A New Triterpene Glycoside from the Sea  Cucumber Holothuria Scabra Collected in Vietnam

Thành, Nguyễn Văn; Dang, Nguyen Hai; Kiệm, Phan Văn; Cường, Nguyễn Xuân; Hương, Hoàng Thanh; Minh, Châu Văn

doi:10.29037/ajstd.113

Cited by 15 publications

(11 citation statements)

References 6 publications

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“…[3] The 1 H-NMR spectrum of 1 revealed four anomeric proton signals at δ in table 1. These data were similar to those reported, [4,5] confirming the sugar chain as 3-Omethyl-β-D-glucopyranosyl-(13)-β-D-glucopyranosyl-(14)-β-D-quinovopyranosyl-(12)-4-Osodium sulfate-β-D-xylopyranoside, one common tetraglycoside chain of saponins obtained from Holothuria species. [3] In addition, the 1 [5] Similarly, detailed analysis of the 1D, 2D NMR, and HR-QTOF-MS data as well as comparison of them with the literature values (table 1) led to identification of 3 and 4 as pervicoside C [7] and holothurin A, [4,5] respectively.…”

Section: Resultssupporting

confidence: 90%

Triterpene tetraglycosides from the Vietnamese sea cucumber Holothuria impatiens

Vien

Hạnh

Hương

et al. 2018

Vietnam Journal of Chemistry

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Four triterpene tetraglycosides were isolated from a methanol extract of the Vietnamese sea cucumber Holothuria impatiens by various chromatographic separations. Their structures were elucidated as 25‐hydroxy fuscocineroside B (1), fuscocineroside B (2), pervicoside C (3), and holothurin A (4) by using extensive NMR spectroscopic analysis as well as comparison of the NMR and MS data with those reported. This is the first report of 1 and 2 from H. impatiens.

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Section: Resultssupporting

confidence: 90%

Triterpene tetraglycosides from the Vietnamese sea cucumber Holothuria impatiens

Vien

Hạnh

Hương

et al. 2018

Vietnam Journal of Chemistry

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“…We recently demonstrated that trepang preparation does not significantly alter the saponin contents, compared to that of fresh animals. However, to the best of our knowledge, the saponin content of the viscera of H. scabra is, to date, not reported [37][38][39][40].…”

Section: Introductionmentioning

confidence: 99%

“…The monodesmosidic triterpene saponins of H. scabra consist of a holostanol-based aglycone and a C3-anchored glycan that is either linear or branched, and may contain up to 6 monosaccharide units (see Figure 1) [17,[37][38][39][40][41]. Honey-Escandón et al reported, in their review, the presence of sulfated and non-sulfated saponins in various organs of sea cucumbers, such as the body wall [17].…”

Section: Introductionmentioning

confidence: 99%

Microwave-Assisted Desulfation of the Hemolytic Saponins Extracted from Holothuria scabra Viscera

et al. 2022

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Saponins are plant and marine animal specific metabolites that are commonly considered as molecular vectors for chemical defenses against unicellular and pluricellular organisms. Their toxicity is attributed to their membranolytic properties. Modifying the molecular structures of saponins by quantitative and selective chemical reactions is increasingly considered to tune the biological properties of these molecules (i) to prepare congeners with specific activities for biomedical applications and (ii) to afford experimental data related to their structure–activity relationship. In the present study, we focused on the sulfated saponins contained in the viscera of Holothuria scabra, a sea cucumber present in the Indian Ocean and abundantly consumed on the Asian food market. Using mass spectrometry, we first qualitatively and quantitatively assessed the saponin content within the viscera of H. scabra. We detected 26 sulfated saponins presenting 5 different elemental compositions. Microwave activation under alkaline conditions in aqueous solutions was developed and optimized to quantitatively and specifically induce the desulfation of the natural saponins, by a specific loss of H2SO4. By comparing the hemolytic activities of the natural and desulfated extracts, we clearly identified the sulfate function as highly responsible for the saponin toxicity.

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“…Please check your intended meaning is retainedOne aglycone and two saponins were tentatively identified comparing their m/z values to those reported in the literature. The peaks appearing at 15.86, 16.81, and 20.68 min are holothurinogenin B, holothurinoside K 1 , and philinopgenin B, respectively [34][35][36]. During this investigation, molecular ions with m/z values ranging from 200-800 [M + H] + were observed in abundance, indicating the presence of aglycones or saponins with low molecular weight.…”

Section: Phytochemical Profile Of H Atra Saponinmentioning

confidence: 79%

Cytotoxic Desulfated Saponin from Holothuria atra Predicted to Have High Binding Affinity to the Oncogenic Kinase PAK1: A Combined In Vitro and In Silico Study

et al. 2018

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Sea cucumbers have long been utilized in foods and Asiatic folk medicines for their nutritive and health benefits. Herein, three sea cucumber species were investigated and showed the highest cytotoxicity among these. Next, a desulfated saponin, desulfated echinoside B (DEB), was purified from through bioassay-guided fractionation. LC-ESI-MS (Liquid chromatography-electrospray ionization mass spectrometry) analysis also showed to be a rich source of saponins. DEB showed cytotoxicity on cancer cells with IC values of 0.5⁻2.5 µM, and on brine shrimps with an IC value of 9.2 µM. In molecular docking studies, DEB was found to bind strongly with the catalytic domain of PAK1 (p21-activated kinase 1) and it showed binding energy of -8.2 kcal/mol compared to binding energy of -7.7 kcal/mol for frondoside A (FRA). Both of them bind to the novel allosteric site close to the ATP-binding cleft. Molecular dynamics (MD) simulation demonstrated that DEB can form a more stable complex with PAK1, remaining inside the allosteric binding pocket and forming the maximum number of hydrogen bonds with the surrounding residues. Moreover, important ligand binding residues were found to be less fluctuating in the DEB-PAK1 complex than in the FRA-PAK1 complex throughout MD simulation. Our experimental and computational studies showed that both DEB and FRA can act as natural allosteric PAK1 inhibitors and DEB appeared to be more promising than FRA.

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A New Triterpene Glycoside from the Sea Cucumber Holothuria Scabra Collected in Vietnam

Cited by 15 publications

References 6 publications

Triterpene tetraglycosides from the Vietnamese sea cucumber Holothuria impatiens

Triterpene tetraglycosides from the Vietnamese sea cucumber Holothuria impatiens

Microwave-Assisted Desulfation of the Hemolytic Saponins Extracted from Holothuria scabra Viscera

Cytotoxic Desulfated Saponin from Holothuria atra Predicted to Have High Binding Affinity to the Oncogenic Kinase PAK1: A Combined In Vitro and In Silico Study

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