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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.

Abstract：

: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.

journal_name

Mar Drugs

journal_title

Marine drugs

authors

Silchenko AS,Kalinovsky AI,Avilov SA,Kalinin VI,Andrijaschenko PV,Dmitrenok PS,Chingizova EA,Ermakova SP,Malyarenko OS,Dautova TN

doi

10.3390/md15080256

subject

Has Abstract

pub_date

2017-08-16 00:00:00

issue

issn

1660-3397

pii

md15080256

journal_volume

pub_type

杂志文章

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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.