Psolusosides C3 and D2-D5, Five Novel Triterpene Hexaosides From the Sea Cucumber Psolus fabricii (Psolidae, Dendrochirotida): Chemical Structures and Bioactivities

Silchenko, Alexandra S.; Avilov, Sergey A.; Kalinovsky, Anatoly I.; Kalinin, Vladimir I.; Andrijaschenko, Pelageya V.; Dmitrenok, Pavel S.; Popov, Roman S.; Chingizova, Ekaterina A.; Kasakin, Marat F.

doi:10.1177/1934578x19861253

Cited by 9 publications

(40 citation statements)

References 11 publications

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“…The signal of the tertiary bearing oxygen carbon C(25) was deduced from the HMBC correlations between the signals of methyl groups H(26) (δ H 1.46, s) and H(27) (δ H 1.48, s) and the signal at δ C 81.3. This chemical shift was also close to that of the corresponding carbon (δ C 80.8, C(25)) in the spectrum of psolusoside D 3 [ 24 ]. So, the NMR and HR-ESI-MS data indicated the presence of a 25-hydroperoxy-23 E -ene fragment in the side chain of 1 .…”

Section: Resultssupporting

confidence: 61%

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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: 61%

“…So, the NMR and HR-ESI-MS data indicated the presence of a 25-hydroperoxy-23 E -ene fragment in the side chain of 1 . This is the third finding of a hydroperoxyl group in the triterpene glycosides aglycones of sea cucumbers [ 24 , 25 ].…”

Section: Resultsmentioning

confidence: 94%

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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“…Seven individual compounds 1-7, including mono-and disulfated, linear, and branched tetraosides, as well as monosulfated triosides, were isolated from the sea cucumber Psolus fabricii in addition to recently obtained non-sulfated hexaosides [14,15]. The structural analysis of the glycosides 1-7 demonstrated the variability of their aglycones and carbohydrate chains.…”

Section: Discussionmentioning

confidence: 98%

“…Really, the signal of C(6) was observed at δ(C) 67.5 and the signal of C(5) at δ(C) 75.5. Hence, these signals were shifted in comparison with corresponding signals (δC (6) at 62.1, δC (5) at 77.8) in non-sulfated glucose residue in the same position of carbohydrate chains of psolusosides, belonging to the group D [15]. The analogous shifting effects were observed for the signals C(2) and C(1) of the glucose occupying the fourth position of the carbohydrate chain of 1 and attached to C(4) of the xylose unit.…”

Section: Structural Elucidation Of the Glycosidesmentioning

confidence: 91%

“…Only two main compounds, 2 of 24 psolusosides A [10,11] and B [12,13], had been isolated in that time. Recently, we have recommenced the studies on the glycosides of P. fabricii that resulted in the isolation of eight new hexaosides, psolusosides C 1 -C 3 and D 1 -D 5 , as well as five previously known compounds [14,15]. Herein, we report the isolation and structural elucidation of six new glycosides, psolusosides E (2), F (3), G (4), H (5), H 1 (6), and I (7), as well as an earlier known psolusoside B (1), whose structure has been revised based on the modern NMR and HR MS techniques.…”

Section: Introductionmentioning

confidence: 99%

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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

et al. 2019

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Seven sulfated triterpene glycosides, psolusosides B (1), E (2), F (3), G (4), H (5), H1 (6), and I (7), along with earlier known psolusoside A and colochiroside D have been isolated from the sea cucumber Psolus fabricii collected in the Sea of Okhotsk. Herein, the structure of psolusoside B (1), elucidated by us in 1989 as a monosulfated tetraoside, has been revised with application of modern NMR and particularly MS data and proved to be a disulfated tetraoside. The structures of other glycosides were elucidated by 2D NMR spectroscopy and HR-ESI mass-spectrometry. Psolusosides E (2), F (3), and G (4) contain holostane aglycones identical to each other and differ in their sugar compositions and the quantity and position of sulfate groups in linear tetrasaccharide carbohydrate moieties. Psolusosides H (5) and H1 (6) are characterized by an unusual sulfated trisaccharide carbohydrate moiety with the glucose as the second sugar unit. Psolusoside I (7) has an unprecedented branched tetrasaccharide disulfated carbohydrate moiety with the xylose unit in the second position of the chain. The cytotoxic activities of the compounds 2–7 against several mouse cell lines—ascite form of Ehrlich carcinoma, neuroblastoma Neuro 2A, normal epithelial JB-6 cells, and erythrocytes—were quite different, at that hemolytic effects of the tested compounds were higher than their cytotoxicity against other cells, especially against the ascites of Ehrlich carcinoma. Interestingly, psolusoside G (4) was not cytotoxic against normal JB-6 cells but demonstrated high activity against Neuro 2A cells. The cytotoxic activity against human colorectal adenocarcinoma HT-29 cells and the influence on the colony formation and growth of HT-29 cells of compounds 1–3, 5–7 and psolusoside A was checked. The highest inhibitory activities were demonstrated by psolusosides E (2) and F (3).

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