Kicha AA et al. (2022), Disulfated Ophiuroid Type Steroids from the Far...

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Mar Drugs 2022 Feb 24;203:. doi: 10.3390/md20030164.

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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.

Kicha AA , Kalinovsky AI , Malyarenko TV , Malyarenko OS , Ermakova SP , Popov RS , Stonik VA , Ivanchina NV .

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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 Δ24-22-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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References [+] :

Amelian, Application of standard cell cultures and 3D in vitro tissue models as an effective tool in drug design and development. 2017, Pubmed

	Figure 1. Structures of compounds 1–5 isolated from P. marsippus.
	Figure 2. COSY and key HMBC correlations of compounds 2–5.
	Figure 3. Key ROESY correlations for compounds 2–5. Colors reveal the atoms of hydrogen (blue), oxygen (red), sulfur (yellow), and carbon (grey) and their bonds.
	Figure 4. The cytotoxic effect of compounds 1–5 on the model of 2D (A) HEK293, (B) SK-MEL-28, (C) HuTu80, and (D) ZR-75-1 cells. Cells monolayer was treated with Doxo at concentrations of 5, 25, 50, and 100 μM or 1, 4, and 5 and the mixture of 2 and 3 at concentrations of 10, 50, and 100 μM and incubated for 24 h. Cell viability was assessed using the MTS test. Data are presented as means ± standard deviation, as determined in three experiments.
	Figure 5. The cytotoxic effect of compounds 1–5 on the model of 3D (A) SK-MEL-28, (B) HuTu80, and (C) ZR-75-1 cells. Spheroids were treated with Doxo at concentrations of 5, 25, 50, and 100 μM or 1, 4, and 5 and the mixture of 2 and 3 at concentrations of 10, 50, and 100 μM and incubated for 24 h. Cell viability was assessed using the MTS test. Data are presented as means ± standard deviation, as determined in three experiments. Photographs (n = 6 for controls or cells treated with polysaccharides or derivatives, where n = number of photographs) of each spheroid were taken with the ZOE ™ Fluorescent Cell Imager. Spheroids were analyzed using ImageJ software.