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Cordycepin
Names
IUPAC name
3′-Deoxyadenosine
Systematic IUPAC name
(2S,3R,5S)-2-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-ol
Other names
Cordycepine
9-(3-Deoxy-β-D-ribofuranosyl)adenine
3-dA
Identifiers
3D model ( JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.720 Edit this at Wikidata
PubChem CID
UNII
  • InChI=1S/C10H13N5O3/c11-8-7-9(13-3-12-8)15(4-14-7)10-6(17)1-5(2-16)18-10/h3-6,10,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,10+/m0/s1 ☒N
    Key: OFEZSBMBBKLLBJ-BAJZRUMYSA-N ☒N
  • O[C@@H]1C[C@@H](CO)O[C@H]1N2C(N=CN=C3N)=C3N=C2
  • n2c1c(ncnc1n(c2)[C@@H]3O[C@@H](C[C@H]3O)CO)N
Properties
C10H13N5O3
Molar mass 251.246 g·mol−1
Melting point 225.5 °C (437.9 °F; 498.6 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N  verify ( what is checkY☒N ?)

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%. [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. ^ a b 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. ^ Hwang IH, Oh SY, Jang HJ, Jo E, Joo JC, Lee KB, Yoo HS, Lee MY, Park SJ, Jang IS (2017-10-18). Ahmad A (ed.). "Cordycepin promotes apoptosis in renal carcinoma cells by activating the MKK7-JNK signaling pathway through inhibition of c-FLIPL expression". PLOS ONE. 12 (10): e0186489. Bibcode: 2017PLoSO..1286489H. doi: 10.1371/journal.pone.0186489. ISSN  1932-6203. PMC  5646797. PMID  29045468.
  13. ^ Lee SY, Debnath T, Kim SK, Lim BO (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. 60: 439–447. doi: 10.1016/j.fct.2013.07.068. PMID  23941773.
  14. ^ Lee D, Lee WY, Jung K, Kwon Y, Kim D, Hwang G, Kim CE, Lee S, Kang K (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. 9 (9): 414. doi: 10.3390/biom9090414. ISSN  2218-273X. PMC  6770402. PMID  31454995.
  15. ^ 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.
  16. ^ 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.
  17. ^ 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.
Retrieved from " https://en.wikipedia.org/?title=Cordycepin&oldid=1225416048"
From Wikipedia, the free encyclopedia
Cordycepin
Names
IUPAC name
3′-Deoxyadenosine
Systematic IUPAC name
(2S,3R,5S)-2-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-ol
Other names
Cordycepine
9-(3-Deoxy-β-D-ribofuranosyl)adenine
3-dA
Identifiers
3D model ( JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.720 Edit this at Wikidata
PubChem CID
UNII
  • InChI=1S/C10H13N5O3/c11-8-7-9(13-3-12-8)15(4-14-7)10-6(17)1-5(2-16)18-10/h3-6,10,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,10+/m0/s1 ☒N
    Key: OFEZSBMBBKLLBJ-BAJZRUMYSA-N ☒N
  • O[C@@H]1C[C@@H](CO)O[C@H]1N2C(N=CN=C3N)=C3N=C2
  • n2c1c(ncnc1n(c2)[C@@H]3O[C@@H](C[C@H]3O)CO)N
Properties
C10H13N5O3
Molar mass 251.246 g·mol−1
Melting point 225.5 °C (437.9 °F; 498.6 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N  verify ( what is checkY☒N ?)

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%. [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. ^ a b 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. ^ Hwang IH, Oh SY, Jang HJ, Jo E, Joo JC, Lee KB, Yoo HS, Lee MY, Park SJ, Jang IS (2017-10-18). Ahmad A (ed.). "Cordycepin promotes apoptosis in renal carcinoma cells by activating the MKK7-JNK signaling pathway through inhibition of c-FLIPL expression". PLOS ONE. 12 (10): e0186489. Bibcode: 2017PLoSO..1286489H. doi: 10.1371/journal.pone.0186489. ISSN  1932-6203. PMC  5646797. PMID  29045468.
  13. ^ Lee SY, Debnath T, Kim SK, Lim BO (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. 60: 439–447. doi: 10.1016/j.fct.2013.07.068. PMID  23941773.
  14. ^ Lee D, Lee WY, Jung K, Kwon Y, Kim D, Hwang G, Kim CE, Lee S, Kang K (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. 9 (9): 414. doi: 10.3390/biom9090414. ISSN  2218-273X. PMC  6770402. PMID  31454995.
  15. ^ 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.
  16. ^ 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.
  17. ^ 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.
Retrieved from " https://en.wikipedia.org/?title=Cordycepin&oldid=1225416048"

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