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 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 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.

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.

Frondoside A. A novel triterpene glycoside from the holothurian Cucumariafrondosa

1990 ◽  
Vol 68 (1) ◽  
pp. 11-18 ◽  
Author(s):  
Michel Girard ◽  
Jacqueline Bélanger ◽  
John W. ApSimon ◽  
François-Xavier Garneau ◽  
Christian Harvey ◽  
...  
Keyword(s):  
Double Bond ◽  
Triterpene Glycoside ◽  
Sea Cucumber ◽  
Acetoxy Group ◽  
Chemical Data ◽  
Triterpene Saponins ◽  
Isolation And Characterization ◽  
Physico Chemical

The isolation and characterization of a novel triterpene glycoside from the sea cucumber Cucumariafrondosa, collected from the Gulf of St. Lawrence, are described. Physico-chemical data obtained on the underivatized saponin are presented in support of structure 1 for frondoside A. The structure is characterized by the presence of a branched oligosaccharidic chain composed of five units. The holostane-type aglycone features an endocyclic double bond at position C-7,8 and a β-acetoxy group at C-16. Keywords: triterpene glycoside; Cucumariafrondosa saponins; saponins, triterpene from holothurians; holothurian saponins; echinoderm triterpene saponins.

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 Structure and Biological Action of Cladolosides B1, B2, C, C1, C2 and D, Six New Triterpene Glycosides from the Sea Cucumber Cladolabes schmeltzii

2013 ◽  
Vol 8 (11) ◽  
pp. 1934578X1300801 ◽  
Author(s):  
Alexandra S. Silchenko ◽  
Anatoly I. Kalinovsky ◽  
Sergey A. Avilov ◽  
Pelageya V. Andryjaschenko ◽  
Pavel S. Dmitrenok ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Sea Cucumber ◽  
Carbohydrate Chain ◽  
2D Nmr ◽  
Biological Action ◽  
Triterpene Glycosides ◽  
2D Nmr Spectroscopy ◽  
New Variant ◽  
Sugar Unit

Six new nonsulfated triterpene glycosides, cladolosides B1(1), B2(2), C (3), C1(4), C2(5) and D (6) and known holotoxin A1(7) have been isolated from the tropical Indo-West Pacific sea cucumber Cladolabes schmeltzii (Cladolabinae, Sclerodactylidae, Dendrochirotida). Structures of the glycosides were elucidated by 2D NMR spectroscopy and mass-spectrometry. Glycosides 1 and 2 have pentasaccharide branched carbohydrate moieties and differ from each other by the aglycone structures. Compounds 3–6 are hexaosides; 3–5 contain identical carbohydrate moieties with two terminal 3- O-methylglucose residues and glucose as the fifth sugar unit and differ from each other in the structures of their aglycones. Cladoloside D (6) has a new variant of carbohydrate chain with xylose and glucose residues as fifth and sixth monosaccharides, correspondingly. All of the substances demonstrated rather strong cytotoxic and hemolytic effects.

scholarly journals Isomadecassoside, a New Ursane-Type Triterpene Glycoside from Centella asiatica Leaves, Reduces Nitrite Levels in LPS-Stimulated Macrophages

Biomolecules ◽  
2021 ◽  
Vol 11 (4) ◽  
pp. 494
Author(s):  
Giuseppina Chianese ◽  
Francesca Masi ◽  
Donatella Cicia ◽  
Daniele Ciceri ◽  
Sabrina Arpini ◽  
...  
Keyword(s):  
Double Bond ◽  
Triterpene Glycoside ◽  
Nmr Spectra ◽  
Nmr Assignment ◽  
Centella Asiatica ◽  
2D Nmr ◽  
Nitrite Production ◽  
2D Nmr Spectra ◽  
And Migration ◽  
Inflammatory Effect

A madecassoside-rich fraction obtained from the industrial purification of Centella asiatica leaves afforded a new triterpene glycoside, named isomadecassoside (4), characterized by an ursane-type skeleton and migration of the double bond at Δ20(21) in ring E. The structure of isomadecassoside was established by means of HR-ESIMS and detailed analysis of 1D and 2D NMR spectra, which allowed a complete NMR assignment. Studies on isolated J774A.1 macrophages stimulated by LPS revealed that isomadecassoside (4) inhibited nitrite production at non-cytotoxic concentrations, thus indicating an anti-inflammatory effect similar to that of madecassoside.

scholarly journals Triterpene Glycosides from the Sea Cucumber Eupentacta fraudatrix. Structure and Cytotoxic action of Cucumarioside D with a Terminal 3-O-Me-Glucose Residue Unique for this Species

2018 ◽  
Vol 13 (2) ◽  
pp. 1934578X1801300 ◽  
Author(s):  
Alexandra S. Silchenko ◽  
Anatoly I. Kalinovsky ◽  
Sergey A. Avilov ◽  
Roman S. Popov ◽  
Vladimir I Kalinin ◽  
...  
Keyword(s):  
Sea Cucumber ◽  
Carbohydrate Chain ◽  
2D Nmr ◽  
Carcinoma Cells ◽  
Triterpene Glycosides ◽  
Cytotoxic Action ◽  
2D Nmr Spectroscopy ◽  
Individual Substance ◽  
Unique Structural Feature ◽  
Eupentacta Fraudatrix

New minor triterpene glycoside, cucumarioside D (1) identified earlier as a candidate to new glycoside using LC-ESI QTOF-MS has been isolated from the sea cucumber Eupentacta fraudatrix as individual substance. The structure of the glycoside was elucidated using 2D NMR spectroscopy and MS. The glycoside has non-sulfated pentasaccharide carbohydrate chain branched by the second sugar (quinovose) and having 3-O-methylglucose as a terminal monosacharide residue that is an unique structural feature of sea cucumber triterpene glycosides from this species. A moderate cytotoxic activity of the glycoside 1 against the ascyte form of Echlich carcinoma cells and hemolytic activity has been found.

scholarly journals A New Triterpene Glycoside from the Sea Cucumber Holothuria Scabra Collected in Vietnam

2017 ◽  
Vol 23 (4) ◽  
pp. 253 ◽  
Author(s):  
Nguyen Van Thanh ◽  
Nguyen Hai Dang ◽  
Phan Van Kiem ◽  
Nguyen Xuan Cuong ◽  
Hoang Thanh Huong ◽  
...  
Keyword(s):  
Spectral Analysis ◽  
Triterpene Glycoside ◽  
Sea Cucumber ◽  
Methanol Extract ◽  
2D Nmr ◽  
Holothuria Scabra ◽  
Bioassay Guided Fractionation

Bioassay guided fractionation led to the isolation of a new triterpene glycoside, holothurinogenin B (1) along with three known compounds, holothurin B (2), holothurin A (3), and holothurin A2 (4), from the methanol extract of the Vietnamese sea cucumber Holothuria scabra. Their structures were deduced from the spectral analysis (1D-NMR, 2D-NMR, MS) and chemical evidences. 

Sign in / Sign up

Export Citation Format

Share Document