来自新几内亚 Culcita 海星的三种新海星皂苷及其生物活性。

Three new asterosaponins from the starfish Culcita novaeguineae and their bioactivity.

作者信息

Tang Hai-Feng, Yi Yang-Hua, Li Ling, Sun Peng, Zhang San-Qi, Zhao Yue-Ping

机构信息

Research Center for Marine Drugs, College of Pharmacy, Second Military Medical University, Shanghai, PR China.

出版信息

Planta Med. 2005 May;71(5):458-63. doi: 10.1055/s-2005-871215.

DOI:10.1055/s-2005-871215

PMID:15931586

Abstract

Bioassay-guided fractionation of the active n-BuOH extract of the starfish Culcita novaeguineae resulted in the isolation of three new sulfated steroidal glycosides (asterosaponins) 1, 2 and 3, as active compounds causing morphological abnormality of Pyricularia oryzae mycelia. Compounds 1-3 possess the same pentasaccharide moiety, beta-D-fucopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->4)-[beta-D-quinovopyranosyl-(1-->2)]-beta-D-xylopyranosyl-(1-->3)-beta-D-quinovopyranosyl, linked to C-6 of 3beta-sulfated steroidal aglycones and differ from each other in the side chains. Their structures were elucidated by extensive spectral studies and chemical evidences. Saponins 1 and 3 showed significant cytotoxicity against two cancer cell lines (IC50 values for 1:3.57 microg/mL [K-562], 2.55 microg/mL [BEL-7402]; for 3:3.75 microg/mL [K-562], 1.89 microg/mL [BEL-7402]), as well as hemolytic activity to rabbit erythrocytes (ED50 values: 16 and 31 microg/mL, respectively), while 2 was inactive in these bioassays.

摘要

对新几内亚 Culcita 海星的活性正丁醇提取物进行生物测定指导的分级分离，得到了三种新的硫酸化甾体糖苷（海星皂苷）1、2 和 3，它们是导致稻瘟病菌丝体形态异常的活性化合物。化合物 1 - 3 具有相同的五糖部分，即β-D-呋喃岩藻糖基-(1→2)-α-L-阿拉伯呋喃糖基-(1→4)-[β-D-奎诺糖基-(1→2)]-β-D-木糖呋喃糖基-(1→3)-β-D-奎诺糖基，连接到 3β-硫酸化甾体苷元的 C-6 位，且侧链彼此不同。通过广泛的光谱研究和化学证据阐明了它们的结构。皂苷 1 和 3 对两种癌细胞系显示出显著的细胞毒性（1 的 IC50 值：对 K-562 为 3.57 μg/mL，对 BEL-7402 为 2.55 μg/mL；3 的 IC50 值：对 K-562 为 3.75 μg/mL，对 BEL-7402 为 1.89 μg/mL），以及对兔红细胞的溶血活性（ED50 值分别为 16 和 31 μg/mL），而 2 在这些生物测定中无活性。