Invertébrés Marins du Lagon Néo-Calédonien, VII. Étude Structurale d'un Nouveau Saponoside Sulfaté Extrait de l'Holothurie, Neothyonidium magnum

Zurita, M. Bedoya; Ahond, A.; Poupat, C.; Potìer, Pierre; Menou, J. L.

doi:10.1021/np50047a008

Cited by 25 publications

(21 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…These aglycones are strongly differing from the holostane-type aglycones found in isolated earlier glycosides, “neothyonidioside” and neothyonidioside C [ 15 , 16 ], from New-Caledonian and Vietnamese collections of N. magnum , correspondingly. In contrast, the aglycone of colochiroside B 2 ( 10 ) found in the investigated sample of N. magnum is biogenetically very close to that of neothyonidioside C which also has the holostane-type aglycone with 16-acetoxygroup and differs in the side chain structure.…”

Section: Resultsmentioning

confidence: 60%

“…The signals of C(4) and C(5) of the first (xylose) residue were observed at δ(C) 76.0 and 63.9, correspondingly, indicating the presence of a sulfate group at C(4) of the sugar unit, analogically to the carbohydrate chains of magnumosides of the group A ( 1 – 4 ). The linear tetrasaccharide monosulfated carbohydrate chain of magnumosides of the group B ( 5 , 6 ), having the xylose as third monosaccharide unit, were found earlier in “neothyonidioside” [ 15 ] isolated from another collection of N. magnum , also coincided with the sugar moiety of colochiroside B 2 ( 9 ) [ 17 ] found in the investigated sample of N. magnum and are widely distributed in the triterpene glycosides of sea cucumbers of the orders Aspidochirotida [ 2 ] and Dendrochirotida [ 2 , 8 , 26 , 27 , 28 ].…”

Section: Resultsmentioning

confidence: 95%

“…The glycosides from the sea cucumber Neothyonidium (= Massinium ) magnum (Phyllophoridae, Dendrochirotida) have been previously investigated. The first studied sample of N. magnum was collected near the shores of New Caledonia [ 15 ]. The main component of glycosidic fraction, monosulfated tetraoside, “neothyоnidioside”, had the holostane-type aglycone with 9(11)- and 25(26)-double bonds and a 16-keto-group.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Nine New Triterpene Glycosides, Magnumosides A1–A4, B1, B2, C1, C2 and C4, from the Vietnamese Sea Cucumber Neothyonidium (=Massinium) magnum: Structures and Activities against Tumor Cells Independently and in Synergy with Radioactive Irradiation

et al. 2017

View full text Add to dashboard Cite

Nine new sulfated triterpene glycosides, magnumosides A1 (1), A2 (2), A3 (3), A4 (4), B1 (5), B2 (6), C1 (7), C2 (8) and C4 (9) as well as a known colochiroside B2 (10) have been isolated from the tropical Indo-West Pacific sea cucumber Neothynidium (=Massinium) magnum (Phyllophoridae, Dendrochirotida) collected in the Vietnamese shallow waters. The structures of new glycosides were elucidated by 2D NMR spectroscopy and mass-spectrometry. All the isolated new glycosides were characterized by the non-holostane type lanostane aglycones having 18(16)-lactone and 7(8)-double bond and differed from each other by the side chains and carbohydrate moieties structures. Magnumoside A1 (1) has unprecedented 20(24)-epoxy-group in the aglycone side chain. Magnumosides of the group A (1–4) contained disaccharide monosulfated carbohydrate moieties, of the group B (5, 6)—tetrasaccharide monosulfated carbohydrate moieties and, finally, of the group C (7–9)—tetrasaccharide disulfated carbohydrate moieties. The cytotoxic activities of the compounds 1–9 against mouse spleen lymphocytes, the ascites form of mouse Ehrlich carcinoma cells, human colorectal carcinoma DLD-1 cells as well as their hemolytic effects have been studied. Interestingly, the erythrocytes were more sensitive to the glycosides action than spleenocytes and cancer cells tested. The compounds 3 and 7 significantly inhibited the colony formation and decreased the size of colonies of DLD-1 cancer cells at non-cytotoxic concentrations. Moreover, the synergism of effects of radioactive irradiation and compounds 3 and 7–9 at subtoxic doses on proliferation of DLD-1 cells was demonstrated.

show abstract

Section: Resultsmentioning

confidence: 60%

Section: Resultsmentioning

confidence: 95%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Nine New Triterpene Glycosides, Magnumosides A1–A4, B1, B2, C1, C2 and C4, from the Vietnamese Sea Cucumber Neothyonidium (=Massinium) magnum: Structures and Activities against Tumor Cells Independently and in Synergy with Radioactive Irradiation

et al. 2017

View full text Add to dashboard Cite

show abstract

“…Three units of xylose and one unit each of 3-0-methyl glucose and quinovose (6-deoxyglucose) were detected while glucose, a sugar usually present in holothurins containing more than two sugar units, was not found. This unusual situation has also been observed in neothyonidioside, the major holothurin from Neothyonidium magnum (12).…”

Section: Oligosaccharide Chainmentioning

confidence: 58%

Frondoside A. A novel triterpene glycoside from the holothurian Cucumariafrondosa

Girard¹,

Bélanger²,

ApSimon³

et al. 1990

Can. J. Chem.

View full text Add to dashboard Cite

1 (1990).The isolation and characterization of a novel triterpene glycoside from the sea cucumber Cucumariaji-ondosa, 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 P-acetoxy group at C-16. On dCcrit l'isolation et 1'Clucidation structurale d'un nouveau triterpkne-glycoside, obtenu de l'holothurie Cucumaria ji-ondosa provenant du golfe du St-Laurent. En se basant sur les donnCes physico-chimiques du produit intact, on propose la structure 1 pour le frondoside A. Le composC est caractCrisC par la presence d'une chaine oligosaccharidique branchke, de cinq unites. L'aglycone de type holostane posskde une insaturation en position C-7,8 et un groupement acCtoxy-P en C-16.

show abstract

“…Only one new representative of the family Stichopodidae, Stichopus mollis, collected near New Zealand shore, was studied during last 5 years (Moraes et al, 2004). The major component of its glycoside fraction was identified as neothyonidioside C (29) (Figure 11) known earlier from sea cucumber Neothyonidium nagnum (family Phyllophoridae, order Dendrochirotida) (Zurita et al, 1986). The glycoside 29 has holotoxinogenin as aglycone and carbohydrate chain with xylose as a third monosaccharide unit.…”

Section: Structures Of the Glycosidesmentioning

confidence: 99%

Sea Cucumbers Triterpene Glycosides, the Recent Progress in Structural Elucidation and Chemotaxonomy

et al. 2005

View full text Add to dashboard Cite

Triterpene glycosides are characteristic metabolites of sea cucumbers (Holothurioidea, Echinodermata). Majority of the glycosides belong to holostane type (lanostane derivatives with 18(20)-lactone). Carbohydrate chains of these glycosides contain xylose, glucose, quinovose, 3-O-methylglucose and 3-O-methylsylose. During the last 5 years, main investigations were focused on holothurians belonging to the order Dendrochirotida collected in the North Pacific, North Atlantic, Antarctic and in subtropical waters. The glycosides of holothurians belonging to the order Aspidochirotida have also been studied. The most uncommon structural features of carbohydrate chains of new glycosides were: (1) the presence of quinovose as fifth terminal monosaccharide unit and the presence of two quinovose residues; (2) the presence of glucose instead of common xylose as fifth terminal monosaccharide unit; (3) trisaccharide carbohydrate chain; (4) the presence of two 3-O-methylxylose terminal monosaccharide units; (5) the presence of sulfate group at C-3 of quinovose residue. New glycosides without lactone or with 18(16)-lactone and having shortened side chains have also been isolated. The presence of 17a and 12a-hydroxyls, which are characteristic for glycosides from holothurians belonging to the family Holothuriidae (Aspidochirotida) in glycosides of dendrochirotids confirms parallel and relatively independent character of evolution of glycosides. All three families belonging to the order Aspidochirotida: Holothuriidae, Stichopodidae and Synallactidae have similar and parallel trends in evolution of the glycosides carbohydrate chains, namely from nonsulfated hexaosides to sulfated tetraosides. Sets of aglycones in glycosides from holothurians belonging to the genus Cucumaria (Cucumariidae, Dendrochirotida) are specific for each species. The carbohydrate chains are similar in all representatives of the genus Cucumaria.

show abstract

Invertébrés Marins du Lagon Néo-Calédonien, VII. Étude Structurale d'un Nouveau Saponoside Sulfaté Extrait de l'Holothurie, Neothyonidium magnum

Cited by 25 publications

References 4 publications

Nine New Triterpene Glycosides, Magnumosides A1–A4, B1, B2, C1, C2 and C4, from the Vietnamese Sea Cucumber Neothyonidium (=Massinium) magnum: Structures and Activities against Tumor Cells Independently and in Synergy with Radioactive Irradiation

Nine New Triterpene Glycosides, Magnumosides A1–A4, B1, B2, C1, C2 and C4, from the Vietnamese Sea Cucumber Neothyonidium (=Massinium) magnum: Structures and Activities against Tumor Cells Independently and in Synergy with Radioactive Irradiation

Frondoside A. A novel triterpene glycoside from the holothurian Cucumariafrondosa

Sea Cucumbers Triterpene Glycosides, the Recent Progress in Structural Elucidation and Chemotaxonomy

Contact Info

Product

Resources

About