Cordycepin

Last updated
Cordycepin
Cordycepin.svg
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 OOjs UI icon edit-ltr-progressive.svg
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 X mark.svgN
    Key: OFEZSBMBBKLLBJ-BAJZRUMYSA-N X mark.svgN
  • 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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.[ 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

Related Research Articles

mir-17 microRNA precursor family

The miR-17 microRNA precursor family are a group of related small non-coding RNA genes called microRNAs that regulate gene expression. The microRNA precursor miR-17 family, includes miR-20a/b, miR-93, and miR-106a/b. With the exception of miR-93, these microRNAs are produced from several microRNA gene clusters, which apparently arose from a series of ancient evolutionary genetic duplication events, and also include members of the miR-19, and miR-25 families. These clusters are transcribed as long non-coding RNA transcripts that are processed to form ~70 nucleotide microRNA precursors, that are subsequently processed by the Dicer enzyme to give a ~22 nucleotide products. The mature microRNA products are thought to regulate expression levels of other genes through complementarity to the 3' UTR of specific target messenger RNA.

<span class="mw-page-title-main">DNA damage-inducible transcript 3</span> Human protein and coding gene

DNA damage-inducible transcript 3, also known as C/EBP homologous protein (CHOP), is a pro-apoptotic transcription factor that is encoded by the DDIT3 gene. It is a member of the CCAAT/enhancer-binding protein (C/EBP) family of DNA-binding transcription factors. The protein functions as a dominant-negative inhibitor by forming heterodimers with other C/EBP members, preventing their DNA binding activity. The protein is implicated in adipogenesis and erythropoiesis and has an important role in the cell's stress response.

<span class="mw-page-title-main">PAK4</span> Mammalian protein found in Homo sapiens

Serine/threonine-protein kinase PAK 4 is an enzyme that in humans is encoded by the PAK4 gene.

<span class="mw-page-title-main">Hippo signaling pathway</span> Signaling pathway that controls organ size

The Hippo signaling pathway, also known as the Salvador-Warts-Hippo (SWH) pathway, is a signaling pathway that controls organ size in animals through the regulation of cell proliferation and apoptosis. The pathway takes its name from one of its key signaling components—the protein kinase Hippo (Hpo). Mutations in this gene lead to tissue overgrowth, or a "hippopotamus"-like phenotype.

mir-221 microRNA

In molecular biology, mir-221 microRNA is a short RNA molecule. MicroRNAs function to regulate the expression levels of other genes by several mechanisms.

mir-210 microRNA

In molecular biology mir-210 microRNA is a short RNA molecule. MicroRNAs function to regulate the expression levels of other genes by several mechanisms.

miR-214

miR-214 is a vertebrate-specific family of microRNA precursors. The ~22 nucleotide mature miRNA sequence is excised from the precursor hairpin by the enzyme Dicer. This sequence then associates with RISC which effects RNA interference.

<i>N</i><sup>6</sup>-Methyladenosine Modification in mRNA, DNA

N6-Methyladenosine (m6A) was originally identified and partially characterised in the 1970s, and is an abundant modification in mRNA and DNA. It is found within some viruses, and most eukaryotes including mammals, insects, plants and yeast. It is also found in tRNA, rRNA, and small nuclear RNA (snRNA) as well as several long non-coding RNA, such as Xist.

In molecular biology mir-301 microRNA is a short RNA molecule. MicroRNAs function to regulate the expression levels of other genes by several mechanisms.

In molecular biology mir-365 microRNA is a short RNA molecule. MicroRNAs function to regulate the expression levels of other genes by several mechanisms.

In molecular biology mir-25 microRNA is a short RNA molecule. MicroRNAs function to regulate the expression levels of other genes by several mechanisms. mir-25 levels increase in human heart failure, and treatment with an anti-sense RNA molecule (antagomiR) was recently reported to halt disease progression and improves cardiac function in a mouse heart failure model.

In molecular biology mir-28 microRNA is a short RNA molecule. MicroRNAs function to regulate the expression levels of other genes by several mechanisms.

In molecular biology mir-153 microRNA is a short RNA molecule. MicroRNAs function to regulate the expression levels of other genes by several mechanisms.

In molecular biology mir-186 microRNA is a short RNA molecule. MicroRNAs function to regulate the expression levels of other genes by several mechanisms.

<i>Cordyceps militaris</i> Species of fungus

Cordyceps militaris is a species of fungus in the family Cordycipitaceae, and the type species of the genus Cordyceps. It was originally described by Carl Linnaeus in 1753 as Clavaria militaris. There are hundreds of species of cordyceps fungi. Special characteristics of Cordyceps Militaris are its use in traditional Chinese medicine, modern pharmaceuticals, and its relationship with insects and how it disperses.

<span class="mw-page-title-main">MicroRNA 495</span>

MicroRNA 495 is a protein that in humans is encoded by the MIR495 gene.

<span class="mw-page-title-main">CHCHD2</span> Protein-coding gene in the species Homo sapiens

Coiled-coil-helix-coiled-coil-helix domain containing 2 is a protein that in humans is encoded by the CHCHD2 gene.

mIR141

MicroRNA 141 is a non-coding RNA molecule that in humans is encoded by the MIR141 gene.

<span class="mw-page-title-main">MIR22HG</span> Non-coding RNA in the species Homo sapiens

MIR22HG, also known as C17orf91, MGC14376, MIRN22, hsa-mir-22, and miR-22 is a human gene that encodes a noncoding RNA (ncRNA).This RNA molecule is not translated into a protein but nonetheless may have important functions.

CKLF-like MARVEL transmembrane domain-containing 5 (CMTM5), previously termed chemokine-like factor superfamily 5, designates any one of the six protein isoforms encoded by six different alternative splices of its gene, CMTM5; CMTM5-v1 is the most studied of these isoforms. The CMTM5 gene is located in band 11.2 on the long arm of chromosome 14.

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. 1 2 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 I, Oh SY, Jang H, Jo E, Joo JC, Lee K, Yoo H, Lee MY, Park SJ, Jang I (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 S, 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 W, Jung K, Kwon Y, Kim D, Hwang G, Kim C, 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.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.