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Three new triterpene glycosides, pacificusosides A-C (1-3), and three previously known triterpene glycosides, cucumariosides C1 (4), C2 (5), and A10 (6), were isolated from the alcoholic extract of the Far Eastern starfish Solaster pacificus. The structures of 1-3 were elucidated by extensive NMR and ESIMS techniques and chemical transformations. Compound 1 has a novel, unique structure, containing an aldehyde group of side chains in its triterpene aglycon. This structural fragment has not previously been found in the sea cucumber triterpene glycosides or starfish steroidal glycosides. Probably, pacificusoside A (1) is a product of the metabolism of the glycoside obtained through dietary means from a sea cucumber in the starfish. Another two new triterpene glycosides (2, 3) have closely related characteristics to sea cucumber glycosides. The cytotoxicity of compounds 1-6 was tested against human embryonic kidney HEK 293 cells, colorectal carcinoma HT-29 cells, melanoma RPMI-7951 cells, and breast cancer MDA-MB-231 cells using MTS assay. Compounds 4-6 revealed the highest cytotoxic activity against the tested cell lines, while the other investigated compounds had moderate or slight cytotoxicity. The cytotoxic effects of 2-6 were reduced by cholesterol like the similar effects of the previously investigated individual triterpene glycosides. Compounds 3, 4, and 5 almost completely suppressed the colony formation of the HT-29, RPMI-7951, and MDA-MB-231 cells at a nontoxic concentration of 0.5 µM.
Figure 1. The structures of compounds 1−6 isolated from S. pacificus.
Figure 2. (A) 1H-1H COSY and key HMBC correlations for aglycon part of compounds 1–3. (B) Key ROESY correlations for aglycon part of compounds 1–3.
Figure 3. Effect of compounds 1–6 on colony formation of human colorectal carcinoma HT-29, melanoma RPMI-7951, and breast cancer MDA-MB-231 cell lines. HT-29, RPMI-7951, and MDA-MB-231 cells (2.4 × 104 /mL) treated with/without investigated 1–6 (0.1, 0.5, and 1 µM) and subjected into a soft agar. The culture was maintained at 37 °C in a 5% CO2 atmosphere for 2 weeks. The colonies were counted under a microscope with the aid of the ImageJ software program (n = 6 for control and each compound, n—quantity of photos). The asterisks (* p < 0.05, ** p < 0.01, *** p < 0.001) indicate a significant decrease in colony formation in cells treated with compounds compared with the nontreated cells (control).
Figure 4. Hypothetic scheme of the biosynthesis of aglycon side chain of compound 1.
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