Cordycepin: Difference between revisions

{{cs1 config|name-list-style=vanc}}

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 389428269

| Name = Cordycepin

| ImageFile = cordycepin.svg

| ImageName =

| IUPACName = 3′-Deoxyadenosine

| SystematicName = (2''S'',3''R'',5''S'')-2-(6-Amino-9''H''-purin-9-yl)-5-(hydroxymethyl)oxolan-3-ol

| OtherNames = Cordycepine<br />9-(3-Deoxy-β-<small>D</small>-ribofuranosyl)adenine <br> 3-dA

|Section1={{Chembox Identifiers

| IUPHAR_ligand = 4630

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 73-03-0

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = GZ8VF4M2J8

| SMILES = O[C@@H]1C[C@@H](CO)O[C@H]1N2C(N=CN=C3N)=C3N=C2

| PubChem = 6303

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 305686

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 6064

| SMILES2 = n2c1c(ncnc1n(c2)[C@@H]3O[C@@H](C[C@H]3O)CO)N

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = OFEZSBMBBKLLBJ-BAJZRUMYSA-N

}}

|Section2={{Chembox Properties

| C=10|H=13|N=5|O=3

| Density =

| MeltingPtC = 225.5

}}

'''Cordycepin''', or '''3'-deoxyadenosine''', is a [[Derivative (chemistry)|derivative]] of the [[nucleoside]] [[adenosine]], differing from the latter by the replacement of the [[hydroxy group]] in the [[Nucleic acid nomenclature|3']] position with a hydrogen. It was initially extracted from the [[fungus]] ''[[Cordyceps militaris]]'',<ref>{{cite journal | author = Cunningham, K. G. | author2 = Manson, W. | author3 = Spring, F. S. | author4 = Hutchinson, S. A. | year = 1950 | title = Cordycepin, a Metabolic Product isolated from Cultures of Cordyceps militaris (Linn.) Link. | journal = Nature | volume = 166 | issue = 4231 | pages = 949 | doi = 10.1038/166949a0 | pmid = 14796634 | bibcode = 1950Natur.166..949C | doi-access = free }}</ref> but can now be produced synthetically.<ref>{{Cite journal |last1=Huang |first1=Shen |last2=Liu |first2=Hui |last3=Sun |first3=Yanhua |last4=Chen |first4=Jian |last5=Li |first5=Xiufang |last6=Xu |first6=Jiangfeng |last7=Hu |first7=Yuwei |last8=Li |first8=Yuqing |last9=Deng |first9=Zhiwei |last10=Zhong |first10=Shian |date=2018-01-01 |title=An effective and convenient synthesis of cordycepin from adenosine |url=https://doi.org/10.1007/s11696-017-0266-9 |journal=Chemical Papers |language=en |volume=72 |issue=1 |pages=149–160 |doi=10.1007/s11696-017-0266-9 |s2cid=90915876 |issn=1336-9075}}</ref> It is also found in other ''[[Cordyceps]]'' species as well as ''[[Ophiocordyceps sinensis]]''.<ref>{{cite journal |last1=Zhou |first1=X |last2=Luo |first2=L |last3=Dressel |first3=W |last4=Shadier |first4=G |last5=Krumbiegel |first5=D |last6=Schmidtke |first6=P |last7=Zepp |first7=F |last8=Meyer |first8=CU |title=Cordycepin is an immunoregulatory active ingredient of Cordyceps sinensis. |journal=The American Journal of Chinese Medicine |date=2008 |volume=36 |issue=5 |pages=967–80 |doi=10.1142/S0192415X08006387 |pmid=19051361}}</ref>

Cordycepin is produced in ''cordyceps'' as a means of infecting insect populations, due to cordycepin's biological activity<ref>{{Cite journal |last1=Raethong |first1=Nachon |last2=Wang |first2=Hao |last3=Nielsen |first3=Jens |last4=Vongsangnak |first4=Wanwipa |date=2020 |title=Optimizing cultivation of Cordyceps militaris for fast growth and cordycepin overproduction using rational design of synthetic media |journal=Computational and Structural Biotechnology Journal |language=en |volume=18 |pages=1–8 |doi=10.1016/j.csbj.2019.11.003 |pmc=6926140 |pmid=31890138}}</ref>

Because cordycepin is similar to [[adenosine]], some [[enzyme]]s 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).<ref>{{cite journal | author = Siev, M. | author2 = Weinberg, R. | author3 = Penman, S. | year = 1969 | title = The selective interruption of nucleolar RNA synthesis in HeLa cells by cordycepin | journal = J. Cell Biol. | volume = 41 | pages = 510–520 | doi = 10.1083/jcb.41.2.510 | pmid = 5783871 | issue = 2 | pmc = 2107749}}</ref><ref name="pmid23118416">{{cite journal| vauthors=Kondrashov A, Meijer HA, Barthet-Barateig A, Parker HN, Khurshid A, Tessier S| title=Inhibition of polyadenylation reduces inflammatory gene induction | journal=RNA | year= 2012 | volume= 18| issue= 12| pages= 2236–50| pmid=23118416 | doi=10.1261/rna.032391.112 | pmc= 3504674| display-authors=etal }}</ref> By acting as an adenosine analog, cordycepin was found to be the most potent molecular circadian clock resetter out of several screened compounds.<ref>{{cite journal |last1=Ju |first1=Dapeng |last2=Zhang |first2=Wei |last3=Yan |first3=Jiawei |last4=Zhao |first4=Haijiao |last5=Li |first5=Wei |last6=Wang |first6=Jiawen |last7=Liao |first7=Meimei |last8=Xu |first8=Zhancong |last9=Wang |first9=Zhiqiang |last10=Zhou |first10=Guanshen |last11=Mei |first11=Long |last12=Hou |first12=Nannan |last13=Ying |first13=Shuhua |last14=Cai |first14=Tao |last15=Chen |first15=She |last16=Xie |first16=Xiaowen |last17=Lai |first17=Luhua |last18=Tang |first18=Chao |last19=Park |first19=Noheon |last20=Takahashi |first20=Joseph S. |last21=Huang |first21=Niu |last22=Qi |first22=Xiangbing |last23=Zhang |first23=Eric Erquan |title=Chemical perturbations reveal that RUVBL2 regulates the circadian phase in mammals |journal=Science Translational Medicine |date=6 May 2020 |volume=12 |issue=542 |pages=eaba0769 |doi=10.1126/scitranslmed.aba0769|pmid=32376767 |s2cid=218533423 }}</ref>

Cordycepin has displayed [[cytotoxicity]] against some [[Leukemia|leukemic]] cell lines ''in vitro''.<ref>{{cite web|author=National Cancer Institute|title=Definition of cordycepin|url=http://www.cancer.gov/publications/dictionaries/cancer-drug?cdrid=42667|website=NCI Drug Dictionary|accessdate=21 December 2015|date=2011-02-02}}</ref><ref name="kodama2000">{{cite journal | last1 = Kodama | first1 = E.M. | last2 = McCaffrey | first2 = R.P. | last3 = Yusa | first3 = K. | last4 = Mitsuya | first4 = H. | title = Antileukemic activity and mechanism of action of cordycepin against terminal deoxynucleotidyl transferase-positive (TdT+) leukemic cells| journal = Biochemical Pharmacology | volume = 59 | issue = 3 | date = February 2000 | pages = 273–281 | doi = 10.1016/S0006-2952(99)00325-1 | pmid = 10609556}}</ref><ref name="chou2014">{{cite journal | last1 = Chou | first1 = S.M. | last2 = Lai | first2 = W.J. | last3 = Hong | first3 = T.W. | last4 = Lai | first4 = J.Y. | last5 = Tsai | first5 = S.H. | last6 = Chen | first6 = Y.H. | last7 = Yu | first7 = S.H. | last8 = Kao | first8 = C.H. | last9 = Chu | first9 = R. | last10 = Ding | first10 = S.T. | last11 = Li | first11 = T.K. | last12 = Shen | first12 = T.L. | title = Synergistic property of cordycepin in cultivated ''Cordyceps militaris''-mediated apoptosis in human leukemia cells | doi = 10.1016/j.phymed.2014.07.014 | journal = Phytomedicine | volume = 21 | issue = 12 | date = October 2014 | pages = 1516–1524 | pmid = 25442260}}</ref> Additionally, cordycepin has been shown to display an effect in some types of other cancers, such as lung,<ref name=":0">{{Cite journal |last1=Tuli |first1=Hardeep Singh |last2=Kumar |first2=Gaurav |last3=Sandhu |first3=Sardul Singh |last4=Sharma |first4=Anil Kumar |last5=Kashyap |first5=Dharmbir |date=2015 |title=Apoptotic effect of cordycepin on A549 human lung cancer cell line |journal=Turkish Journal of Biology |url=https://journals.tubitak.gov.tr/biology/vol39/iss2/16 |volume=39 |pages=306–311 |doi=10.3906/biy-1408-14|doi-access=free }}</ref> renal,<ref>{{Cite journal |last1=Hwang |first1=In-Hu |last2=Oh |first2=Seung Yoon |last3=Jang |first3=Hyun-Jin |last4=Jo |first4=Eunbi |last5=Joo |first5=Jong Cheon |last6=Lee |first6=Kyung-Bok |last7=Yoo |first7=Hwa-Seung |last8=Lee |first8=Mi Young |last9=Park |first9=Soo Jung |last10=Jang |first10=Ik-Soon |date=2017-10-18 |editor-last=Ahmad |editor-first=Aamir |title=Cordycepin promotes apoptosis in renal carcinoma cells by activating the MKK7-JNK signaling pathway through inhibition of c-FLIPL expression |journal=PLOS ONE |language=en |volume=12 |issue=10 |pages=e0186489 |doi=10.1371/journal.pone.0186489 |issn=1932-6203 |pmc=5646797 |pmid=29045468 |bibcode=2017PLoSO..1286489H |doi-access=free }}</ref> colon,<ref>{{Cite journal |last1=Lee |first1=Seung Yuan |last2=Debnath |first2=Trishna |last3=Kim |first3=Si-Kwan |last4=Lim |first4=Beong Ou |date=October 2013 |title=Anti-cancer effect and apoptosis induction of cordycepin through DR3 pathway in the human colonic cancer cell HT-29 |url=https://linkinghub.elsevier.com/retrieve/pii/S0278691513005231 |journal=Food and Chemical Toxicology |language=en |volume=60 |pages=439–447 |doi=10.1016/j.fct.2013.07.068|pmid=23941773 }}</ref> and breast cancer.<ref>{{Cite journal |last1=Lee |first1=Dahae |last2=Lee |first2=Won-Yung |last3=Jung |first3=Kiwon |last4=Kwon |first4=Yong |last5=Kim |first5=Daeyoung |last6=Hwang |first6=Gwi |last7=Kim |first7=Chang-Eop |last8=Lee |first8=Sullim |last9=Kang |first9=Ki |date=2019-08-26 |title=The Inhibitory Effect of Cordycepin on the Proliferation of MCF-7 Breast Cancer Cells, and Its Mechanism: An Investigation Using Network Pharmacology-Based Analysis |journal=Biomolecules |language=en |volume=9 |issue=9 |pages=414 |doi=10.3390/biom9090414 |issn=2218-273X |pmc=6770402 |pmid=31454995 |doi-access=free }}</ref> Cordycepin has been shown to reduce viable A549 lung cancer cell populations by 50%.<ref name=":0" />

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.<ref name="LiHou2016">{{cite journal|last1=Li|first1=Bai|last2=Hou|first2=Yangyang|last3=Zhu|first3=Ming|last4=Bao|first4=Hongkun|last5=Nie|first5=Jun|last6=Zhang|first6=Grace Y.|last7=Shan|first7=Liping|last8=Yao|first8=Yao|last9=Du|first9=Kai|last10=Yang|first10=Hongju|last11=Li|first11=Meizhang|last12=Zheng|first12=Bingrong|last13=Xu|first13=Xiufeng|last14=Xiao|first14=Chunjie|last15=Du|first15=Jing|title=3'-Deoxyadenosine (Cordycepin) Produces a Rapid and Robust Antidepressant Effect via Enhancing Prefrontal AMPA Receptor Signaling Pathway|journal=International Journal of Neuropsychopharmacology|volume=19|issue=4|year=2016|pages=pyv112|issn=1461-1457|doi=10.1093/ijnp/pyv112|pmid=26443809|pmc=4851261}}</ref>

Cordycepin has been shown to have anti-inflammatory qualities,<ref>{{Cite journal |last1=Tan |first1=Lu |last2=Song |first2=Xiaominting |last3=Ren |first3=Yali |last4=Wang |first4=Miao |last5=Guo |first5=Chuanjie |last6=Guo |first6=Dale |last7=Gu |first7=Yucheng |last8=Li |first8=Yuzhi |last9=Cao |first9=Zhixing |last10=Deng |first10=Yun |date=March 2021 |title=Anti-inflammatory effects of cordycepin: A review |url=https://onlinelibrary.wiley.com/doi/10.1002/ptr.6890 |journal=Phytotherapy Research |language=en |volume=35 |issue=3 |pages=1284–1297 |doi=10.1002/ptr.6890 |pmid=33090621 |s2cid=224828245 |issn=0951-418X}}</ref> as well as the ability to defend against injury from cerebral ischemia in mice.<ref>{{Cite journal |last1=Cheng |first1=Zhenyong |last2=He |first2=Wei |last3=Zhou |first3=Xiaoxia |last4=Lv |first4=Qing |last5=Xu |first5=Xulin |last6=Yang |first6=Shanshan |last7=Zhao |first7=Chenming |last8=Guo |first8=Lianjun |date=2011-08-16 |title=Cordycepin protects against cerebral ischemia/reperfusion injury in vivo and in vitro |url=https://www.sciencedirect.com/science/article/pii/S0014299911004717 |journal=European Journal of Pharmacology |language=en |volume=664 |issue=1 |pages=20–28 |doi=10.1016/j.ejphar.2011.04.052 |pmid=21554870 |issn=0014-2999}}</ref>

* 2'-[[Deoxyadenosine]]

{{Reflist|2}}

[[Category:Alkaloids found in fungi]]

[[Category:Antidepressants]]

[[Category:Nucleosides]]