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Mar Drugs
2020 Jul 28;188:. doi: 10.3390/md18080394.
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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.
Silchenko AS
,
Kalinovsky AI
,
Avilov SA
,
Andrijaschenko PV
,
Popov RS
,
Dmitrenok PS
,
Chingizova EA
,
Ermakova SP
,
Malyarenko OS
,
Dautov SS
,
Kalinin VI
.
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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%.
Figure 1. Chemical structures of glycosides isolated from Colochirus quadrangularis:
1âquadrangularisoside A; 2âquadrangularisoside A1; 3âquadrangularisoside B; 4âquadrangularisoside B1; 5âquadrangularisoside B2; 6âquadrangularisoside C; 7âquadrangularisoside C1; 8âquadrangularisoside D; 9âquadrangularisoside D1, 10âquadrangularisoside D2; 11âquadrangularisoside D3; 12âquadrangularisoside D4; 13âquadrangularisoside E.
Figure 2. The effect of radioactive irradiation and a combination of radioactive irradiation and glycosides 1â13 on HT-29 cancer cells colony formation. HT-29 cells (8.0 à 103) were cultured in the presence or absence of 0.02 μM compounds for an additional 24 h before irradiation at the dose of 1 Gy. Immediately after irradiation, cells were returned to the incubator for recovery. Three hours later, the cells were harvested and used for soft agar assay. Data are represented as the mean ± SD as determined from triplicate experiments. A Studentâs t-test was used to evaluate the data with the following significance levels: ** p < 0.01.
Figure 3. The biosynthetic network of triterpene glycosides from C. quadrangularis.
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