New methymycin derivatives of Streptomyces venezuelae ATCC 15439 and their inhibitory effects on human T cell proliferation mediated by PMA/ionomycin

Archives of Pharmacal Research

Volumn 35, Issue 9, 2012, Pages 1567-1572

  Ding, Rong ^a   Tang, Jinshan ^b   Gao, Hao ^b   Li, Ting ^c   Zhou, Hua ^c   Liu, Liang ^c   Yao, Xin Sheng ^a,b  

^a SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

^b JINAN UNIVERSITY   (China)

^c MACAU UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Macao)

Author keywords

12 and 14 membered macrolides; Anti inflammatory activity; Methymycin derivatives; Streptomyces venezuelae ATCC 15439

Indexed keywords

3' DEMETHYLDEOXYMETHYMYCIN; 3' DEMETHYLMETHYMYCIN; 3' DEMETHYLNEOMETHYMYCIN; 3' N OXIDE; ANTIINFLAMMATORY AGENT; IONOMYCIN; KROMYCIN; METHYMYCIN; NEOMETHYMYCIN; NOVAMETHYMYCIN; UNCLASSIFIED DRUG; YC 17;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; BACTERIAL STRAIN; CELL PROLIFERATION; DRUG EFFECT; DRUG STRUCTURE; HUMAN; HUMAN CELL; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; STREPTOMYCES VENEZUELAE; T LYMPHOCYTE;

EID: 84872108544     PISSN: 02536269     EISSN: 19763786     Source Type: Journal    
DOI: 10.1007/s12272-012-0907-z     Document Type: Article

References (22)

1. Borisova, S. A., Zhao, L. S., Sherman, D. H., and Liu, H. W., Biosynthesis of desosamine: Construction of a new macrolide carrying a genetically designed sugar moiety. Org. Lett., 1, 133-136 (1999).
2. Cane, D. E., Liang, T. C., Taylor, P. B., Chang, C., and Yang, C. C., Macrolide biosynthesis. 3. Stereochemistry of the chain-elongation steps of erythromycin biosynthesis. J. Am. Chem. Soc., 108, 4957-4964 (1986).
3. Cane, D. E., Lambalot, R. H., Prabhakaran, P. C., and Ott, W. R., Macrolide Biosynthesis .7. Incorporation of polyketide chain elongation intermediates into methymycin. J. Am. Chem. Soc., 115, 522-526 (1993).
4. Cane, D. E. and Graziani, E. I., Methymycin biosynthesis. Isolation of P450 monooxygenase activity in a cell-free system from Streptomyces venezuelae. J. Am. Chem. Soc., 120, 2682-2683 (1998).
5. Chang, C. W., Zhao, L. H., Yamase, H., and Liu, H. W., DesVI: A new member of the sugar N,N-dimethyltransferase family involved in the biosynthesis of desosamine. Angew. Chem. Int. Edit., 39, 2160-2163 (2000).
6. Djerassi, C., Bowers, A., and Khastgir, H. N., Methymycin. Reduction and oxidation studies. J. Am. Chem. Soc., 78, 1729-1732 (1956a).
7. Djerassi, C. and Zderic, J. A., The structure of the antibiotic methymycin. J. Am. Chem. Soc., 78, 2907-2908 (1956b).
8. Donin, M. N., Pagano, J., Dutcher, J. D., and Mckee, C. M., Methymycin, a new crystalline antibiotic. Antibiot. Annu., 179-185 (1953).
9. Ghittoni, R., Patrussi, L., Pirozzi, K., Pellegrini, M., Lazzerini, P. E., Capecchi, P. L., Pasini, F. L., and Baldari, C. T., Simvastatin inhibits T-cell activation by selectively impairing the function of Ras superfamily GTPases. FASEB. J., 19, 605-607 (2005).
10. Gunnes, S., Romming, C., and Undheim, K., Selective substitutions in the C10-methyl group in erythromycin derivatives. Tetrahedron, 62, 6090-6099 (2006).
11. Hong, J. S. J., Kim, W. S., Lee, S. K., Koh, H. S., Park, H. S., Park, S. J., Kim, Y. S., and Yoon, Y. J., The role of a second protein (DesVIII) in glycosylation for the biosynthesis of hybrid macrolide antibiotics in Streptomyces venezuelae. J. Microbiol. Biotechnol., 15, 640-645 (2005).
12. Ishimoto, H., Mukae, H., Sakamoto, N., Amenomori, M., Kitazaki, T., Imamura, Y., Fujita, H., Ishii, H., Nakayama, S., Yanagihara, K., and Kohno, S., Different effects of telithromycin on MUC5AC production induced by human neutrophil peptide-1 or lipopolysaccharide in NCI-H292 cells compared with azithromycin and clarithromycin. J. Antimicrob. Chemother., 63, 109-114 (2009).
13. Kao, C. L., Borisova, S. A., Kim, H. J., and Liu, H. W., Linear aglycones are the substrates for glycosyltransferase DesVII in methymycin biosynthesis: Analysis and implications. J. Am. Chem. Soc., 128, 5606-5607 (2006).
14. Li, T., Wong, V. K. W., Yi, X. Q., Wong, Y. F., Zhou, H., and Liu, L., Pseudolaric acid B suppresses T lymphocyte activation through inhibition of NF-êB signaling pathway and p38 phosphorylation. J. Cell. Biochem., 108, 87-95 (2009).
15. Lu, Y. J., Chen, T. H., Lin, L. H., Shen, C. M., and Huang, C. H., Macrolide use shortens fever duration in mycoplasma pneumoniae infection in children: a 2-year experience. J. Microbiol. Immunol. Infect., 41, 307-310 (2008).
16. Marjanovic, N., Bosnar, M., Michielin, F., Wille, D. R., Anic-Milic, T., Culic, O., Popovic-Grle, S., Bogdan, M., Parnham, M. J., and Haber, V. E., Macrolide antibiotics broadly and distinctively inhibit cytokine and chemokine production by COPD sputum cells in vitro. Pharmacol. Res., 63, 389-397 (2011).
17. Masamune, S., Kim, C. U., Wilson, K. E., Spessard, G. O., Georghiou, P. E., and Bates, G. S., Syntheses of macrolide antibiotics. I. methymycin. J. Am. Chem. Soc., 97, 3512-3513 (1975).
18. Mcpherson, M., Khosla, C., and Cane, D. E., Erythromycin biosynthesis: The ?-ketoreductase domains catalyze the stereospecific transfer of the 4-pro-S hydride of NADPH. J. Am. Chem. Soc., 120, 3267-3268 (1998).
19. Munic, V., Banjanac, M., Kostrun, S., Nujic, K., Bosnar, M., Marjanovic, N., Ralic, J., Matijasic, M., Hlevnjak, M., and Haber, V. E., Intensity of macrolide anti-inflammatory activity in J774A.1 cells positively correlates with cellular accumulation and phospholipidosis. Pharmacol. Res., 64, 298-307 (2011).
20. Ogura, H., Furuhata, K., Kuwano, H., and Harada, N., Stereochemistry of macrolides. I. Conformation of aglycones of pikromycin and narbomycin and their derivatives. J. Am. Chem. Soc., 97, 1930-1934 (1975).
21. Zhang, Q. B. and Sherman, D. H., Isolation and structure determination of novamethymycin, a new bioactive metabolite of the methymycin biosynthetic pathway in Streptomyces venezuelae. J. Nat. Prod., 64, 1447-1450 (2001).
22. Zhao, L. S., Sherman, D. H., and Liu, H. W., Biosynthesis of desosamine: Construction of a new methymycin/neomethymycin analogue by deletion of a desosamine biosynthetic gene. J. Am. Chem. Soc., 120, 10256-10257 (1998).