Synthesis of cordycepin: Current scenario and future perspectives
Tài liệu tham khảo
Ahn, 2000, Cordycepin: selective growth inhibitor derived from liquid culture of Cordyceps militaris against Clostridium spp, J. Agric. Food Chem., 48, 2744, 10.1021/jf990862n
Ajikumar, 2010, Isoprenoid pathway optimization for Taxol precursor overproduction in Escherichia coli, Science, 330, 70, 10.1126/science.1191652
Aman, S., A.D., Connolly, T.J., Crittall, A.J., Ji, G., 2000. From adenosine to 3'-deoxyadenosine: development and scale up. Org. Process Res. Dev. 4.
Baeshen, 2015, Production of biopharmaceuticals in E. coli: current scenario and future perspectives, J. Microbiol. Biotechnol., 25, 953, 10.4014/jmb.1412.12079
Biggs, 2016, Overcoming heterologous protein interdependency to optimize P450-mediated Taxol precursor synthesis in Escherichia coli, Proc. Natl. Acad. Sci. U. S. A., 113, 3209, 10.1073/pnas.1515826113
Zhang, C., M.X., Weng, L., 2008. Effects of Cordyceps militaris space mutation treatment on active constituent content. Food Sci., 29.
Cho, 2007, Cordycepin (3'-deoxyadenosine) inhibits human platelet aggregation in a cyclic AMP- and cyclic GMP-dependent manner, Eur. J. Pharmacol., 558, 43, 10.1016/j.ejphar.2006.11.073
Cunningham, 1950, Cordycepin, a metabolic product isolated from cultures of Cordyceps militaris (Linn.) link, Nature, 166, 949, 10.1038/166949a0
Das, 2008, A new approach for improving cordycepin productivity in surface liquid culture of Cordyceps militaris using high-energy ion beam irradiation, Lett. Appl. Microbiol., 47, 534, 10.1111/j.1472-765X.2008.02456.x
de Julian-Ortiz, 1999, Virtual combinatorial syntheses and computational screening of new potential anti-herpes compounds, J. Med. Chem., 42, 3308, 10.1021/jm981132u
Dong, 2005, Nutritional requirements of mycelial growth of Cordyceps sinensis in submerged culture, J. Appl. Microbiol., 99, 483, 10.1111/j.1365-2672.2005.02640.x
Fan, D.D., W.W., Zhong, J.J., 2012. Enhancement of cordycepin production in submerged cultures of Cordyceps militaris by addition of ferrous sulfate. Biochem. Eng. J., 60.
Ho, 2019, Cordycepin enhances radiosensitivity in oral squamous carcinoma cells by inducing autophagy and apoptosis through cell cycle arrest, Int. J. Mol. Sci., 20, 10.3390/ijms20215366
Huang, 2001, Engineering Escherichia coli for the synthesis of taxadiene, a key intermediate in the biosynthesis of taxol, Bioorg. Med. Chem., 9, 2237, 10.1016/S0968-0896(01)00072-4
Huang, 2017, An effective and convenient synthesis of cordycepin from adenosine, Chem. Pap., 72, 149, 10.1007/s11696-017-0266-9
Jan Vonk, 2019, High-throughput targeted gene deletion in the model mushroom Schizophyllum commune using pre-assembled Cas9 ribonucleoproteins, Sci. Rep., 9, 7632, 10.1038/s41598-019-44133-2
Jeong, 2010, Anti-inflammatory effects of cordycepin via suppression of inflammatory mediators in BV2 microglial cells, Int. Immunopharmacol., 10, 1580, 10.1016/j.intimp.2010.09.011
Jeong, 2011, Induction of apoptosis by cordycepin via reactive oxygen species generation in human leukemia cells, Toxicol. In Vitro, 25, 817, 10.1016/j.tiv.2011.02.001
Ji, 2015, Enhanced production of polysaccharide through the overexpression of homologous uridine diphosphate glucose pyrophosphorylase gene in a submerged culture of lingzhi or reishi medicinal mushroom, Ganoderma lucidum (higher basidiomycetes), Int. J. Med. Mushrooms, 17, 435, 10.1615/IntJMedMushrooms.v17.i5.30
Jiang, 2019, Antimicrobial effect and proposed action mechanism of cordycepin against Escherichia coli and Bacillus subtilis, J. Microbiol., 57, 288, 10.1007/s12275-019-8113-z
Jiao, 2019, Developing a CRISPR/Cas9 system for genome editing in the basidiomycetous yeast Rhodosporidium toruloides, Biotechnol. J., 14, 10.1002/biot.201900036
Jiapeng, 2014, Optimization of fermentation conditions and purification of cordycepin from Cordyceps militaris, Prep. Biochem. Biotech., 44, 90, 10.1080/10826068.2013.833111
Jin, 2012, Suppression of alpha-MSH and IBMX-induced melanogenesis by cordycepin via inhibition of CREB and MITF, and activation of PI3K/Akt and ERK-dependent mechanisms, Int. J. Mol. Med., 29, 119
Jung, 2007, A mushroom lectin from ascomycete Cordyceps militaris, BBA, 1770, 833
Kaczka, 1964, Isolation and inhibitory effects of KB cell cultures of 3'-deoxyandenosine from Aspergillus nidulans (Eidam) Wint, Biochem. Biophys. Res. Commun., 14, 452, 10.1016/0006-291X(64)90085-3
Kang, 2017, Development of high cordycepin-producing Cordyceps militaris strains, Mycobiology, 45, 31, 10.5941/MYCO.2017.45.1.31
Khan, 2018, Cordycepin in anticancer research: molecular mechanism of therapeutic effects, Curr. Med. Chem.
Kondrashov, 2012, Inhibition of polyadenylation reduces inflammatory gene induction, RNA, 18, 2236, 10.1261/rna.032391.112
Kredich, 1961, Studies on the biosynthesis of cordycepin, BBA, 47, 529
Kunhorm, 2019, Enrichment of cordycepin for cosmeceutical applications: culture systems and strategies, Appl. Microbiol. Biotechnol., 10.1007/s00253-019-09623-3
Lee, 2019, 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, 10.3390/biom9090414
Lee, 2009, Cordycepin inhibits UVB-induced matrix metalloproteinase expression by suppressing the NF-kappaB pathway in human dermal fibroblasts, Exp. Mol. Med., 41, 548, 10.3858/emm.2009.41.8.060
Lennon, 1976, Biosynthesis of 3'-deoxyadenosine by Cordyceps militaris. Mechanism of reduction, BBA, 425, 532
Li, Q., Y.R., Ruan, Z., Hu, T., Ding, H., Xiao, Q., 2013. Total synthesis of cordycepin. Chin. J. Organ. Chem., 33.
Lim, 2012, Optimization of solid state culture conditions for the production of adenosine, cordycepin, and D-mannitol in fruiting bodies of medicinal caterpillar fungus Cordyceps militaris (L.:Fr.) Link (Ascomycetes), Int. J. Med. Mushrooms, 14, 181, 10.1615/IntJMedMushr.v14.i2.60
Lin, 2016, Biosynthetic pathway analysis for improving the cordycepin and cordycepic acid production in Hirsutella sinensis, Appl. Biochem. Biotechnol., 179, 633, 10.1007/s12010-016-2020-0
Liu Hong, M.H., Mao Lirong, Li Yangming, Zhang Tian, Bao Jianzhong, Chen Xiulan, Sun Ye, 2017. Breeding of high yield Cordyceps militaris mutant strains by protoplast mutagenesis. Sci. Sericulture 03.
Liu, 2020, Dual sgRNA-directed gene deletion in basidiomycete Ganoderma lucidum using the CRISPR/Cas9 system, Microb. Biotechnol., 13, 386, 10.1111/1751-7915.13534
Liu, 2018, Identification of cordycepin biosynthesis-related genes through de novo transcriptome assembly and analysis in Cordyceps cicadae, R. Soc. Open Sci., 5, 10.1098/rsos.181247
Ma, 2015, Cordycepin from Cordyceps militaris prevents hyperglycemia in alloxan-induced diabetic mice, Nutr. Res., 35, 431, 10.1016/j.nutres.2015.04.011
Mao, X.B., E.T., Chauvatcharin, S., Zhong, J.J., 2005. Optimization of carbon source/nitrogen ratio for cordycepin production by submerged cultivation of medicinal mushroom cordyceps militaris. Process. Biochem., 40.
Mao, 2004, Hyperproduction of cordycepin by two-stage dissolved oxygen control in submerged cultivation of medicinal mushroom Cordyceps militaris in bioreactors, Biotechnol. Prog., 20, 1408, 10.1021/bp049765r
Mao XB, Z.J., 2006. Significant effect of NH+ 4 on cordycepin production by submerged cultivation of medicinal mushroom Cordyceps militaris. Enzyme Microbial. Technol., 38.
Martin, 2003, Engineering a mevalonate pathway in Escherichia coli for production of terpenoids, Nat. Biotechnol., 21, 796, 10.1038/nbt833
Masuda, 2011, Production of cordycepin by a repeated batch culture of a Cordyceps militaris mutant obtained by proton beam irradiation, J. Biosci. Bioeng., 111, 55, 10.1016/j.jbiosc.2010.08.018
Masuda, M., U.E., Honda, H., 2007. Enhanced production of cordycepin by surface culture using the medicinal mushroom Cordyceps militaris. Enzyme Microbial. Technol., 40.
McDonald, F.E., G.M., 1996. Asymmetric synthesis of nucleosides via molybdenum-catalyzed alkynol cycloisomerization coupled with stereoselective glycosylations of deoxyfuranose glycals and 3-amidofuranose glycals. J. Am. Chem. Soc., 118.
Moreau, C., K.T., Swarbrick, J.M., Bartlett, S.J., Fliegert, R., Yorgan, T., Bauche, A., Harneit, A., Guse, A.H., Potter, B.V., 2013. Structure-activity relationship of adenosine 5'-diphosphoribose at the transient receptor potential melastatin2 (TRPM2) channel: rational design of antagonists. J. Med. Chem., 56.
Nakamura, 2005, Effect of cordycepin (3'-deoxyadenosine) on hematogenic lung metastatic model mice, Vivo, 19, 137
Ni, 2009, Column chromatographic extraction and preparation of cordycepin from Cordyceps militaris waster medium, J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 877, 2135, 10.1016/j.jchromb.2009.06.009
Pang, 2018, Transcriptome analysis of Paecilomyces hepiali at different growth stages and culture additives to reveal putative genes in cordycepin biosynthesis, Genomics, 110, 162, 10.1016/j.ygeno.2017.09.008
Park, 2014, Cordyceps militaris extract protects human dermal fibroblasts against oxidative stress-induced apoptosis and premature senescence, Nutrients, 6, 3711, 10.3390/nu6093711
Ping, 2019, Building microbial hosts for heterologous production of N-methylpyrrolinium, ACS Synth. Biol., 8, 257, 10.1021/acssynbio.8b00483
Qin, 2019, Therapeutic potential and biological applications of cordycepin and metabolic mechanisms in cordycepin-producing fungi, Molecules, 24, 10.3390/molecules24122231
Quy, 2019, Xanthine oxidase inhibitory potential, antioxidant and antibacterial activities of Cordyceps militaris (L.) link fruiting body, Medicines (Basel), 6
Quy, 2019, Cordycepin isolated from Cordyceps militaris: Its newly discovered herbicidal property and potential plant-based novel alternative to glyphosate, Molecules, 24, 10.3390/molecules24162901
Raethong, 2018, Uncovering global metabolic response to cordycepin production in Cordyceps militaris through transcriptome and genome-scale network-driven analysis, Sci. Rep., 8, 9250, 10.1038/s41598-018-27534-7
Ro, 2006, Production of the antimalarial drug precursor artemisinic acid in engineered yeast, Nature, 440, 940, 10.1038/nature04640
Santos, 2011, Optimization of a heterologous pathway for the production of flavonoids from glucose, Metab. Eng., 13, 392, 10.1016/j.ymben.2011.02.002
Sheng, 2011, An exopolysaccharide from cultivated Cordyceps sinensis and its effects on cytokine expressions of immunocytes, Appl. Biochem. Biotechnol., 163, 669, 10.1007/s12010-010-9072-3
Shin, 2009, Cordycepin suppresses expression of diabetes regulating genes by inhibition of lipopolysaccharide-induced inflammation in macrophages, Immune Netw., 9, 98, 10.4110/in.2009.9.3.98
Sugar, 1998, Antifungal activity of 3'-deoxyadenosine (cordycepin), Antimicrob. Agents Chemother., 42, 1424, 10.1128/AAC.42.6.1424
Tang, 2018, Enhancing cordycepin production in liquid static cultivation of Cordyceps militaris by adding vegetable oils as the secondary carbon source, Bioresour. Technol., 268, 60, 10.1016/j.biortech.2018.07.128
Terpe, 2006, Overview of bacterial expression systems for heterologous protein production: from molecular and biochemical fundamentals to commercial systems, Appl. Microbiol. Biotechnol., 72, 211, 10.1007/s00253-006-0465-8
Todd, A., U.T., 1960. Deoxynucleosides and related compounds Part IX A synthesis of 3'-deoxyadenosine. J. Chem. Soc.
Tuli, 2014, Pharmacological and therapeutic potential of Cordyceps with special reference to Cordycepin, 3 Biotech, 4, 1, 10.1007/s13205-013-0121-9
Wei, 2008, Investigations on cordycepin production by solid culture of Cordyceps militaris, Zhongguo Zhong Yao Za Zhi, 33, 2159
Wongsa, 2020, Alternative metabolic routes in channeling xylose to cordycepin production of Cordyceps militaris identified by comparative transcriptome analysis, Genomics, 112, 629, 10.1016/j.ygeno.2019.04.015
Wu, 2019, Radical scavenging and antiproliferative effects of cordycepin-rich ethanol extract from brown rice-cultivated Cordyceps militaris (ascomycetes) mycelium on breast cancer cell lines, Int. J. Med. Mushrooms, 21, 657, 10.1615/IntJMedMushrooms.2019031138
Xia, Y., L.F., Shang, Y., Chen, P., Lu, Y., Wang, C., 2017. Fungal cordycepin biosynthesis is coupled with the production of the safeguard molecule pentostatin. Cell. Chem. Biol. 24(12), 11.
Xiang, 2014, Transcriptome analysis of the Ophiocordyceps sinensis fruiting body reveals putative genes involved in fruiting body development and cordycepin biosynthesis, Genomics, 103, 154, 10.1016/j.ygeno.2014.01.002
Xu, 2015, Increased polysaccharide production and biosynthetic gene expressions in a submerged culture of Ganoderma lucidum by the overexpression of the homologous alpha-phosphoglucomutase gene, Bioprocess Biosyst. Eng., 38, 399, 10.1007/s00449-014-1279-1
Xu, 2010, Production of individual ganoderic acids and expression of biosynthetic genes in liquid static and shaking cultures of Ganoderma lucidum, Appl. Microbiol. Biotechnol., 85, 941, 10.1007/s00253-009-2106-5
Xu, 2012, Enhancement of ganoderic acid accumulation by overexpression of an N-terminally truncated 3-hydroxy-3-methylglutaryl coenzyme A reductase gene in the basidiomycete Ganoderma lucidum, Appl. Environ. Microbiol., 78, 7968, 10.1128/AEM.01263-12
Xu, 2019, Enhanced production of individual ganoderic acids by integrating Vitreoscilla haemoglobin expression and calcium ion induction in liquid static cultures of Ganoderma lingzhi, Microb. Biotechnol., 12, 1180, 10.1111/1751-7915.13381
An, 2018, Cordycepin reduces weight through regulating gut microbiota in high-fat diet-induced obese rats, Lipids Health Dis., 17, 10.1186/s12944-018-0910-6
Yin, 2017, Transcriptome-wide analysis reveals the progress of Cordyceps militaris subculture degeneration, PLoS ONE, 12, 10.1371/journal.pone.0186279
Yoo, 2004, Effects of Cordyceps militaris extract on angiogenesis and tumor growth, Acta Pharmacol. Sin., 25, 657
Yoshikawa, 2007, Reinforcement of antitumor effect of Cordyceps sinensis by 2'-deoxycoformycin, an adenosine deaminase inhibitor, Vivo, 21, 291
Yue, 2013, The genus Cordyceps: a chemical and pharmacological review, J. Pharm. Pharmacol., 65, 474, 10.1111/j.2042-7158.2012.01601.x
Zhao, 2019, Cordycepin and pentostatin biosynthesis gene identified through transcriptome and proteomics analysis of Cordyceps kyushuensis Kob, Microbiol. Res., 218, 12, 10.1016/j.micres.2018.09.005
Zheng, 2011, Genome sequence of the insect pathogenic fungus Cordyceps militaris, a valued traditional Chinese medicine, Genome Biol., 12, R116, 10.1186/gb-2011-12-11-r116
Zhou, 2018, Improved polysaccharide production by homologous co-overexpression of phosphoglucomutase and UDP glucose pyrophosphorylase genes in the mushroom Coprinopsis cinerea, J. Agric. Food Chem., 66, 4702, 10.1021/acs.jafc.8b01343
Zhou Lihong, W.S., LuoLimei, 2009. Breeding of high yield Cordyceps militaris mutant strains by UV mutagenesis. Edible fungi, 31(4).
Zhou, 2002, Effect of cordycepin on interleukin-10 production of human peripheral blood mononuclear cells, Eur. J. Pharmacol., 453, 309, 10.1016/S0014-2999(02)02359-2
Zhu, 2016, Influence of fermentation conditions on polysaccharide production and the activities of enzymes involved in the polysaccharide synthesis of Cordyceps militaris, Appl. Microbiol. Biotechnol., 100, 3909, 10.1007/s00253-015-7235-4