An effective and convenient synthesis of cordycepin from adenosine

Huang, Shen; Liu, Hui; Sun, Yanhua; Chen, Jian; Li, Xiufang; Xu, Jingmang; Hu, Yuwei; Li, Yuqing; Deng, Zhiwei; Zhong, Shian

doi:10.1007/s11696-017-0266-9

Cited by 17 publications

(10 citation statements)

References 30 publications

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“…The chemical structure of cordycepin is very similar to adenosine, with exception of a missing hydroxyl group on carbon number 3 [47]. Therefore, cordycepin can easily be synthetized from adenosine, a natural chemical present in all human cells [48]. The isolation of cordycepin has been described in the literature using various methods [11,16,17,47,48].…”

Section: Discussionmentioning

confidence: 99%

“…Therefore, cordycepin can easily be synthetized from adenosine, a natural chemical present in all human cells [48]. The isolation of cordycepin has been described in the literature using various methods [11,16,17,47,48]. The present study improved the isolation procedure, provided a rapid isolation method, and conducted bioassay-guided isolation and identification of plant growth inhibitors from C. militaris (Figure 1 and Figure 8; Table 2), resulting in a detailed description of the inhibitory activity of this fungus with its active cordycepin (Table 4).…”

Section: Discussionmentioning

confidence: 99%

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Cordycepin Isolated from Cordyceps militaris: Its Newly Discovered Herbicidal Property and Potential Plant-Based Novel Alternative to Glyphosate

et al. 2019

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There is currently much interest in finding new phytochemicals among plants and fungi as nature-based alternatives to replace problematic herbicides such as glyphosate, which are preferentially used in agricultural production n. We discovered striking herbicidal potency in Cordyceps militaris (L.) and identified cordycepin as its principal plant growth inhibitor. Cordycepin obtained as an ethyl acetate extract was subjected to column chromatography and evaluated for its bioassay-guided phytotoxic capacity against Raphanus sativus (radish), showing a maximum inhibition on germination and growth of radish (IC50 = 0.052–0.078 mg/mL). Gas chromatography-mass spectrometry (GC-MS) (m/z: 251.2) and liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS) ([M + Na]+ m/z: 274.1; [M + H]+ m/z: 252.1) analyses confirmed cordycepin as the major component of the tested column fraction (55.38%). At 0.04 mg/mL, cordycepin showed 3.8–5.9- and 3.3–3.7-fold greater inhibition of the germination and growth of radish than benzoic acid (BA) and glyphosate, respectively. Compared with BA, isolated cordycepin reduced plant chlorophyll and carotenoid contents (2.0–9.5 -fold), while proline, total phenolic and total flavonoid contents were increased 1.2–1.8-fold. Finally, cordycepin promoted electrolyte leakage and malondialdehyde accumulation in radish aerial parts. Thus, cordycepin successfully isolated from Cordyceps militaris is a highly potent plant growth inhibitor with pending worldwide patent and may become a potential plant-based novel alternative to the disputed glyphosate.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Cordycepin Isolated from Cordyceps militaris: Its Newly Discovered Herbicidal Property and Potential Plant-Based Novel Alternative to Glyphosate

et al. 2019

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“…The NMR spectrum of cordycepin shows a singlet at 3.4 ppm, attributed to the C-H proton and a -NH 2 peak reported to be present at 4.6 ppm, whereas, the peaks due to the different -OH groups are found to in the 8-8.5 ppm range [47]. The concentration of cordycepin in C. militaris, i.e., around 2-3 mg/kg, is very low compared to the needs of the commercial market, therefore various synthetic and semi-synthetic methods have been reported for the preparation of cordycepin [49]. Cordycepin can be synthesized chemically by replacing an OH group with an H group at the 3 -position of the ribofuranosyl moiety to produce an adenosine analogue [50].…”

Section: Cordycepin and Its Chemical Featuresmentioning

confidence: 99%

“…Cordycepin can be synthesized chemically by replacing an OH group with an H group at the 3 -position of the ribofuranosyl moiety to produce an adenosine analogue [50]. Cordycepin is found to be structurally very similar to adenosine except for the lack of a 3 -hydroxyl group [49,51] Due to its very close structural similarity with adenosine, it is considered to be a very potent bioactive component with essential properties for its nutraceutical applications. There are various reports suggesting that cordycepin competitively inhibits the courses of synthesis and metabolism of DNA and RNA, as well as it affects the activity of adenosine deaminase and the mTOR signaling pathway [52].…”

Section: Cordycepin and Its Chemical Featuresmentioning

confidence: 99%

“…There are various reports suggesting that cordycepin competitively inhibits the courses of synthesis and metabolism of DNA and RNA, as well as it affects the activity of adenosine deaminase and the mTOR signaling pathway [52]. Therefore, cordycepin has been reported to have a wide variety of pharmacological actions such as antioxidant, immunological, hypolipidemic, anti-inflammatory, anticancer, antimicrobial, antiviral, and hypoglycemic properties [49].…”

Section: Cordycepin and Its Chemical Featuresmentioning

confidence: 99%

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Cordycepin for Health and Wellbeing: A Potent Bioactive Metabolite of an Entomopathogenic Medicinal Fungus Cordyceps with Its Nutraceutical and Therapeutic Potential

et al. 2020

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Cordyceps is a rare naturally occurring entomopathogenic fungus usually found at high altitudes on the Himalayan plateau and a well-known medicinal mushroom in traditional Chinese medicine. Cordyceps contains various bioactive components, out of which, cordycepin is considered most vital, due to its utmost therapeutic as well as nutraceutical potential. Moreover, the structure similarity of cordycepin with adenosine makes it an important bioactive component, with difference of only hydroxyl group, lacking in the 3′ position of its ribose moiety. Cordycepin is known for various nutraceutical and therapeutic potential, such as anti-diabetic, anti-hyperlipidemia, anti-fungal, anti-inflammatory, immunomodulatory, antioxidant, anti-aging, anticancer, antiviral, hepato-protective, hypo-sexuality, cardiovascular diseases, antimalarial, anti-osteoporotic, anti-arthritic, cosmeceutical etc. which makes it a most valuable medicinal mushroom for helping in maintaining good health. In this review, effort has been made to bring altogether the possible wide range of cordycepin’s nutraceutical potential along with its pharmacological actions and possible mechanism. Additionally, it also summarizes the details of cordycepin based nutraceuticals predominantly available in the market with expected global value. Moreover, this review will attract the attention of food scientists, nutritionists, pharmaceutical and food industries to improve the use of bioactive molecule cordycepin for nutraceutical purposes with commercialization to aid and promote healthy lifestyle, wellness and wellbeing.

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A novel complementary pathway of cordycepin biosynthesis in Cordyceps militaris

Zhang,

Yang,

Luo

et al. 2023

Int Microbiol

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We determined whether there exists a complementary pathway of cordycepin biosynthesis in wild-type Cordyceps militaris, high-cordycepin-producing strain C. militaris GYS60, and low-cordycepin-producing strain C. militaris GYS80. Differentially expressed genes were identified from the transcriptomes of the three strains. Compared with C. militaris, in GYS60 and GYS80, we identified 145 and 470 upregulated and 96 and 594 downregulated genes. Compared with GYS80, in GYS60, we identified 306 upregulated and 207 downregulated genes. Gene Ontology analysis revealed that upregulated genes were mostly involved in detoxification, antioxidant, and molecular transducer in GYS60. By Clusters of Orthologous Groups of Proteins and Kyoto Encyclopedia of Genes and Genomes analyses, eight genes were significantly upregulated: five genes related to purine metabolism, one to ATP production, one to secondary metabolite transport, and one to RNA degradation. In GYS60, cordycepin was significantly increased by upregulation of ATP production, which promoted 3′,5′-cyclic AMP production. Cyclic AMP accelerated 3′-AMP accumulation, and cordycepin continued to be synthesized and exported. We verified the novel complementary pathway by adding the precursor adenosine and analyzing the expression of four key genes involved in the main pathway of cordycepin biosynthesis. Adenosine addition increased cordycepin production by 51.2% and 10.1%, respectively, in C. militaris and GYS60. Four genes in the main pathway in GYS60 were not upregulated.

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An effective and convenient synthesis of cordycepin from adenosine

Cited by 17 publications

References 30 publications

Cordycepin Isolated from Cordyceps militaris: Its Newly Discovered Herbicidal Property and Potential Plant-Based Novel Alternative to Glyphosate

Cordycepin Isolated from Cordyceps militaris: Its Newly Discovered Herbicidal Property and Potential Plant-Based Novel Alternative to Glyphosate

Cordycepin for Health and Wellbeing: A Potent Bioactive Metabolite of an Entomopathogenic Medicinal Fungus Cordyceps with Its Nutraceutical and Therapeutic Potential

A novel complementary pathway of cordycepin biosynthesis in Cordyceps militaris

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