Studies On The Bioactive Constituents From Cucumaria Frondosa Gunnerus

Cucumaria frondosa Gunnerus distributed from the north east coast of Scotland, Shetland and Orkney. The range may have retracted northwards in the last hundred years as there are old records from the west coast of Scotland. Lives in rocky areas, with the body attached to elevated rock surfaces, often just below low tide mark and in shallow water.Anti-cancer and anti-fungal constituents of Cucumaria frondosa Gunnerus have been investigated by various chromatography methods including LPLC, MPLC, HPLC on silica gel, ODS RP C₁₈and Zorbax SB C₁₈ respectively. Eighteen compounds were isolated and structures of nine compounds were elucidated by chemical and spectral analysis (IR, EI-MS, ESI-MS, HRESI-MS, ¹HNMR, ¹³CNMR, ¹H-¹H COSY, DQCOSY, TOCSY, HMQC, HMBC, NOESY, etc.).From the ethanolic extracts of Cucumaria frondosa Gunnerus five glycosides were isolated and identified, including one new triterpene glycosides . Their chemical structures were: CF-1 : 16-acetoxy-3-P -β-{3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D-Xylopyra nosy1 -(1→4)-β-D-quinovopyranosyl-( 1→2)-O-β-D-4-sulfonatoxylopyranosyl-β-D-xylopyranosyl }-7-ene-3β-ol(named frondosideA6);CF-216-acetoxy-3--O-{3-O-methyl-β-D-Glucopyranosyl-(1→3)-β-D- xylopyranosyl -(1→4)-β-D- quinovopyranosyl- (1→2)-4-O-sodium sulfate-P-D-xylopyranosyl-β-D-xylopyranosyl }-7-ene-3β-ol(frondoside A); CF-3: 16-acetoxy-3- P -β-{3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D- xylopyranosyl-(1→4)-β-D-quinovopyranosyl-( 1→2)-4-O-sodiumsulfate-β-D-xylopyranosyl} -7-ene-3β-ol (frondosideAl) ;CF-4: 3--O-{3-O-memyl-β-D-glucopyranosyl-(1→3)-β-D-6-Sulfonaro glucopyranosyl-( 1→4)-β-D-xylopyranosyl-( 1→2)-β-D-quinovopyranosyl-( 1→2)-4-O-sodi um sulfate-P-D-xylopyranosyl}-7-,24-diene sodium salt (frondoside B);CF-5: 16-acetoxy -3-β-O-{3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D- xylopyranosyl-(1→4)-p-D-xylopy ranosyl -(1→2)-β-D-quinovopyranosyl-(1→2)-4-O-sodium sulfate-β-D-xylopyranosyl-23 S-hydroxy-holost-7-ene-3β-ol(frondoside D).Five triterpene glycosides showed activity against P.oryzae. Our studies focused on bioactive constituents of Cucumaria frondosa Gunnerus have established a foundation for further research and development of the kind sea cucumber with abundant resources i, and provided important leading compounds for the development of new anti-cancer and anti fungus drugs.Three sphingosine-type glucocerebrosides, CF-6 ,CF-7 and CF-8 , were isolated by means of highperformance liquid chromatography (HPLC) from a cerebroside molecular species which was obtained from the less polar fraction of the methanol extract of the sea cucumber Cucumaria frondosa Gunnerus . The structures of these cerebrosides were determined on the basis of chemical and spectroscopic evidences.