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Molecules 2016, 21(7), 939; doi:10.3390/molecules21070939

Structures and Biogenesis of Fallaxosides D4, D5, D6 and D7, Trisulfated Non-Holostane Triterpene Glycosides from the Sea Cucumber Cucumaria fallax

1
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, 690022 Vladivostok, Russia
2
P.P. Shirshov Institute of Oceanology of the Russian Academy of Sciences, Nakhimovsky Pr., 36, 117997 Moscow, Russia
*
Author to whom correspondence should be addressed.
Academic Editors: Vassilios Roussis and Efstathia Ioannou
Received: 24 June 2016 / Revised: 15 July 2016 / Accepted: 15 July 2016 / Published: 20 July 2016
(This article belongs to the Special Issue Triterpenes and Triterpenoids 2016)
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Abstract

Four new trisulfated triterpene glycosides, fallaxosides D4 (1), D5 (2), D6 (3) and D7 (4) have been isolated from the sea cucumber Cucumaria fallax (Cucumariidae, Dendrochirotida). The structures of the glycosides have been elucidated by 2D NMR spectroscopy and HRESIMS. All the glycosides have the lanostane aglycones of a rare non-holostane type with 7(8)-, 8(9)- or 9(11)-double bonds, one or two hydroxyl groups occupying unusual positions in the polycyclic nucleus and shortened or normal side chains. The pentasaccharide carbohydrate moieties of 14 have three sulfate groups. The cytotoxic activity of glycosides 14 against the ascite form of mouse Ehrlich carcinoma cells and mouse spleen lymphocytes and hemolytic activity against mouse erythrocytes have been studied. View Full-Text
Keywords: sea cucumbers; Cucumaria fallax; triterpene glycosides; fallaxosides; non-holostane glycosides sea cucumbers; Cucumaria fallax; triterpene glycosides; fallaxosides; non-holostane glycosides
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Silchenko, A.S.; Kalinovsky, A.I.; Avilov, S.A.; Andryjaschenko, P.V.; Dmitrenok, P.S.; Kalinin, V.I.; Chingizova, E.A.; Minin, K.V.; Stonik, V.A. Structures and Biogenesis of Fallaxosides D4, D5, D6 and D7, Trisulfated Non-Holostane Triterpene Glycosides from the Sea Cucumber Cucumaria fallax. Molecules 2016, 21, 939.

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