DOI QR코드

DOI QR Code

Chemical Constituents Identified from Fruit Body of Cordyceps bassiana and Their Anti-Inflammatory Activity

  • Suh, Wonse (School of Biotechnology, Yeungnam University) ;
  • Nam, Gyeongsug (Department of Genetic Engineering, Sungkyunkwan University) ;
  • Yang, Woo Seok (Department of Genetic Engineering, Sungkyunkwan University) ;
  • Sung, Gi-Ho (Institute for Bio-Medical Convergence, International St. Mary's Hospital and College of Medicine, Catholic Kwandong University) ;
  • Shim, Sang Hee (College of Pharmacy, Duksung Women's University) ;
  • Cho, Jae Youl (Department of Genetic Engineering, Sungkyunkwan University)
  • 투고 : 2016.03.21
  • 심사 : 2016.06.20
  • 발행 : 2017.03.01

초록

Cordyceps bassiana is one of Cordyceps species with anti-oxidative, anti-cancer, anti-inflammatory, anti-diabetic, anti-obesity, anti-angiogenic, and anti-nociceptive activities. This mushroom has recently demonstrated to have an ability to reduce 2,4-dinitrofluorobenzene-induced atopic dermatitis symptoms in NC/Nga mice. In this study, we further examined phytochemical properties of this mushroom by column chromatography and HPLC analysis. By chromatographic separation and spectroscopic analysis, 8 compounds, such as 1,9-dimethylguanine (1), adenosine (2), uridine (3), nicotinamide (4), 3-methyluracil (5), 1,7-dimethylxanthine (6), nudifloric acid (7), and mannitol (8) were identified from 6 different fractions and 4 more subfractions. Through evaluation of their anti-inflammatory activities using reporter gene assay and mRNA analysis, compound 1 was found to block luciferase activity induced by $NF-{\kappa}B$ and AP-1, suppress the mRNA levels of cyclooxygenase (COX)-2 and tumor necrosis factor $(TNF)-{\alpha}$. Therefore, our data strongly suggests that compound 1 acts as one of major principles in Cordyceps bassiana with anti-inflammatory and anti-atopic dermatitis activities.

키워드

참고문헌

  1. Bagno, A., Rastrelli, F. and Saielli, G. (2008) Predicting the NMR spectra of nucleotides by DFT calculations: cyclic uridine monophosphate. Magn. Reson. Chem. 46, 518-524. https://doi.org/10.1002/mrc.2204
  2. Byeon, S. E., Lee, J., Yoo, B. C., Sung, G. H., Kim, T. W., Park, H. J. and Cho, J. Y. (2011a) p38-targeted inhibition of interleukin-12 expression by ethanol extract from Cordyceps bassiana in lipopolysaccharide-activated macrophages. Immunopharmacol. Immunotoxicol. 33, 90-96. https://doi.org/10.3109/08923973.2010.482137
  3. Byeon, S. E., Lee, S. Y., Kim, A. R., Lee, J., Sung, G. H., Jang, H. J., Kim, T. W., Park, H. J., Lee, S. J., Hong, S. and Cho, J. Y. (2011b) Inhibition of cytokine expression by a butanol extract from Cordyceps bassiana. Pharmazie 66, 58-62.
  4. Bock, K. and Pedersen, C. (1983) Carbon-13 nuclear magnetic resonance of monosaccharides. Adv. Carbohydr. Chem. Biochem. 41, 27-66.
  5. Chen, L., Xiao, H., Wang, Z. H., Huang, Y., Liu, Z. P., Ren, H. and Song, H. (2014) miR-29a suppresses growth and invasion of gastric cancer cells in vitro by targeting VEGF-A. BMB Rep. 47, 39-44. https://doi.org/10.5483/BMBRep.2014.47.1.079
  6. Ciuffreda, P., Casati, S. and Manzocchi, A. (2007) Complete (1)H and (13)C NMR spectral assignment of alpha- and beta-adenosine, 2'-deoxyadenosine and their acetate derivatives. Magn. Reson. Chem. 45, 781-784. https://doi.org/10.1002/mrc.2036
  7. Gil, M., Pak, H. K., Park, S. J., Lee, A. N., Park, Y. S., Lee, H., Lee, H., Kim, K. E., Lee, K. J., Yoon, D. H., Chung, Y. S. and Park, C. S. (2015) Engagement of CD99 reduces AP-1 activity by inducing BATF in the human multiple myeloma cell line RPMI8226. Immune Netw. 15, 260-267. https://doi.org/10.4110/in.2015.15.5.260
  8. Hyun, S. H., Lee, S. Y., Park, S. J., Kim, D. Y., Chun, Y. J., Sung, G. H., Kim, S. H. and Choi, H. K. (2013) Alteration of media composition and light conditions change morphology, metabolic profile, and beauvericin biosynthesis in cordyceps bassiana mycelium. J. Microbiol. Biotechnol. 23, 47-55. https://doi.org/10.4014/jmb.1208.08058
  9. Jiang, M., Kameda, K., Han, L. K., Kimura, Y. and Okuda, H. (1998) Isolation of lipolytic substances caffeine and 1,7-dimethylxanthine from the stem and rhizome of Sinomenium actum. Planta Med. 64, 375-377. https://doi.org/10.1055/s-2006-957456
  10. Jung, J. Y., Kim, I. Y., Kim, Y. N., Kim, J. S., Shin, J. H., Jang, Z. H., Lee, H. S., Hwang, G. S. and Seong, J. K. (2012) 1H NMR-based metabolite profiling of diet-induced obesity in a mouse mode. BMB Rep. 45, 419-424. https://doi.org/10.5483/BMBRep.2012.45.7.248
  11. Lee, N., Jung, Y. S., Lee, H. Y., Kang, N., Park, Y. J., Hwang, J. S., Bahk, Y. Y., Koo, J. and Bae, Y. S. (2014) Mouse neutrophils express functional umami taste receptor T1R1/T1R3. BMB Rep. 47, 649-654. https://doi.org/10.5483/BMBRep.2014.47.11.185
  12. Lee, Y. G., Lee, J., Byeon, S. E., Yoo, D. S., Kim, M. H., Lee, S. Y. and Cho, J. Y. (2011) Functional role of Akt in macrophage-mediated innate immunity. Front. Biosci. (Landmark Ed.) 16, 517-530. https://doi.org/10.2741/3702
  13. Liang, C., Ding, Y., Song, S. B., Kim, J. A., Cuong, N. M., Ma, J. Y. and Kim, Y. H. (2013) Oleanane-triterpenoids from Panax stipuleanatus inhibit NF-${\kappa}B$. J. Ginseng Res. 37, 74-79. https://doi.org/10.5142/jgr.2013.37.74
  14. Madsen, A. M., Hansen, V. M., Meyling, N. V. and Eilenberg, J. (2007) Human exposure to airborne fungi from genera used as biocontrol agents in plant production. Ann. Agric. Environ. Med. 14, 5-24.
  15. Moon, S. J., Jeong, J. H., Jhun, J. Y., Yang, E. J., Min, J. K., Choi, J. Y. and Cho, M. L. (2014) Ursodeoxycholic Acid ameliorates pain severity and cartilage degeneration in monosodium iodoacetateinduced osteoarthritis in rats. Immune Netw. 14, 45-53. https://doi.org/10.4110/in.2014.14.1.45
  16. Ng, T. B. and Wang, H. X. (2005) Pharmacological actions of Cordyceps, a prized folk medicine. J. Pharm. Pharmacol. 57, 1509-1519. https://doi.org/10.1211/jpp.57.12.0001
  17. Rehner, S. A., Minnis, A. M., Sung, G. H., Luangsa-ard, J. J., Devotto, L. and Humber, R. A. (2011) Phylogeny and systematics of the anamorphic, entomopathogenic genus Beauveria. Mycologia 103, 1055-1073. https://doi.org/10.3852/10-302
  18. Sigel, R. K., Freisinger, E. and Lippert, B. (2000) Effects of N7-methylation, N7-platination, and C8-hydroxylation of guanine on H-bond formation with cytosine: platinum coordination strengthens the Watson-Crick pair. J. Biol. Inorg. Chem. 5, 287-299. https://doi.org/10.1007/PL00010657
  19. Vo, H. T., Cho, J. Y., Choi, Y. E., Choi, Y. S. and Jeong, Y. H. (2015) Kinetic study for the optimization of ginsenoside Rg3 production by heat treatment of ginsenoside Rb1. J. Ginseng Res. 39, 304-313. https://doi.org/10.1016/j.jgr.2015.02.003
  20. Wong, P., Bachki, A., Banerjee, K. and Leyland-Jones, B. (2002) Identification of N1-methyl-2-pyridone-5-carboxamide and N1-methyl-4-pyridone-5-carboxamide as components in urine extracts of individuals consuming coffee. J. Pharm. Biomed. Anal. 30, 773-780. https://doi.org/10.1016/S0731-7085(02)00384-9
  21. Wu, G., Li, L., Sung, G. H., Kim, T. W., Byeon, S. E., Cho, J. Y., Park, C. W. and Park, H. J. (2011) Inhibition of 2,4-dinitrofluorobenzeneinduced atopic dermatitis by topical application of the butanol extract of Cordyceps bassiana in NC/Nga mice. J. Ethnopharmacol. 134, 504-509. https://doi.org/10.1016/j.jep.2010.12.012
  22. Yang, Y., Lee, J., Rhee, M. H., Yu, T., Baek, K. S., Sung, N. Y., Kim, Y., Yoon, K., Kim, J. H., Kwak, Y. S., Hong, S., Kim, J. H. and Cho, J.Y. (2015) Molecular mechanism of protopanaxadiol saponin fractionmediated anti-inflammatory actions. J. Ginseng Res. 39, 61-68. https://doi.org/10.1016/j.jgr.2014.06.002
  23. Yu, T., Yi, Y. S., Yang, Y., Oh, J., Jeong, D. and Cho, J. Y. (2012) The Pivotal Role of TBK1 in Inflammatory Responses Mediated by Macrophages. Mediators Inflamm. 2012, 979105.
  24. Yuyama, S. and Suzuki, T. (1991) The excretion of N'-methyl-2-pyridone-5-carboxylic acid and related compounds in human subjects after oral administration of nicotinic acid, trigonelline, and N'-methyl- 2-pyridone-5-carboxylic acid. Adv. Exp. Med. Biol. 294, 475-479.
  25. Zhou, X., Gong, Z., Su, Y., Lin, J. and Tang, K. (2009) Cordyceps fungi: natural products, pharmacological functions and developmental products. J. Pharm. Pharmacol. 61, 279-291. https://doi.org/10.1211/jpp.61.03.0002

피인용 문헌

  1. -(2-hydroxyethyl)-adenosine–producing fungus vol.8, pp.4, 2017, https://doi.org/10.1080/21501203.2017.1375040
  2. B Inhibition vol.2019, pp.1741-4288, 2019, https://doi.org/10.1155/2019/1548125
  3. Inhibitory Activity of Cordyceps bassiana Extract on LPS-induced Inflammation in RAW 264.7 Cells by Suppressing NF-κB Activation vol.23, pp.3, 2017, https://doi.org/10.20307/nps.2017.23.3.162
  4. Adenosine Induces EBV Lytic Reactivation through ADORA1 in EBV-Associated Gastric Carcinoma vol.20, pp.6, 2019, https://doi.org/10.3390/ijms20061286
  5. Quercetin Synergistically Inhibit EBV-Associated Gastric Carcinoma with Ganoderma lucidum Extracts vol.24, pp.21, 2019, https://doi.org/10.3390/molecules24213834
  6. Cordyceps spp.: A Review on Its Immune-Stimulatory and Other Biological Potentials vol.11, pp.None, 2017, https://doi.org/10.3389/fphar.2020.602364