Cytotoxic sulfated triterpene glycosides from the sea cucumber Pseudocolochirus violaceus.
Bioassay-guided fractionation of the active BuOH extract of the sea cucumber Pseudocolochirus violaceus resulted in the isolation of three new sulfated triterpene glycosides, i.e., violaceusides I, II, and III (1-3, resp.), as active compounds causing morphological abnormality of Pyricularia oryzae mycelia. Their structures were elucidated by spectroscopic methods including 2D-NMR and MS experiments, as well as chemical evidence. Compounds 1-3 exhibit the same structural features, i.e., the presence of a 16-oxo group in the holostane-type triterpene aglycone with the C(7)=C(8) bond, but differ in the side chains and the tetrasaccharide moieties. Compound 1 possesses one sulfate group, while 2 and 3 are disulfated glycosides. All the glycosides showed significant in vitro cytotoxicities against human gastric cancer MKN-45 and human colon cancer HCT-116 cells.
Zhang
Shu-Yu
SY
Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guohe Road, Shanghai 200433, PR China.
Yi
Yang-Hua
YH
Tang
Hai-Feng
HF
D000818:Animals; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D006027:Glycosides / Q000737:chemistry* / Q000633:toxicity*; D006801:Humans; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012616:Sea Cucumbers / Q000737:chemistry*; D013455:Sulfur / Q000737:chemistry*; D014315:Triterpenes / Q000737:chemistry*
D006027:Glycosides; D014315:Triterpenes; D013455:Sulfur