Triterpene Saponins from the Sea Cucumber Stichopus chloronotus (original) (raw)
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Saponins Isolated from the Vietnamese Sea Cucumber Stichopus Chloronotus
Using various chromatographic methods, three triterpene saponins neothyonidioside (1), stichoposide D (2), and holothurin B (3), were isolated from the methanol extract of the sea cucumber Stichopus chloronotus. Their structures were elucidated by 1D and 2D-NMR experiments and comparison of their NMR data with reported values. Compound 1 was isolated from S. chloronotus for the first time.
Rapid Profiling of Saponin Extracts from Stichopus horrens Sea Cucumbers by Mass Spectrometry
Philippine Journal of Science
Sea cucumbers produce bioactive compounds known as saponins. Structurally, these triterpene glycosides contain different sugar moieties that are attached to a lanostane-based aglycone backbone. This study aims to rapidly profile the saponins of the Philippine sea cucumber, Stichopus cf. horrens, by mass spectrometry (MS). MS and tandem MS (MS/MS) were acquired using a UPLC-QToF (ultra-performance liquid chromatography–quadrupole time-of-flight) mass spectrometer. The aglycone and glycan components of the saponins were determined from the corresponding MS2 spectra. A total of 22 saponins were detected, nine of which were similar to known sea cucumber saponins. Some of these saponins – such as holothurinoside C, holothurinoside H, impatienoside A, and stichloroside A2/B2 – have been shown to be effective as antitumor, anti-cancer, or antifungal compounds. The other 13 saponins we detected appear to be unique as these have not been previously reported. Glycan and potential aglycone com...
Article Discovery of Novel Saponins from the Viscera of the Sea Cucumber Holothuria lessoni
2014
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
The edible portion of sea cucumber, body walls, is a source of natural bioactive compounds. Triterpene saponins are the main chemical constituents in sea cucumber that have potential interest for the body health and food industry. Twenty-one lanostane-type non-sulphated triterpene glycosides were isolated from the methanol/ methylene chloride extract of the body walls of Bohadschia cousteaui. Ten new saponins called coustesides A (1), B (3), C (9), D (10), E (11), F (12), G (15), H (16), I (17) and J (18), including two pentasaccharide and eight hexasaccharide saponins, together with eleven known triterpene glycosides, were isolated by reversed-phase semi-preparative HPLC. Their structures were mainly determined by 1D- and 2D-NMR (1H, 13C, COSY, TOCSY, HSQC, HMBC and ROESY) as well as MS experiments and acid hydrolysis. Most of the isolated compounds showed good antifungal activity against Candida albicans. Moreover, sea cucumber B. cousteaui is a rich source of biologically active saponins. Therefore, sea cucumbers are eaten for their therapeutic values as a functional food than for their seafood taste.
Marine Drugs, 2014
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.
Structural Elucidation of Novel Saponins in the Sea Cucumber Holothuria lessoni
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.
Structure Elucidation of Novel Saponins in the Sea Cucumber Holothuria lessoni
Marine Drugs
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.
Discovery of Novel Saponins from the Viscera of the Sea Cucumber Holothuria lessoni
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
Saponins of North Atlantic Sea Cucumber: Chemistry, Health Benefits, and Future Prospectives
Marine Drugs
Frondosides are the major saponins (triterpene glycosides) of the North Atlantic sea cucumber (Cucumaria frondosa). Frondosides possess amphiphilic characteristics due to the presence of various hydrophilic sugar moieties and hydrophobic genin (sapogenin). Saponins are abundant in holothurians, especially in sea cucumbers that are widely distributed across the Northern Atlantic Ocean. Over 300 triterpene glycosides have been isolated, identified, and categorized from many species of sea cucumbers. Furthermore, specific saponins from C. frondosa are broadly classified into frondosides, fallaxosides, lefevreiosides, cucumariosides, and colochirosides. Recent studies have shown that frondoside-containing extracts from C. frondosa exhibit anticancer, anti-obesity, anti-hyperuricemic, anticoagulant, antioxidant, antimicrobial, antiangiogenic, antithrombotic, anti-inflammatory, antitumor, and immunomodulatory activities. However, the exact mechanism(s) of action of biological activities o...
Marine Drugs
Sea cucumbers are an important ingredient of traditional folk medicine in many Asian countries, which are well-known for their medicinal, nutraceutical, and food values due to producing an impressive range of distinctive natural bioactive compounds. Triterpene glycosides are the most abundant and prime secondary metabolites reported in this species. They possess numerous biological activities ranging from anti-tumour, wound healing, hypolipidemia, pain relieving, the improvement of nonalcoholic fatty livers, anti-hyperuricemia, the induction of bone marrow hematopoiesis, anti-hypertension, and cosmetics and anti-ageing properties. This study was designed to purify and elucidate the structure of saponin contents of the body wall of sea cucumber Holothuria lessoni and to compare the distribution of saponins of the body wall with that of the viscera. The body wall was extracted with 70% ethanol, and purified by a liquid-liquid partition chromatography, followed by isobutanol extraction...