Constituents of the sea cucumber Cucumaria okhotensis. Structures of okhotosides B1-B3 and cytotoxic activities of some glycosides from this species.
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).
Silchenko
Alexandra S
AS
Pacific Institute of Biorganic Chemistry, Russian Academy of Science, Vladivostok, Russian Federation.
Avilov
Sergey A
SA
Kalinin
Vladimir I
VI
Kalinovsky
Anatoly I
AI
Dmitrenok
Pavel S
PS
Fedorov
Sergey N
SN
Stepanov
Vadim G
VG
Dong
Zigang
Z
Stonik
Valentin A
VA
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D048016:Cucumaria / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D004815:Epidermal Growth Factor / Q000494:pharmacology; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006367:HeLa Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D016328:NF-kappa B / Q000378:metabolism; D012426:Russia; D015533:Transcriptional Activation / Q000187:drug effects; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
D000970:Antineoplastic Agents; D006027:Glycosides; D016328:NF-kappa B; D014315:Triterpenes; C529248:okhotoside B1; C529249:okhotoside B2; C529250:okhotoside B3; D004815:Epidermal Growth Factor