Abstract
Two new polyhydroxysteroidal glycosides, anthenosides A1 (1) and A2 (2), and one previously known steroidal glycoside anthenoside A (3) were isolated from extract of the tropical starfish Anthenea aspera. Structures of 1–3 were determined by analysis of the spectroscopic data as well as chemical transformations. As a result, the structure of anthenoside A has been revised and the structures of 1 and 2 were established. Glycosides 1–3 contain a 2-acetamido-2-deoxy-4-O-methyl-β-d-glucopyranosyl residue, found in the starfish steroidal glycosides for the first time. All the isolated compounds slightly inhibited cell viability of human cancer T-47D cells and did not show cytotoxic effects against RPMI-7951 cells. Glycoside 1 slightly inhibited colony formation of human cancer RPMI-7951 cells by 16% while compound 2 decreased the number of colonies of T-47D cells by 40%.
Highlights
As characteristic secondary metabolites of starfish (Echinodermata, Asteroidea) steroidal glycosides may be divided into three major classes: glycosides of polyhydroxysteroids, cyclic glycosides, and asterosaponins [1,2,3,4,5,6,7]
Based on these data the tetracyclic moiety of the aglycon of 1 was determined as ∆8(14) -3α,6β,7β,16α-tetrahydroxysteroidal moiety glycosylated at C-16 position which is characteristic of starfish steroidal glycosides of the genus Anthenea [8,9,10]
It was shown that only compound 1 but not 2 and 3 slightly inhibited colony formation of RPMI-7951 cancer cells by 16% (Figure 3A)
Summary
As characteristic secondary metabolites of starfish (Echinodermata, Asteroidea) steroidal glycosides may be divided into three major classes: glycosides of polyhydroxysteroids, cyclic glycosides, and asterosaponins [1,2,3,4,5,6,7]. In particular β-N-acetyl- and β-N-formylgalactosamines, were found in oligosaccharide chains of gangliosides isolated from the starfish of genus Evasterias [13,14]. It has been previously reported, that some polyhydroxysteroidal glycosides from the starfish. We have established the structures of ten related new polyhydroxysteroidal glycosides, anthenosides L–U, from the starfish Anthenea aspera. Some of these glycosides showed hemolytic activity and anthenoside O exhibited reduction of ROS level, when RAW 264.7 murine macrophages cells were co-stimulated with pro-inflammatory endotoxin, lipopolysaccharide (LPS) from. We examined the effect of these compounds on the colony formation of melanoma and breast cancer cells using soft agar assay
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