Browse > Article

Cyclo(Dehydrohistidyl-L-Tryptophyl), an Inhibitor of Nitric Oxide Production from a Fungal Strain, Fb956  

Noh, Hyun-Jeong (Functional Metabolite Research Center, Korea Research Institute of Bioscience and Biotechnology)
Sohn, Mi-Jin (Functional Metabolite Research Center, Korea Research Institute of Bioscience and Biotechnology)
Yu, Hyung-Eun (Functional Metabolite Research Center, Korea Research Institute of Bioscience and Biotechnology)
Yoo, Ick-Dong (Functional Metabolite Research Center, Korea Research Institute of Bioscience and Biotechnology)
Kim, Won-Gon (Functional Metabolite Research Center, Korea Research Institute of Bioscience and Biotechnology)
Publication Information
Journal of Microbiology and Biotechnology / v.17, no.10, 2007 , pp. 1717-1720 More about this Journal
Abstract
In the course of screening for nitric oxide inhibitors in activated microglial BV-2 cells, cyclo(dehydrohistidyl-L-tryptophyl) was isolated from solid-state fermentation cultures of an unidentified fungal strain, Fb956. Its structure was determined by spectroscopic methods including 2D NMR and chiral TLC analyses. Cyclo(dehydrohistidyl-L-tryptophyl) was found to have an inhibitory activity on nitric oxide production with an $IC_{50}$ of $6.5\;{\mu}M$ in activated BV-2 cells. The structure determination and biological activity of cyclo(dehydrohistidyl-L-tryptophyl) was reported for the first time in this study.
Keywords
Cyclo(dehydrohistidyl-L-tryptophyl); cyclic peptide; nitric oxide; microglia;
Citations & Related Records
Times Cited By KSCI : 5  (Citation Analysis)
Times Cited By Web Of Science : 2  (Related Records In Web of Science)
연도 인용수 순위
1 Song, H. H., J.-H. Ahn, Y. H. Lim, and C. Lee. 2006. Analysis of beauvericin and unusual enniatins co-produced by Fusarium oxysporum FB1501 (KFCC 11363P). J. Microbiol. Biotechnol. 16: 1111-1119   과학기술학회마을
2 Alvi, K. A., D. D. Baker, V. Stienecker, M. Hosken, and B. G. Nair. 2000. Identification of inhibitors of inducible nitric oxide synthase from microbial extracts. J. Antibiot. 53: 496-501   DOI   ScienceOn
3 Chabrier, P.-E., C. Demerle-Pallardy, and M. Auguet. 1999. Nitric oxide synthases: Targets for therapeutic strategies in neurological diseases. Cell. Mol. Life Sci. 55: 1029-1035   DOI
4 Fukushima, K., K. Yazawa, and T. Arai. 1972. Biological activities of albonoursin. J. Antibiot. 26: 175-176
5 Gonzalez-Scarano, F. and G. Baltuch. 1999. Microglial as mediators of inflammatory and degenerative diseases. Annu. Rev. Neurosci. 22: 219-240   DOI   ScienceOn
6 Kimura, Y., A. Sawada, M. Kuramata, M. Kusano, S. Fujioka, T. Kawano, and A. Shimada. 2005. Brevicompanine C, cyclo-(D-Ile-L-Trp), and cyclo-(D-Leu-L-Trp), plant growth regulators from Penicillium brevicompactum. J. Nat. Prod. 68: 237-239   DOI   ScienceOn
7 Kimura, Y., K. Tani, A. Kojima, G. Sotoma, K. Okada, and A. Shimada. 1996. Cycol-(L-tryptophyl-L-phenylalanyl), a plant growth regulator produced by the fungus Penicillium sp. Phytochemistry 41: 665-669   DOI   ScienceOn
8 Nathan, C. 1997. Inducible nitric oxide synthase: What difference does it make? J. Clin. Invest. 100: 2417-2423   DOI   ScienceOn
9 Nathan, C. and Q. W. Xie. 1994. Nitric oxide synthases: Roles, tolls, and controls. Cell 78: 915-918   DOI   ScienceOn
10 Salerno, I., V. Sorrenti, C. Di Giacomo, G. Romeo, and M. A. Siracusa. 2002. Progress in the development of selective nitric oxide synthase inhibitors. Curr. Pharm. Des. 8: 177-200   DOI   ScienceOn
11 Griffith, O. W. and D. J. Stuehr. 1995. Nitric oxide synthases: Properties and catalytic mechanism. Annu. Rev. Physiol. 57: 707-736   DOI   ScienceOn
12 Kim, W.-G., I.-J. Ryoo, S.-H. Park, D.-S. Kim, S. Lee, K.-C. Park, and I.-D. Yoo. 2005. Terrein, a melanin biosynthesis inhibitor from Penicillium sp. 2013. J. Microbiol. Biotechnol. 15: 891-894   과학기술학회마을
13 Kim, H. J., J. H. Kim, C. H. Lee, and H. J. Kwon. 2006. Gentisyl alcohol, an antioxidant from microbial metabolite, induces angiogenesis in vitro. J. Microbiol. Biotechnol. 16: 475-479   과학기술학회마을
14 Prasad, C. 1995. Bioactive cyclic peptides. Peptides 16: 151-164   DOI   ScienceOn
15 Song, M. K., M. J. Rosenthal, S. Hong, D. M. Harris, I. Hwang, I. Yip, M. S. Golub, M. E. Ament, and V. L. Go. 2001. Synergistic antidiabetic activities of zinc, cyclo(hispro), and arachinoic acid. Metabolism 50: 53-59   DOI   ScienceOn
16 Gross, S. S. and M. S. Wolin. 1995. Nitric oxide: Pathophysiological mechanisms. Annu. Rev. Physiol. 57: 737-769   DOI   ScienceOn
17 Kozlovskii, A. G., N. G. Vinokurova, V. P. Zhelifonova, and V. M. Adanin. 1997. Secondary metabolites of fungi belonging to the species Penicillium janczewskii. Prikladnaya Biokhimiya I Mikrobiologiya 33: 70-74
18 Shimi, I. R. and S. Fathey. 1981. Isolation of cairomycins A and C. Antimicrobiol. Agents Chemother. 19: 941-944   DOI   ScienceOn
19 Zelenkova, N. F., N. G. Vinokurova, and M. U. Arinbasarov. 2003. Analysis of secondary metabolites of microscopic fungi of the genus Penicillium by chromatographic techniques. Appl. Biochem. Microbiol. 39: 52-62
20 Bredt, D. S. and S. H. Snyder. 1994. Nitric oxide: A physiologic messenger molecule. Annu. Rev. Biochem. 63: 175-195   DOI   ScienceOn
21 Kim, W.-G., N.-K. Song, and I.-D. Yoo. 2002. Trienomycin G, a new inhibitor of nitric oxide production in microglia cells from Streptomyces sp. 91614. J. Antibiot. 55: 204-207   DOI   ScienceOn
22 Green, L. C., D. A. Wagner, J. Glogowski, P. L. Skipper, J. S. Wishnok, and S. R. Tannenbaum. 1982. Analysis of nitrate, nitrite, and [$^{15}N$] nitrate in biological fluids. Anal. Biochem. 126: 131-138   DOI   ScienceOn
23 Zielasek, J. and H.-P. Hartung. 1996. Molecular mechanisms of microglial activation. Adv. Neuroimmunol. 6: 191-222   DOI   ScienceOn
24 Marletta, M. A. 1994. Nitric oxide synthase: Aspects concerning structure and catalysis. Cell 78: 927-930   DOI   ScienceOn
25 Hobbs A. J., A. Higgs, and S. Moncada. 1999. Inhibition of nitric oxide synthase as a potential therapeutic target. Annu. Rev. Pharmacol. Toxicol. 39: 191-220   DOI   ScienceOn
26 Davey, D. D., M. Alder, D. Arnaiz, K. Eagen, S. Erickson, W. Guiford, M. Kenrick, M. M. Morrissey, M. Ohlmeyer, G. Pan, V. M. Paradkar, J. Parkinson, M. Polokoff, K. Saionz, C. Santos, B. Subramanyam, R. Vergona, R. G. Wei, M. Whitlow, B. Ye, J. J. Devlin, and G. Phillips. 2007. Design, synthesis, and activity of 2-imidazol-1-ylpyrimidine derived inducible nitric oxide synthase dimerization inhibitors. J. Med. Chem. 50: 1146-1157   DOI   ScienceOn
27 Song, M. K., I. K. Hwang, M. J. Rosenthal, D. M. Harris, D. T. Yamaguchi, I. Yip, and V. L. W. Go. 2003. Antihyperglycemic activity of zinc plus cyclo(his-pro) in genetically diabetic Goto-Kakizaki and aged rats. Exp. Biol. Med. 228: 1338-1345   DOI
28 Li, X., S.-K. Kim, J. S. Kang, H. D. Choi, and B. W. Son. 2006. Radical scavenging hydroxyphenyl ethanoic acid derivatives from a marine-derived fungus. J. Microbiol. Biotechnol. 16: 637-638   과학기술학회마을
29 Zhang, D., X. Li, J. S. Kang, H. D. Choi, J. H. Jung, and B. W. Son. 2007. Redoxcitrinin, a biogenetic precursor of citrinin from marine isolate of fungus Penicillium sp. J. Microbiol. Biotechnol. 17: 865-867   과학기술학회마을