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Structures and Biogenesis of Fallaxosides D(4), D(5), D(6) and D(7), Trisulfated Non-Holostane Triterpene Glycosides from the Sea Cucumber Cucumaria fallax
Four new trisulfated triterpene glycosides, fallaxosides D(4) (1), D(5) (2), D(6) (3) and D(7) (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 h...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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MDPI
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6274125/ https://www.ncbi.nlm.nih.gov/pubmed/27447601 http://dx.doi.org/10.3390/molecules21070939 |
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author | Silchenko, Alexandra S. Kalinovsky, Anatoly I. Avilov, Sergey A. Andryjaschenko, Pelageya V. Dmitrenok, Pavel S. Kalinin, Vladimir I. Chingizova, Ekaterina A. Minin, Kirill V. Stonik, Valentin A. |
author_facet | Silchenko, Alexandra S. Kalinovsky, Anatoly I. Avilov, Sergey A. Andryjaschenko, Pelageya V. Dmitrenok, Pavel S. Kalinin, Vladimir I. Chingizova, Ekaterina A. Minin, Kirill V. Stonik, Valentin A. |
author_sort | Silchenko, Alexandra S. |
collection | PubMed |
description | Four new trisulfated triterpene glycosides, fallaxosides D(4) (1), D(5) (2), D(6) (3) and D(7) (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 1–4 have three sulfate groups. The cytotoxic activity of glycosides 1–4 against the ascite form of mouse Ehrlich carcinoma cells and mouse spleen lymphocytes and hemolytic activity against mouse erythrocytes have been studied. |
format | Online Article Text |
id | pubmed-6274125 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-62741252018-12-28 Structures and Biogenesis of Fallaxosides D(4), D(5), D(6) and D(7), Trisulfated Non-Holostane Triterpene Glycosides from the Sea Cucumber Cucumaria fallax Silchenko, Alexandra S. Kalinovsky, Anatoly I. Avilov, Sergey A. Andryjaschenko, Pelageya V. Dmitrenok, Pavel S. Kalinin, Vladimir I. Chingizova, Ekaterina A. Minin, Kirill V. Stonik, Valentin A. Molecules Article Four new trisulfated triterpene glycosides, fallaxosides D(4) (1), D(5) (2), D(6) (3) and D(7) (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 1–4 have three sulfate groups. The cytotoxic activity of glycosides 1–4 against the ascite form of mouse Ehrlich carcinoma cells and mouse spleen lymphocytes and hemolytic activity against mouse erythrocytes have been studied. MDPI 2016-07-20 /pmc/articles/PMC6274125/ /pubmed/27447601 http://dx.doi.org/10.3390/molecules21070939 Text en © 2016 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Silchenko, Alexandra S. Kalinovsky, Anatoly I. Avilov, Sergey A. Andryjaschenko, Pelageya V. Dmitrenok, Pavel S. Kalinin, Vladimir I. Chingizova, Ekaterina A. Minin, Kirill V. Stonik, Valentin A. Structures and Biogenesis of Fallaxosides D(4), D(5), D(6) and D(7), Trisulfated Non-Holostane Triterpene Glycosides from the Sea Cucumber Cucumaria fallax |
title | Structures and Biogenesis of Fallaxosides D(4), D(5), D(6) and D(7), Trisulfated Non-Holostane Triterpene Glycosides from the Sea Cucumber Cucumaria fallax |
title_full | Structures and Biogenesis of Fallaxosides D(4), D(5), D(6) and D(7), Trisulfated Non-Holostane Triterpene Glycosides from the Sea Cucumber Cucumaria fallax |
title_fullStr | Structures and Biogenesis of Fallaxosides D(4), D(5), D(6) and D(7), Trisulfated Non-Holostane Triterpene Glycosides from the Sea Cucumber Cucumaria fallax |
title_full_unstemmed | Structures and Biogenesis of Fallaxosides D(4), D(5), D(6) and D(7), Trisulfated Non-Holostane Triterpene Glycosides from the Sea Cucumber Cucumaria fallax |
title_short | Structures and Biogenesis of Fallaxosides D(4), D(5), D(6) and D(7), Trisulfated Non-Holostane Triterpene Glycosides from the Sea Cucumber Cucumaria fallax |
title_sort | structures and biogenesis of fallaxosides d(4), d(5), d(6) and d(7), trisulfated non-holostane triterpene glycosides from the sea cucumber cucumaria fallax |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6274125/ https://www.ncbi.nlm.nih.gov/pubmed/27447601 http://dx.doi.org/10.3390/molecules21070939 |
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