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Mar Drugs
2014 May 09;125:2633-67. doi: 10.3390/md12052633.
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Discovery of novel saponins from the viscera of the sea cucumber Holothuria lessoni.
Bahrami Y
,
Zhang W
,
Franco C
.
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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.
Figure 1. The thin-layer chromatography (TLC) pattern of a saponin mixture (A) and the high performance centrifugal partition chromatography (HCPCP) fractions (B) from the purified extracts of the viscera of the Holothuria lessoni sea cucumber using the lower phase of CHCl3-MeOH-H2O (7:13:8) system. The numbers under each lane indicate the fraction number of fractions in the fraction collector. Here, only the fractions 52 to 61 of one analysis (of 110 fractions) are shown as a representative.
Figure 2. The full-scan matrix-assisted laser desorption/ionization mass spectrometry (MALDI) mass spectrum of HPCPC Fraction 55 in the (+) ion mode.
Figure 3. Schematic fragmentation patterns of the ion detected at m/z 1303.6; (A) Fraction 15; (B) Fraction 14 and (C) Fraction 12. Full and dotted arrows show the two main feasible fragmentation pathways. The predominant peak (A and B) at m/z 507 corresponds to the key sugar residue and aglycone moiety. The major abundant peak (C) at m/z 523 corresponds to both the key sugar residue and aglycone moiety. Abbreviations; G = Glc, MG = MeGlc, Q = Qui, X = Xyl.
Figure 4. The full-scan MALDI mass spectrum of the isobutanol-enriched saponin extract from the viscera of the H. lessoni. A mass range of 600 to 1500 Da is shown here. It is noted that this spectrum is unique for this species.
Figure 5. The schematic diagram of the proposed isomeric structures of ion at m/z 1303.6.
Figure 6. (+) ion mode ESI-MS/MS spectrum of saponins detected at m/z 1287.6. This spectrum shows the presence of two different aglycones, which led to the isomeric saponins. Full and dotted arrows illustrate the two main possible fragmentation pathways.
Figure 7. A schematic diagram of the proposed isomeric structures of ion at m/z 1287.6.
Figure 8. Positive tandem MALDI spectrum analysis of the precursor ion (saponin) detected at m/z 1243.5. The figure shows the collision-induced fragmentation of parent ions at m/z 1243.5. The consecutive losses of sulfate group, aglycone, xylose (Xyl), quinovose (Qui) and 3-O-methylglucose (MeGlc) residues affords product ions detected at m/z 1123, 639, 507, 361and 185, respectively.
Figure 9. The structure of identified saponins in the viscera of H. lessoni.
Figure 10. (+) ESI-MS spectrum of saponins extract from the viscera of H. lessoni.
Figure 11. (+) ion mode ESI-MS spectrum of saponins extract from Fraction 14.
Figure 12. (+) Ion mode ESI-MS/MS spectrum of saponin detected at 1243.5 (Holothurin A). Full and dotted arrows show the two main feasible fragmentation pathways. The structure of saponin was elucidated on the base of tandem mass spectrometry.
Aminin,
Antitumor activity of the immunomodulatory lead Cumaside.
2010, Pubmed,
Echinobase
Aminin,
Antitumor activity of the immunomodulatory lead Cumaside.
2010,
Pubmed
,
Echinobase
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
Avilov,
Triterpene glycosides from the Far Eastern sea cucumber Cucumaria conicospermium.
2003,
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,
Triterpene glycosides from the far eastern sea cucumber Pentamera calcigera II: disulfated glycosides.
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
Bankefors,
Electrospray ionization ion-trap multiple-stage mass spectrometry of Quillaja saponins.
2011,
Pubmed
Bondoc,
Chemical fingerprinting and phylogenetic mapping of saponin congeners from three tropical holothurian sea cucumbers.
2013,
Pubmed
,
Echinobase
Bordbar,
High-value components and bioactives from sea cucumbers for functional foods--a review.
2011,
Pubmed
,
Echinobase
Caulier,
When a repellent becomes an attractant: harmful saponins are kairomones attracting the symbiotic Harlequin crab.
2013,
Pubmed
,
Echinobase
Chludil,
Cytotoxic and antifungal triterpene glycosides from the Patagonian sea cucumber Hemoiedema spectabilis.
2002,
Pubmed
,
Echinobase
Cui,
Rapid identification of saponins in plant extracts by electrospray ionization multi-stage tandem mass spectrometry and liquid chromatography/tandem mass spectrometry.
2000,
Pubmed
Cui,
Metal ion adducts in the structural analysis of ginsenosides by electrospray ionization with multi-stage mass spectrometry.
2001,
Pubmed
Dang,
Two new triterpene glycosides from the Vietnamese sea cucumber Holothuria scabra.
2007,
Pubmed
,
Echinobase
Du,
Isolation of dammarane saponins from Panax notoginseng by high-speed counter-current chromatography.
2003,
Pubmed
Fang,
Rapid analysis of steroidal saponin mixture using electrospray ionization mass spectrometry combined with sequential tandem mass spectrometry.
1998,
Pubmed
Francis,
The biological action of saponins in animal systems: a review.
2002,
Pubmed
Habermehl,
Aglycones of the toxins from the Cuvierian organs of Holothuria forskåli and a new nomenclature for the aglycones from holothurioideae.
1971,
Pubmed
,
Echinobase
Han,
Two new cytotoxic triterpene glycosides from the sea cucumber Holothuria scabra.
2009,
Pubmed
,
Echinobase
Han,
A novel sulfated holostane glycoside from sea cucumber Holothuria leucospilota.
2010,
Pubmed
,
Echinobase
Han,
Antifungal active triterpene glycosides from sea cucumber Holothuria scabra.
2009,
Pubmed
,
Echinobase
Iñiguez-Martinez,
Triterpenoid oligoglycosides from the sea cucumber Stichopus parvimensis.
2005,
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,
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,
Triterpene glycosides from sea cucumbers and their biological activities.
2012,
Pubmed
,
Echinobase
Kitagawa,
Marine natural products. XIV. Structures of echinosides A and B, antifungal lanostane-oligosides from the sea cucumber Actinopyga echinites (Jaeger).
1985,
Pubmed
,
Echinobase
Kitagawa,
Saponin and sapogenol. XV. Antifungal glycosides from the sea cucumber Stichopus japonicus selenka. (2). Structures of holotoxin A and holotoxin B.
1976,
Pubmed
,
Echinobase
Kupchan,
Bruceantin, a new potent antileukemic simaroubolide from Brucea antidysenterica.
1973,
Pubmed
Liu,
Structural analysis of saponins from medicinal herbs using electrospray ionization tandem mass spectrometry.
2004,
Pubmed
Liu,
Structure analysis of triterpene saponins in Polygala tenuifolia by electrospray ionization ion trap multiple-stage mass spectrometry.
2007,
Pubmed
Liu,
Argusides D and E, two new cytotoxic triterpene glycosides from the sea cucumber Bohadschia argus Jaeger.
2008,
Pubmed
,
Echinobase
Liu,
Argusides B and C, two new cytotoxic triterpene glycosides from the sea cucumber Bohadschia argus Jaeger.
2008,
Pubmed
,
Echinobase
Maier,
Two new cytotoxic and virucidal trisulfated triterpene glycosides from the Antarctic sea cucumber Staurocucumis liouvillei.
2001,
Pubmed
,
Echinobase
Matsuno,
Distribution and seasonal variation of toxic principles of sea-cucumber (Holothuria leucospilota Brandt).
1969,
Pubmed
,
Echinobase
Mercier,
Endogenous and exogenous control of gametogenesis and spawning in echinoderms.
2009,
Pubmed
,
Echinobase
Miyamoto,
Structures of four new triterpenoid oligoglycosides: DS-penaustrosides A, B, C, and D from the sea cucumber Pentacta australis.
1992,
Pubmed
,
Echinobase
Mohammadizadeh,
Evaluation of antibacterial, antifungal and cytotoxic effects of Holothuria scabra from the North Coast of the Persian Gulf.
2013,
Pubmed
,
Echinobase
Osbourn,
The saponins: polar isoprenoids with important and diverse biological activities.
2011,
Pubmed
,
Echinobase
Schöpke,
Structure elucidation of a glycoside of 2 beta, 3 beta, 23-trihydroxy-16-oxoolean-12-en-28-oic acid from Bellis bernardii using mass spectrometry for the sugar sequence determination.
1995,
Pubmed
Silchenko,
Holothurins B(2), B(3), and B(4), new triterpene glycosides from mediterranean sea cucumbers of the genus holothuria.
2005,
Pubmed
,
Echinobase
Song,
Multiple-stage tandem mass spectrometry for differentiation of isomeric saponins.
2004,
Pubmed
Stonik,
Toxins from sea cucumbers (holothuroids): chemical structures, properties, taxonomic distribution, biosynthesis and evolution.
1999,
Pubmed
,
Echinobase
Van Dyck,
Elucidation of molecular diversity and body distribution of saponins in the sea cucumber Holothuria forskali (Echinodermata) by mass spectrometry.
2009,
Pubmed
,
Echinobase
Van Dyck,
Qualitative and quantitative saponin contents in five sea cucumbers from the Indian ocean.
2010,
Pubmed
,
Echinobase
Van Dyck,
The triterpene glycosides of Holothuria forskali: usefulness and efficiency as a chemical defense mechanism against predatory fish.
2011,
Pubmed
,
Echinobase
Van Dyck,
Localization of secondary metabolites in marine invertebrates: contribution of MALDI MSI for the study of saponins in Cuvierian tubules of H. forskali.
2010,
Pubmed
,
Echinobase
Wang,
Determination of ginsenosides in plant extracts from Panax ginseng and Panax quinquefolius L. by LC/MS/MS.
1999,
Pubmed
Wu,
Nobilisides A - C, three new triterpene glycosides from the sea cucumber Holothuria nobilis.
2006,
Pubmed
,
Echinobase
Yuan,
Two new holostan-type triterpene glycosides from the sea cucumber Bohadschia marmorata JAEGER.
2008,
Pubmed
,
Echinobase
Yuan,
Antifungal triterpene glycosides from the sea cucumber Holothuria (Microthele) axiloga.
2009,
Pubmed
,
Echinobase
Zhang,
Philinopsides E and F, two new sulfated triterpene glycosides from the sea cucumber Pentacta quadrangularis.
2006,
Pubmed
,
Echinobase
Zhang,
Bioactive triterpene glycosides from the sea cucumber Holothuria fuscocinerea.
2006,
Pubmed
,
Echinobase
Zhang,
Cytotoxic sulfated triterpene glycosides from the sea cucumber Pseudocolochirus violaceus.
2006,
Pubmed
,
Echinobase
Zhang,
Cytotoxic triterpene glycosides from the sea cucumber Pseudocolochirus violaceus.
2007,
Pubmed
,
Echinobase
Zhang,
Two new bioactive triterpene glycosides from the sea cucumber Pseudocolochirus violaceus.
2006,
Pubmed
,
Echinobase
Zheng,
Rapid identification of C21 steroidal saponins in Cynanchum versicolor Bunge by electrospray ionization multi-stage tandem mass spectrometry and liquid chromatography/tandem mass spectrometry.
2007,
Pubmed
van Setten,
Multiple-stage tandem mass spectrometry for structural characterization of saponins.
1998,
Pubmed