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Vibsane-type Diterpenoids from Viburnum odoratissimum and Their Cytotoxic Activities
Bioorganic Chemistry ( IF 4.5 ) Pub Date : 2020-11-24 , DOI: 10.1016/j.bioorg.2020.104498
Shi-Fang Li 1 , Xiao-Qi Yu 1 , Ya-Ling Li 1 , Ming Bai 1 , Bin Lin 2 , Guo-Dong Yao 1 , Shao-Jiang Song 1
Affiliation  

Seven new diterpenoids (1-7), including five 7-membered ring vibsane-type diterpenoids, vibsanolide A-E (1-5) and a pair of epimers of 14,15,16,17-tetranorvibsane-type diterpenoids possessing bicyclo [4.2.1] nonane moiety, vibsanolide F-G (6-7), together with twelve known analogues (8-19) were isolated from the crude extracts of the leaves of Viburnum odoratissimum using Small Molecule Accurate Recognition Technology (SMART). These structures including absolute configurations were elucidated by means of comprehensive analyses of spectroscopic data, as well as comparison of the experimental and calculated electronic circular dichroism (ECD) spectra. These compounds were evaluated for their cytotoxic activities against A549 and HepG2 cells by MTT assay. The results showed that compound 2 exhibited potent cytotoxic activity against A549 cells with IC50 value of 1.11 μM. Further staining experiments indicated that 2 could promote apoptosis induction, enhance reactive oxygen species (ROS) level and attenuate mitochondrial membrane potential (MMP) in A549 cells. Taken together, these findings provided new insights into understanding the cytotoxic activity of vibsane-type diterpenoids and it is meaningful to further investigate the application potential of V. odoratissimum.



中文翻译:

Viburum odoratissimum中的Vibsane型二萜及其细胞毒活性

七种新二萜类化合物 ( 1-7 ),包括 5 种 7 元环 vibsane 型二萜、vibsanolide AE ( 1-5 ) 和一对具有双环的 14,15,16,17- tetranorvibsane 型二萜差向异构体 [4.2. 1] 壬烷部分,vibsanolide FG ( 6-7 ),连同十二个已知的类似物 ( 8-19 ) 是从荚莲( Viburnum odoratissimum)叶子的粗提取物中分离出来的使用小分子精确识别技术(SMART)。通过对光谱数据的综合分析以及实验和计算电子圆二色性 (ECD) 光谱的比较,阐明了包括绝对构型在内的这些结构。通过 MTT 测定评估这些化合物对 A549 和 HepG2 细胞的细胞毒活性。结果表明,化合物2对A549细胞表现出较强的细胞毒活性,IC 50值为1.11 μ M。进一步染色实验表明,2可促进 A549 细胞凋亡诱导,提高活性氧 (ROS) 水平并减弱线粒体膜电位 (MMP)。综上所述,这些发现为了解 vibsane 型二萜类化合物的细胞毒活性提供了新的见解,对进一步研究V. odoratissimum的应用潜力具有重要意义。

更新日期:2020-11-25
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