Triterpene Glycosides from Sea Cucucmbers (Holothurioidea, Echinodermata). Biological Activities and Functions

Kalinin, Vladimir I.; Aminin, Dmitry L.; Avilov, Sergey A.; Silchenko, Alexandra S.; Stonik, Valentin A.

doi:10.1016/s1572-5995(08)80006-3

Cited by 90 publications

(174 citation statements)

References 64 publications

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“…Some recent studies have highlighted the large diversity of triterpene glycosides present in holothuroid tissues (Kobayashi et al, 1991;Kalinin et al, 2008;Maier, 2008). In H. forskali, 26 different saponins have been described in the Cuvierian tubules and 12 have been described in the body wall (Rodrigez et al, 1991;Van Dyck et al, 2009).…”

Section: Discussionmentioning

confidence: 99%

The triterpene glycosides of Holothuria forskali: usefulness and efficiency as a chemical defense mechanism against predatory fish

Dyck

Caulier

Todesco

et al. 2011

Journal of Experimental Biology

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SUMMARYMore than 100 triterpene glycosides (saponins) have been characterized in holothuroids in the past several decades. In particular, Holothuria forskali contains 26 saponins in its Cuvierian tubules and 12 in its body wall. This high diversity could be linked to a chemical defense mechanism, the most commonly accepted biological role for these secondary metabolites. We performed an integrated study of the body-wall saponins of H. forskali. The saponins are mainly localized in the epidermis and in the mesothelium of the body wall and appear to be released when the holothuroid is stressed. Among the saponins present in the epidermis, one (holothurinoside G) was detected in the seawater surrounding non-stressed holothuroids and three others (holohurinosides C and F, and desholothurin A) were secreted when the animals were stressed. In addition, two new congeners (detected at m/z 1301 and 1317) were also present in the immediate surroundings of stressed holothuroids. These new saponins do not originate from the epidermis and could come from an internal organ. Quantities of secreted saponins were very low compared with the body wall and Cuvierian tubules concentrations. At natural concentrations, saponins do not represent a threat to the health of predatory fish. The deterrent effect of saponins seems therefore to act as an aposematic signal, warning potential predators of the unpalatability of the holothuroid tissues.

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Section: Discussionmentioning

confidence: 99%

The triterpene glycosides of Holothuria forskali: usefulness and efficiency as a chemical defense mechanism against predatory fish

Dyck

Caulier

Todesco

et al. 2011

Journal of Experimental Biology

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“…None of these glycosides were active in these tests at the dosage studied (IC 50 > 100 µM/mL). This could be explained by the absence of the 18(20)-lactone moiety that is essential for the membranolytic action of sea cucumber glycosides and by the presence of three sulfate groups that decreased the membranolytic activity of the glycosides [12].…”

Section: Resultsmentioning

confidence: 99%

“…Non-holostane glycosides may play only a regulatory role and are evolutionary precursors of holostane glycosides [12].…”

Section: Resultsmentioning

confidence: 99%

Structures and Biogenesis of Fallaxosides D4, D5, D6 and D7, Trisulfated Non-Holostane Triterpene Glycosides from the Sea Cucumber Cucumaria fallax

et al. 2016

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Four new trisulfated triterpene glycosides, fallaxosides D 4 ( 1 ), D 5 ( 2 ), D 6 ( 3 ) and D 7 ( 4 ) have been isolated from the sea cucumber Cucumaria fallax (Cucumariidae, Dendrochirotida). The structures of the glycosides have been elucidated by 2D NMR spectroscopy and HRESIMS. All the glycosides have the lanostane aglycones of a rare non-holostane type with 7(8)-, 8(9)- or 9(11)-double bonds, one or two hydroxyl groups occupying unusual positions in the polycyclic nucleus and shortened or normal side chains. The pentasaccharide carbohydrate moieties of 1 – 4 have three sulfate groups. The cytotoxic activity of glycosides 1 – 4 against the ascite form of mouse Ehrlich carcinoma cells and mouse spleen lymphocytes and hemolytic activity against mouse erythrocytes have been studied.

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“…The basis of membranotropic action is the ability of glycosides to attach to cell biomembranes and form nonselective ion-conducting complexes with 5(6)-nonsaturated sterols of cell membranes, preferably with cholesterol. Such sterol/saponin interactions result in an efflux of some ions, substances of the nucleotide pool and peptides, disruption of ion homeostasis and osmolarity followed by lysis and cell death [5,6,7]. …”

Section: Introductionmentioning

confidence: 99%

“…These studies have shown that triterpene glycosides may inhibit the growth of pathogenic fungal microflora and block egg cleavage and the development of sea urchin embryos. They also suppress the proliferation of different types of human tumor cells in vitro, including leukemia P-388, KB, lymphoidal leukemia L 1210, Schabel, A-549, HT-29, Mel-28, MICF-1, IA9, CAKI-1, U-87-MG, PC-3, SK-MEL, and HCT-8 [7]. Some glycosides may induce tumor cell apoptosis in vitro [8,9,10].…”

Section: Introductionmentioning

confidence: 99%

Antitumor Activity of Cucumarioside A<sub>2</sub>-2

et al. 2013

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Background: The cytotoxic activity of sea cucumber glycosides against different types of cells and cell lines, including human tumor cell lines, has been studied for many years. However, the molecular mechanism(s) of the antitumor action of triterpene glycosides on cancer cells remain unclear. This article reports a continuation of investigations of triterpene glycoside cucumarioside A₂-2 isolated from the Far-Eastern sea cucumber Cucumaria japonica. It describes a study of glycoside anticancer activity in vivo and glycoside interaction with mouse Ehrlich carcinoma cells in vitro. Methods: The cytotoxicity of cucumarioside A₂-2 and its effect on apoptosis, the cell cycle, DNA biosynthesis and p53 activity, and glycoside anticancer action against Ehrlich carcinoma cells were studied. Results: Cucumarioside A₂-2 influences tumor cell viability at micromolar concentrations. The EC₅₀ for glycoside estimated by nonspecific esterase assay and MTT assay was 2.1 and 2.7 μM, respectively. Cucumarioside A₂-2 at a subcytotoxic range of concentrations exhibits a cytostatic effect by blocking cell proliferation and DNA biosynthesis in the S phase. It may induce apoptosis in tumor cells in a caspase-dependent way, bypassing the activation of the p53-dependent segment. Conclusion: The anticancer and proapoptotic properties of cucumarioside A₂-2 may be due to direct interaction of the glycoside with tumor cells. The in vivo anticancer effect of cucumarioside A₂-2 may be associated with the ability of the drug to arrest the cell cycle in the synthetic phase and induce programmed tumor cell death.

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Triterpene Glycosides from Sea Cucucmbers (Holothurioidea, Echinodermata). Biological Activities and Functions

Cited by 90 publications

References 64 publications

The triterpene glycosides of Holothuria forskali: usefulness and efficiency as a chemical defense mechanism against predatory fish

The triterpene glycosides of Holothuria forskali: usefulness and efficiency as a chemical defense mechanism against predatory fish

Structures and Biogenesis of Fallaxosides D4, D5, D6 and D7, Trisulfated Non-Holostane Triterpene Glycosides from the Sea Cucumber Cucumaria fallax

Antitumor Activity of Cucumarioside A<sub>2</sub>-2

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