Cordycepin from Cordyceps militaris

Cordycepin O -deoxyadenosine 152), isolated from Cordyceps militaris (Cunningham et al., 1951 Bentley et al., 1951), is a deoxynucleoside possessing antifungal, antiviral, and antitumor activity. Although (152) was isolated 50 years ago, there are still an increasing number of publications on the biochemistry of this compound and other nucleoside mimics. It should be noted that an adenosine derivative, N 6-(2-hydroxyethyl) adenosine (153), was isolated, together with (152) and adenosine, from several species of Cordycepsand Isaria (Furuya et al., 1983). 

Bentley HR, Cunningham KG, Spring FS. Cordycepin, a metabolic product from cultures of Cordyceps militaris (Linn.) Link. Part II. The structure of cordycepin. J Chem Soc 2301-2305, 1951. 

The nucleoside cordycepin was isolated from cultures of the fungus Cordyceps militaris and found to be 3 -deoxyadenosine. Write its structural formula. 

Cordycepin was one of the first adenine-nucleoside analogs isolated from growing cultures of fungi (Cunningham et al., 1951). This nucleoside is produced by Cordyceps militaris, Bentley et al. (1951) reported cordycepin as an adenine-sugar nucleoside (I). Their structural elucidation of the sugar moiety, cordy-... 

Frederiksen, S., H. Malling, and H. Klenow. Isolation of 3 -deoxy-adenosine (cordycepin) from the liquid medium of Cordyceps militaris (L. ex Fr.) Link. Biochim et Biophys. Acta 95, I89 (1965). 

Our recent studies have shown that during the time of cordycepin biosynthesis, DNA synthesis is completely stopped. When adenosine-U- C is added to cordycepin producing cultures of Cordyceps militaris and the RNA and DNA isolated, the RNA is radioactive, while the DNA is not. Both adenine and guanine isolated from the RNA are radioactive. 

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