Cordycepin

Cordycepin

Cordycepin

Chemical compound


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]

Quick Facts Names, Identifiers ...

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.[citation needed] 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%.[11]

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


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. Bibcode:1950Natur.166..949C. doi:10.1038/166949a0. PMID 14796634.
  2. Huang S, Liu H, Sun Y, Chen J, Li X, Xu J, Hu Y, Li Y, Deng Z, Zhong S (2018-01-01). "An effective and convenient synthesis of cordycepin from adenosine". Chemical Papers. 72 (1): 149–160. doi:10.1007/s11696-017-0266-9. ISSN 1336-9075. S2CID 90915876.
  3. Zhou X, Luo L, Dressel W, Shadier G, Krumbiegel D, Schmidtke P, Zepp F, Meyer CU (2008). "Cordycepin is an immunoregulatory active ingredient of Cordyceps sinensis". The American Journal of Chinese Medicine. 36 (5): 967–80. doi:10.1142/S0192415X08006387. PMID 19051361.
  4. Raethong N, Wang H, Nielsen J, Vongsangnak W (2020). "Optimizing cultivation of Cordyceps militaris for fast growth and cordycepin overproduction using rational design of synthetic media". Computational and Structural Biotechnology Journal. 18: 1–8. doi:10.1016/j.csbj.2019.11.003. PMC 6926140. PMID 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 (2): 510–520. doi:10.1083/jcb.41.2.510. PMC 2107749. PMID 5783871.
  6. Kondrashov A, Meijer HA, Barthet-Barateig A, Parker HN, Khurshid A, Tessier S, et al. (2012). "Inhibition of polyadenylation reduces inflammatory gene induction". RNA. 18 (12): 2236–50. doi:10.1261/rna.032391.112. PMC 3504674. PMID 23118416.
  7. Ju D, Zhang W, Yan J, Zhao H, Li W, Wang J, Liao M, Xu Z, Wang Z, Zhou G, Mei L, Hou N, Ying S, Cai T, Chen S, Xie X, Lai L, Tang C, Park N, Takahashi JS, Huang N, Qi X, Zhang EE (6 May 2020). "Chemical perturbations reveal that RUVBL2 regulates the circadian phase in mammals". Science Translational Medicine. 12 (542): eaba0769. doi:10.1126/scitranslmed.aba0769. PMID 32376767. S2CID 218533423.
  8. National Cancer Institute (2011-02-02). "Definition of cordycepin". NCI Drug Dictionary. Retrieved 21 December 2015.
  9. Kodama E, McCaffrey R, Yusa K, Mitsuya H (February 2000). "Antileukemic activity and mechanism of action of cordycepin against terminal deoxynucleotidyl transferase-positive (TdT+) leukemic cells". Biochemical Pharmacology. 59 (3): 273–281. doi:10.1016/S0006-2952(99)00325-1. PMID 10609556.
  10. Chou S, Lai W, Hong T, Lai J, Tsai S, Chen Y, Yu S, Kao C, Chu R, Ding S, Li T, Shen T (October 2014). "Synergistic property of cordycepin in cultivated Cordyceps militaris-mediated apoptosis in human leukemia cells". Phytomedicine. 21 (12): 1516–1524. doi:10.1016/j.phymed.2014.07.014. PMID 25442260.
  11. Tuli HS, Kumar G, Sandhu SS, Sharma AK, Kashyap D (2015). "Apoptotic effect of cordycepin on A549 human lung cancer cell line". Turkish Journal of Biology. 39: 306–311. doi:10.3906/biy-1408-14.
  12. Li B, Hou Y, Zhu M, Bao H, Nie J, Zhang GY, Shan L, Yao Y, Du K, Yang H, Li M, Zheng B, Xu X, Xiao C, Du J (2016). "3'-Deoxyadenosine (Cordycepin) Produces a Rapid and Robust Antidepressant Effect via Enhancing Prefrontal AMPA Receptor Signaling Pathway". International Journal of Neuropsychopharmacology. 19 (4): pyv112. doi:10.1093/ijnp/pyv112. ISSN 1461-1457. PMC 4851261. PMID 26443809.
  13. Tan L, Song X, Ren Y, Wang M, Guo C, Guo D, Gu Y, Li Y, Cao Z, Deng Y (March 2021). "Anti-inflammatory effects of cordycepin: A review". Phytotherapy Research. 35 (3): 1284–1297. doi:10.1002/ptr.6890. ISSN 0951-418X. PMID 33090621. S2CID 224828245.
  14. Cheng Z, He W, Zhou X, Lv Q, Xu X, Yang S, Zhao C, Guo L (2011-08-16). "Cordycepin protects against cerebral ischemia/reperfusion injury in vivo and in vitro". European Journal of Pharmacology. 664 (1): 20–28. doi:10.1016/j.ejphar.2011.04.052. ISSN 0014-2999. PMID 21554870.

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