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Three new polyhydroxysteroid glycosides, regulusosides A-C (1-3) along with the previously known five steroid compounds (4-8) were isolated from the tropical starfish Pentaceraster regulus. The structures of compounds 1-3 were established by extensive NMR and ESI-MS techniques. New glycosides have the same aglycon, (24 S)-5α-cholestane-3β,5,6β,8,15α,24-hexol, and various disaccharide moieties: β-D-xylopyranosyl-(1→2)-3- O-methyl-α-L-arabinofuranosyl (1), β-D-xylopyranosyl-(1→2)-α-L-arabinofuranosyl (2), and 2- O-methyl-β-D-xylopyranosyl-(1→2)-3- O-methyl-α-L-arabinofuranosyl (3), attached at C-24 of the side chain. Compounds 1, 2 and 6 exhibit potential immunomodulatory properties, inducing intracellular ROS (reactive oxygen species) formation in the RAW 264.7 murine macrophage cells.

Regulusosides A, B, and C, Three New Polyhydroxysteroid Glycosides from the Starfish Pentaceraster regulus