Trisulfated glycosides from the holothurianCucumaria japonica

Drozdova, O. A.; Авилов, С. А.; Калиновский, А. И.; Stonik, V. A.; Mil'grom, Yu. M.; Rashkes, Ya. V.

doi:10.1007/bf00630529

Cited by 20 publications

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“…The characteristic proton resonances of the methyl groups at δ 1.59 ppm (d, J = 6.4 Hz) and δ 3.79 (s) indicated the presence of a quinovose and 3-O-methyl glucose residues in the oligosaccharide chain. Comparison of the carbon resonances due to the carbohydrate chain of 1 and 2 (Table 1) showed complete coincidence with those of the trisulfated pentaoside cucumarioside A 7 -1, isolated from Cucumaria japonica (4), and those of the desulfated derivative of cucumarioside A 7 -1, respectively. Therefore we assume that compound 1 and cucumarioside A 7 -1 share identical carbohydrate chains.…”

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confidence: 67%

“…Therefore we assume that compound 1 and cucumarioside A 7 -1 share identical carbohydrate chains. The location of sulfate groups of 1 at C-4 of internal xylose (Xyl 1 ) and at C-6 of glucose and 3-O-methyl glucose units was confirmed by the comparison of the carbon resonances of 1 with those of its desulfated derivative 2 (Table 1) and other holostane and nonholostane sea-cucumber glycosides (4)(5)(6).…”

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confidence: 85%

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Article

Avilov¹,

Drozdova²,

Kalinin³

et al. 1998

Can. J. Chem.

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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.Résumé : On a isolé un nouveau glycoside sulfaté du triterpène nonholostane, le frondoside C (1) (comportant des glycosides de la structure aglycone comme impuretés), à partir du concombre de mer Cucumaria frondosa. On a déterminé sa structure en se basant sur des données spectrales (RMN et SM) du composé 1 et de son dérivé désulfaté (2) obtenu par solvolyse. Le frondoside C (1) n'est que le septième glycoside à avoir été observé dans les concombres de mer, avec un aglycone de type lanostane ne comportant pas de cycle lactone typique en 18(20).Mots clés : Cucumaria frondosa, concombres de mer, frondosides, glycosides de triterpène, activité antitumorale. [Traduit par la rédaction]The sea cucumber Cucumaria frondosa Gunnerus (Cucumariidae) is a widespread benthic animal inhabiting the North Atlantic and western Arctic seas. Previous studies of this sea cucumber have yielded two new holostane pentaglycosides, the monosulfated frondoside A (1) and the disulfated frondoside B (2). More recently, we have isolated a new minor monosulfated tetraoside frondoside A 1 , along with frondoside A, from specimens of C. frondosa collected in Barents Sea (3).Continuing with our investigations on bioactive secondary metabolites of marine origin, we report here our results on the study of the more polar triterpene glycosides from C. frondosa, with the isolation of a new saponin that we named frondoside C. Column chromatography on polychrom-1 (powdered Teflon) of the ethanolic extract of C. frondosa gave a mixture of glycosides that was separated by column chromatography on silica gel, affording frondoside C (1) accompanied by very small amounts of other polar glycosides with identical carbohydrate chain. Attempts to purify 1 by HPLC were unsuccessful. To establish wholly its structure, we resorted to spectroscopic analysis of impure 1 and the pure compound 2 that resulted from solvolysis of 1. Thus, solvolysis of 1 with pyridine-dioxane mixture afforded, after HPLC purification, the pure desulfated derivative 2.

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Article

Avilov¹,

Drozdova²,

Kalinin³

et al. 1998

Can. J. Chem.

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“…Cucumaria japonica is very important harvesting species of the sea cucumber from the Sea of Japan and Southern part of the Sea of Okhotsk. The glycosides from the sea cucumbers were very intensively studied earlier [1][2][3][4]. The main components of the glycoside fractions were branched pentaosides having quinovose residue as the second monosaccharide unit having one [2], two [3] and three sulfate groups [4].…”

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confidence: 99%

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

Silchenko

Kalinovsky

Dmitrenok

et al. 2015

Natural Product Communications

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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.

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“…Frondoside A (compound 3) and cucumariosides are derived from the edible sea cucumbers Cucumaria frondosa and C. japonica , respectively (Girard et al, 1990 ; Stonik et al, 1999 ) (Figure 2 ). C. japonica is a source of several different cucumariosides such as cucumarioside A 2 -2 (compound 4), A 4 -2 (compound 5), and A 7 -1 (compound 6) (Figure 2 ) (Avilov et al, 1990 ; Drozdova et al, 1993 , 1997 ; Stonik et al, 1999 ). Frondoside A and cucumariosides are pentaosides, with the main structural difference between the two compounds being the functional group at C-16 of the aglycone (acetoxy or keto group) and the third carbohydrate unit in the carbohydrate chain (indicated by an asterisk in compound 3 and 4).…”

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confidence: 99%

Relationships between chemical structures and functions of triterpene glycosides isolated from sea cucumbers

et al. 2014

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Many marine triterpene glycosides have in vitro and in vivo activities with very low toxicity, suggesting that they are suitable agents for the prevention and treatment of different diseases, particularly cancer. However, the molecular mechanisms of action of natural marine compounds in cancer, immune, and other various cells are not fully known. This review focuses on the structural characteristics of marine triterpene glycosides and how these affect their biological activities and molecular mechanisms. In particular, the membranotropic and membranolytic activities of frondoside A and cucumariosides from sea cucumbers and their ability to induce cytotoxicity and apoptosis have been discussed, with a focus on structure-activity relationships. In addition, the structural characteristics and antitumor effects of stichoposide C and stichoposide D have been reviewed along with underlying their molecular mechanisms.

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Trisulfated glycosides from the holothurianCucumaria japonica

Cited by 20 publications

References 2 publications

Article

Article

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

Relationships between chemical structures and functions of triterpene glycosides isolated from sea cucumbers

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