Glycosides from the sea cucumber Cucumaria frondosa. IV. Structure of frondosides A2-4, A2-7, and A2-8, three new minor monosulfated triterpene glycosides

2005 ◽  
Vol 83 (12) ◽  
pp. 2120-2126 ◽  
Author(s):  
Alexandra S Silchenko ◽  
Sergey A Avilov ◽  
Alexandr S Antonov ◽  
Anatoly I Kalinovsky ◽  
Pavel S Dmitrenok ◽  
...  
Keyword(s):  
Double Bond ◽  
Spectral Data ◽  
Sea Cucumber ◽  
2D Nmr ◽  
Triterpene Glycosides ◽  
Sea Cucumbers ◽  
Cucumaria Frondosa

Frondosides A2-4 (1), A2-7 (2), and A2-8 (3) are new monosulfated triterpene glycosides isolated from the sea cucumber Cucumaria frondosa. Their structures have been elucidated on the basis of spectral data (2D NMR and MS). Frondosides A2-7 (2) and A2-8 (3) are isomers and differ from each other only by the position of a double bond in their non-holostane-type aglycones.Key words: Cucumaria frondosa, sea cucumbers, frondosides, triterpene glycosides.

Glycosides from the sea cucumber Cucumaria frondosa. III. Structure of frondosides A2-1, A2-2, A2-3, and A2-6, four new minor monosulfated triterpene glycosides

2005 ◽  
Vol 83 (1) ◽  
pp. 21-27 ◽  
Author(s):  
Alexandra S Silchenko ◽  
Sergey A Avilov ◽  
Alexandr S Antonov ◽  
Anatoly I Kalinovsky ◽  
Pavel S Dmitrenok ◽  
...  
Keyword(s):  
Spectral Data ◽  
Sea Cucumber ◽  
2D Nmr ◽  
Triterpene Glycosides ◽  
Side Chain ◽  
Unsaturated Ketone ◽  
Sea Cucumbers ◽  
Cucumaria Frondosa

Frondosides A2-1 (1), A2-2 (2), A2-3 (3), and A2-6 (4) are new monosulfated holostane pentaosides isolated from the sea cucumber Cucumaria frondosa. Their structures have been elucidated on the basis of spectral data (2D NMR and MS). Frondoside A2-2 (2) contains an α,β-unsaturated ketone fragment in the side chain of the aglycon, unique for triterpene glycosides of sea cucumbers.Key words: Cucumaria frondosa, sea cucumbers, frondosides, triterpene glycosides.

scholarly journals Structure of Cucumariosides H5, H6, H7 and H8, Triterpene Glycosides from the Sea Cucumber Eupentacta fraudatrix and Unprecedented Aglycone with 16,22-Epoxy-group

2011 ◽  
Vol 6 (8) ◽  
pp. 1934578X1100600 ◽  
Author(s):  
Alexandra S. Silchenko ◽  
Anatoly I. Kalinovsky ◽  
Sergey A. Avilov ◽  
Pelageya V. Andryjaschenko ◽  
Pavel S. Dmitrenok ◽  
...  
Keyword(s):  
Spectral Data ◽  
Sea Cucumber ◽  
Epoxy Group ◽  
2D Nmr ◽  
Triterpene Glycosides ◽  
Sulfate Group ◽  
Sea Cucumbers ◽  
Far Eastern ◽  
Mouse Lymphocytes ◽  
Eupentacta Fraudatrix

Four new triterpene glycosides cucumariosides H5 (1), H6 (2), H7 (3) and H8 (4) along with the known cucumarioside H (5) have been isolated from the Far Eastern sea cucumber Eupentacta fraudatrix. The structures of glycosides 1–4 were elucidated on the basis of spectral data (2D NMR and MS). Glycosides 1–4 belong to the group of cucumariosides H, having branched rare pentasaccharide carbohydrate moieties with one sulfate group and 3- O-methyl-D-xylose as a terminal monosaccharide unit. Glycosides 1–3 and 5 differ from each other in structures of side chains of the aglycones, while cucumarioside H8 (4) has a novel aglycone with unprecedented 16(22)-epoxy-group, never found in the sea cucumbers glycosides. Glycosides 1–3, and 5 were cytotoxic against mouse lymphocytes and hemolytic against mouse erythrocytes. Glycoside 2 was less active in comparison with others.

Article

1998 ◽  
Vol 76 (2) ◽  
pp. 137-141
Author(s):  
Sergey A Avilov ◽  
Olga A Drozdova ◽  
Vladimir I Kalinin ◽  
Anatoly I Kalinovsky ◽  
Valentin A Stonik ◽  
...  
Keyword(s):  
Antitumor Activity ◽  
Spectral Data ◽  
Triterpene Glycoside ◽  
Sea Cucumber ◽  
Sea Cucumbers ◽  
Cucumaria Frondosa

Frondoside C (1) is a new sulfated nonholostane triterpene glycoside obtained (with the glycosides closed by aglycone structure as impurities) from the sea cucumber Cucumaria frondosa. Its structure has been elucidated on the basis of spectral data (NMR and MS) of compound 1 and of its desulfated derivative (2) obtained by solvolysis. Frondoside C (1) is just the seventh glycoside reported from sea cucumbers, having a lanostane-type aglycone devoid of the typical 18(20)- lactone ring.Key words: Cucumaria frondosa, sea cucumbers, frondosides, triterepene glycosides, antitumor activity.

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.

Glycosides from the North Atlantic sea cucumber Cucumaria frondosa V - Structures of five new minor trisulfated triterpene oligoglycosides, frondosides A7-1, A7-2, A7-3, A7-4, and isofrondoside C

2007 ◽  
Vol 85 (9) ◽  
pp. 626-636 ◽  
Author(s):  
Alexandra S Silchenko ◽  
Sergey A Avilov ◽  
Anatoly I Kalinovsky ◽  
Pavel S Dmitrenok ◽  
Vladimir I Kalinin ◽  
...  
Keyword(s):  
North Atlantic ◽  
Sea Cucumber ◽  
Lactone Ring ◽  
Triterpene Glycosides ◽  
Biosynthetic Pathways ◽  
Sea Cucumbers ◽  
The North ◽  
The North Atlantic ◽  
Cucumaria Frondosa ◽  
Oxygen Functionality

Seven highly polar trisulfated triterpene glycosides belonging to the frondoside A7 group have been isolated from the North Atlantic sea cucumber Cucumaria frondosa. The structures of five new glycosides, frondosides A7-1 (1), A7-2 (2), A7-3 (3), A7-4 (4), and isofrondoside C (5) were elucidated, three of which contained lanostane aglycons without a lactone-ring. Three pairs of the glycosides proved to be isomers by virture of the positions of double bonds in the aglycons nuclei; two pairs of the glycosides differed from each other by the character of the oxygen functionality at C-22. The results from these studies provided the basis for postulating the biosynthetic pathways of norlanostane glycosides in the sea cucumber.Key words: Cucumaria frondosa, sea cucumbers, frondosides, triterpene glycosides.

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 Colochiroside E, an Unusual Non-holostane Triterpene Sulfated Trioside from the Sea Cucumber Colochirus Robustus and Evidence of the Impossibility of a 7(8)-Double Bond Migration in Lanostane Derivatives having an 18(16)-Lactone

2016 ◽  
Vol 11 (6) ◽  
pp. 1934578X1601100 ◽  
Author(s):  
Alexandra S. Silchenko ◽  
Anatoly L Kalinovsky ◽  
Sergey A. Avilov ◽  
Pelageya V. Andryjaschenko ◽  
Pavel S. Dmitrenok ◽  
...  
Keyword(s):  
Double Bond ◽  
Triterpene Glycoside ◽  
Sea Cucumber ◽  
Carbohydrate Chain ◽  
2D Nmr ◽  
Double Bond Migration ◽  
Chlorine Derivative ◽  
Rare Group

The unusual non-holostane triterpene glycoside, colochiroside E (1) was isolated from the sea cucumber Colochirus robustus (Cucumariidae, Dendrochirotida). The structure of 1 was established by analysis of ID, 2D NMR and HRESI MS data. Colochiroside E (1) belongs to a rare group of glycosylated 9β-H-lanosta-18(16)-lactones and has an unprecedented sulfated trisaccharide carbohydrate chain consisting of two glucose and one xylose units. In contrast with (9β-H)-7(8)-unsaturated holostane glycosides, the 7(8)-double bond in the having (9β-H)-configuration aglycone of colochiroside E is not capable of migration into the 8(9)- and then into the 9(11)-position on treatment with HC1. The formation of a chlorine derivative of 1 was observed under these conditions.

scholarly journals Cucumarioside E from the Far Eastern Sea Cucumber Cucumaria japonica (Cucumariidae, Dendrochirotida), New Minor Monosulfated Holostane Triterpene Pentaoside with Glucose as the Second Monosaccharide Residue

2015 ◽  
Vol 10 (6) ◽  
pp. 1934578X1501000 ◽  
Author(s):  
Alexandra S. Silchenko ◽  
Anatoly I. Kalinovsky ◽  
Pavel S. Dmitrenok ◽  
Vladimir I. Kalinin ◽  
Andrey N. Mazeika ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Structural Feature ◽  
Sea Cucumber ◽  
2D Nmr ◽  
Monosaccharide Residue ◽  
Sea Cucumbers ◽  
Unique Structural Feature ◽  
Far Eastern ◽  
Cucumaria Japonica ◽  
Carbohydrate Chains

New minor triterpene glycoside, cucumarioside E (1) has been isolated from the Far Eastern sea cucumber Cucumaria japonica. The structure of the glycoside was elucidated by 2D-NMR specroscopy and mass-spectrometry. The glycoside has glucose instead of quinovose as the second monosaccharide residue and xylose as third monosaccharide residue that is unique structural feature for triterpene glycosides carbohydrate chains from sea cucumbers belonging to the genus Cucumaria.

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 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.

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