ECB-ART-43631
Front Chem
2014 Jan 01;2:77. doi: 10.3389/fchem.2014.00077.
Show Gene links
Show Anatomy links
Relationships between chemical structures and functions of triterpene glycosides isolated from sea cucumbers.
Park JI
,
Bae HR
,
Kim CG
,
Stonik VA
,
Kwak JY
.
???displayArticle.abstract???
Many marine triterpene glycosides have in vitro and in vivo activities with very low toxicity, suggesting that they are suitable agents for the prevention and treatment of different diseases, particularly cancer. However, the molecular mechanisms of action of natural marine compounds in cancer, immune, and other various cells are not fully known. This review focuses on the structural characteristics of marine triterpene glycosides and how these affect their biological activities and molecular mechanisms. In particular, the membranotropic and membranolytic activities of frondoside A and cucumariosides from sea cucumbers and their ability to induce cytotoxicity and apoptosis have been discussed, with a focus on structure-activity relationships. In addition, the structural characteristics and antitumor effects of stichoposide C and stichoposide D have been reviewed along with underlying their molecular mechanisms.
???displayArticle.pubmedLink??? 25250309
???displayArticle.pmcLink??? PMC4159031
???displayArticle.link??? Front Chem
Genes referenced: LOC100887844
???attribute.lit??? ???displayArticles.show???
References [+] :
Agafonova,
Influence of cucumariosides upon intracellular [Ca2+]i and lysosomal activity of macrophages.
2003, Pubmed,
Echinobase
Agafonova, Influence of cucumariosides upon intracellular [Ca2+]i and lysosomal activity of macrophages. 2003, Pubmed , Echinobase
Al Marzouqi, Frondoside A inhibits human breast cancer cell survival, migration, invasion and the growth of breast tumor xenografts. 2011, Pubmed , Echinobase
Aminin, Triterpene glycoside cucumarioside A(2)-2 from sea cucumber stimulates mouse immune cell adhesion, spreading, and motility. 2011, Pubmed , Echinobase
Aminin, Immunomodulatory properties of Cumaside. 2006, Pubmed , Echinobase
Aminin, Antitumor activity of the immunomodulatory lead Cumaside. 2010, Pubmed , Echinobase
Aminin, Immunomodulatory Properties of Cucumariosides from the Edible Far-Eastern Holothurian Cucumaria japonica. 2001, Pubmed , Echinobase
Anisimov, [Triterpene glycosides and the structural-functional properties of membranes]. 1987, Pubmed
Antonov, Triterpene glycosides from Antarctic sea cucumbers III. Structures of liouvillosides A(4) and A(5), two minor disulphated tetraosides containing 3-O-methylquinovose as terminal monosaccharide units from the sea cucumber Staurocucumis liouvillei (Vaney). 2011, Pubmed , Echinobase
Antonov, Triterpene glycosides from Antarctic sea cucumbers. 1. Structure of liouvillosides A1, A2, A3, B1, and B2 from the sea cucumber Staurocucumis liouvillei: new procedure for separation of highly polar glycoside fractions and taxonomic revision. 2008, Pubmed , Echinobase
Antonov, Triterpene glycosides from Antarctic sea cucumbers. 2. Structure of Achlioniceosides A(1), A(2), and A(3) from the sea cucumber Achlionice violaecuspidata (=Rhipidothuria racowitzai). 2009, Pubmed , Echinobase
Attoub, Frondoside a suppressive effects on lung cancer survival, tumor growth, angiogenesis, invasion, and metastasis. 2013, Pubmed , Echinobase
Avilov, Koreoside A, a new nonholostane triterpene glycoside from the sea cucumber Cucumaria koraiensis. 1997, Pubmed , Echinobase
Avilov, Triterpene glycosides from the Far-Eastern sea cucumber Pentamera calcigera. 1. Monosulfated glycosides and cytotoxicity of their unsulfated derivatives. 2000, Pubmed , Echinobase
Avilov, Synaptosides A and A1, triterpene glycosides from the sea cucumber Synapta maculata containing 3-O-methylglucuronic acid and their cytotoxic activity against tumor cells. 2008, Pubmed , Echinobase
Avilov, Triterpene glycosides from the Far Eastern sea cucumber Cucumaria conicospermium. 2003, Pubmed , Echinobase
Avilov, Triterpene glycosides from the far eastern sea cucumber Pentamera calcigera II: disulfated glycosides. 2000, Pubmed , Echinobase
Bordbar, High-value components and bioactives from sea cucumbers for functional foods--a review. 2011, Pubmed , Echinobase
Brown, Functions of lipid rafts in biological membranes. 1998, Pubmed
Choi, Ginsenoside Rg(3) decelerates hERG K(+) channel deactivation through Ser631 residue interaction. 2011, Pubmed
Choi, Ginsenoside Rg3 enhances large conductance Ca2+-activated potassium channel currents: a role of Tyr360 residue. 2011, Pubmed
Colorado-Ríos, HPLC-ESI-IT-MS/MS analysis and biological activity of triterpene glycosides from the Colombian marine sponge Ectyoplasia ferox. 2013, Pubmed
Dang, Two new triterpene glycosides from the Vietnamese sea cucumber Holothuria scabra. 2007, Pubmed , Echinobase
Fu, Glycyrrhizin inhibits the inflammatory response in mouse mammary epithelial cells and a mouse mastitis model. 2014, Pubmed
Gorshkova, Two different modes of inhibition of the rat brain Na+, K(+)-ATPase by triterpene glycosides, psolusosides A and B from the holothurian Psolus fabricii. 1999, Pubmed , Echinobase
Goñi, Sphingomyelinases: enzymology and membrane activity. 2002, Pubmed
Gulbins, Acid sphingomyelinase-derived ceramide signaling in apoptosis. 2002, Pubmed
Hannun, Principles of bioactive lipid signalling: lessons from sphingolipids. 2008, Pubmed
Holt, Modulation of host natural killer cell functions in breast cancer via prostaglandin E2 receptors EP2 and EP4. 2012, Pubmed
Hwang, 20-O-β-d-glucopyranosyl-20(S)-protopanaxadiol, a metabolite of ginseng, inhibits colon cancer growth by targeting TRPC channel-mediated calcium influx. 2013, Pubmed
Im, Yin and Yang of ginseng pharmacology: ginsenosides vs gintonin. 2013, Pubmed
Itoh, Effects of glycyrrhizin and glycyrrhetinic acid on (Na+ + K+)-ATPase of renal basolateral membranes in vitro. 1989, Pubmed
Iñiguez-Martinez, Triterpenoid oligoglycosides from the sea cucumber Stichopus parvimensis. 2005, Pubmed , Echinobase
Jin, Differential effects of triterpene glycosides, frondoside A and cucumarioside A2-2 isolated from sea cucumbers on caspase activation and apoptosis of human leukemia cells. 2009, Pubmed , Echinobase
Kalinin, System-theoretical (Holistic) approach to the modelling of structural-functional relationships of biomolecules and their evolution: an example of triterpene glycosides from sea cucumbers (Echinodermata, holothurioidea). 2000, Pubmed , Echinobase
Kalinin, Hemolytic activities of triterpene glycosides from the holothurian order Dendrochirotida: some trends in the evolution of this group of toxins. 1996, Pubmed , Echinobase
Kalinin, Glycosides from marine sponges (Porifera, Demospongiae): structures, taxonomical distribution, biological activities and biological roles. 2012, Pubmed
Kalinin, Structure of eximisoside A, a novel triterpene glycoside from the Far-Eastern sea cucumber psolus eximius. 1997, Pubmed , Echinobase
Kerr, In vivo and in vitro biosynthesis of saponins in sea cucumbers. 1995, Pubmed , Echinobase
Kim, Inhibitory effect of ginsenosides on NMDA receptor-mediated signals in rat hippocampal neurons. 2002, Pubmed
Kim, Triterpene glycosides from sea cucumbers and their biological activities. 2012, Pubmed , Echinobase
Kitagawa, [Bioactive marine natural products]. 1988, Pubmed
Kolesnick, Compartmentalization of ceramide signaling: physical foundations and biological effects. 2000, Pubmed
Kuznetsova, A comparative study in vitro of physiological activity of triterpene glycosides of marine invertebrates of echinoderm type. 1982, Pubmed , Echinobase
Lee, Effects of ginsenoside Rg3 on α9α10 nicotinic acetylcholine receptor-mediated ion currents. 2013, Pubmed
Lee, 20(S)-ginsenoside Rh2, a newly identified active ingredient of ginseng, inhibits NMDA receptors in cultured rat hippocampal neurons. 2006, Pubmed
Lee, Ginsenoside Rg₃ regulates GABAA receptor channel activity: involvement of interaction with the γ₂ subunit. 2013, Pubmed
Lee, Involvement of batrachotoxin binding sites in ginsenoside-mediated voltage-gated Na+ channel regulation. 2008, Pubmed
Lee, The effects of ginsenoside Rg(3) on human Kv1.4 channel currents without the N-terminal rapid inactivation domain. 2009, Pubmed
Levade, Signalling sphingomyelinases: which, where, how and why? 1999, Pubmed
Li, Astragaloside IV reduces cerebral edema post-ischemia/reperfusion correlating the suppression of MMP-9 and AQP4. 2013, Pubmed
Li, Echinoside A, a new marine-derived anticancer saponin, targets topoisomerase2alpha by unique interference with its DNA binding and catalytic cycle. 2010, Pubmed , Echinobase
Li, Review of the apoptosis pathways in pancreatic cancer and the anti-apoptotic effects of the novel sea cucumber compound, Frondoside A. 2008, Pubmed , Echinobase
Li, Proapoptotic triterpene electrophiles (avicins) form channels in membranes: cholesterol dependence. 2005, Pubmed
Lin, Ginsenoside Rb1 selectively inhibits the activity of L-type voltage-gated calcium channels in cultured rat hippocampal neurons. 2012, Pubmed
Lorent, Induction of highly curved structures in relation to membrane permeabilization and budding by the triterpenoid saponins, α- and δ-Hederin. 2013, Pubmed
Ma, Frondoside A inhibits breast cancer metastasis and antagonizes prostaglandin E receptors EP4 and EP2. 2012, Pubmed , Echinobase
McManus, An activator of calcium-dependent potassium channels isolated from a medicinal herb. 1993, Pubmed
Menchinskaya, Antitumor activity of cucumarioside A2-2. 2013, Pubmed , Echinobase
Mimaki, Cytotoxic activities and structure-cytotoxic relationships of steroidal saponins. 2001, Pubmed
Moraes, Mollisosides A, B1, and B2: minor triterpene glycosides from the New Zealand and South Australian sea cucumber Australostichopus mollis. 2005, Pubmed , Echinobase
Nah, Ginseng ginsenoside pharmacology in the nervous system: involvement in the regulation of ion channels and receptors. 2014, Pubmed
Nigrelli, Substances of potential biomedical importance from marine organisms. 1967, Pubmed
Pan, Ginsenoside Rg3 attenuates cell migration via inhibition of aquaporin 1 expression in PC-3M prostate cancer cells. 2012, Pubmed
Park, Frondoside A has an anti-invasive effect by inhibiting TPA-induced MMP-9 activation via NF-κB and AP-1 signaling in human breast cancer cells. 2012, Pubmed
Park, Relationships between chemical structures and functions of triterpene glycosides isolated from sea cucumbers. 2014, Pubmed
Pislyagin, Interaction of holothurian triterpene glycoside with biomembranes of mouse immune cells. 2012, Pubmed , Echinobase
Polikarpova, [Cytogenetic study of the mutagenicity of cucumarioside]. 1990, Pubmed , Echinobase
Robertson, Differential regulation of the aggressive phenotype of inflammatory breast cancer cells by prostanoid receptors EP3 and EP4. 2010, Pubmed
Roginsky, Anti-pancreatic cancer effects of a polar extract from the edible sea cucumber, Cucumaria frondosa. 2010, Pubmed , Echinobase
Shang, Ginsenoside Rb1 stimulates glucose uptake through insulin-like signaling pathway in 3T3-L1 adipocytes. 2008, Pubmed
Sil'chenko, [Monosulfated triterpene glycosides from Cucumaria okhotensis Levin et Stepanov, a new species of sea cucumbers from Sea of Okhotsk]. 2007, Pubmed , Echinobase
Silchenko, Structure of cucumarioside I2 from the sea cucumber Eupentacta fraudatrix (Djakonov et Baranova) and cytotoxic and immunostimulatory activities of this saponin and relative compounds. 2013, Pubmed , Echinobase
Silchenko, Triterpene glycosides from the sea cucumber Eupentacta fraudatrix. Structure and biological activity of cucumariosides B1 and B2, two new minor non-sulfated unprecedented triosides. 2012, Pubmed , Echinobase
Silchenko, Triterpene glycosides from the sea cucumber Eupentacta fraudatrix. Structure and biological action of cucumariosides A1, A3, A4, A5, A6, A12 and A15, seven new minor non-sulfated tetraosides and unprecedented 25-keto, 27-norholostane aglycone. 2012, Pubmed , Echinobase
Silchenko, Triterpene glycosides from the deep-water North-Pacific sea cucumber Synallactes nozawai Mitsukuri. 2002, Pubmed , Echinobase
Silchenko, Holothurins B(2), B(3), and B(4), new triterpene glycosides from mediterranean sea cucumbers of the genus holothuria. 2005, Pubmed , Echinobase
Silchenko, Triterpene glycosides from the sea cucumber Eupentacta fraudatrix. Structure and cytotoxic action of cucumariosides A2, A7, A9, A10, an, A13 and A14, seven new minor non-sulfated tetraosides and an aglycone with an uncommon 18-hydroxy group. 2012, Pubmed , Echinobase
Silchenko, Triterpene glycosides from the sea cucumber Eupentacta fraudatrix. Structure and biological action of cucumariosides I1, I3, I4, three new minor disulfated pentaosides. 2013, Pubmed , Echinobase
Silchenko, Structure and biological action of cladolosides B1, B2, C, C1, C2 and D, six new triterpene glycosides from the sea cucumber Cladolabes schmeltzii. 2013, Pubmed , Echinobase
Silchenko, Constituents of the sea cucumber Cucumaria okhotensis. Structures of okhotosides B1-B3 and cytotoxic activities of some glycosides from this species. 2008, Pubmed , Echinobase
Silchenko, Structure of cucumariosides H5, H6, H7 and H8, triterpene glycosides from the sea cucumber Eupentacta fraudatrix and unprecedented aglycone with 16,22-epoxy-group. 2011, Pubmed , Echinobase
Silchenko, Structures and cytotoxic properties of cucumariosides H₂, H₃ and H₄ from the sea cucumber Eupentacta fraudatrix. 2012, Pubmed , Echinobase
Silchenko, Structures and biological activities of typicosides A1, A2, B1, C1 and C2, triterpene glycosides from the sea cucumber Actinocucumis typica. 2013, Pubmed , Echinobase
Stonik, Toxins from sea cucumbers (holothuroids): chemical structures, properties, taxonomic distribution, biosynthesis and evolution. 1999, Pubmed , Echinobase
Strum, Lipid second messengers. A role in cell growth regulation and cell cycle progression. 1997, Pubmed
Taha, A house divided: ceramide, sphingosine, and sphingosine-1-phosphate in programmed cell death. 2006, Pubmed
Tian, PE, a new sulfated saponin from sea cucumber, exhibits anti-angiogenic and anti-tumor activities in vitro and in vivo. 2005, Pubmed , Echinobase
Tian, Philinopside E, a new sulfated saponin from sea cucumber, blocks the interaction between kinase insert domain-containing receptor (KDR) and alphavbeta3 integrin via binding to the extracellular domain of KDR. 2007, Pubmed , Echinobase
Timoshenko, Role of prostaglandin E2 receptors in migration of murine and human breast cancer cells. 2003, Pubmed
Tong, Philinopside A, a novel marine-derived compound possessing dual anti-angiogenic and anti-tumor effects. 2005, Pubmed , Echinobase
Uyama, Effects of cyclopiazonic acid, a novel Ca(2+)-ATPase inhibitor, on contractile responses in skinned ileal smooth muscle. 1992, Pubmed
Wang, Eicosanoids and cancer. 2010, Pubmed
Wang, Ginsenoside Re suppresses electromechanical alternans in cat and human cardiomyocytes. 2008, Pubmed
Wink, Secondary Metabolites from Plants Inhibiting ABC Transporters and Reversing Resistance of Cancer Cells and Microbes to Cytotoxic and Antimicrobial Agents. 2012, Pubmed
Wong, Saikosaponin-d, a novel SERCA inhibitor, induces autophagic cell death in apoptosis-defective cells. 2013, Pubmed
Xu, Astragaloside IV improved intracellular calcium handling in hypoxia-reoxygenated cardiomyocytes via the sarcoplasmic reticulum Ca-ATPase. 2008, Pubmed
Xu, Effect of the ginsenoside Rb1 on the spontaneous contraction of intestinal smooth muscle in mice. 2012, Pubmed
Yamasaki, Alterations by saponins of passive Ca2+ permeability and Na+-Ca2+ exchange activity of canine cardiac sarcolemmal vesicles. 1987, Pubmed
Yun, Stichoposide C induces apoptosis through the generation of ceramide in leukemia and colorectal cancer cells and shows in vivo antitumor activity. 2012, Pubmed , Echinobase
Yun, Lipid raft modulation by Rp1 reverses multidrug resistance via inactivating MDR-1 and Src inhibition. 2013, Pubmed
Zhang, Cytotoxic sulfated triterpene glycosides from the sea cucumber Pseudocolochirus violaceus. 2006, Pubmed , Echinobase
Zhang, Bioactive triterpene glycosides from the sea cucumber Holothuria fuscocinerea. 2006, Pubmed , Echinobase
Zhang, Two new bioactive triterpene glycosides from the sea cucumber Pseudocolochirus violaceus. 2006, Pubmed , Echinobase
Zhang, Philinopsides E and F, two new sulfated triterpene glycosides from the sea cucumber Pentacta quadrangularis. 2006, Pubmed , Echinobase
Zhao, Ds-echinoside A, a new triterpene glycoside derived from sea cucumber, exhibits antimetastatic activity via the inhibition of NF-κB-dependent MMP-9 and VEGF expressions. 2011, Pubmed , Echinobase
Zhao, In vitro and in vivo anti-tumour activities of echinoside A and ds-echinoside A from Pearsonothuria graeffei. 2012, Pubmed , Echinobase
Zou, Intercedensides D-I, cytotoxic triterpene glycosides from the sea cucumber Mensamaria intercedens Lampert. 2005, Pubmed , Echinobase