Pectiniferosides A-J: Diversified Glycosides of Polyhydroxy Steroids Isolated from the Sea Star Patiria (=Asterina) pectinifera.

Abstract

To optimize the utilization of the sea star Patiria (=Asterina) pectinifera, which has demonstrated potential pharmaceutical properties in Chinese folk medicine, ten glycosides of polyhydroxy steroids, pectiniferosides A-J (1-10), were isolated and characterized. These compounds possess 3β, 6α, 8, 15α (or β), 16β-pentahydroxycholestane aglycones with sulfated and (or) methylated monosaccharides. The chemical structures of 1-10 were determined using NMR spectroscopy and HR-ESI-MS. The discovery of saponins with multiple substitution patterns in sea stars exemplified the molecular diversity of secondary metabolites in marine echinoderms. These compounds exhibited no embryotoxicity or teratogenicity at a concentration of 100 μM in a bioassay with marine medaka (Oryzias melastigma) embryos, implying that these compounds may not be ecologically toxic to marine fish embryos. In addition, none of the compounds exhibited significant cytotoxicity against five human cancer cell lines at 40 μM or anti-inflammatory activities at 50 μM, suggesting their potential for further structural optimization to enhance bioactivity. The research on the constituents of P. pectinifera provides a potential foundation for drug development and marine ecotoxicology.