a G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Division of the Russian Academy of Sciences , Pr. 100-letya Vladivostoka 159, 690022 , Vladivostok , Russian Federation.
Nat Prod Res. 2013;27(19):1776-83. doi: 10.1080/14786419.2013.778851. Epub 2013 Apr 11.
A new triterpene glycoside cucumarioside I2 (1) has been isolated from holothurian Eupentacta fraudatrix. The structure of 1 was elucidated using extensive NMR spectroscopy ((1)H and (13)C NMR, (1)H-(1)H COSY, 1D TOCSY, HSQC, H2BC, HMBC and NOESY) and MALDI-TOF-MS. Glycoside 1 is a disulfated branched pentaoside having rare 3-O-methyl-D-xylose. Cytotoxic activity of the glycoside 1 and known cucumariosides H (2), A5 (3), A6 (4), B2 (5) and B1 (6) against mouse Ehrlich carcinoma cells and their influence on lysosomal activity of mouse peritoneal macrophages have been studied. Glycosides 1 and 5 possessed low cytotoxicities, glycoside 6 was not cytotoxic while compounds 2, 3 and 4 possessed moderate cytotoxicities. Glycosides 1, 3 and 5 increased the lysosomal activity of macrophages on 15-17% at doses of 1-5 μg/mL. Hence lysosomal activity depends on structures of both aglycone and carbohydrate chain and does not have a direct correlation with cytotoxicities of the glycosides.
从海参 Eupentacta fraudatrix 中分离得到一种新的三萜糖苷 cucumarioside I2（1）。通过广泛的 NMR 光谱（（1）H 和（13）C NMR、（1）H-（1）H COSY、1D TOCSY、HSQC、H2BC、HMBC 和 NOESY）和 MALDI-TOF-MS 确定了 1 的结构。糖苷 1 是一种双硫酸化的支化五糖苷，具有罕见的 3-O-甲基-D-木糖。糖苷 1 和已知的 cucumariosides H（2）、A5（3）、A6（4）、B2（5）和 B1（6）对小鼠艾氏腹水癌细胞的细胞毒性活性及其对小鼠腹腔巨噬细胞溶酶体活性的影响进行了研究。糖苷 1 和 5 具有低细胞毒性，糖苷 6 无细胞毒性，而化合物 2、3 和 4 具有中等细胞毒性。糖苷 1、3 和 5 在 1-5 μg/mL 剂量下使巨噬细胞的溶酶体活性增加了 15-17%。因此，溶酶体活性取决于糖苷配基和糖链的结构，与糖苷的细胞毒性没有直接关系。
