2. Academic Validation
  3. α-Pyrone derivatives with cytotoxic activities, from the endophytic fungus Phoma sp. YN02-P-3

α-Pyrone derivatives with cytotoxic activities, from the endophytic fungus Phoma sp. YN02-P-3

  • Bioorg Med Chem Lett. 2017 Aug 15;27(16):3723-3725. doi: 10.1016/j.bmcl.2017.06.079.
Xia-Nan Sang 1,  Shao-Fei Chen 1,  Ming-Xu Tang 1,  Hai-Feng Wang 1,  Xiao An 1,  Xiao-Jie Lu 1,  Dan Zhao 1,  Yu-Bo Wang 2,  Jiao Bai 1,  Hui-Ming Hua 1,  Gang Chen 3,  Yue-Hu Pei 4
Affiliations

Affiliations

  • 1 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.
  • 2 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.
  • 3 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. Electronic address: [email protected].
  • 4 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. Electronic address: [email protected].
PMID: 28697923 DOI: 10.1016/j.bmcl.2017.06.079
Abstract

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 IC50 values in the range 0.52-9.85μM. while compounds 1, 4 and 6-8 that possess no acetyl group showed no inhibitory activity (IC50>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.

Keywords

Cytotoxic activities; Phoma sp.; Phomones; Structure-activity relationships; α-Pyrone derivatives.

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