Levina Eleonora V, Kalinovsky Anatoly I, Andriyashenko Polina V, Dmitrenok Pavel S, Aminin Dmitry L, Stonik Valentin A
Laboratory of the MaNaPro Chemistry, Pacific Institute of Bioorganic Chemistry of the Russian Academy of Sciences, 690022 Vladivostok-22, Russian Federation.
J Nat Prod. 2005 Oct;68(10):1541-4. doi: 10.1021/np049610t.
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).
新型含环丙烷甾体化合物弗氏海星甾醇（1）和甾体糖苷弗氏糖苷B（2），以及先前已知的北方糖苷C（2a）和（20R，24S）-5α-胆甾-3β，6α，8，15α，24-戊醇（3），已从太平洋海星弗氏海盘车中分离得到。基于光谱分析，采用一维和二维核磁共振技术以及一些化学转化方法，确定了1和2的结构分别为（20R，24R，25R）-24，26-环-5α-胆甾-3β，6α，8，15α，16β，27-己醇（1）和（20R，24S）-24-O-（3-O-甲基-4-O-硫酸-β-D-吡喃木糖基）-5α-胆甾-3β，6α，8，15α，24-戊醇的钠盐（2）。化合物1对艾氏癌细胞的生长具有抑制作用，IC50为50μg/mL，而化合物2可诱导相同细胞凋亡（EC50 = 70μg/mL），并抑制Ca2+流入小鼠脾细胞（EC50 = 20μg/mL）。
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