Cargando…

New Conjugates of Polyhydroxysteroids with Long-Chain Fatty Acids from the Deep-Water Far Eastern Starfish Ceramaster patagonicus and Their Anticancer Activity

Four new conjugates, esters of polyhydroxysteroids with long-chain fatty acids (1–4), were isolated from the deep-water Far Eastern starfish Ceramaster patagonicus. The structures of 1–4 were established by NMR and ESIMS techniques as well as chemical transformations. Unusual compounds 1–4 contain t...

Descripción completa

Detalles Bibliográficos
Autores principales: Malyarenko, Timofey V., Kicha, Alla A., Malyarenko, Olesya S., Zakharenko, Viktor M., Kotlyarov, Ivan P., Kalinovsky, Anatoly I., Popov, Roman S., Svetashev, Vasily I., Ivanchina, Natalia V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7281419/
https://www.ncbi.nlm.nih.gov/pubmed/32429281
http://dx.doi.org/10.3390/md18050260
_version_ 1783543915519934464
author Malyarenko, Timofey V.
Kicha, Alla A.
Malyarenko, Olesya S.
Zakharenko, Viktor M.
Kotlyarov, Ivan P.
Kalinovsky, Anatoly I.
Popov, Roman S.
Svetashev, Vasily I.
Ivanchina, Natalia V.
author_facet Malyarenko, Timofey V.
Kicha, Alla A.
Malyarenko, Olesya S.
Zakharenko, Viktor M.
Kotlyarov, Ivan P.
Kalinovsky, Anatoly I.
Popov, Roman S.
Svetashev, Vasily I.
Ivanchina, Natalia V.
author_sort Malyarenko, Timofey V.
collection PubMed
description Four new conjugates, esters of polyhydroxysteroids with long-chain fatty acids (1–4), were isolated from the deep-water Far Eastern starfish Ceramaster patagonicus. The structures of 1–4 were established by NMR and ESIMS techniques as well as chemical transformations. Unusual compounds 1–4 contain the same 5α-cholestane-3β,6β,15α,16β,26-pentahydroxysteroidal moiety and differ from each other in the fatty acid units: 5′Z,11′Z-octadecadienoic (1), 11′Z-octadecenoic (2), 5′Z,11′Z-eicosadienoic (3), and 7′Z-eicosenoic (4) acids. Previously, only one such steroid conjugate with a fatty acid was known from starfish. After 72 h of cell incubation, using MTS assay it was found that the concentrations of compounds 1, 2, and 3 that caused 50% inhibition of growth (IC(50)) of JB6 Cl41 cells were 81, 40, and 79 µM, respectively; for MDA-MB-231 cells, IC(50) of compounds 1, 2, and 3 were 74, 33, and 73 µM, respectively; for HCT 116 cells, IC(50) of compounds 1, 2, and 3 were 73, 31, and 71 µM, respectively. Compound 4 was non-toxic against tested cell lines even in three days of treatment. Compound 2 (20 µM) suppressed colony formation and migration of MDA-MB-231 and HCT 116 cells.
format Online
Article
Text
id pubmed-7281419
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-72814192020-06-19 New Conjugates of Polyhydroxysteroids with Long-Chain Fatty Acids from the Deep-Water Far Eastern Starfish Ceramaster patagonicus and Their Anticancer Activity Malyarenko, Timofey V. Kicha, Alla A. Malyarenko, Olesya S. Zakharenko, Viktor M. Kotlyarov, Ivan P. Kalinovsky, Anatoly I. Popov, Roman S. Svetashev, Vasily I. Ivanchina, Natalia V. Mar Drugs Article Four new conjugates, esters of polyhydroxysteroids with long-chain fatty acids (1–4), were isolated from the deep-water Far Eastern starfish Ceramaster patagonicus. The structures of 1–4 were established by NMR and ESIMS techniques as well as chemical transformations. Unusual compounds 1–4 contain the same 5α-cholestane-3β,6β,15α,16β,26-pentahydroxysteroidal moiety and differ from each other in the fatty acid units: 5′Z,11′Z-octadecadienoic (1), 11′Z-octadecenoic (2), 5′Z,11′Z-eicosadienoic (3), and 7′Z-eicosenoic (4) acids. Previously, only one such steroid conjugate with a fatty acid was known from starfish. After 72 h of cell incubation, using MTS assay it was found that the concentrations of compounds 1, 2, and 3 that caused 50% inhibition of growth (IC(50)) of JB6 Cl41 cells were 81, 40, and 79 µM, respectively; for MDA-MB-231 cells, IC(50) of compounds 1, 2, and 3 were 74, 33, and 73 µM, respectively; for HCT 116 cells, IC(50) of compounds 1, 2, and 3 were 73, 31, and 71 µM, respectively. Compound 4 was non-toxic against tested cell lines even in three days of treatment. Compound 2 (20 µM) suppressed colony formation and migration of MDA-MB-231 and HCT 116 cells. MDPI 2020-05-15 /pmc/articles/PMC7281419/ /pubmed/32429281 http://dx.doi.org/10.3390/md18050260 Text en © 2020 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.
Kicha, Alla A.
Malyarenko, Olesya S.
Zakharenko, Viktor M.
Kotlyarov, Ivan P.
Kalinovsky, Anatoly I.
Popov, Roman S.
Svetashev, Vasily I.
Ivanchina, Natalia V.
New Conjugates of Polyhydroxysteroids with Long-Chain Fatty Acids from the Deep-Water Far Eastern Starfish Ceramaster patagonicus and Their Anticancer Activity
title New Conjugates of Polyhydroxysteroids with Long-Chain Fatty Acids from the Deep-Water Far Eastern Starfish Ceramaster patagonicus and Their Anticancer Activity
title_full New Conjugates of Polyhydroxysteroids with Long-Chain Fatty Acids from the Deep-Water Far Eastern Starfish Ceramaster patagonicus and Their Anticancer Activity
title_fullStr New Conjugates of Polyhydroxysteroids with Long-Chain Fatty Acids from the Deep-Water Far Eastern Starfish Ceramaster patagonicus and Their Anticancer Activity
title_full_unstemmed New Conjugates of Polyhydroxysteroids with Long-Chain Fatty Acids from the Deep-Water Far Eastern Starfish Ceramaster patagonicus and Their Anticancer Activity
title_short New Conjugates of Polyhydroxysteroids with Long-Chain Fatty Acids from the Deep-Water Far Eastern Starfish Ceramaster patagonicus and Their Anticancer Activity
title_sort new conjugates of polyhydroxysteroids with long-chain fatty acids from the deep-water far eastern starfish ceramaster patagonicus and their anticancer activity
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7281419/
https://www.ncbi.nlm.nih.gov/pubmed/32429281
http://dx.doi.org/10.3390/md18050260
work_keys_str_mv AT malyarenkotimofeyv newconjugatesofpolyhydroxysteroidswithlongchainfattyacidsfromthedeepwaterfareasternstarfishceramasterpatagonicusandtheiranticanceractivity
AT kichaallaa newconjugatesofpolyhydroxysteroidswithlongchainfattyacidsfromthedeepwaterfareasternstarfishceramasterpatagonicusandtheiranticanceractivity
AT malyarenkoolesyas newconjugatesofpolyhydroxysteroidswithlongchainfattyacidsfromthedeepwaterfareasternstarfishceramasterpatagonicusandtheiranticanceractivity
AT zakharenkoviktorm newconjugatesofpolyhydroxysteroidswithlongchainfattyacidsfromthedeepwaterfareasternstarfishceramasterpatagonicusandtheiranticanceractivity
AT kotlyarovivanp newconjugatesofpolyhydroxysteroidswithlongchainfattyacidsfromthedeepwaterfareasternstarfishceramasterpatagonicusandtheiranticanceractivity
AT kalinovskyanatolyi newconjugatesofpolyhydroxysteroidswithlongchainfattyacidsfromthedeepwaterfareasternstarfishceramasterpatagonicusandtheiranticanceractivity
AT popovromans newconjugatesofpolyhydroxysteroidswithlongchainfattyacidsfromthedeepwaterfareasternstarfishceramasterpatagonicusandtheiranticanceractivity
AT svetashevvasilyi newconjugatesofpolyhydroxysteroidswithlongchainfattyacidsfromthedeepwaterfareasternstarfishceramasterpatagonicusandtheiranticanceractivity
AT ivanchinanataliav newconjugatesofpolyhydroxysteroidswithlongchainfattyacidsfromthedeepwaterfareasternstarfishceramasterpatagonicusandtheiranticanceractivity