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Mar Drugs
2019 Feb 01;172:. doi: 10.3390/md17020086.
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Molecular Networking-Based Analysis of Cytotoxic Saponins from Sea Cucumber Holothuria atra.
Grauso L
,
Yegdaneh A
,
Sharifi M
,
Mangoni A
,
Zolfaghari B
,
Lanzotti V
.
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The saponin composition of a specimen of black sea cucumber, Holothuria atra collected in the Persian Gulf was studied by a combined approach including LC-MS/MS, Molecular Networking, pure compound isolation, and NMR spectroscopy. The saponin composition of Holothuria atra turned out to be more complex than previously reported. The most abundant saponins in the extract (1⁻4) were isolated and characterized by 1D- and 2D-NMR experiments. Compound 1 was identified as a new triterpene glycoside saponin, holothurin A5. The side chain of the new saponin 1, unprecedented among triterpene glycosides, is characterized by an electrophilic enone function, which can undergo slow water or methanol addition under neutral conditions. The cytotoxic activity of compounds 1⁻4, evaluated on the human cervix carcinoma HeLa cell line, was remarkable, with IC50 values ranging from 1.2 to 2.5 µg/mL.
Figure 1. Major holothurins from black sea cucumber Holothuria atra collected in Persian Gulf.
Figure 2. MS/MS-based molecular network of the BuOH extract of H. atra. Each node is labeled with the parent mass. Node size is relative to ion count, edge thickness is relative to cosine score. Nodes with the same parent mass refer to isomeric compounds. They were automatically recognized by the MS-Cluster module of GNPS based on their different MS/MS spectra.
Figure 3. Diagnostic HMBC correlations for the oligosaccharide chain (green arrows), the holostane nucleus (blue arrows), and the side chain (red arrows) of compound 1.
Figure 4. (a) Scheme of the solvolysis reaction occurring between the α,β-unsaturated ketone in the side chain of holothurin A5 (1) and a solution of MeOH/H2O (1:1); (b) LC-MS analysis of compound 1 after having left the compound in a solution of MeOH/H2O (1:1). Two isomeric saponins at 1229.5 (addition of H2O) and two isomeric saponins at 1243.5 (addition of MeOH) appeared in the spectrum; (c) LC-MS analysis of compound 1 left in the same solution of MeOH/H2O (1:1) repeated after 16 weeks. The peaks of the additional saponins showed an increasing intensity.
Figure 5. A comparison of major triterpene glycosides found in the specimens of Holothuria atra studied so far.
Bordbar,
High-value components and bioactives from sea cucumbers for functional foods--a review.
2011, 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
Chambers,
A cross-platform toolkit for mass spectrometry and proteomics.
2012,
Pubmed
Dang,
Two new triterpene glycosides from the Vietnamese sea cucumber Holothuria scabra.
2007,
Pubmed
,
Echinobase
Farshadpour,
Antiviral activity of Holothuria sp. a sea cucumber against herpes simplex virus type 1 (HSV-1).
2014,
Pubmed
,
Echinobase
Haug,
Antibacterial activity in Strongylocentrotus droebachiensis (Echinoidea), Cucumaria frondosa (Holothuroidea), and Asterias rubens (Asteroidea).
2002,
Pubmed
,
Echinobase
Janakiram,
Sea Cucumbers Metabolites as Potent Anti-Cancer Agents.
2015,
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
Khotimchenko,
Pharmacological Potential of Sea Cucumbers.
2018,
Pubmed
,
Echinobase
Kicha,
Furostane Series Asterosaponins and Other Unusual Steroid Oligoglycosides from the Tropical Starfish Pentaceraster regulus.
2017,
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
Kupchan,
Bruceantin, a new potent antileukemic simaroubolide from Brucea antidysenterica.
1973,
Pubmed
Liu,
Antioxidant and antihyperlipidemic activities of polysaccharides from sea cucumber Apostichopus japonicus.
2012,
Pubmed
,
Echinobase
Mashjoor,
Holothurians antifungal and antibacterial activity to human pathogens in the Persian Gulf.
2017,
Pubmed
,
Echinobase
Mena-Bueno,
Sea cucumbers with an anti-inflammatory effect on endothelial cells and subcutaneous but not on epicardial adipose tissue.
2016,
Pubmed
,
Echinobase
Moosmann,
Cyanobacterial ent-Sterol-Like Natural Products from a Deviated Ubiquinone Pathway.
2017,
Pubmed
Shannon,
Cytoscape: a software environment for integrated models of biomolecular interaction networks.
2003,
Pubmed
Suleria,
Marine-Based Nutraceuticals: An Innovative Trend in the Food and Supplement Industries.
2015,
Pubmed
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
Wang,
Sharing and community curation of mass spectrometry data with Global Natural Products Social Molecular Networking.
2016,
Pubmed
Wu,
Anticoagulant and antithrombotic evaluation of native fucosylated chondroitin sulfates and their derivatives as selective inhibitors of intrinsic factor Xase.
2015,
Pubmed
Xu,
Three new cucurbitane triterpenoids from Hemsleya penxianensis and their cytotoxic activities.
2014,
Pubmed
Yuan,
Antifungal triterpene glycosides from the sea cucumber Bohadschia marmorata.
2009,
Pubmed
,
Echinobase
Zhu,
Cucurbitane-type triterpenes from the tubers of Hemsleya penxianensis and their bioactive activity.
2018,
Pubmed
