Zhu Wanfang, Su Shengzhi, Xu Yunhui, Xie Zijian, Bai Yidan, Liu Wenyuan, Abe Masahiko, Akihisa Toshihiro, Feng Feng, Zhang Jie
School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing 211198, PR China.
Marshall University, Marshall Institute for Interdisciplinary Research, Weisberg Engn Complex, RM 4117, 1628 Third Ave, Huntington, WV 25703, USA.
Steroids. 2018 Dec;140:167-172. doi: 10.1016/j.steroids.2018.09.016. Epub 2018 Oct 6.
Three new C steroids, i.e., (3β,17α,20S)-pregn-5(6)-ene-3, 17, 20-triol-3-O-β-d-digitalopyranosyl-(1 → 4)-β-d-digitalopyranoside (4), (3β,17α,20S)-pregn-5(6)-ene-3, 17, 20-triol-20-O-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl-(1 → 2)-β-d-digital-opyranoside (8), (3β, 20R)-pregn-14(15)-ene-3, 20, 21-triol-3-O-β-d-glucopy-ranoside (10), along with ten known C steroids were isolated from Streptocaulon juventas. Their structures were elucidated on the basis of 1D and 2D NMR spectroscopic techniques, mass spectrometry as well as comparison with the literature. All the isolated compounds were screened for their in vitro cytotoxicity against human liver cancer cells (HepG2) and the structure-activity relationships were also analyzed. Moreover, compounds 1-3, 5, 10-12, which displayed cytotoxic activities in HepG2 cells, were tested for the selective index (SI) by the ratio of cytotoxic effect on human hepatocytes (LO2) to that on HepG2. As a result, new compound 10 exhibited a good inhibitory activity against HepG2 with IC value 11.7 μM as well as high SI value 3.5. Furthermore, compound 10 could induce HepG2 cells apoptosis by flow cytometry.
从长花链珠藤中分离出三种新的C甾体化合物，即(3β,17α,20S)-孕甾-5(6)-烯-3,17,20-三醇-3-O-β-D-洋地黄吡喃糖基-(1→4)-β-D-洋地黄吡喃糖苷(4)、(3β,17α,20S)-孕甾-5(6)-烯-3,17,20-三醇-20-O-β-D-吡喃葡萄糖基-(1→6)-β-D-吡喃葡萄糖基-(1→2)-β-D-洋地黄吡喃糖苷(8)、(3β,20R)-孕甾-14(15)-烯-3,20,21-三醇-3-O-β-D-吡喃葡萄糖苷(10)，以及十种已知的C甾体化合物。通过一维和二维核磁共振光谱技术、质谱分析并与文献对比，阐明了它们的结构。对所有分离得到的化合物进行了体外抗人肝癌细胞(HepG2)的细胞毒性筛选，并分析了构效关系。此外，对在HepG2细胞中表现出细胞毒性活性的化合物1-3、5、10-12，通过对人肝细胞(LO2)与HepG2细胞的细胞毒性作用比值来测定其选择性指数(SI)。结果表明，新化合物10对HepG2具有良好的抑制活性，IC值为11.7 μM，SI值高达3.5。此外，化合物10可通过流式细胞术诱导HepG2细胞凋亡。
