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Disulfated Ophiuroid Type Steroids from the Far Eastern Starfish Pteraster marsippus and Their Cytotoxic Activity on the Models of 2D and 3D Cultures

New steroidal 3β,21-disulfates (2–4), steroidal 3β,22-disulfate (5), and the previously known related steroidal 3β,21-disulfate (1) were isolated from the ethanolic extract of the Far Eastern starfish Pteraster marsippus, collected off Urup Island in the Sea of Okhotsk. The structures of these compo...

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Autores principales: Kicha, Alla A., Kalinovsky, Anatoly I., Malyarenko, Timofey V., Malyarenko, Olesya S., Ermakova, Svetlana P., Popov, Roman S., Stonik, Valentin A., Ivanchina, Natalia V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8951248/
https://www.ncbi.nlm.nih.gov/pubmed/35323463
http://dx.doi.org/10.3390/md20030164
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author Kicha, Alla A.
Kalinovsky, Anatoly I.
Malyarenko, Timofey V.
Malyarenko, Olesya S.
Ermakova, Svetlana P.
Popov, Roman S.
Stonik, Valentin A.
Ivanchina, Natalia V.
author_facet Kicha, Alla A.
Kalinovsky, Anatoly I.
Malyarenko, Timofey V.
Malyarenko, Olesya S.
Ermakova, Svetlana P.
Popov, Roman S.
Stonik, Valentin A.
Ivanchina, Natalia V.
author_sort Kicha, Alla A.
collection PubMed
description New steroidal 3β,21-disulfates (2–4), steroidal 3β,22-disulfate (5), and the previously known related steroidal 3β,21-disulfate (1) were isolated from the ethanolic extract of the Far Eastern starfish Pteraster marsippus, collected off Urup Island in the Sea of Okhotsk. The structures of these compounds were determined by intensive NMR and HRESIMS techniques as well as by chemical transformations. Steroids 2 and 3 have an oxo-group in the tetracyclic nucleus at position C-7 and differ from each other by the presence of the 5(6)-double bond. The Δ(24)-22-sulfoxycholestane side chain of the steroid 5 has not been found previously in the starfish or ophiuroid steroids. The cytotoxic activities of 1, 4, 5, and the mixture of 2 and 3 were determined on the models of 2D and 3D cultures of human epithelial kidney cells (HEK293), melanoma cells (SK-MEL-28), small intestine carcinoma cells (HuTu80), and breast carcinoma cells (ZR-75-1). The mixture of 2 and 3 revealed a significant inhibitory effect on the cell viability of human breast carcinoma ZR-75-1 cells, but other tested compounds were less effective.
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spelling pubmed-89512482022-03-26 Disulfated Ophiuroid Type Steroids from the Far Eastern Starfish Pteraster marsippus and Their Cytotoxic Activity on the Models of 2D and 3D Cultures Kicha, Alla A. Kalinovsky, Anatoly I. Malyarenko, Timofey V. Malyarenko, Olesya S. Ermakova, Svetlana P. Popov, Roman S. Stonik, Valentin A. Ivanchina, Natalia V. Mar Drugs Article New steroidal 3β,21-disulfates (2–4), steroidal 3β,22-disulfate (5), and the previously known related steroidal 3β,21-disulfate (1) were isolated from the ethanolic extract of the Far Eastern starfish Pteraster marsippus, collected off Urup Island in the Sea of Okhotsk. The structures of these compounds were determined by intensive NMR and HRESIMS techniques as well as by chemical transformations. Steroids 2 and 3 have an oxo-group in the tetracyclic nucleus at position C-7 and differ from each other by the presence of the 5(6)-double bond. The Δ(24)-22-sulfoxycholestane side chain of the steroid 5 has not been found previously in the starfish or ophiuroid steroids. The cytotoxic activities of 1, 4, 5, and the mixture of 2 and 3 were determined on the models of 2D and 3D cultures of human epithelial kidney cells (HEK293), melanoma cells (SK-MEL-28), small intestine carcinoma cells (HuTu80), and breast carcinoma cells (ZR-75-1). The mixture of 2 and 3 revealed a significant inhibitory effect on the cell viability of human breast carcinoma ZR-75-1 cells, but other tested compounds were less effective. MDPI 2022-02-24 /pmc/articles/PMC8951248/ /pubmed/35323463 http://dx.doi.org/10.3390/md20030164 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/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 (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Kicha, Alla A.
Kalinovsky, Anatoly I.
Malyarenko, Timofey V.
Malyarenko, Olesya S.
Ermakova, Svetlana P.
Popov, Roman S.
Stonik, Valentin A.
Ivanchina, Natalia V.
Disulfated Ophiuroid Type Steroids from the Far Eastern Starfish Pteraster marsippus and Their Cytotoxic Activity on the Models of 2D and 3D Cultures
title Disulfated Ophiuroid Type Steroids from the Far Eastern Starfish Pteraster marsippus and Their Cytotoxic Activity on the Models of 2D and 3D Cultures
title_full Disulfated Ophiuroid Type Steroids from the Far Eastern Starfish Pteraster marsippus and Their Cytotoxic Activity on the Models of 2D and 3D Cultures
title_fullStr Disulfated Ophiuroid Type Steroids from the Far Eastern Starfish Pteraster marsippus and Their Cytotoxic Activity on the Models of 2D and 3D Cultures
title_full_unstemmed Disulfated Ophiuroid Type Steroids from the Far Eastern Starfish Pteraster marsippus and Their Cytotoxic Activity on the Models of 2D and 3D Cultures
title_short Disulfated Ophiuroid Type Steroids from the Far Eastern Starfish Pteraster marsippus and Their Cytotoxic Activity on the Models of 2D and 3D Cultures
title_sort disulfated ophiuroid type steroids from the far eastern starfish pteraster marsippus and their cytotoxic activity on the models of 2d and 3d cultures
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8951248/
https://www.ncbi.nlm.nih.gov/pubmed/35323463
http://dx.doi.org/10.3390/md20030164
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