Kicha AA et al. (2024), Rare Ophiuroid-Type Steroid 3β,21-, 3β,22-, and...

ECB-ART-52721

Mar Drugs 2024 Jan 12;221:. doi: 10.3390/md22010043.

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Rare Ophiuroid-Type Steroid 3β,21-, 3β,22-, and 3α,22-Disulfates from the Slime Sea Star Pteraster marsippus and Their Colony-Inhibiting Effects against Human Breast Cancer Cells.

Kicha AA , Malyarenko TV , Kuzmich AS , Malyarenko OS , Kalinovsky AI , Popov RS , Tolkanov DK , Ivanchina NV .

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Two new steroid 3β,21-disulfates (1, 2) and two new steroid 3β,22- and 3α,22-disulfates (3, 4), along with the previously known monoamine alkaloid tryptamine (5) were found in the ethanolic extract of the Far Eastern slime sea star Pteraster marsippus. Their structures were determined on the basis of detailed analysis of one-dimensional and two-dimensional NMR, HRESIMS, and HRESIMS/MS data. Compounds 1 and 2 have a Δ22-21-sulfoxy-24-norcholestane side chain. Compounds 3 and 4 contain a Δ24(28)-22-sulfoxy-24-methylcholestane side chain, which was first discovered in the polar steroids of starfish and brittle stars. The influence of substances 1-4 on cell viability, colony formation, and growth of human breast cancer T-47D, MCF-7, and MDA-MB-231 cells was investigated. It was shown that compounds 1 and 2 possess significant colony-inhibiting activity against T-47D cells, while compounds 3 and 4 were more effective against MDA-MB-231 cells.

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References [+] :

Carvalhal, SULFATION PATHWAYS: Sources and biological activities of marine sulfated steroids. 2018, Pubmed

	Figure 1. Chemical structures of steroids 1−4 and compound 5.
	Figure 2. 1H-1H COSY and main HMBC correlations of steroids 1–4.
	Figure 3. Main ROESY correlations for steroids 1–4.
	Figure 4. The cytotoxic activity of compounds 1–4 against human breast cancer cells. (a) T-47D, (b) MCF-7, and (c) MDA-MB-231 cells were incubated with 1–4 (6.25, 12.5, 25, and 50 µM) or cisplatin (Cis) (6.25, 12.5, 25, and 50 µM) for 72 h. MTS assay was used to evaluate cytotoxicity of compounds. The results are presented as the mean ± SD for triplicate experiments. The asterisk () indicates a significant decrease in cell viability of cancer cells treated with different concentrations of investigated compounds at a time point 72 h as compared to control ( p < 0.05, p < 0.01, * p < 0.001).
	Figure 5. The colony-inhibiting activity of compounds 1–4 in human breast cancer cells. (a) T-47D, (b) MCF-7, and (c) MDA-MB-231 cells were treated by 1–4 (12.5, 25, and 50 µM) in soft agar. Microscope (at a total magnification of 40×) using the ImageJ software version 1.50i bundled with 64 bit Java 1.6.0_24 (“NIH”, Bethesda, MD, USA) were used to count the number of colonies. Results are presented as the mean ± standard deviation (SD). A one-way ANOVA and Tukey’s HSD test for multiple comparisons indicated the statistical significance (* p < 0.05, p < 0.01, * p < 0.001).