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...
Autores principales: | , , , , , , , , |
---|---|
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 |