Malyarenko TV et al. (2023), New Rare Triterpene Glycosides from Pacific Sun...

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Mar Drugs 2023 Dec 28;221:. doi: 10.3390/md22010019.

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New Rare Triterpene Glycosides from Pacific Sun Star, Solaster pacificus, and Their Anticancer Activity.

Malyarenko TV , Kicha AA , Kuzmich AS , Malyarenko OS , Kalinovsky AI , Popov RS , Dmitrenok PS , Ivanchina NV , Stonik VA .

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Six previously unknown triterpene glycosides, pacificusosides L-Q (1-6), and two previously known triterpene glycosides, cucumariosides B1 (7) and A5 (8), were isolated from an alcoholic extract of Pacific sun star, Solaster pacificus. The structures of 1-6 were determined using 1D and 2D NMR, ESIMS, and chemical modifications. Compound 1 is a rare type of triterpene glycoside with non-holostane aglycon, having a linear trisaccharide carbohydrate chain. Pacificusosides M-P (2-5) have new structures containing a Δ8(9)-3,16,18-trihydroxy tetracyclic triterpene moiety. This tetracyclic fragment in sea star or sea cucumber triterpene glycosides was described for the first time. All the compounds under study exhibit low or moderate cytotoxic activity against colorectal carcinoma HCT 116 cells, and breast cancer MDA-MB-231 cells were assessed by MTS assay. Compound 2 effectively suppresses the colony formation of cancer cells at a non-toxic concentration, using the soft-agar assay. A scratch assay has shown a significant anti-invasive potential of compound 2 against HCT 116 cells, but not against MDA-MB-231 cells.

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Al Marzouqi, Frondoside A inhibits human breast cancer cell survival, migration, invasion and the growth of breast tumor xenografts. 2011, Pubmed, Echinobase

	Figure 1. The structures of compounds 1–8 isolated from S. pacificus.
	Figure 2. 1H-1H COSY and key HMBC correlations for aglycons of compounds 1–6.
	Figure 3. Key ROESY correlations for aglycons of compounds 1–6.
	Figure 4. (−)ESIMS/MS spectrum of compound 1.
	Figure 5. (−)ESIMS/MS spectrum of compound 2.
	Figure 6. The inhibiting effect of compound 2 on the colony formation activity of human colorectal carcinoma (HCT 116) and breast cancer (MDA-MB-231) cells. (a,b) HCT 116 or (c,d) MDA-MB-231 cells were treated with 2 (at 0.6, 1.25, 2.5, and 5 µM) on soft agar. Number of colonies was counted under a microscope (at a total magnification of 40×) using the ImageJ v. 1.50i software, bundled with 64-bit Java 1.6.0_24. Results are presented as mean ± standard deviation (SD). The one-way ANOVA and Tukey’s HSD test for multiple comparisons showed statistical significance: * p < 0.05, p < 0.01, and * p < 0.001.
	Figure 7. The effect of compound 2 on migration of human colorectal carcinoma HCT 116 cells and breast cancer MDA-MB-231 cells. (a,b) HCT 116 and (c,d) MDA-MB-231 cells were treated with 2 (0.6, 1.25, 2.5, 5 µM) for 24, 48, and 72 h. The cell migration distance was estimated by measuring the width of the wound, and was expressed as the percentage of each control in relation to the mean of the wound-closure area. All experiments were set up at least in triplicate (n = 9 for control and compound; n is the number of photographs). The magnification of the representative photos is ×10. The results are expressed as mean ± standard deviation (SD). The asterisks (* p < 0.05, ** p < 0.01) indicate a significant decrease in migration of cells treated with the compound, compared to control.