Cordycepin Explained

Cordycepin, or 3'-deoxyadenosine, is a derivative of the nucleoside adenosine, differing from the latter by the replacement of the hydroxy group in the 3' position with a hydrogen. It was initially extracted from the fungus Cordyceps militaris,[1] but can now be produced synthetically.[2] It is also found in other Cordyceps species as well as Ophiocordyceps sinensis.[3]

Cordycepin is produced in cordyceps as a means of infecting insect populations, due to cordycepin's biological activity[4]

Because cordycepin is similar to adenosine, some enzymes cannot discriminate between the two. It can therefore participate in certain biochemical reactions (for example, 3-dA can trigger the premature termination of mRNA synthesis).[5] [6] By acting as an adenosine analog, cordycepin was found to be the most potent molecular circadian clock resetter out of several screened compounds.[7]

Cordycepin has displayed cytotoxicity against some leukemic cell lines in vitro.[8] [9] [10] Additionally, cordycepin has been shown to display an effect in some types of other cancers, such as lung,[11] renal,[12] colon,[13] and breast cancer.[14] Cordycepin has been shown to reduce viable A549 lung cancer cell populations by 50%.

Cordycepin has been found to produce rapid, robust imipramine-like antidepressant effects in animal models of depression, and these effects, similarly to those of imipramine, are dependent on enhancement of AMPA receptor signaling.[15]

Cordycepin has been shown to have anti-inflammatory qualities,[16] as well as the ability to defend against injury from cerebral ischemia in mice.[17]

See also

Notes and References

  1. Cunningham, K. G. . Manson, W. . Spring, F. S. . Hutchinson, S. A. . 1950 . Cordycepin, a Metabolic Product isolated from Cultures of Cordyceps militaris (Linn.) Link. . Nature . 166 . 4231 . 949 . 10.1038/166949a0 . 14796634 . 1950Natur.166..949C . free .
  2. Huang . Shen . Liu . Hui . Sun . Yanhua . Chen . Jian . Li . Xiufang . Xu . Jiangfeng . Hu . Yuwei . Li . Yuqing . Deng . Zhiwei . Zhong . Shian . 2018-01-01 . An effective and convenient synthesis of cordycepin from adenosine . Chemical Papers . en . 72 . 1 . 149–160 . 10.1007/s11696-017-0266-9 . 90915876 . 1336-9075.
  3. Zhou . X . Luo . L . Dressel . W . Shadier . G . Krumbiegel . D . Schmidtke . P . Zepp . F . Meyer . CU . Cordycepin is an immunoregulatory active ingredient of Cordyceps sinensis. . The American Journal of Chinese Medicine . 2008 . 36 . 5 . 967–80 . 10.1142/S0192415X08006387 . 19051361.
  4. Raethong . Nachon . Wang . Hao . Nielsen . Jens . Vongsangnak . Wanwipa . 2020 . Optimizing cultivation of Cordyceps militaris for fast growth and cordycepin overproduction using rational design of synthetic media . Computational and Structural Biotechnology Journal . en . 18 . 1–8 . 10.1016/j.csbj.2019.11.003 . 6926140 . 31890138.
  5. Siev, M. . Weinberg, R. . Penman, S. . 1969 . The selective interruption of nucleolar RNA synthesis in HeLa cells by cordycepin . J. Cell Biol. . 41 . 510–520 . 10.1083/jcb.41.2.510 . 5783871 . 2 . 2107749.
  6. Kondrashov A, Meijer HA, Barthet-Barateig A, Parker HN, Khurshid A, Tessier S. Inhibition of polyadenylation reduces inflammatory gene induction . RNA . 2012 . 18. 12. 2236–50. 23118416 . 10.1261/rna.032391.112 . 3504674. etal .
  7. Ju . Dapeng . Zhang . Wei . Yan . Jiawei . Zhao . Haijiao . Li . Wei . Wang . Jiawen . Liao . Meimei . Xu . Zhancong . Wang . Zhiqiang . Zhou . Guanshen . Mei . Long . Hou . Nannan . Ying . Shuhua . Cai . Tao . Chen . She . Xie . Xiaowen . Lai . Luhua . Tang . Chao . Park . Noheon . Takahashi . Joseph S. . Huang . Niu . Qi . Xiangbing . Zhang . Eric Erquan . Chemical perturbations reveal that RUVBL2 regulates the circadian phase in mammals . Science Translational Medicine . 6 May 2020 . 12 . 542 . eaba0769 . 10.1126/scitranslmed.aba0769. 32376767 . 218533423 .
  8. Web site: National Cancer Institute. Definition of cordycepin. NCI Drug Dictionary. 21 December 2015. 2011-02-02.
  9. Kodama . E.M. . McCaffrey . R.P. . Yusa . K. . Mitsuya . H. . Antileukemic activity and mechanism of action of cordycepin against terminal deoxynucleotidyl transferase-positive (TdT+) leukemic cells. Biochemical Pharmacology . 59 . 3 . February 2000 . 273–281 . 10.1016/S0006-2952(99)00325-1 . 10609556.
  10. Chou . S.M. . Lai . W.J. . Hong . T.W. . Lai . J.Y. . Tsai . S.H. . Chen . Y.H. . Yu . S.H. . Kao . C.H. . Chu . R. . Ding . S.T. . Li . T.K. . Shen . T.L. . Synergistic property of cordycepin in cultivated Cordyceps militaris-mediated apoptosis in human leukemia cells . 10.1016/j.phymed.2014.07.014 . Phytomedicine . 21 . 12 . October 2014 . 1516–1524 . 25442260.
  11. Tuli . Hardeep Singh . Kumar . Gaurav . Sandhu . Sardul Singh . Sharma . Anil Kumar . Kashyap . Dharmbir . 2015 . Apoptotic effect of cordycepin on A549 human lung cancer cell line . Turkish Journal of Biology . 39 . 306–311 . 10.3906/biy-1408-14. free .
  12. Hwang . In-Hu . Oh . Seung Yoon . Jang . Hyun-Jin . Jo . Eunbi . Joo . Jong Cheon . Lee . Kyung-Bok . Yoo . Hwa-Seung . Lee . Mi Young . Park . Soo Jung . Jang . Ik-Soon . 2017-10-18 . Ahmad . Aamir . Cordycepin promotes apoptosis in renal carcinoma cells by activating the MKK7-JNK signaling pathway through inhibition of c-FLIPL expression . PLOS ONE . en . 12 . 10 . e0186489 . 10.1371/journal.pone.0186489 . 1932-6203 . 5646797 . 29045468 . 2017PLoSO..1286489H . free .
  13. Lee . Seung Yuan . Debnath . Trishna . Kim . Si-Kwan . Lim . Beong Ou . October 2013 . Anti-cancer effect and apoptosis induction of cordycepin through DR3 pathway in the human colonic cancer cell HT-29 . Food and Chemical Toxicology . en . 60 . 439–447 . 10.1016/j.fct.2013.07.068. 23941773 .
  14. Lee . Dahae . Lee . Won-Yung . Jung . Kiwon . Kwon . Yong . Kim . Daeyoung . Hwang . Gwi . Kim . Chang-Eop . Lee . Sullim . Kang . Ki . 2019-08-26 . The Inhibitory Effect of Cordycepin on the Proliferation of MCF-7 Breast Cancer Cells, and Its Mechanism: An Investigation Using Network Pharmacology-Based Analysis . Biomolecules . en . 9 . 9 . 414 . 10.3390/biom9090414 . 2218-273X . 6770402 . 31454995 . free .
  15. Li. Bai. Hou. Yangyang. Zhu. Ming. Bao. Hongkun. Nie. Jun. Zhang. Grace Y.. Shan. Liping. Yao. Yao. Du. Kai. Yang. Hongju. Li. Meizhang. Zheng. Bingrong. Xu. Xiufeng. Xiao. Chunjie. Du. Jing. 3'-Deoxyadenosine (Cordycepin) Produces a Rapid and Robust Antidepressant Effect via Enhancing Prefrontal AMPA Receptor Signaling Pathway. International Journal of Neuropsychopharmacology. 19. 4. 2016. pyv112. 1461-1457. 10.1093/ijnp/pyv112. 26443809. 4851261.
  16. Tan . Lu . Song . Xiaominting . Ren . Yali . Wang . Miao . Guo . Chuanjie . Guo . Dale . Gu . Yucheng . Li . Yuzhi . Cao . Zhixing . Deng . Yun . March 2021 . Anti-inflammatory effects of cordycepin: A review . Phytotherapy Research . en . 35 . 3 . 1284–1297 . 10.1002/ptr.6890 . 33090621 . 224828245 . 0951-418X.
  17. Cheng . Zhenyong . He . Wei . Zhou . Xiaoxia . Lv . Qing . Xu . Xulin . Yang . Shanshan . Zhao . Chenming . Guo . Lianjun . 2011-08-16 . Cordycepin protects against cerebral ischemia/reperfusion injury in vivo and in vitro . European Journal of Pharmacology . en . 664 . 1 . 20–28 . 10.1016/j.ejphar.2011.04.052 . 21554870 . 0014-2999.

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