具有细胞毒性活性的α-吡喃酮衍生物，来自内生真菌茎点霉属YN02-P-3。
α-Pyrone derivatives with cytotoxic activities, from the endophytic fungus Phoma sp. YN02-P-3.
作者信息
Sang Xia-Nan, Chen Shao-Fei, Tang Ming-Xu, Wang Hai-Feng, An Xiao, Lu Xiao-Jie, Zhao Dan, Wang Yu-Bo, Bai Jiao, Hua Hui-Ming, Chen Gang, Pei Yue-Hu
机构信息
Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China; School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China.
Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China; School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China; School of Pharmacy, Jinzhou Medical University, Jinzhou 121001, China.
出版信息
Bioorg Med Chem Lett. 2017 Aug 15;27(16):3723-3725. doi: 10.1016/j.bmcl.2017.06.079. Epub 2017 Jun 29.
Four new α-pyrone derivatives phomones C-F (1-4) together with four known compounds (5-8) were isolated from the endophytic fungus Phoma sp. YN02-P-3. Compound 1 is the first example of 6-α,β-unsaturated ester-2-pyrone dimers via intermolecular symmetrical [2+2] cycloaddition. The chemical structures of these compounds were determined from spectroscopic data (1D/2D NMR, MS and IR). The acetylated product (9) of 1 along with compounds 1-8 were then tested for their cytotoxicity against HL-60, PC-3 and HCT-116 cell lines. Compounds 2, 3, 5 and 9 with acetyl groups showed significant inhibitory activities against the three cell lines with IC values in the range 0.52-9.85μM. while compounds 1, 4 and 6-8 that possess no acetyl group showed no inhibitory activity (IC>50μM), indicating that the acetyl group at 10- or 12- are essential for their cytotoxic activities. The structure-activity relationships of these phomones were also reported.
从内生真菌茎点霉属YN02-P-3中分离得到4个新的α-吡喃酮衍生物茎点霉毒素C-F（1-4）以及4个已知化合物（5-8）。化合物1是通过分子间对称[2+2]环加成形成的6-α,β-不饱和酯-2-吡喃酮二聚体的首个实例。这些化合物的化学结构通过光谱数据（一维/二维核磁共振、质谱和红外光谱）确定。随后测试了1的乙酰化产物（9）以及化合物1-8对HL-60、PC-3和HCT-116细胞系的细胞毒性。带有乙酰基的化合物2、3、5和9对这三种细胞系显示出显著的抑制活性，IC值在0.52-9.85μM范围内。而不具有乙酰基的化合物1、4和6-8没有显示出抑制活性（IC>50μM），这表明10-或12-位的乙酰基对其细胞毒性活性至关重要。还报道了这些茎点霉毒素的构效关系。
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