Nucleosides, a valuable chemical marker for quality control in traditional Chinese medicine Cordyceps

Recent Patents on Biotechnology

Volumn 7, Issue 2, 2013, Pages 153-166

  Xiao, Jian Hui ^a   Qi, Ying ^a   Xiong, Qing ^a  

^a ZUNYI MEDICAL UNIVERSITY   (China)

Author keywords

Bioactivity; Chemical marker; Cordyceps; Nucleoside; Quality control

Indexed keywords

BIOACTIVITY; BIOMOLECULES; MEDICINE; QUALITY ASSURANCE;

ACTIVE COMPONENTS; BIOPRODUCTS; CHEMICAL MARKERS; CORDYCEP; CURATIVE EFFECTS; MACROFUNGI; NUCLEOSIDE; SYMBIOTICS; TRADITIONAL CHINESE MEDICINE; VALUABLE CHEMICALS;

QUALITY CONTROL;

2' METHOXYADENOSINE; 2',3' DIDEOXYADENOSINE; 3' METHOXYADENOSINE; ACICLOVIR; ADENINE; ADENOSINE; CHOLINE; CORDYCEPIN; CYTIDINE; CYTOSINE; DEOXYADENOSINE; DEOXYGUANOSINE; DEOXYURIDINE; DOCOSAHEXAENOIC ACID; FAMCICLOVIR; FLUOROURACIL; GANCICLOVIR; GUANINE; GUANOSINE; HYPOXANTHINE; IDOXURIDINE; INOSINE; NUCLEOSIDE; PENCICLOVIR; THYMIDINE; THYMINE; UNCLASSIFIED DRUG; UNINDEXED DRUG; URACIL; URIDINE; VALACICLOVIR; BIOLOGICAL MARKER; DRUG;

ANALYTIC METHOD; ANTICONVULSANT ACTIVITY; ANTIDEPRESSANT ACTIVITY; ANTIDIABETIC ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; CAPILLARY ELECTROPHORESIS; CELL PROTECTION; CHICKENPOX; CORDYCEPS; CORDYCEPS GUNNII; CORDYCEPS JIANGXIENSIS; CORDYCEPS KYUSHUENSIS; CORDYCEPS PRUINOSA; CORDYCEPS TAII; DIGESTIVE SYSTEM CANCER; DRUG BIOAVAILABILITY; DRUG METABOLISM; DRUG STRUCTURE; HERPES SIMPLEX; HERPES SIMPLEX KERATITIS; HERPES ZOSTER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; IMMUNOMODULATION; MEDICAL HISTORY; NONHUMAN; OPHIOCORDYCEPS; PATENT; PRIORITY JOURNAL; QUALITY CONTROL; REVIEW; THIN LAYER CHROMATOGRAPHY; CHINESE MEDICINE; STANDARDS;

ARTHROPODA; CORDYCEPS; HEXAPODA;

BIOLOGICAL MARKERS; CORDYCEPS; MEDICINE, CHINESE TRADITIONAL; NUCLEOSIDES; PATENTS AS TOPIC; PHARMACEUTICAL PREPARATIONS; QUALITY CONTROL;

EID: 84884217446     PISSN: 18722083     EISSN: None     Source Type: Journal    
DOI: 10.2174/1872208311307020007     Document Type: Review

References (100)

1. Xiao JH, Zhong JJ. Secondary metabolites from Cordyceps species and their antitumor activity studies. Recent Pat Biotechnol 2007; 1: 123-7.
2. Zhong JJ, Xiao JH. Secondary metabolites from higher fungi: Discovery, bioactivity, and bioproduction. Adv Biochem Engin Biotechnol 2009; 113: 79-150.
3. Zhong H, Yi M, Lu J, et al. Use of the traditional Chinese Medicine composition for manufacturing a health food or medicament for preventing and alleviating physical fatigue. WO2012034534, 2012.
4. Wu B. Product of functional health food that enhances organ immunity. WO2012034498, 2012.
5. Sim JH, Kim JK. Composition for lowering blood sugar, comprising extract of Smilax chine L., Momordica charantia and Cordyceps militaris as active ingredient. WO2011052935, 2011.
6. Katsuyuki U, Yukio O, Yoshitatsu I, Lipid metabolism improving composition. JP2011000075091, 2011.
7. Makoto K. Method for producing immunomodulator. JP 2010215580 A, 2010.
8. Koichi S, Masaaki T, Fumio S. Cerebral function-improving agent comprising hot-water extract from Paecilomyces tenuipes powder. JP2012056867, 2012.
9. Holliday J, Cleaver M. Medicinal value of the caterpillar fungi species of the genus Cordyceps (Fr.) Link (Ascomycetes), a review. Int J Med Mushr 2008; 10: 219-34.
10. Cleaver PD, Holliday JC, Powers ML. Method for growing Cordyceps sinensis on a substrate and novel method for hybridizing different strains of Cordyceps sinensis. US 20060014267 A1, 2006.
11. Chen S. Culturing method for Cordyceps militaris. WO2011116649, 2011.
12. Yang CH, Huang KS, Hsieh YH. Formula of medium for culturing Cordyceps spp. US20110300606A1, 2011.
13. Hsu TH, Shiao LH, Hsieh C, Chang DM. A comparison of the chemical composition and bioactive ingredients of the Chinese medicinal mushroom DongChongXiaCao, its counterfeit and mimic, and fermented mycelium of Cordyceps sinensis. Food Chem 2002; 78: 463-9.
14. Liang XM, Jin Y, Wang YP, Jin GW, Fu Q, Xiao YS. Qualitative and quantitative analysis in quality control of traditional Chinese medicines. J Chromatogr A 2009; 1216: 2033-44.
15. Xiao JH, Xiao DM, Sun ZH, Xiong Q, Liang ZQ, Zhong JJ. Chemical compositions and antimicrobial property of three edible and medicinal Cordyceps species. J Food Agric Environ 2009; 7(3&4): 91-100.
16. Editorial Committee of the Pharmacopoeia of People's Republic of China, Pharmacopoeia of the People's Republic of China (2005 Edition), Beijing: Chemical Industry Press, 2005.
17. Li SP, Yang FQ, Tsimb KWK. Quality control of Cordyceps sinensis, a valued traditional Chinese medicine. J Pharma Biomed Anal 2006; 41: 1571-84.
18. Cunningham KG, Manson W, Spring FS, Hutchison SA. Cordycepin, a metabolic product isolated from cultures of Cordyceps militaris (Linn.) Link. Nature 1950; 166: 949.
19. Yang FQ, Guan J, Li SP. Fast simultaneous determination of 14 nucleosides and nucleobases in cultured Cordyceps using ultraperformance liquid chromatography. Talanta 2007; 73: 269-73.
20. Chen C, Pan WD, Xiao JH, Liang GY. Investigation of chemical constituents of methanolic extract from Penicillium jiangxiense. Chin J Exp Trad Med Formul 2011; 17: 242-6.
21. Sun ZH, Xiao JH, Pan WD, Zhang MS, Xu P. Study on the chemical constituents of submerged cultivation mycelium of Cordyceps jiangxiensis. J Chin Med Mat 2010; 33: 1887-91.
22. Kitakaze M, Hori M. Adenosine therapy: A new approach to chronic heart failure. Expert Opin Investig Drugs 2000; 9, 2519-35.
23. Nakav S, Chaimovitz C, Sufaro Y, et al. Anti-inflammatory preconditioning by agonists of adenosine A1 receptor. PLoS ONE 2008; 7; 3: e2107.
24. Ballarin M, Herrera-Marschitz M, Casas M, Ungerstedt U. Striatal adenosine levels measured 'in vivo' by microdialysis in rats with unilateral dopamine denervation. Neurosci Lett. 1987; 83: 338-44.
25. Latini S, Pedata F. Adenosine in the central nervous system: release mechanisms and extracellular concentrations. J Neurochem. 2001; 79: 463-84.
26. Ribeizo JA. Purinergic inhibition of neurotransmitter release in the central nervous system. Pharmacol Toxicol 1995; 77: 299-305.
27. Won SY, Park EH. Anti-inflammatory and related pharmacological activities of cultured mycelia and fruiting bodies of Cordyceps militaris. J Ethnopharmacol 2005; 96: 555-61.
28. Lee SJ, Kim SK, Choi WS, Kim WJ, Moon SK. Cordycepin causes p21WAF1-mediated G2/M cell-cycle arrest by regulating c-Jun Nterminal kinase activation in human bladder cancer cells. Arch Biochem Biophys 2009; 490: 103-9.
29. Hwang IK, Lim SS, Yoo KY, et al. A phytochemically characterized extract of Cordyceps militaris and cordycepin protect hippocampal neurons from ischemic injury in gerbils. Planta Med 2008; 74: 114-9.
30. Chang W, Lim S, Song H, et al. Cordycepin inhibits vascular smooth muscle cell proliferation. Eur J Pharm 2008; 597: 64-9.
31. Won KJ, Lee SC, Lee CK, et al. Cordycepin attenuates neointimal formation by inhibiting reactive oxygen species-mediated responses in vascular smooth muscle cells in rats. J Pharmacol Sci 2009; 109: 403-12.
32. Guo P, Kai Q, Gao J, et al. Cordycepin prevents hyperlipidemia in hamsters fed a high-fat diet via activation of AMP-activated protein kinase. J Pharmacol Sci 2010; 113: 395-403.
33. Shin S, Lee S, Kwon J, et al. Cordycepin suppresses expression of diabetes regulating genes by inhibition of lipopolysaccharideinduced inflammation in macrophages. Immune Network 2009; 9: 98-105.
34. Noh EM, Kim JS, Hur H, et al. Cordycepin inhibits IL-1b-induced MMP-1 and MMP-3 expression in rheumatoid arthritis synovial fibroblasts. Rheumatology 2009; 48: 45-8.
35. Kim HG, Shrestha B, Lim SY, et al. Cordycepin inhibits lipopolysaccharide- induced inflammation by the suppression of NF-κB through Akt and p38 inhibition in RAW 264.7 macrophage cells. Eur J Pharma 2006; 545: 192-9.
36. Zhou X, Luo L, Dressel W, et al. Cordycepin is an immunoregulatory active ingredient of Cordyceps sinensis. Am J Chin Med 2008; 36: 967-980.
37. Nakamura K, Konoha K, Yoshikawaet al. Effect of cordycepin (3'-deoxyadenosine) on hematogenic lung metastatic model mice. In Vivo 2005; 19: 137-42.
38. Nakamura K, Yoshikawa N, Yamaguchi Y, Kagota S, Shinozuka K, Kunitomo M. Antitumor effect of cordycepin (3'- deoxyadenosine) on mouse melanoma and lung carcinoma cells involves adenosine A3 receptor stimulation. Anticancer Res 2006; 26: 43-8.
39. Yoshikawa N, Nakamura K, Yamaguchi Y, Kagota S, Shinozuka K, Kunitomo M. Cordycepin and Cordyceps sinensis reduce the growth of human promyelocytic leukaemia cells through the Wnt signalling pathway. Clin Exp Pharmacol Physiol 2007; 34: S61-3.
40. Yoshikawa N, Yamada S, Takeuchi C, et al. Cordycepin (3′- deoxyadenosine) inhibits the growth of B16-BL6 mouse melanoma cells through the stimulation of adenosine A3 receptor followed by glycogen synthase kinase-3′ activation and cyclin D1 suppression. Naunyn-Schmiedeberg's Arch Pharmacol 2008; 377: 591-5.
41. Yoshikawa N, Kunitomo M, Kagota S, Shinozuka K, Nakamura K. Inhibitory effect of cordycepin on hematogenic metastasis of B16- F1 mouse melanoma cells accelerated by adenosine-5'- diphosphate. Anticancer Res 2009; 29: 3857-60.
42. Lee EJ, Kim WJ, Moon SK. Cordycepin suppresses TNF-alphainduced invasion, migration and matrix metalloproteinase-9 expression in human bladder cancer cells. Phytother Res 2010; 24: 1755-61.
43. Furuya T, Hirotani M, Matsuzawa M. N6-(2-hydroxyethyl) adenosine, a biologically active compound from cultured mycelia of Cordyceps and Isaria species. Phytochemistry 1983; 22: 2509-12.
44. Holliday JC, Cleaver P, Loomis-Power M, Patel D. Analysis of quality and techniques for hybridization of medicinal fungus Cordyceps sinensis (Berk.)Sacc. (Ascomycetes). Int J med mushr 2004; 6: 151-64.
45. Xiao JH, Sun ZH, Pan WD, Chen C, Zhong JJ. Chemical compounds of medicinal macrofungus Cordyceps jiangxiensis mycelium. In: Proceedings of 2010 International Conference of Natural Product and Traditional Medicine. USA: Scientific and Technical Development Press, 2010: pp 199-202.
46. Yu L, Zhao J, Li SP, et al. Quality evaluation of Cordyceps through simultaneous determination of eleven nucleosides and bases by RPHPLC. J Sep Sci 2006; 29: 953-8.
47. Benowitz LI, Goldberg DE, Irwin N. Inosine stimulates axon growth in vitro and in the adult CNS, Prog Brain Res 2002; 137: 389-99.
48. Ikeda R, Nishimura M, Sun Y, Wada M, Nakashima K. Simple HPLC-UV determination of nucleosides and its application to the authentication of Cordyceps and its allies. Biomed Chromatogr 2008; 22: 630-36.
49. Clercq ED, Field HJ. Antiviral prodrugs - the development of successful prodrug strategies for antiviral chemotherapy. Br J Pharmacol 2006; 147: 1-11.
50. Klubes P, Cerna I. Use of uridine rescue to enhance the antitumor selectivity of 5-fluorouracil. Cancer Res 1983; 43: 3182-6.
51. Chen C, Pan WD, Xiao JH, Liang GY. Secondary metabolites from Penicillium jiangxiense. Nat Prod Res Dev 2011; 23: 664-6.
52. Martin DS, Stolfi RL, Sawyer RC, Spiegelman S, Young CW. High-dose 5-fluorouracil with delayed uridine "rescue" in mice. Cancer Res 1982; 42: 3964-70.
53. Ashour OM., Naguib FNM., Khalifa MMA, Abdel-Raheem MH, Panzica RP, Kouni MH. Enhancement of 5-fluoro-2'-deoxyuridine antitumor efficacy by the uridine phosphorylase inhibitor 5- (benzyloxybenzyl)barbituric acid acyclonucleoside. Cancer Res 1995; 55: 1092-8.
54. Wagner CR. Nucleosides with antiviral and antitumor activity. US 20090306007 A1, 2009.
55. Prusoff WH. Synthesis and biological activities of iododeoxyuridine, an analog of thymidine. Biochim Biophys Acta 1959; 32: 295-6.
56. Field HJ, De Clercq E. Antiviral drugs - a short history of their discovery and development. Microbiol Today 2004; 31: 58-61.
57. Wurtman RJ, Ulus IH, Cansev M, Watkins CJ, Wang L, Marzloff G. Synaptic proteins and phospholipids are increased in gerbil brain by administering uridine plus docosahexaenoic acid orally. Brain Res 2006; 1088: 83-92.
58. Holguin S, Martinez J, Chow C, Wurtman R. Enhances the improvement in learning and memory produced by administering DHA to gerbils. FASEB J 2008; 22: 3938-46.
59. Carlezon WA, Mague SD, Parow AM, Stoll AL, Cohen BM, Renshaw PF. Antidepressant-like effects of uridine and omega-3 fatty acids are potentiated by combined treatment in rats. Biol Psychiatry 2005; 57: 343-50.
60. Wurtman RJ, Regan M, Ulus I, Yu L. Effect of oral CDP-choline on plasma choline and uridine levels in humans. Biochem Pharmacol 2000; 60: 989-92.
61. Carlezon WA, Pliakas AM, Parow AM, Detke MJ, Cohen BM, Renshaw PF. Antidepressant-like effects of cytidine in the forced swim test in rats. Biol Psychiatry 2002; 51: 882-9.
62. Matsuda A, Sasaki T. Antitumor activity of sugar-modified cytosine nucleosides. Cancer Sci 2004; 95: 105-11.
63. Yoshida T, Endo Y, Obata T, Kosugi Y, Sakamoto K, Sasaki T. Influence of cytidine deaminase on antitumor activity of 2'- deoxycytidine analogs in vitro and in vivo. Drug Metab Disp 2010; 38: 1814-9.
64. Jansen RS, Rosing H, Schellens JHM, Beijnen JH. Deoxyuridine analog nucleotides in deoxycytidine analog treatment: secondary active metabolites? Fund Clin Pharmacol 2011; 25: 172-85.
65. Suzuki N, Emura T, Fukushima M. Mode of action of trifluorothymidine (TFT) against DNA replication and repair enzymes. Int J Oncol 2011; 39: 263-70.
66. Suzuki N, Nakagawa F, Nukatsuka M, Fukushima M. Trifluorothymidine exhibits potent antitumor activity via the induction of DNA double-strand breaks. Exp Ther Med 2011; 2: 393-7.
67. Bijnsdorp IV, Kruyt FAE, Fukushima M, Smid K, Gokoel S, Peters GJ. Molecular mechanism underlying the synergistic interaction between trifluorothymidine and the epidermal growth factor receptor inhibitor erlotinib in human colorectal cancer cell lines. Cancer Sci 2010; 101: 440-7.
68. Chun BK, Clark J, Sarma K, Wang P. Antiviral nucleosides. US 20070197463 A1, 2007.
69. Ahn YJ, Kim JR, Yoen SH. Anticancer agent cordycepin extracted from Cordyceps militaris and producing method thereof. KR1054264A, 2001.
70. Ma KW, Chau FT, Wu JY. Analysis of the nucleoside content of Cordyceps sinensis using the stepwise gradient elution technique of thin-layer chromatography. Chin J Chem 2004; 22: 85-91.
71. Fan H, Yang FQ, Li SP. Determination of purine and pyrimidine bases in natural and cultured Cordyceps using optimum acid hydrolysis followed by high performance liquid chromatography. J Pharm Biomed Anal 2007; 45: 141-4.
72. Yu R, Ye B, Yan C, et al. Fingerprint analysis of fruiting bodies of cultured Cordyceps militaris by high-performance liquid chromatography- photodiode array detection. J Pharm Biomed Anal 2007; 44: 818-23.
73. Xie JW, Huang LF, Hu W, He YB, Wong KP. Analysis of the main nucleosides in Cordyceps sinensis by LC/ESI-MS. Molecules 2010; 15: 305-14.
74. Guo FQ, Li A, Huang LF, Liang YZ, Chen BM. Identification and determination of nucleosides in Cordyceps sinensis and its substitutes by high performance liquid chromatography with mass spectrometric detection. J Pharm Biomed Anal 2006; 40: 623-30.
75. Ganzera M. Quality control of herbal medicines by capillary electrophoresis: Potential, requirements and applications. Electrophoresis 2008; 29: 3489-503.
76. Li SP, Li P, Dong TTX, Tsim KWK. Determination of nucleosides in natural Cordyceps sinensis and cultured Cordyceps mycelia by capillary electrophoresis. Electrophoresis 2001; 22: 144-50.
77. Rao YK, Chou CH, Tzeng YM. A simple and rapid method for identification and determination of cordycepin in Cordyceps militaris by capillary electrophoresis. Anal Chim Acta 2006; 566: 253-8.
78. Gong YX, Li SP, Li P, Liu JJ, Wang YT. Simultaneous determination of six main nucleosides and bases in natural and cultured Cordyceps by capillary electrophoresis. J Chromatogr A 2004; 1055: 215-21.
79. Ling JY, Sun YJ, Zhang H, Lu P, Zhang CK. Measurement of cordycepin and adenosine in stroma of Cordyceps sp. by capillary zone electrophoresis (CZE). J Biosci Bioeng 2002; 94: 371-4.
80. Sun YJ, Ling JY, Lu P, Zhang HX, Zhang CK. Determination of cordycepin in Cordyceps kyushuensis by capillary electrophoresis and its antitumour activity. Chin Chem Lett 2003; 14: 724-7.
81. Wang S, Zhao X, Mao Y, Cheng Y. Novel approach for developing urinary nucleosides profile by capillary electrophoresis-mass spectrometry. J Chromatogr A 2007; 1147: 254-60.
82. Stillwell WG, Xu HX, Adkins JA, Wishnok JS, Tannenbaum SR. Analysis of methylated and oxidized purines in urine by capillary gas chromatography-mass spectrometry. Chem Res Toxicol 1989; 2: 94-9.
83. Teixeira AJR, Gommers-Ampt JH, deWerken GV, Westra JG, Stavenuiter JFC, de Jong APJM. Methods for the analysis of oxidized nucleosides by gas chromatography-mass spectrometry. Anal Biochem 1993; 214: 474-83.
84. Furst W, Hallstrom S. Simultaneousdetermination of myocardialnucleotides, nucleosides, purinebases and creatinephosphate by ion-pair high-performance liquid chromatography. J Chromatogr B 1992; 578: 39-44.
85. Childs KF, Ning XH, Bolling SF. Simultaneous detection of nucleotides, nucleosides and oxidative metabolites in myocardial biopsies. J Chromatogr B 1996; 678: 181-6.
86. Itoh K, Aida S, Ishiwata S, Sasaki S, Ishida N, Mizugaki M. Urinary excretion patterns of modified nucleosides, pseudouridine and 1-methyladenosine, in healthy individuals. Clin Chim Acta 1993; 217: 221-3.
87. Itoh K, Konno T, Sasaki T, Ishiwata S, Ishida N, Misugaki M. Relationship of urinary pseudouridine and l-methyladenosine to activity of leukemia and lymphoma. Clin Chim Acta 1992; 206: 181-9.
88. Holliday J, Cleaver M, Wasser SP. Cordyceps. Encyclopedia of Dietary Supplements 2005, 1-13. doi: 10.1081/E-EDS-120024882.
89. Li SP, Li P, Ji H, Zhang P, Dong TTX, Tsim KWK. The contents and their change of nucleosides from natural Cordyceps sinensis and cultured Cordyceps mycelia. Acta Pharma Sin 2001; 36: 436-9.
90. Cleaver PD, Holliday JC, Powers ML. Method for growing Cordyceps sinensis on a substrate and novel method for hybridizing different strains of Cordyceps sinensis. US 20060014267 A1, 2006.
91. Zheng JH, Xiang K. A large-scale production method for the fruiting body of Cordyceps militaris. CN 101622941, 2009.
92. Li H. Artificial cultivating method of enriched selenium Cordyceps militaris and application of fruiting body. CN1861782, 2006.
93. Yang FQ, Li SP. Effects of sample preparation methods on the quantification of nucleosides in natural and cultured Cordyceps. J Pharm Biomed Anal 2008; 48: 231-5.
94. Huang SJ, Tsai SY, Lee YL, Mau JL. Nonvolatile taste components of fruit bodies and mycelia of Cordyceps militaris. LWT 2006; 39: 577-83.
95. Yu L, Zhao J, Zhu Q, Li SP. Macrophage biospecific extraction and high performance liquid chromatography for hypothesis of immunological active components in Cordyceps sinensis. J Pharm Biomed Anal 2007; 44: 439-43.
96. Fan H, Li SP, Xiang JJ, et al. Qualitative and quantitative determination of nucleosides, bases and their analogues in natural and cultured Cordyceps by pressurized liquid extraction and high performance liquid chromatography-electrospray ionization tandem mass spectrometry (HPLC-ESI-MS/MS). Anal Chim Acta 2006, 567: 218-28.
97. Li SP, Li P, Lai CM, et al. Simultaneous determination of ergosterol, nucleosides and their bases from natural and cultured Cordyceps by pressurised liquid extraction and high-performance liquid chromatography. J Chromatogr A 2004; 1036: 239-43.
98. Huang LF, Liang YZ, Guo FQ, Zhou ZF, Cheng BM. Simultaneous separation and determination of active components in Cordyceps sinensis and Cordyceps militaris by LC/ESI-MS. J Pharm Biomed Anal 2003; 33: 1155-62.
99. Valavanidis A, Vlachogianni T, Fiotakis C. 8-Hydroxy-2' - deoxyguanosine (8-OHdG): a critical biomarker of oxidative stress and carcinogenesis. J Environ Sci Health C Environ Carcinog Ecotoxicol Rev 2009; 27: 120-39.
100. Xiao JH, Sun ZH, Zhang XJ, Xiong Q, Zhong JJ. Efficient extraction and rapid quantitative determination of nucleoside compounds from Cordyceps jiangxiensis, a new Cordyceps producingcordycepin. Lat Am J Pharm 2012; 31: 1161-9.