Structures and Bioactivities of Six New Triterpene Glycosides, Psolusosides E, F, G, H, H1, and I and the Corrected Structure of Psolusoside B from the Sea Cucumber Psolus fabricii

Silchenko, Alexandra S.; Kalinovsky, Anatoly I.; Avilov, Sergey A.; Kalinin, Vladimir I.; Andrijaschenko, Pelageya V.; Dmitrenok, Pavel S.; Popov, Roman S.; Chingizova, Ekaterina A.; Ermakova, Svetlana P.; Malyarenko, Olesya S.

doi:10.3390/md17060358

Cited by 18 publications

(64 citation statements)

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“…In the 1 H and 13 C NMR spectra of the aglycone part of 4 , the signals of holostane-type aglycone having 7(8)- and 25(26)-double bonds as well as a 16 β -acetoxy-group were observed ( Table 6 ). This aglycone is identical to that of pentactasides C [ 14 ] and II [ 15 ] isolated earlier from the same species and is frequently occurred in the glycosides of the sea cucumbers of the order Dendrochirotida [ 2 , 4 , 5 , 21 , 30 ].…”

Section: Resultssupporting

confidence: 68%

“…The analysis of the NMR data provided in the paper [ 14 ] allowed supposing the erroneous interpretation of these data by the authors. When the sulfate group is bonded to C(2) of the monosaccharide residue in the pyranose form, it resulted in the up-field shifting of the signal of anomeric carbon to δ C approximately 100 [ 30 ]. Whenever the signals of C(1) of a quinovose unit in pentactasides B and C were observed, δ C 102.5 and 102.9, correspondingly, indicating the absence of a sulfate group at C(2) of this residue.…”

Section: Resultsmentioning

confidence: 99%

“…Triterpene glycosides of the sea cucumbers are metabolites that are formed by the mosaic type of biosynthesis [ 30 , 37 ], i.e., the aglycones and carbohydrate moieties are biosynthesized simultaneously and independently from each other. One of the results of such biosynthesis is the appearance of the glycosides having sugar chains identical to each other but structurally diverse aglycones.…”

Section: Discussionmentioning

confidence: 99%

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Structures and Bioactivities of Quadrangularisosides A, A1, B, B1, B2, C, C1, D, D1–D4, and E from the Sea Cucumber Colochirus quadrangularis: The First Discovery of the Glycosides, Sulfated by C-4 of the Terminal 3-O-Methylglucose Residue. Synergetic Effect on Colony Formation of Tumor HT-29 Cells of these Glycosides with Radioactive Irradiation

et al. 2020

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Thirteen new mono-, di-, and trisulfated triterpene glycosides, quadrangularisosides A–D4 (1−13) have been isolated from the sea cucumber Colochirus quadrangularis, which was collected in Vietnamese waters. The structures of these glycosides were established by 2D NMR spectroscopy and HR-ESI (High Resolution Electrospray Ionization) mass spectrometry. The novel carbohydrate moieties of quadrangularisosides D–D4 (8−12), belonging to the group D, and quadrangularisoside E (13) contain three sulfate groups, with one of them occupying an unusual position—at C(4) of terminal 3-O-methylglucose residue. Quadrangularisosides A (1) and D3 (11) as well as quadrangularisosides A1 (2) and D4 (12) are characterized by the new aglycones having 25-hydroperoxyl or 24-hydroperoxyl groups in their side chains, respectively. The cytotoxic activities of compounds 1–13 against mouse neuroblastoma Neuro 2a, normal epithelial JB-6 cells, erythrocytes, and human colorectal adenocarcinoma HT-29 cells were studied. All the compounds were rather strong hemolytics. The structural features that most affect the bioactivity of the glycosides are the presence of hydroperoxy groups in the side chains and the quantity of sulfate groups. The membranolytic activity of monosulfated quadrangularisosides of group A (1, 2) against Neuro 2a, JB-6 cells, and erythrocytes was relatively weak due to the availability of the hydroperoxyl group, whereas trisulfated quadrangularisosides D3 (11) and D4 (12) with the same aglycones as 1, 2 were the least active compounds in the series due to the combination of these two structural peculiarities. The erythrocytes were more sensitive to the action of the glycosides than Neuro 2a or JB-6 cells, but the structure–activity relationships observed for glycosides 1–13 were similar in the three cell lines investigated. The compounds 3−5, 8, and 9 effectively suppressed the cell viability of HT-29 cells. Quadrangularisosides A1 (2), C (6), C1 (7), and E (13) possessed strong inhibitory activity on colony formation in HT-29 cells. Due to the synergic effects of these glycosides (0.02 μM) and radioactive irradiation (1 Gy), a decreasing of number of colonies was detected. Glycosides 1, 3, and 9 enhanced the effect of radiation by about 30%.

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Section: Resultssupporting

confidence: 68%

Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

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Structures and Bioactivities of Quadrangularisosides A, A1, B, B1, B2, C, C1, D, D1–D4, and E from the Sea Cucumber Colochirus quadrangularis: The First Discovery of the Glycosides, Sulfated by C-4 of the Terminal 3-O-Methylglucose Residue. Synergetic Effect on Colony Formation of Tumor HT-29 Cells of these Glycosides with Radioactive Irradiation

et al. 2020

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“…The cytotoxic activity against human colorectal adenocarcinoma HT-29 cells and the influence on the colony formation and growth of HT-29 cells by psolusosides B, E, F, H, H 1 , and I, along with psolusoside A as a control, were examined. The highest inhibitory activities were shown for psolusosides E and F [13].…”

mentioning

confidence: 95%

“…The third article concerns the function of the immunity of a lectin in producing this compound crinoid. Two articles concern steroid glycosides from starfish [11,12], and two others concern triterpene glycosides from sea cucumbers [13,14]. One article describes the effect of a glycosaminoglycan from the sea cucumber Apostichopus japonicus on hyperglycemia in the liver of insulin-resistant mice [17].…”

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confidence: 99%

Marine Glycoconjugates: Trends and Perspectives

2020

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Glycoconjugates play significant roles in biological systems and are used in medicine, for example as vaccines. Glycoproteins, peptidoglycans, lipopolysaccharides, and other biopolymer glycoconjugates are responsible for cellular interactions, including cell-cell recognition and the binding of cells to the intercellular matrix. These molecules perform signal, antigenic and transport functions, and participate in the formation of receptors and other important membrane and blood constituents. Due to the negative charges of some sulfated glycoconjugates and the binding of water, they are critical for maintaining the physical status of connective tissue [1]. Low molecular weight glycoconjugates, such as triterpene and steroidal glycosides [2][3][4], glycolipids, are also well known as molecules playing important internal and exterior roles. Diverse glycoconjugates show a very wide spectrum of biological activities, including defensive, cytotoxic, antitumor, immunomodulatory, and antioxidant properties. The water environment requires high solubility for signal or anti-predatory exometabolites of marine organisms, and carbohydrate moieties provide this property. All these peculiarities explain the very wide diversity of glycoconjugates of marine origin, including those presented in the current Special Issue.Sterol and sphingolipid glycoconjugates, which are widespread, but insufficiently studied metabolites of microalgae, were discussed by Stonik and Stonik in the review article. Glycosylated sterols play important biological roles in microalgae and show different beneficial properties useful for medicine and healthy food. Dietary sterols and their glycoconjugates of microalgae enter into marine invertebrates through food chains and may be converted into 7(8)-unsaturated sterols and their derivatives, such as polyhydroxylated sterols and, probably, glycosides of starfishes and sea cucumbers. The knowledge of microalgal glycosphingolipids still remains poor, despite intensive investigations. Some of them are important for their interactions with pathogens and may induce apoptosis in microalgae. They also participate in the termination of microalgal blooms [5].In their experimental article, Galasso et al. have discussed the obtaining and properties of a water-soluble bioactive fraction isolated from the toxic dinoflagellate Alexandrium minutem. This substance is a glycoprotein with a molecular weight above 20 kDa. It demonstrates specific antiproliferative activity (IC 50 = 0.4 µg/mL) against the A549 cell line (the human lung adenocarcinoma cells). Moreover, the glycoconjugate did not reveal a cytotoxicity against human normal lung fibroblasts (WI38), but induced cell death, triggered by mitochondrial autophagy (mitophagy) in tumor cells. No mitophagic events were activated by it in normal WI38 cells [6].Kostetsky et al. from the Far East Federal University (Vladivostok, Russia) have compared the fatty acid composition and thermal transitions of membrane lipids from green macroalgae Ulva lactuca, collected in the Sea of...

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Triterpene Glycosides from the Viscera of Sea Cucumber Apostichopus japonicus with Embryotoxicity

Liu,

Lu,

Yan

et al. 2024

Chemistry & Biodiversity

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Sea cucumbers release chemical repellents from their guts when they are in danger from predators or a hostile environment. To investigate the chemical structure of the repellent, we collected and chemically analyzed the viscera of stressed sea cucumbers (Apostichopus japonicus) in the Yellow Sea of China. Two undescribed triterpene glycosides (1 and 2), together with a known cladoloside A (3), were identified and elucidated as 3β‐O‐{2‐O‐[β‐D‐quinovopyranosyl]‐4‐O‐[3‐O‐methyl‐β‐D‐glucopyranosyl‐(1→3)‐β‐D‐glucopyranosyl]‐β‐D‐xylopyranosyl}‐holosta‐9(11),25(26)‐dien‐16‐one (1), 3β‐O‐{2‐O‐[β‐D‐glucopyranosyl]‐4‐O‐[3‐O‐methyl‐β‐D‐glucopyranosyl‐(1→3)‐β‐D‐glucopyranosyl]‐β‐D‐xylopyranosyl}‐holosta‐9(11),25(26)‐dien‐16‐one (2), 3β‐O‐{2‐O‐[3‐O‐methyl‐β‐D‐glucopyranosyl‐(1→3)‐β‐D‐xylopyranosyl‐(1→4)‐β‐D‐quinovopyranosyl]‐β‐D‐xylopyranosyl}‐holosta‐9(11),25(26)‐dien‐16‐one (3) by spectroscopic analysis, including HR‐ESI‐MS and NMR spectra. Compounds 1, 2, and 3 display embryonic toxicity, as indicated by their 96‐hour post‐fertilization lethal concentration (96 hpf‐LC50) values of 0.289, 0.536, and 0.091 μM, respectively. Our study discovered a class of triterpene glycoside compounds consisting of an oligosaccharide with four sugar units and a holostane aglycone. These compounds possess embryotoxicity and may serve as chemical defense molecules in marine benthic ecosystems.

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Structures and Bioactivities of Six New Triterpene Glycosides, Psolusosides E, F, G, H, H1, and I and the Corrected Structure of Psolusoside B from the Sea Cucumber Psolus fabricii

Cited by 18 publications

References 28 publications

Marine Glycoconjugates: Trends and Perspectives

Triterpene Glycosides from the Viscera of Sea Cucumber Apostichopus japonicus with Embryotoxicity

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