| Starfish or sea stars are marine echinoderms belonging to the class Asteroidea,are know to yield a lot of significant bioactive compounds such as polyhydroxysteroids,saponins,alkaloids,polysaccharides and so on.These compouds have been reported to exhibit cytotoxic,anti-cancer,anti-bacterial,anti-viral and anti-inflammatory activeities.Especially polyhydroxysteroids and steroidal saponins,have attracted the attention of marine drug researchers around the world because of their significant bioactivities.Herein in order to obtain those active steroids,we systematically studied the chemical constituents of the starfish Pentaceraster chinensis(family Oreasteridae),collected in the South China Sea,which is endemic to China and abundantly distributed in the South China Sea.Partial isolated compouds from the starfish have been studied on anticancer activitities against two human cancer cell lines in vitro.The animal materials were extracted with 75% Et OH,and the extract was portioned with petroleum ether and n-butanol sequentially,the n-butanol section was isolated by silica gel,ODS and Sephadex LH-20 column chromatographies,and semi-preparativeHPLC.Twenty-onecompounds were isolated and 16 of them were elucidated by chemical and spectroscopic methods as(20R,24S)-5?-cholestan-3?,6?,8?,15?,24-pentol(1),(22E)-3?,6?,15?,24-tetrahydroxy-5?-cholestan-22-en(2),(22E)-3?,6?,8?,15?,24-pen tahydroxy-5?-cholestan-22-en(3),(22E)-3?,4?,6?,8?,15?,24-hexahydroxy-5?-cholestan-22-en(4),5?-cholestan-3?,6?,15?,16?,24-pentol(5),5?-cholestan-3?,6?,8?,15?,16?,26-hexol(6),sodium 3?-O-[2-O-methyl-?-D-xylopyranosyl]-6?,8?,16?,29-te trahydroxy-5?-stigmastan-15?-yl sulfate(7),sodium 6?-O-{?-D-fucopyranosyl-(1?2)-?-D-galactopyranosyl-(1?4)-[?-D-quinovopyranosyl-(1?2)]-?-D-xylopyranosyl-(1?3)-?-D-quinovopyranosyl}-5?-pregn-9(11)-en-20-one-3?-yl sulfate(8),sodium 6?-O-{?-Dfucopyranosyl-(1?2)-?-D-glucopyranosyl-(1?4)-[?-D-quinovopyranosyl-(1?2)]-?-Dquinovopyranosyl-(1?3)-?-D-quinovopyranosyl}-5?-pregn-9(11)-en-20-one-3?-yl sulfate(9),sodium 6?-O-{?-D-fucopyranosyl-(1?2)-?-D-quinovopyranosyl-(1?4)-[?-D-quino vopyranosyl-(1?2)]-?-D-glucopyranosyl-(1?3)-?-D-quinovopyranosyl}-20-hydroxy-5?-cholestan-9(11)-en-23-one-3?-yl sulfate(10),sodium(20E)-6?-O-{?-D-fucopyranosyl-(1?2)-?-D-glucopyranosyl-(1?4)-[?-D-quinovopyranosyl-(1?2)]-?-D-xylopyranosyl-(1?3)-?-D-quinovopyranosyl}-5?-cholestan-9(11),20(22)-dien-23-one-3?-yl sulfate(11),sodium(20E)-6?-O-{?-D-fucopyranosyl-(1?2)-?-D-fucopyranosyl-(1?4)-[?-D-quinovo pyranosyl-(1?2)]-?-D-glucopyranosyl-(1?3)-?-D-quinovopyranosyl}-5?-cholestan-9(11),20(22)-dien-23-one-3?-yl sulfate(12),asterubine(13),phenylalanine(14),guanosine(15)and inosine(16),respectively.All of the compounds were isolated from Pentanceraster chinensis for the first time.Compound(11)is a novel compound with a relatively rare side chain.The isolated compounds were tested for cytotoxicity against Hep G2 and U87 MG cells in vitro.Asterosaponins10,11 and 12 have cytotoxicity to Hep G2 cells and U87 MG cells.Polyhydroxysteroidal glycoside 7 has cytotoxicity to U87 MG cells.Analysis of the cytotoxicity data and comparison with those reported in the literature which have a similarstructure showed that asterosaponins and polyhydroxysteroidal glycolsides are generally more potent then free sterols.Innovations and significance: 1.The chemical constituents of Pentaceraster chinensis were systematically studied.Twenty-one compounds were isolated and 16 compounds were elucidated,including 6 polyhydroxysteroids,1 polyhydroxysteroidal glycoside,5 asterosaponins,asterubine,phenylalanine,guanosine and inosine.2.A new compound was found with a relatively rare side chain structure and all 16 elucidated compounds were firstly isolated from Pentaceraster chinensis.3.The cytotoxicity of the compounds was studied and the structure-activity relationship was discussed.4.This topic provides new information for the study of Pentaceraster chinensis and a new scientific basis for utilization. |
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