FOOD SCIENCE ›› 2021, Vol. 42 ›› Issue (8): 235-242.doi: 10.7506/spkx1002-6630-20191017-168

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Separation, Structural Identification and Anti-tumor Effects of New Compounds from Cordyceps militaris

XIANG Ting, XIA Chen, LIU Jianhua, WANG Chaoran, SHEN Jianfu   

  1. (1. Natural Products and Human Health Research Center, College of Biosystems Engineering and Food Science, Zhejiang University, Hangzhou 310058, China; 2. SHENGTAI Tea Oil Technology Co. Ltd., Changshan 324200, China; 3. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China; 4. Institute of Biomedical Innovation, China National Pharmaceutical City, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Taizhou 225300, China)
  • Online:2021-04-25 Published:2021-05-14

Abstract: Preparative high performance liquid chromatography with C18 and C18-HCE columns was used to prepare nucleoside compounds from Cordyceps militaris including cordycepin, adenosine and two monomeric compounds, and their structures were identified by ultra-high performance liquid chromatography-quadrupole time-of-flight mass spectrometry (UPLC-QTOF MS) and nuclear magnetic resonance (NMR) spectroscopy. The inhibitory effects of cordycepin, compound I and compound II on the proliferation of HepG2 liver cancer cells were comparatively evaluated by methylthiazolyldiphenyl-tetrazolium bromide (MTT) assay. The results showed that the C18-HCE column could effectively improve the retention and selectivity of polar compounds, facilitating the separation and purification of nucleosides. The purities of adenosine, cordycepin, compound I and compound II were 90.49%, 98.11%, 96.34%, and 98.33% and their yields were 0.053%, 0.253%, 0.368%, and 0.231%, respectively. Compound II was identified as a new substance, which was similar to compound I in structure, both being nucleoside-type compounds substituted with amino acids or amino acid derivatives. Anti-tumor activity experiments showed that all compounds could significantly inhibit the proliferation of HepG2 hepatoma cells, and their effects decreased in the order: compound I > cordycepin > compound II.

Key words: amino acid derivatives; nucleosides; separation and purification; structure identification; anti-tumor

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