Biologically Active Triterpene Glycosides from Sea Cucumbers (Holothuroidea, Echinodermata)

Chludil, Hugo D.; Murray, Ana Paula; Seldes, Alicia M.; Maier, Marta S.

doi:10.1016/s1572-5995(03)80150-3

Cited by 28 publications

(30 citation statements)

References 32 publications

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“…Triterpene glycosides of sea cucumbers have unique chemical structures, significantly differing from those of terrestrial plants. These compounds possess a variety of biological and pharmacological effects including cytotoxic [1,2], antifungal [3,4], bactericidal, hemolytic, antiviral and antiparasitic properties [5]. Some glycosides are capable to induce apoptosis, inhibit the growth of tumor cells [6] and have immunomodulatory properties [7].…”

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

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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.

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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

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“…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%

“…In sea cucumber saponins, sulfation of the oligosaccharide chain in the Xyl, Glc and MeGlc residues has been reported [38,40,46,53,54]. Most of them are mono-sulfated glycosides with few occurrences of di- and tri-sulfated glycosides.…”

Section: Introductionmentioning

confidence: 99%

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

2014

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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.

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“…The majority of these saponins contain an aglycon based on a “holostanol” skeleton [3β,20 S -dihydroxy-5α-lanostano-18,20-lactone] and a sugar chain of two to six monosaccharide units linked to the C-3 of the aglycon [1]. These substances have a wide spectrum of biological effects: antifungal, cytotoxic, hemolytic, cytostatic, and immunomodulatory activities [2].…”

Section: Introductionmentioning

confidence: 99%

Patagonicosides B and C, Two Antifungal Sulfated Triterpene Glycosides from the Sea Cucumber Psolus patagonicus

Careaga

Muniain

Maier

2011

Chemistry & Biodiversity

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Two new triterpene glycosides, patagonicosides B (2) and C (3), together with the known patagonicoside A (1), have been isolated from the ethanolic extract of the sea cucumber Psolus patagonicus. The structures of the new compounds were established on the basis of extensive NMR spectroscopy (1H and13C NMR,1H–1H COSY, HMBC, HSQC, TOCSY, and NOESY), HRESIMS, and chemical transformations. Compounds 1–3 and their desulfated analogs showed antifungal activity against the phytopathogenic fungus Cladosporium cladosporoides in a dose dependent activity.

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Biologically Active Triterpene Glycosides from Sea Cucumbers (Holothuroidea, Echinodermata)

Cited by 28 publications

References 32 publications

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

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

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

Patagonicosides B and C, Two Antifungal Sulfated Triterpene Glycosides from the Sea Cucumber Psolus patagonicus

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