Phrygiasterol, a cytotoxic cyclopropane-containing polyhydroxysteroid, and related compounds from the pacific starfish Hippasteria phrygiana.
The new cyclopropane-containing steroid phrygiasterol (1) and steroid glycoside phrygioside B (2), along with previously known borealoside C (2a) and (20R,24S)-5alpha-cholesta-3beta,6alpha,8,15alpha,24-pentaol (3), have been isolated from the Pacific starfish Hippasteria phrygiana. On the basis of spectroscopic analyses, using 1D and 2D NMR techniques and some chemical transformations, the structures of 1 and 2 have been established as (20R,24R,25R)-24,26-cyclo-5alpha-cholesta-3beta,6alpha,8,15alpha,16beta,27-hexaol (1) and the sodium salt of (20R,24S)-24-O-(3-O-methyl-4-O-sulfate-beta-d-xylopyranosyl)-5alpha-cholesta-3beta,6alpha,8,15alpha,24-pentaol (2), respectively. Compound 1 inhibited the growth of Ehrlich carcinoma cells with an IC(50) of 50 microg/mL, whereas 2 induced apoptosis of the same cells (EC(50)=70 microg/mL) and inhibited Ca(2+) influx into mouse spleenocytes (EC(50)=20microg/mL).
Levina
Eleonora V
EV
Laboratory of the MaNaPro Chemistry, Pacific Institute of Bioorganic Chemistry of the Russian Academy of Sciences, 690022 Vladivostok-22, Russian Federation.
Kalinovsky
Anatoly I
AI
Andriyashenko
Polina V
PV
Dmitrenok
Pavel S
PS
Aminin
Dmitry L
DL
Stonik
Valentin A
VA
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002118:Calcium / Q000037:antagonists & inhibitors; D004354:Drug Screening Assays, Antitumor; D020128:Inhibitory Concentration 50; D051379:Mice; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010140:Pacific Ocean; D013154:Spleen / Q000166:cytology / Q000187:drug effects; D013215:Starfish / Q000737:chemistry*; D013256:Steroids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D013256:Steroids; C505679:phrygiasterol; D002118:Calcium