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Mar. Drugs 2017, 15(8), 256; doi:10.3390/md15080256

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

1
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, Vladivostok 690022, Russia
2
A.V. Zhirmunsky Institute of Marine Biology Far East Branch of Russian Academy of Sciences, Palchevsky St. 17, Vladivostok 690041, Russia
*
Author to whom correspondence should be addressed.
Received: 25 July 2017 / Revised: 8 August 2017 / Accepted: 11 August 2017 / Published: 16 August 2017
(This article belongs to the Special Issue Marine Glycosides)
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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 (14) contained disaccharide monosulfated carbohydrate moieties, of the group B (5, 6)—tetrasaccharide monosulfated carbohydrate moieties and, finally, of the group C (79)—tetrasaccharide disulfated carbohydrate moieties. The cytotoxic activities of the compounds 19 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 79 at subtoxic doses on proliferation of DLD-1 cells was demonstrated. View Full-Text
Keywords: Neothyonidium magnum; triterpene glycosides; magnumosides; sea cucumber; cytotoxic activity; radioactive irradiation Neothyonidium magnum; triterpene glycosides; magnumosides; sea cucumber; cytotoxic activity; radioactive irradiation
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Silchenko, A.S.; Kalinovsky, A.I.; Avilov, S.A.; Kalinin, V.I.; Andrijaschenko, P.V.; Dmitrenok, P.S.; Chingizova, E.A.; Ermakova, S.P.; Malyarenko, O.S.; Dautova, T.N. 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. Mar. Drugs 2017, 15, 256.

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