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Mar Drugs
2017 Aug 16;158:. doi: 10.3390/md15080256.
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Nine New Triterpene Glycosides, Magnumosides A₁-A₄, B₁, B₂, C₁, C₂ and C₄, from the Vietnamese Sea Cucumber Neothyonidium (=Massinium) magnum: Structures and Activities against Tumor Cells Independently and in Synergy with Radioactive Irradiation.
Silchenko AS
,
Kalinovsky AI
,
Avilov SA
,
Kalinin VI
,
Andrijaschenko PV
,
Dmitrenok PS
,
Chingizova EA
,
Ermakova SP
,
Malyarenko OS
,
Dautova TN
.
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Nine new sulfated triterpene glycosides, magnumosides A₁ (1), A₂ (2), A₃ (3), A₄ (4), B₁ (5), B₂ (6), C₁ (7), C₂ (8) and C₄ (9) as well as a known colochiroside B₂ (10) have been isolated from the tropical Indo-West Pacific sea cucumber Neothynidium (=Massinium) magnum (Phyllophoridae, Dendrochirotida) collected in the Vietnamese shallow waters. The structures of new glycosides were elucidated by 2D NMR spectroscopy and mass-spectrometry. All the isolated new glycosides were characterized by the non-holostane type lanostane aglycones having 18(16)-lactone and 7(8)-double bond and differed from each other by the side chains and carbohydrate moieties structures. Magnumoside A₁ (1) has unprecedented 20(24)-epoxy-group in the aglycone side chain. Magnumosides of the group A (1-4) contained disaccharide monosulfated carbohydrate moieties, of the group B (5, 6)-tetrasaccharide monosulfated carbohydrate moieties and, finally, of the group C (7-9)-tetrasaccharide disulfated carbohydrate moieties. The cytotoxic activities of the compounds 1-9 against mouse spleen lymphocytes, the ascites form of mouse Ehrlich carcinoma cells, human colorectal carcinoma DLD-1 cells as well as their hemolytic effects have been studied. Interestingly, the erythrocytes were more sensitive to the glycosides action than spleenocytes and cancer cells tested. The compounds 3 and 7 significantly inhibited the colony formation and decreased the size of colonies of DLD-1 cancer cells at non-cytotoxic concentrations. Moreover, the synergism of effects of radioactive irradiation and compounds 3 and 7-9 at subtoxic doses on proliferation of DLD-1 cells was demonstrated.
Figure 1. Chemical structure of the glycosides 1–10 isolated from Neothyonidium magnum.
Figure 2. 1H,1H-COSY (—) and key HMBC (H→C) correlations for the aglycones of compounds 1–9.
Figure 3. Key ROESY correlations for the aglycones of compounds 1–9.
Figure 4. The aglycones fragmentation observed in the (−)ESI-MS/MS of compounds 1–9.
Figure 5. The hypothetic scheme of the aglycones biosynthesis of glycosides of N. magnum.
Figure 6. The effect of the glycosides 3, 7–9 on colony formation of DLD-1 cells. (A) The compounds decreased the number of colonies of cancer cells. (B) The compounds decreased the size of colonies of cancer cells. Data are shown as means ± standard deviation and the asterisks (* p < 0.05) indicates a significant decrease in colony formation of cells treated with the compounds compared with the control.
Figure 7. The effect of radioactive irradiation and a combination of radioactive irradiation and the compounds 3, 7–9 on DLD-1 cancer cell proliferation. DLD-1 cells (8.0 × 103) were treated with radiation 4 Gy and the compounds 3, 7–9 (2 µM) for 96 h. Cell viability was estimated using the MTS assay. Data are represented as the mean ± SD as determined from triplicate experiments. A Student’s t-test was used to evaluate the data with the following significance levels: * p < 0.05, ** p < 0.01.
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