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Open AccessArticle

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

1
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, Vladivostok 690022, Russia
2
Department of Bioorganic Chemistry and Biotechnology, School of Natural Sciences, Far Eastern Federal University, Sukhanova Str. 8, Vladivostok 690000, Russia
3
A.V. Zhirmunsky National Scientific Center of Marine Biology, Far Eastern Branch of the Russian Academy of Sciences, 17 Palchevsky St., Vladivostok 690041, Russia
*
Author to whom correspondence should be addressed.
Mar. Drugs 2020, 18(5), 260; https://doi.org/10.3390/md18050260
Received: 27 April 2020 / Revised: 8 May 2020 / Accepted: 13 May 2020 / Published: 15 May 2020
Four new conjugates, esters of polyhydroxysteroids with long-chain fatty acids (14), were isolated from the deep-water Far Eastern starfish Ceramaster patagonicus. The structures of 14 were established by NMR and ESIMS techniques as well as chemical transformations. Unusual compounds 14 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 (IC50) of JB6 Cl41 cells were 81, 40, and 79 µM, respectively; for MDA-MB-231 cells, IC50 of compounds 1, 2, and 3 were 74, 33, and 73 µM, respectively; for HCT 116 cells, IC50 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. View Full-Text
Keywords: polyhydroxysteroidal esters; NMR spectra; fatty acids; starfish; Ceramaster patagonicus; cytostatic activity; soft agar assay; wound healing assay polyhydroxysteroidal esters; NMR spectra; fatty acids; starfish; Ceramaster patagonicus; cytostatic activity; soft agar assay; wound healing assay
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Malyarenko, T.V.; Kicha, A.A.; Malyarenko, O.S.; Zakharenko, V.M.; Kotlyarov, I.P.; Kalinovsky, A.I.; Popov, R.S.; Svetashev, V.I.; Ivanchina, N.V. New Conjugates of Polyhydroxysteroids with Long-Chain Fatty Acids from the Deep-Water Far Eastern Starfish Ceramaster patagonicus and Their Anticancer Activity. Mar. Drugs 2020, 18, 260.

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