Triterpene Glycosides from Sea Cucumbers and Their Biological Activities

Kim, Se‐Kwon; Himaya, S.W.A.

doi:10.1016/b978-0-12-416003-3.00020-2

Cited by 83 publications

(109 citation statements)

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“…It was also found that some sulphated saponins have potential antitumor activity (Yu et al, 2015). Overall, sea cucumber saponins have been widely studied for their biological activities, such as anticancer and antiviral activities (Kim & Himaya, 2012). Despite the biological activity and the pharmacological actions of sea cucumber saponins being well-known, limited studies about digestion and absorption characteristics of sea cucumber saponins have been reported.…”

Section: Introductionmentioning

confidence: 99%

Absorption and pharmacokinetic study of two sulphated triterpenoid saponins in rat after oral and intravenous administration of saponin extracts of Pearsonothuria graeffei by HPLC-MS

Song

Cong

et al. 2016

Journal of Functional Foods

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Section: Introductionmentioning

confidence: 99%

Absorption and pharmacokinetic study of two sulphated triterpenoid saponins in rat after oral and intravenous administration of saponin extracts of Pearsonothuria graeffei by HPLC-MS

Song

Cong

et al. 2016

Journal of Functional Foods

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“…They are reported primarily as typical metabolites of terrestrial plants [25]. A few marine species belonging to the phylum Echinodermata [26] namely holothuroids (sea cucumbers) [7,10,13,27,28,29,30,31,32,33] and asteroids, and sponges from the phylum Porifera [13,34,35] produce saponins.…”

Section: Introductionmentioning

confidence: 99%

“…The majority of sea cucumber saponins, generally known as Holothurins, are usually triterpene glycosides, belonging to the holostane type group rather than nonholostane [36,37], which is comprised of a lanostane-3β-ol type aglycone containing a γ-18 (20)-lactone in the d -ring of tetracyclic triterpene (3β,20 S -dihydroxy-5α-lanostano-18,20-lactone) [25] sometimes containing shortened side chains, and a carbohydrate moiety consisting of up to six monosaccharide units covalently connected to C-3 of the aglycone [7,8,13,37,38,39,40,41,42]. …”

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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“…Toxinology DOI 10.1007/978-94-007-6650-1_3-1 # Springer Science+Business Media Dordrecht 2014 During the last decade there have been several reviews of the published investigations of the cytotoxic activities of triterpene glycosides. These summaries have shown specific correlations between the structure of the triterpenoid saponins and their cytotoxicity and most common biological mechanisms of action (Kalinin et al 2008;Podolak et al 2010;Osbourn et al 2011;Kim and Himaya 2012).…”

Section: Sea Cucumber Triterpene Glycosides Immunomodulatory Propertiesmentioning

confidence: 96%

“…Cytotoxic activity of sea cucumber glycosides against different cell types and cell lines, including human tumor cell lines, has been extensively studied. These studies have shown strong cytolytic effects upon tumor cells in vitro (Kalinin et al 2008;Podolak et al 2010;Osbourn et al 2011;Kim and Himaya 2012).…”

Section: Sea Cucumber Triterpene Glycosides Immunomodulatory Propertiesmentioning

confidence: 96%

Immunomodulatory Properties of Sea Cucumber Triterpene Glycosides

Aminin

2014

Marine and Freshwater Toxins

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Sea cucumbers (or holothurians) belonging to the class Holothuroidea (Echinodermata) are marine invertebrate habitually found in the benthic areas and deep seas across the world. Many holothurians are known to be toxic. Triterpene glycosides are the main poison compounds of the sea cucumbers and play a role in the defense of holothuroids as a toxin. The triterpene glycosides are composed of a carbohydrate chain and triterpene aglycone and are widely distributed in sea cucumbers. Most aglycones have 18(20)-lactones and belong to the holostane type. Carbohydrate chains of sea cucumber glycosides have from two to six monosaccharide residues including xylose, quinovose, glucose and 3-O-methylglucose and sometimes 3-O-methylxylose, 3-О-methylquinovose, 3-О-methylglucuronic acid and 6-О-acetylglucose. They may contain one, two or three sulfate groups. At the micromolar concentrations sea cucumber glycosides show hemolytic, cytotoxic, antifungal and other biological activities caused by membranotropic action. Some sea cucumber glycosides show an immunostimulatory effect at sub-toxic nanomolar concentrations. Incubation of immune cells with the glycosides induces their activation resulting in an increase of immune cell adhesion on an extracellular matrix, enhancement of cell spreading and motility, increase of macrophage lysosomal activity, ROS formation and phagocytic activity. Injection of sub-toxic doses of some glycosides induces an increase in the number of antibody-producing plaque-forming cells in mouse spleens, an increase in the number, size and acidity of lysosomes of peritoneal macrophages, an increase of phagocytic index. It was shown that glycosides moderately induce production of some cytokines, restore the level of some CD-markers of lymphocytes, increase bactericidal activity of leucocytes and induce a significant increase in mouse resistance to lethal doses of some pathogenic microorganisms and radiation. A novel nanoparticulate antigen delivery system, tubular immunostimulating complex, consisting of cholesterol, triterpene glycoside cucumarioside A 2 -2, and glycolipid monogalactosyldiacylglycerol from marine macrophytes was developed. This complex influences cytokine mechanisms of immunological regulation and its adjuvant effect varied depending on its composition. Proteomic methods have demonstrated that the mechanism of immunomodulatory action of some sea cucumber glycosides on immune cells includes regulation of the expression of certain proteins involved in formation of the immune response. These glycosides regulate the expression of proteins associated with lysosome maturation, activation and merging, phagocytosis, cytoskeletal reorganization, cell adhesion, motility and proliferation of immune cells. It was found that the most likely membrane targets of cucumarioside A 2 -2 can be purinergic receptors of P2X family. These findings suggest that this glycoside can act as an allosteric regulator which able to withdraw purine receptor inactivation by extracellular ATP and provide a recovery ...

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Triterpene Glycosides from Sea Cucumbers and Their Biological Activities

Cited by 83 publications

References 48 publications

Absorption and pharmacokinetic study of two sulphated triterpenoid saponins in rat after oral and intravenous administration of saponin extracts of Pearsonothuria graeffei by HPLC-MS

Absorption and pharmacokinetic study of two sulphated triterpenoid saponins in rat after oral and intravenous administration of saponin extracts of Pearsonothuria graeffei by HPLC-MS

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

Immunomodulatory Properties of Sea Cucumber Triterpene Glycosides

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