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Two New Steroidal Monoglycosides, Anthenosides A(1) and A(2), and Revision of the Structure of Known Anthenoside A with Unusual Monosaccharide Residue from the Starfish Anthenea aspera

Two new polyhydroxysteroidal glycosides, anthenosides A(1) (1) and A(2) (2), and one previously known steroidal glycoside anthenoside A (3) were isolated from extract of the tropical starfish Anthenea aspera. Structures of 1–3 were determined by analysis of the spectroscopic data as well as chemical...

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Autores principales: Malyarenko, Timofey V., Ivanchina, Natalia V., Malyarenko, Olesya S., Kalinovsky, Anatoly I., Dmitrenok, Pavel S., Evtushenko, Evgeny V., Minh, Chau Van, Kicha, Alla A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6102596/
https://www.ncbi.nlm.nih.gov/pubmed/29751557
http://dx.doi.org/10.3390/molecules23051077
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author Malyarenko, Timofey V.
Ivanchina, Natalia V.
Malyarenko, Olesya S.
Kalinovsky, Anatoly I.
Dmitrenok, Pavel S.
Evtushenko, Evgeny V.
Minh, Chau Van
Kicha, Alla A.
author_facet Malyarenko, Timofey V.
Ivanchina, Natalia V.
Malyarenko, Olesya S.
Kalinovsky, Anatoly I.
Dmitrenok, Pavel S.
Evtushenko, Evgeny V.
Minh, Chau Van
Kicha, Alla A.
author_sort Malyarenko, Timofey V.
collection PubMed
description Two new polyhydroxysteroidal glycosides, anthenosides A(1) (1) and A(2) (2), and one previously known steroidal glycoside anthenoside A (3) were isolated from extract of the tropical starfish Anthenea aspera. Structures of 1–3 were determined by analysis of the spectroscopic data as well as chemical transformations. As a result, the structure of anthenoside A has been revised and the structures of 1 and 2 were established. Glycosides 1–3 contain a 2-acetamido-2-deoxy-4-O-methyl-β-d-glucopyranosyl residue, found in the starfish steroidal glycosides for the first time. All the isolated compounds slightly inhibited cell viability of human cancer T-47D cells and did not show cytotoxic effects against RPMI-7951 cells. Glycoside 1 slightly inhibited colony formation of human cancer RPMI-7951 cells by 16% while compound 2 decreased the number of colonies of T-47D cells by 40%.
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spelling pubmed-61025962018-11-13 Two New Steroidal Monoglycosides, Anthenosides A(1) and A(2), and Revision of the Structure of Known Anthenoside A with Unusual Monosaccharide Residue from the Starfish Anthenea aspera Malyarenko, Timofey V. Ivanchina, Natalia V. Malyarenko, Olesya S. Kalinovsky, Anatoly I. Dmitrenok, Pavel S. Evtushenko, Evgeny V. Minh, Chau Van Kicha, Alla A. Molecules Article Two new polyhydroxysteroidal glycosides, anthenosides A(1) (1) and A(2) (2), and one previously known steroidal glycoside anthenoside A (3) were isolated from extract of the tropical starfish Anthenea aspera. Structures of 1–3 were determined by analysis of the spectroscopic data as well as chemical transformations. As a result, the structure of anthenoside A has been revised and the structures of 1 and 2 were established. Glycosides 1–3 contain a 2-acetamido-2-deoxy-4-O-methyl-β-d-glucopyranosyl residue, found in the starfish steroidal glycosides for the first time. All the isolated compounds slightly inhibited cell viability of human cancer T-47D cells and did not show cytotoxic effects against RPMI-7951 cells. Glycoside 1 slightly inhibited colony formation of human cancer RPMI-7951 cells by 16% while compound 2 decreased the number of colonies of T-47D cells by 40%. MDPI 2018-05-03 /pmc/articles/PMC6102596/ /pubmed/29751557 http://dx.doi.org/10.3390/molecules23051077 Text en © 2018 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
Malyarenko, Timofey V.
Ivanchina, Natalia V.
Malyarenko, Olesya S.
Kalinovsky, Anatoly I.
Dmitrenok, Pavel S.
Evtushenko, Evgeny V.
Minh, Chau Van
Kicha, Alla A.
Two New Steroidal Monoglycosides, Anthenosides A(1) and A(2), and Revision of the Structure of Known Anthenoside A with Unusual Monosaccharide Residue from the Starfish Anthenea aspera
title Two New Steroidal Monoglycosides, Anthenosides A(1) and A(2), and Revision of the Structure of Known Anthenoside A with Unusual Monosaccharide Residue from the Starfish Anthenea aspera
title_full Two New Steroidal Monoglycosides, Anthenosides A(1) and A(2), and Revision of the Structure of Known Anthenoside A with Unusual Monosaccharide Residue from the Starfish Anthenea aspera
title_fullStr Two New Steroidal Monoglycosides, Anthenosides A(1) and A(2), and Revision of the Structure of Known Anthenoside A with Unusual Monosaccharide Residue from the Starfish Anthenea aspera
title_full_unstemmed Two New Steroidal Monoglycosides, Anthenosides A(1) and A(2), and Revision of the Structure of Known Anthenoside A with Unusual Monosaccharide Residue from the Starfish Anthenea aspera
title_short Two New Steroidal Monoglycosides, Anthenosides A(1) and A(2), and Revision of the Structure of Known Anthenoside A with Unusual Monosaccharide Residue from the Starfish Anthenea aspera
title_sort two new steroidal monoglycosides, anthenosides a(1) and a(2), and revision of the structure of known anthenoside a with unusual monosaccharide residue from the starfish anthenea aspera
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6102596/
https://www.ncbi.nlm.nih.gov/pubmed/29751557
http://dx.doi.org/10.3390/molecules23051077
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