Constituents of the sea cucumber Cucumaria okhotensis. Structures of okhotosides B1-B3 and cytotoxic activities of some glycosides from this species

J Nat Prod. 2008 Mar;71(3):351-6. doi: 10.1021/np0705413. Epub 2008 Feb 21.

Abstract

Three new triterpene oligoglycosides, okhotosides B 1 ( 1), B 2 ( 2), and B 3 ( 3), have been isolated from the sea cucumber Cucumaria okhotensis along with the known compounds frondoside A ( 4), frondoside A 1, cucumarioside A 2-5, and koreoside A. The structures of 1- 3 were elucidated on the basis of their spectroscopic data (2D NMR and MS). Compounds 1- 3 were moderately toxic against HeLa tumor cells. Frondoside A ( 4) showed more potent cytotoxicity against THP-1 and HeLa tumor cell lines (with IC 50 values of 4.5 and 2.1 microg/mL, respectively) and decreased both the AP-1-dependent trascriptional activities induced by UVB, EGF, or TPA in JB6-LucAP-1 cells and the EGF-induced NF-kappaB-dependent transcriptional activity in JB6-LucNF-kB cells at doses of about 1 microg/mL. At the same doses, it increased the p53-dependent transcriptional activity in nonactivated JB6-Lucp53 cells and inhibited the colony formation of JB6 P (+) Cl 41 cells activated with EGF (INCC 50 = 0.8 microg/mL).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology*
  • Cucumaria / chemistry*
  • Drug Screening Assays, Antitumor
  • Epidermal Growth Factor / pharmacology
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology*
  • HeLa Cells
  • Humans
  • Inhibitory Concentration 50
  • Molecular Structure
  • NF-kappa B / metabolism
  • Russia
  • Transcriptional Activation / drug effects
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification*
  • Triterpenes / pharmacology*

Substances

  • Antineoplastic Agents
  • Glycosides
  • NF-kappa B
  • Triterpenes
  • okhotoside B1
  • okhotoside B2
  • okhotoside B3
  • Epidermal Growth Factor