Cytotoxic Lathyrane-Type Diterpenes from Seeds of Euphorbia lathyris
Cytotoxic Lathyrane-Type Diterpenes from Seeds of Euphorbia lathyris
复制标题
大戟种子中具有细胞毒性的黧豆烷型二萜
DOI：
10.1248/cpb.c17-00946
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发表时间：
2018-06-01
影响因子：
1.7
通讯作者：
Zhou, Xian-Li
中科院分区：
文献类型：
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作者：
Wang, Jia-Xi;Wang, Qian;Zhou, Xian-Li
从大戟种子中分离得到两个新的二萜化合物L-27(1)和L-28(2)，以及7个已知化合物(3-9)。化合物经核磁共振、高分辨电喷雾电离(HR-ESI)-MS和红外光谱确证。对化合物1和2进行了核磁共振氢谱、碳谱、极化无失真增强谱(DEPT)、相关谱(COSY)、异核多量子相干谱(HMQC)、异核多键连接性谱(HMBC)和核Overhauser效应谱(NOESY)的归属。通过对其核Overhauser效应(NOE)关系的综合解释，证实了1和2的立体构型，表明它们是第一个在C-3上具有α构型取代基的天然二萜类化合物。分别对乳腺癌细胞株MCF-7、MDA-MB-231、786-0和肝癌细胞株HepG2进行了细胞毒实验。结果表明，一品红因子L-28(2)对人肝癌细胞株具有较强的细胞毒作用，其IC50值分别为9.43和13.22mU，初步表明大戟二萜C-3位的构型对其生物活性有显著影响。
We isolated two new lathyrane-type diterpenes L-27 (1) and L-28 (2) along with seven known compounds (3-9) from the seeds of Euphorbia lathyris. These compounds were identified by NMR, high-resolution electrospray ionisation (HR-ESI)-MS as well as IR spectroscopy. Compounds 1 and 2 were assigned NMR spectrums with H-1-NMR, C-13-NMR, distortionless enhancement by polarization (DEPT), correlation spectroscopy (COSY), heteronuclear multiple quantum coherence (HMQC), heteronuclear multiple bond connectivity (HMBC) and nuclear Overhauser effect spectroscopy (NOESY). Stereo configuration of 1 and 2 were confirmed by comprehensive interpretation of their nuclear Overhauser effect (NOE) relationship and showed they were first natural lathyrane-type diterpenes possessing alpha-configuration substitutes at C-3. Cytotoxicity assay of isolated compounds were evaluated against breast cancer cell lines MCF-7 or MDA-MB-231, 786-0 and liver cancer cell lines HepG2. As a result, Euphorbia factor L-28 (2) showed strongly cytotoxicity to the 786-0 and HepG2 cell lines, with an IC50 value of 9.43 and 13.22 mu M, respectively, which preliminarily suggested that the configuration of lathyrane-type diterpene at C-3 has a significant effect on its bioactivity.