Cytotoxic Action of Triterpene Glycosides from Sea Cucumbers from the genus Cucumaria on Mouse Spleen Lymphocytes. Inhibition of Nonspecific Esterase

Four triterpene glycosides from sea cucumbers belonging to the genus Cucumaria, okhotoside A1-1 (1), cucumarioside A0-1 (2), frondoside A (3) and cucumarioside A2-2 (4) inhibit the activity of nonspecific esterase of mouse spleen lymphocytes. The dependence of the inhibitory activity of the glycosides on their structure is similar to that for hemolytic activity. The absence of inhibitory activity for the preparation Cumaside, which is a complex of cucumarioside A2-2 and related compounds with cholesterol, shows a cholesterol-dependent character of the inhibitory action of the glycosides. The effective inhibitory concentrations of frondoside A and cucumarioside A2-2 are significantly higher than the immunomodulatory doses of these glycosides.

Download Full-text

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

Natural Product Communications ◽

10.1177/1934578x1200700912 ◽

2012 ◽

Vol 7 (9) ◽

pp. 1934578X1200700 ◽

Cited By ~ 1

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.

Download Full-text

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

Natural Product Communications ◽

10.1177/1934578x1601100718 ◽

2016 ◽

Vol 11 (7) ◽

pp. 1934578X1601100 ◽

Cited By ~ 1

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.

Download Full-text

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

Natural Product Communications ◽

10.1177/1934578x1200700710 ◽

2012 ◽

Vol 7 (7) ◽

pp. 1934578X1200700 ◽

Cited By ~ 2

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.

Download Full-text