Kicha AA et al. (2020), Unusual Polyhydroxylated Steroids from the Star...

ECB-ART-48504

Molecules 2020 Mar 23;256:. doi: 10.3390/molecules25061440.

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Unusual Polyhydroxylated Steroids from the Starfish Anthenoides laevigatus, Collected off the Coastal Waters of Vietnam.

Kicha AA , Ha DT , Malyarenko TV , Kalinovsky AI , Popov RS , Malyarenko OS , Thuy TTT , Long PQ , Ha NTT , Ivanchina NV .

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Four new polyhydroxylated steroids 1-4 were isolated along with two previously known related steroids 5 and 6 from the methanolic extract of the starfish Anthenoides laevigatus collected off the coastal waters of Vietnam. Structures of new compounds were substantially elucidated by one-dimensional (1D) and two-dimensional (2D) NMR spectroscopy and HRESIMS techniques. Heptaol 1 and hexaol 2 contain the common 5α-cholestane skeleton, while hexaol 3 and heptaol 4 have the rare among starfish steroid compounds 5β-cholestane skeleton. Compounds 1, 5, and 6 do not show cytotoxic effects against normal JB6 Cl41 and cancer HT-29 and MDA-MB-231 cells, however they inhibit cell proliferation and colony formation of cancer HT-29 and MDA-MB-231 cells.

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Genes referenced: LOC115919910

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References [+] :

Dong, Chemical constituents and bioactivities of starfish. 2011, Pubmed, Echinobase

	Figure 1. Structures of compounds 1−6 isolated from A. laevigatus.
	Figure 2. (A) COSY and key HMBC correlations for compound 1; (B) Key ROESY correlations for compound 1. Colors reveal the atoms of hydrogen (blue), oxygen (red) and carbon (grey) and their bonds.
	Figure 3. (A) COSY and key HMBC correlations for compound 3; (B) Key ROESY correlations for compound 3. Colors reveal the atoms of hydrogen (blue), oxygen (red) and carbon (grey) and their bonds.
	Figure 4. The effect of compounds 1, 5, and 6 on cell proliferation. (A) JB6 Cl41; (B) HT-29; or (C) MDA-MB-231 cells were treated with compounds 1, 5, and 6 at concentration of 20 µM for 24 h, 48 h, and 72 h. Cell viability was estimated using the MTS assay. Data are represented as the mean ± SD as determined from triplicate experiments. A Student’s t-test was used to evaluate the data with the following significance levels: p < 0.05, p < 0.01, **p < 0.001.
	Figure 5. The effect of compounds 1, 5, and 6 on colony formation in human cancer cells. (A) HT-29; or (B) MDA-MB-231 cells (2.4 × 104) with or without investigated compounds (20 µM) treatment were subcultured onto 0.3% Basal Medium Eagle (BME) agar containing 10% FBS, 2 mM L-glutamine, and 25 µg/mL gentamicin. After 14 days of incubation, the number of colonies was evaluated under a microscope with the aid of the ImageJ software program. Results are expressed as the mean ± standard deviation (SD). The asterisk () indicates a significant decrease in colony number of cancer cells treated by compounds as compared with the control (p < 0.05, p < 0.01, *p < 0.001).