Triterpene Glycosides of Sea Cucumbers (Holothuroidea, Echinodermata) as Taxonomic Markers

Kalinin, Vladimir I.; Avilov, Sergey A.; Silchenko, Alexandra S.; Stonik, Valentin A.

doi:10.1177/1934578x1501000108

Cited by 27 publications

(35 citation statements)

References 31 publications

(51 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It opens a possibility to study this compound on models of neurodegenerative diseases. Noteworthy, the cytotoxicity of psolusosides H (5) and H 1 (6) (the glycosides having trisaccharide chains) and psolusoside I (7) (the compound with tetrasaccharide branched carbohydrate chain and a xylose as the second unit) are similar to that of linear tetraosides-psolusosides A, E (2), F (3), and G (4)-whereas it is known that the presence of linear tetrasaccharide chain is one of the necessary conditions for the displaying of membranolytic activity [4,6]. The influence of the psolusosides A, B (1), E (2), F (3), H (5), H 1 (6), and I (7) on cell viability, formation, and growth of colonies of human colorectal adenocarcinoma HT-29 cells was checked.…”

Section: Bioactivity Of the Glycosidesmentioning

confidence: 99%

See 1 more Smart Citation

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

et al. 2019

Self Cite

View full text Add to dashboard Cite

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).

show abstract

Section: Bioactivity Of the Glycosidesmentioning

confidence: 99%

“…The sea cucumbers triterpene glycosides are long-time investigated natural compounds characterized by significant structural diversity, exhibiting a broad spectrum of biological activity [1][2][3][4][5][6][7][8][9]. Some of them are under study as marine drugs.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2019

Self Cite

View full text Add to dashboard Cite

show abstract

“…The glycoside structures are specific for one genus or a group of genera for the sea cucumbers of the order Aspidochirotida. However, these compounds are usually species-specific for the representatives of the order Dendrochirotida [12]. …”

Section: Introductionmentioning

confidence: 99%

Metabolite Profiling of Triterpene Glycosides of the Far Eastern Sea Cucumber Eupentacta fraudatrix and Their Distribution in Various Body Components Using LC-ESI QTOF-MS

et al. 2017

View full text Add to dashboard Cite

The Far Eastern sea cucumber Eupentacta fraudatrix is an inhabitant of shallow waters of the south part of the Sea of Japan. This animal is an interesting and rich source of triterpene glycosides with unique chemical structures and various biological activities. The objective of this study was to investigate composition and distribution in various body components of triterpene glycosides of the sea cucumber E. fraudatrix. We applied LC-ESI MS (liquid chromatography–electrospray mass spectrometry) of whole body extract and extracts of various body components for metabolic profiling and structure elucidation of triterpene glycosides from the E. fraudatrix. Totally, 54 compounds, including 26 sulfated, 18 non-sulfated and 10 disulfated glycosides were detected and described. Triterpene glycosides from the body walls, gonads, aquapharyngeal bulbs, guts and respiratory trees were extracted separately and the distributions of the detected compounds in various body components were analyzed. Series of new glycosides with unusual structural features were described in E. fraudatrix, which allow clarifying the biosynthesis of these compounds. Comparison of the triterpene glycosides contents from the five different body components revealed that the profiles of triterpene glycosides were qualitatively similar, and only some quantitative variabilities for minor compounds were observed.

show abstract

“…The apolar part is constructed around a sterol or a triterpenoid base . Those biomolecules are present in numerous plants but also in different classes of echinoderms, in particular in sea stars and sea cucumbers . Thanks to their amphiphilic property and to their broad structural diversity, saponin molecules are considered to be important candidates in the pharmaceutical and food industries as well as in agronomy .…”

Section: Introductionmentioning

confidence: 99%

“…1,2 Those biomolecules are present in numerous plants [3][4][5][6] but also in different classes of echinoderms, in particular in sea stars [7][8][9][10][11] and sea cucumbers. [12][13][14][15][16][17] Thanks to their amphiphilic property and to their broad structural diversity, saponin molecules are considered to be important candidates in the pharmaceutical and food industries as well as in agronomy. 5,9,[18][19][20][21][22][23] Nevertheless, as for other natural products, the principal issues to the industrial/medicinal application of saponins remain their challenging purification as well as their in-depth structural characterization.…”

Section: Introductionmentioning

confidence: 99%

Ion mobility mass spectrometry of saponin ions

Decroo

Colson

Lemaur

et al. 2018

Rapid Comm Mass Spectrometry

View full text Add to dashboard Cite

Rationale Saponins are natural compounds presenting a high structural diversity whose structural characterization remains extremely challenging. Ideally, saponin structures are best established using nuclear magnetic resonance experiments conducted on isolated molecules. However, saponins are also increasingly characterized using tandem mass spectrometry (MS/MS) coupled with liquid chromatography, even if collision‐induced dissociation (CID) experiments are often quite limited in accurately determining the saponin structure. Methods We consider here ion mobility mass spectrometry (IMMS) as an orthogonal tool for the structural characterization of saponin isomers by comparing the experimental collisional cross sections (CCSs) of saponin ions with theoretical CCSs for candidate ion structures. Indeed, state‐of‐the‐art theoretical calculations perfectly complement the experimental results, allowing the ion structures to be deciphered at the molecular level. Results We demonstrate that ion mobility can contribute to the structural characterization of saponins because different saponin ions present significantly distinct CCSs. Depending on the nature of the cation (in the positive ion mode), the differences in CCSs can also be exacerbated, optimizing the gas‐phase separation. When associated with molecular dynamics simulations, the CCS data can be used to describe the interactions between the cations, i.e. H+, Na+ and K+, and the saponin molecules at a molecular level. Conclusions Our work contributes to resolve the relationship between the primary and secondary structures of saponin ions. However, it is obvious that the structural diversity and complexity of the saponins cannot be definitively unraveled by measuring a single numerical value, here the CCS. Consequently, the structural characterization of unknown saponins will be difficult to achieve based on IMMS alone. Nevertheless, we demonstrated that monodesmosidic and bidesmosidic saponins can be distinguished via IMMS.

show abstract

Triterpene Glycosides of Sea Cucumbers (Holothuroidea, Echinodermata) as Taxonomic Markers

Cited by 27 publications

References 31 publications

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

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

Metabolite Profiling of Triterpene Glycosides of the Far Eastern Sea Cucumber Eupentacta fraudatrix and Their Distribution in Various Body Components Using LC-ESI QTOF-MS

Ion mobility mass spectrometry of saponin ions

Contact Info

Product

Resources

About