Triterpene Glycosides from the Far-Eastern Sea Cucumber <i>Pentamera calcigera.</i> 1. Monosulfated Glycosides and Cytotoxicity of Their Unsulfated Derivatives

Avilov, Sergey A.; Антонов, А. С.; Drozdova, O. A.; Kalinin, Vladimir I.; Kalinovsky, Anatoly I.; Stonik, Valentin A.; Riguera, Ricardo; Lenis, Luis A.; Jiménez, Carlos

doi:10.1021/np9903447

Cited by 43 publications

(40 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For example, a series of very interesting from the point of view of their structures relationship mono-and disulfated glycosides was isolated from sea cucumber Pentamera calcigera (the subfamily Thyoninae, the family Phyllophoridae) collected in the Sea of Japan ( Figure 2). Monosulfated glycosides were presented by cucumarioside G 2 (2), earlier isolated from Eupentacta fraudatrix (Avilov et al, 1994) and three new glycosides, calcigerosides B (3), C 1 (4) and C 2 (5) (Avilov et al, 2000a). New glycosides contain branched pentasaccharide carbohydrate chains with 3-O-methylxylose as a terminal residue that is a rare feature for sea cucumber glycosides.…”

Section: Structures Of the Glycosidesmentioning

confidence: 99%

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

et al. 2005

Self Cite

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

Section: Structures Of the Glycosidesmentioning

confidence: 99%

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

et al. 2005

Self Cite

View full text Add to dashboard Cite

show abstract

“…They are classified into four main structural categories based on their aglycone moieties; three holostane type glycoside group saponins containing a (1) 3β-hydroxyholost-9 (11)-ene aglycone skeleton; (2) saponins with a 3β-hydroxyholost-7-ene skeleton and (3) saponins with an aglycone moiety different to the other two holostane type aglycones (other holostane type aglycones); and (4) a nonholostane aglycone [25,38,46,51,52]. …”

Section: Introductionmentioning

confidence: 99%

Discovery of Novel Saponins from the Viscera of the Sea Cucumber Holothuria lessoni

2014

View full text Add to dashboard Cite

Sea cucumbers, sometimes referred to as marine ginseng, produce numerous compounds with diverse functions and are potential sources of active ingredients for agricultural, nutraceutical, pharmaceutical and cosmeceutical products. We examined the viscera of an Australian sea cucumber Holothuria lessoni Massin et al. 2009, for novel bioactive compounds, with an emphasis on the triterpene glycosides, saponins. The viscera were extracted with 70% ethanol, and this extract was purified by a liquid-liquid partition process and column chromatography, followed by isobutanol extraction. The isobutanol saponin-enriched mixture was further purified by high performance centrifugal partition chromatography (HPCPC) with high purity and recovery. The resultant purified polar samples were analyzed using matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS)/MS and electrospray ionization mass spectrometry (ESI-MS)/MS to identify saponins and characterize their molecular structures. As a result, at least 39 new saponins were identified in the viscera of H. lessoni with a high structural diversity, and another 36 reported triterpene glycosides, containing different aglycones and sugar moieties. Viscera samples have provided a higher diversity and yield of compounds than observed from the body wall. The high structural diversity and novelty of saponins from H. lessoni with potential functional activities presents a great opportunity to exploit their applications for industrial, agricultural and pharmaceutical use.

show abstract

“…Over 500 triterpene glycosides have been reported from various species of sea cucumbers [11,12,14,20,25,36,46,47,55,59] and are classified into four main structural categories based on their aglycone moieties; three holostane type glycoside group saponins containing a (1) 3β-hydroxyholost-9 (11)-ene aglycone skeleton; (2) saponins with a 3β-hydroxyholost-7-ene skeleton; and (3) saponins with an aglycone moiety different to the other two holostane type aglycones (other holostane type aglycones); and (4) a nonholostane aglycone [46,48,54,60,61]. …”

Section: Introductionmentioning

confidence: 99%

Structural Elucidation of Novel Saponins in the Sea Cucumber Holothuria lessoni

et al. 2014

View full text Add to dashboard Cite

Sea cucumbers are prolific producers of a wide range of bioactive compounds. This study aimed to purify and characterize one class of compound, the saponins, from the viscera of the Australian sea cucumber Holothuria lessoni. The saponins were obtained by ethanolic extraction of the viscera and enriched by a liquid-liquid partition process and adsorption column chromatography. A high performance centrifugal partition chromatography (HPCPC) was applied to the saponin-enriched mixture to obtain saponins with high purity. The resultant purified saponins were profiled using MALDI-MS/MS and ESI-MS/MS which revealed the structure of isomeric saponins to contain multiple aglycones and/or sugar residues. We have elucidated the structure of five novel saponins, Holothurins D/E and Holothurinosides X/Y/Z, along with seven reported triterpene glycosides, including sulfated and non-sulfated saponins containing a range of aglycones and sugar moieties, from the viscera of H. lessoni. The abundance of novel compounds from this species holds promise for biotechnological applications.

show abstract

Triterpene Glycosides from the Far-Eastern Sea Cucumber Pentamera calcigera. 1. Monosulfated Glycosides and Cytotoxicity of Their Unsulfated Derivatives

Cited by 43 publications

References 9 publications

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

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

Discovery of Novel Saponins from the Viscera of the Sea Cucumber Holothuria lessoni

Structural Elucidation of Novel Saponins in the Sea Cucumber Holothuria lessoni

Contact Info

Product

Resources

About