoside 3 with an aglycone with an 18(16)-lactone and shortened side chain have either low activity or are non-active.

Structures of Violaceusosides C, D, E and G, Sulfated Triterpene Glycosides from the Sea Cucumber Pseudocolochirus violaceus (Cucumariidae, Dendrochirotida)

2014 ◽  
Vol 9 (3) ◽  
pp. 1934578X1400900 ◽  
Author(s):  
Alexandra S. Silchenko ◽  
Anatoly I. Kalinovsky ◽  
Sergey A. Avilov ◽  
Pelageya V. Andryjaschenko ◽  
Pavel S. Dmitrenok ◽  
...  
Keyword(s):  
Sea Cucumber ◽  
2D Nmr ◽  
Triterpene Glycosides ◽  
Ehrlich Carcinoma ◽  
Cytotoxic Activities ◽  
Sugar Composition ◽  
2D Nmr Spectroscopy ◽  
Chemical Structures ◽  
The Family ◽  
Carbohydrate Chains

Four new triterpene glycosides, violaceusosides C (1), D (2), E (3) and G (4) have been isolated from the sea cucumber Pseudocolochirus violaceus (Cucumariidae, Dendrochirotida). Eight known glycosides, DS-holothurin A and holothurinoside A, isolated earlier from Holothuria forskalii (order Aspidochirotida); and violaceuside A, lefevreoside C, philinopside E, intercedenside B, violaceuside II and liovilloside A isolated earlier from representatives of the family Cucumariidae, order Dendrochirotida have also been found in P. violaceus. The chemical structures of the glycosides were elucidated by 2D NMR spectroscopy and mass spectrometry. Violaceusosides C (1), D (2), E (3) and G (4) have holostane-type aglycones and tetrasaccharide linear carbohydrate chains differing in the sugar composition and the number and position of sulfate groups. Violaceusosides E (3) and G (4) are characterized by the presence of a sulfate group at C-3 of the quinovose residue that is very rare among sea cucumber glycosides. Cytotoxic activities of the glycosides 1–4 against cells of the ascite form of mouse Ehrlich carcinoma and hemolytic activities against mouse erythrocytes have been studied. Violaceusosides C (1) and D (2) demonstrated moderate cytotoxic and hemolytic effects, while violaceusosides E (3) and G (4) have more powerful activities.

scholarly journals Colochirosides A1, A2, A3, and D, Four Novel Sulfated Triterpene Glycosides from the Sea Cucumber Colochirus Robustus (Cucumariidae, Dendrochirotida)

2016 ◽  
Vol 11 (3) ◽  
pp. 1934578X1601100 ◽  
Author(s):  
Alexandra S. Silchenko ◽  
Anatoly I. Kalinovsky ◽  
Sergey A. Avilov ◽  
Pelageya V. Andryjaschenko ◽  
Pavel S. Dmitrenok ◽  
...  
Keyword(s):  
Hemolytic Activity ◽  
Sea Cucumber ◽  
Carbohydrate Chain ◽  
2D Nmr ◽  
Triterpene Glycosides ◽  
Ehrlich Carcinoma ◽  
Cytotoxic Activities ◽  
Moderate Activity ◽  
Monosaccharide Residue ◽  
2D Nmr Spectroscopy

Four new triterpene glycosides, colochirosides A1 (1), A2 (2), A3 (3) and D (4), have been isolated from the sea cucumber Colochirus robustus (Cucumariidae, Dendrochirotida). Structures of the glycosides have been elucidated by 2D NMR spectroscopy and mass-spectrometry. Colochiroside D (4) has a new type of carbohydrate chain having the only sulfate group attached to C-6 of the third (glucose) monosaccharide residue. Cytotoxic activities of glycosides 1–4 against the ascite form of mouse Ehrlich carcinoma cells and hemolytic activity against mouse erythrocytes have been studied. Hemolytic activity of the glycosides was higher than cytotoxic. Glycosides 1, 3 and 4 demonstrated strong effects, whereas compound 2 showed only moderate activity.

scholarly journals Colochirosides B1, B2, B3 and C, Novel Sulfated Triterpene Glycosides from the Sea Cucumber Colochirus robustus (Cucumariidae, Dendrochirotida)

2015 ◽  
Vol 10 (10) ◽  
pp. 1934578X1501001 ◽  
Author(s):  
Alexandra S. Silchenko ◽  
Anatoly I. Kalinovsky ◽  
Sergey A. Avilov ◽  
Pelageya V. Andryjaschenko ◽  
Pavel S. Dmitrenok ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Hemolytic Activity ◽  
Sea Cucumber ◽  
2D Nmr ◽  
Carcinoma Cells ◽  
Triterpene Glycosides ◽  
Ehrlich Carcinoma ◽  
Cytotoxic Activities ◽  
2D Nmr Spectroscopy ◽  
Carbohydrate Chains

Four new triterpene glycosides, colochirosides B1 (1), B2 (2), B3 (3) and C (4) have been isolated from the sea cucumber Colochirus robustus (Cucumariidae, Dendrochirotida). Six known earlier glycosides from representatives of two families of the order Dendrochirotida have also been found in C. robustus. Structures of the glycosides have been elucidated by 2D NMR spectroscopy and mass spectrometry. All the glycosides belong to the holostane series and contain tetrasaccharide linear carbohydrate chains with one or two sulfate groups. Cytotoxic activities of glycosides 1-4 against the ascite form of mouse Ehrlich carcinoma cells and hemolytic activities against mouse erythrocytes have been studied. Hemolytic activity of the glycosides was higher than cytotoxic. Glycosides 3 and 4 demonstrated strong effects, whereas compounds 1 and 2 containing the hydroxy-group in the side chains showed moderate hemolytic activity and were not cytotoxic.

scholarly journals Triterpene Glycosides from the Sea Cucumber Eupentacta fraudatrix. Structure and Cytotoxic Action of Cucumariosides A2, A7, A9, A10, A11, A13 and A14, Seven New Minor Non-Sulfated Tetraosides and an Aglycone with an Uncommon 18-Hydroxy Group

2012 ◽  
Vol 7 (7) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Alexandra S. Silchenko ◽  
Anatoly I. Kalinovsky ◽  
Sergey A. Avilov ◽  
Pelageya V. Andryjaschenko ◽  
Pavel S. Dmitrenok ◽  
...  
Keyword(s):  
Hydroxy Group ◽  
Sea Cucumber ◽  
2D Nmr ◽  
Triterpene Glycosides ◽  
Ehrlich Carcinoma ◽  
Cytotoxic Activities ◽  
Cytotoxic Action ◽  
2D Nmr Spectroscopy ◽  
Spleen Lymphocytes ◽  
Eupentacta Fraudatrix

Seven new minor triterpene glycosides, cucumariosides A2 (1), A7 (2), A9 (3), A10 (4), A11 (5), A13 (6) and A14 (7) have been isolated from the Far Eastern sea cucumber Eupentacta fraudatrix. Structures of the glycosides were elucidated by 2D NMR spectroscopy and MS. Glycosides 1–7 belong to the group of cucumariosides A, having linear tetrasaccharide carbohydrate moieties without any sulfate group and possessing 3- O-methyl-D-xylose as a terminal monosaccharide unit. Glycosides 1, 2, 5-7 differ from each other in side chain structures in aglycone moieties, while cucumarioside A10 (4) has a 23,24,25,26,27-pentanorlanostane aglycone with 18(16)-lactone. Cucumarioside A9 (3), having an uncommon 18-hydroxy group, is the second representative of the unique metabolically active glycosides that are regarded as intermediates of glycoside biosynthesis in sea cucumbers. Cytotoxic activities of glycosides 1–7 and cucumarioside A8 (8) against mouse spleen lymphocytes and the cells of the ascite form of mouse Ehrlich carcinoma, along with hemolytic activity against mouse erythrocytes and antifungal activity were studied. Cucumariosides A2 (1), A8 (8) and A13 (6) demonstrated high hemolytic activities. Glycosides 1, 4 and 6 showed moderate cytotoxic activity. Only cucumarioside A8 (8), having an 18-oxymethylene group and a 24(25)-double bond, was very active in all the tests.

scholarly journals Structures and Biological Activities of Typicosides A1, A2, B1, C1 and C2, Triterpene Glycosides from the Sea Cucumber Actinocucumis typica

2013 ◽  
Vol 8 (3) ◽  
pp. 1934578X1300800
Author(s):  
Alexandra S. Silchenko ◽  
Anatoly I. Kalinovsky ◽  
Sergey A. Avilov ◽  
Pelageya V. Andryjaschenko ◽  
Pavel S. Dmitrenok ◽  
...  
Keyword(s):  
Sea Cucumber ◽  
Biological Activities ◽  
Monosaccharide Composition ◽  
Triterpene Glycosides ◽  
Ehrlich Carcinoma ◽  
Cytotoxic Activities ◽  
Monosaccharide Residue ◽  
2D Nmr Spectroscopy ◽  
The Third ◽  
Carbohydrate Chains

Five new minor triterpene glycosides, typicosides A1 (1), A2 (2), B1 (3), C1 (4) and C2 (5), along with two known glycosides, intercedenside A and holothurin B3, have been isolated from the sea cucumber Actinocucumis typica. Structures of the glycosides were elucidated by 2D NMR spectroscopy and MS. Glycosides 1–5 are linear mono- and disulfated tetraosides differing from each other in both aglycone structures and monosaccharide composition of the carbohydrate chains. Typicosides A1 (1) and A2 (2) have identical monosulfated carbohydrate moieties with a xylose residue as the third monosaccharide unit and differ from each other in aglycon structures. Typicoside B1 (3) has glucose as the third monosaccharide residue. Typicosides C1 (4) and C2 (5) contain the same disulfated carbohydrate chains and differ from each other in structures of aglycone side chains. Antifungal activity of glycosides 1–5 against three species of fungi along with cytotoxic activity against mouse spleen lymphocytes and mouse Ehrlich carcinoma cells (ascite form), as well as hemolytic activities against mouse erythrocytes have been studied. All new glycosides, except for typicoside C1 (4), containing a hydroxy-group in the aglycone side chain, demonstrate rather strong hemolytic and cytotoxic activities.

scholarly journals Triterpene Glycosides from the Sea Cucumber Cladolabes schmeltzii. II. Structure and Biological Action of Cladolosides A1-A6

2014 ◽  
Vol 9 (10) ◽  
pp. 1934578X1400901 ◽  
Author(s):  
Alexandra S. Silchenko ◽  
Anatoly I. Kalinovsky ◽  
Sergey A. Avilov ◽  
Pelageya V. Andryjaschenko ◽  
Pavel S. Dmitrenok ◽  
...  
Keyword(s):  
Sea Cucumber ◽  
Carbohydrate Chain ◽  
2D Nmr ◽  
Biological Action ◽  
Triterpene Glycosides ◽  
Side Chain ◽  
Cytotoxic Activities ◽  
2D Nmr Spectroscopy ◽  
Sugar Chain ◽  
The Third

Six new triterpene glycosides, cladolosides A1–A6(1–6), have been isolated from the Vietnamese sea cucumber Cladolabes schmeltzii (Cladolabinae, Sclerodactylidae, Dendrochirotida). Structures of the glycosides were elucidated by 2D NMR spectroscopy and MS. All the glycosides have nonsulfated tetrasaccharide linear carbohydrate moieties. Glycoside 6 has a glucose residue as the third monosaccharide unit, while the rest of the compounds comprise a xylose in this postion of the carbohydrate chain. Glycosides 1–6 differ from each other in the structures of their holostane aglycones. Cytotoxic activities of glycosides 1–6 were studied against mouse spleenocytes, along with hemolytic activities against mouse erythrocytes. All the compounds, except cladoloside A5(5) posessing a hydroxy-group in the aglycone side chain, demonstrated rather strong cytotoxic and hemolytic effects. The most active glycosides were cladolosides A1(1) and A2(2) having two O-acetic groups and the xylose residue in the third position of the sugar chain.

scholarly journals Fallaxosides C1, C2, D1 and D2, Unusual Oligosulfated Triterpene Glycosides from the Sea Cucumber Cucumaria fallax (Cucumariidae, Dendrochirotida, Holothurioidea) and Taxonomic Status of this Animal

2016 ◽  
Vol 11 (7) ◽  
pp. 1934578X1601100 ◽  
Author(s):  
Alexandra S. Silchenko ◽  
Anatoly I. Kalinovsky ◽  
Sergey A. Avilov ◽  
Pelageya V. Andryjaschenko ◽  
Pavel S. Dmitrenok ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Hemolytic Activity ◽  
Sea Cucumber ◽  
Taxonomic Status ◽  
2D Nmr ◽  
Carcinoma Cells ◽  
Triterpene Glycosides ◽  
Ehrlich Carcinoma ◽  
2D Nmr Spectroscopy ◽  
Spleen Lymphocytes

Four new triterpene glycosides, fallaxosides C1 (1), C2 (2), D1 (3) and D2 (4) along with the known cucumarioside A3-2 (5) and koreoside A (6) have been isolated from the sea cucumber Cucumaria fallax (Cucumariidae, Dendrochirotida). Structures of the glycosides have been elucidated by 2D NMR spectroscopy and mass spectrometry. All of the glycosides are rare non-holostane derivatives having shortened side chains and contain pentasaccharide carbohydrate moieties with two or three sulfate groups. Structures of these triterpene glycosides and their comparison with those earlier isolated from Cucumaria spp. and Pseudocnus dubiosus leoninus allow us to suggest that the present assignment of C. fallax to the genus Pseudocnus is not correct, and this species should be assigned to the genus Cucumaria. Cytotoxic activity of glycosides 1–5 against the ascite form of mouse Ehrlich carcinoma cells and mouse spleen lymphocytes and hemolytic activity against mouse erythrocytes have been studied. The glycosides were expectedly not active in all the tests due to the absence of an 18(20)-lactone in their aglycones and the presence of several sulfate groups. There was one exception, cucumarioside A3-2 (5), which demonstrated a weak cytotoxicity against lymphocytes and moderate hemolytic activity.

scholarly journals 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

Marine Drugs ◽  
2020 ◽  
Vol 18 (11) ◽  
pp. 551
Author(s):  
Alexandra S. Silchenko ◽  
Anatoly I. Kalinovsky ◽  
Sergey A. Avilov ◽  
Pelageya V. Andrijaschenko ◽  
Roman S. Popov ◽  
...  
Keyword(s):  
Sea Cucumber ◽  
2D Nmr ◽  
Cytotoxic Activities ◽  
Glucose Residue ◽  
Monosaccharide Residue ◽  
2D Nmr Spectroscopy ◽  
Sugar Chain ◽  
Sugar Unit ◽  
Esi Mass Spectrometry ◽  
Far Eastern

Six new monosulfated triterpene tetra-, penta- and hexaosides, namely, the kurilosides A1 (1), A2 (2), C1 (3), D (4), E (5) and F (6), as well as the known earlier kuriloside A (7), having unusual non-holostane aglycones without lactone, have been isolated from the sea cucumber Thyonidium (= Duasmodactyla) kurilensis (Levin) (Cucumariidae, Dendrochirotida), collected in the Sea of Okhotsk near Onekotan Island from a depth of 100 m. Structures of the glycosides were established by 2D NMR spectroscopy and HR-ESI mass spectrometry. Kurilosides of the groups A and E contain carbohydrate moieties with a rare architecture (a pentasaccharide branched by C(4) Xyl1), differing from each other in the second monosaccharide residue (quinovose or glucose, correspondingly); kurilosides of the group C are characterized by a unique tetrasaccharide branched by a C(4) Xyl1 sugar chain; and kurilosides of the groups D and F are hexaosides differing from each other in the presence of an O-methyl group in the fourth (terminal) sugar unit. All these glycosides contain a sulfate group at C-6 of the glucose residue attached to C-4 Xyl1 and the non-holostane aglycones have a 9(11) double bond and lack γ-lactone. The cytotoxic activities of compounds 1–7 against mouse neuroblastoma Neuro 2a, normal epithelial JB-6 cells and erythrocytes were studied. Kuriloside A1 (1) was the most active compound in the series, demonstrating strong cytotoxicity against the erythrocytes and JB-6 cells and a moderate effect against Neuro 2a cells.

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