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Marine Drugs  2012 

Identification and Characterization of an Anti-Fibrotic Benzopyran Compound Isolated from Mangrove-Derived Streptomyces xiamenensis

DOI: 10.3390/md10030639

Keywords: Streptomyces xiamenensis, mangrove, benzopyran, fibroblast, anti-fibrosis, anti-contractile capacity

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Abstract:

An anti-fibrotic compound produced by Streptomyces xiamenensis, found in mangrove sediments, was investigated for possible therapeutic effects against fibrosis . The compound, N-[[3,4-dihydro-3 S-hydroxy-2 S-methyl-2-(4¢ R-methyl-3¢ S-pentenyl)- 2H-1-benzopyran-6-yl]carbonyl]-threonine (1), was isolated from crude extracts and its structure, including the absolute configuration was determined by extensive spectroscopic data analyses, Mosher’s method, Marfey’s reagent and quantum mechanical calculations. In terms of biological effects, this compound inhibits the proliferation of human lung fibroblasts (WI26), blocks adhesion of human acute monocytic leukemia cells (THP-1) to a monolayer of WI26 cells, and reduces the contractile capacity of WI26 cells in three-dimensional free-floating collagen gels. Altogether, these data indicate that we have identified a bioactive alkaloid (1) with multiple inhibitory biological effects on lung excessive fibrotic characteristics, that are likely involved in fibrosis, suggesting that this molecule might indeed have therapeutic potential against fibrosis.

References

[1]  Wynn, T.A. Cellular and molecular mechanisms of fibrosis. J. Pathol. 2008, 214, 199–210.
[2]  Borm, P. Toxicity of Selected: Toxicology of Fibers and Particles; John Wiley & Sons Ltd.: Hoboken, NJ, USA, 2008.
[3]  Gurtner, G.C.; Werner, S.; Barrandon, Y.; Longaker, M.T. Wound repair and regeneration. Nature 2008, 453, 314–321.
[4]  Nathan, C.; Ding, A.H. Nonresolving Inflammation. Cell 2010, 140, 871–882.
[5]  Guan, S.; Grabley, S.; Groth, I.; Lin, W.; Christner, A.; Guo, D.; Sattler, I. Structure determination of germacrane-type sesquiterpene alcohols from an endophyte Streptomyces griseus subsp. Magn. Reson. Chem. 2005, 43, 1028–1031, doi:10.1002/mrc.1710.
[6]  Guan, S.H.; Sattler, I.; Lin, W.H.; Guo, D.A.; Grabley, S. p-Aminoacetophenonic acids produced by a mangrove endophyte: Streptomyces griseus subsp. J. Nat. Prod. 2005, 68, 1198–1200, doi:10.1021/np0500777.
[7]  Lin, W.; Li, L.; Fu, H.; Sattler, I.; Huang, X.; Grabley, S. New cyclopentenone derivatives from an endophytic Streptomyces sp. isolated from the mangrove plant Aegiceras comiculatum. J. Antibiot. (Tokyo) 2005, 58, 594–598, doi:10.1038/ja.2005.81.
[8]  Wang, F.; Xu, M.; Li, Q.; Sattler, I.; Lin, W. p-Aminoacetophenonic acids produced by a mangrove endophyte Streptomyces sp. (strain HK10552). Molecules 2010, 15, 2782–2790.
[9]  Xu, M.; Gessner, G.; Groth, I.; Lange, C.; Christner, A.; Bruhn, T.; Deng, Z.; Li, X.; Heinemann, S.H.; Grabley, S.; et al. Shearinines D-K, new indole triterpenoids from an endophytic Penicillium sp. (strain HKI0459) with blocking activity on large-conductance calcium-activated potassium channels. Tetrahedron 2007, 63, 435–444.
[10]  Ravangpai, W.; Sommit, D.; Teerawatananond, T.; Sinpranee, N.; Palaga, T.; Pengpreecha, S.; Muangsin, N.; Pudhom, K. Limonoids from seeds of Thai Xylocarpus moluccensis. Bioorg. Med. Chem. Lett. 2011, 21, 4485–4489.
[11]  Li, Y.; Liu, J.; Yu, S.; Proksch, P.; Gu, J.; Lin, W. TNF-alpha inhibitory diterpenoids from the Chinese mangrove plant Excoecaria agallocha L. Phytochemistry 2010, 71, 2124–2131, doi:10.1016/j.phytochem.2010.08.011.
[12]  Gurtner, G.C.; Dauskardt, R.H.; Wong, V.W.; Bhatt, K.A.; Wu, K.; Vial, I.N.; Padois, K.; Korman, J.M.; Longaker, M.T. Improving cutaneous scar formation by controlling the mechanical environment: Large animal and phase I studies. Ann. Surg. 2011, 254, 217–225.
[13]  Xu, J.; Wang, Y.; Xie, S.J.; Xu, J.; Xiao, J.; Ruan, J.S. Streptomyces xiamenensis sp. nov., isolated from mangrove sediment. Int. J. Syst. Evol. Microbiol. 2009, 59, 472–476.
[14]  Kawamura, N.; Tsuji, E.; Watanabe, Y.; Tsuchihashi, K.; Takako, T. Benzopyran derivatives, their manufacture with Streptomyces species, and their use for treatment of asthma and rheumatoid arthritis. Mercian Corp.: Kyoto, Japan, 2000.
[15]  Plavec, J.; Tong, W.; Chattopadhyaya, J. How do the gauche and anomeric effects drive the pseudorotational equilibrium of the pentofuranose moiety of nucleosides? J. Am. Chem. Soc. 1993, 115, 9734–9746.
[16]  Goodlett, D.R.; Abuaf, P.A.; Savage, P.A.; Kowalski, K.A.; Mukherjee, T.K.; Tolan, J.W.; Corkum, N.; Goldstein, G.; Crowther, J.B. Peptide chiral purity determination: Hydrolysis in deuterated acid, derivatization with Marfey’s reagent and analysis using high-performance liquid chromatography-electrospray ionization-mass spectrometry. J. Chromatogr. A 1995, 707, 233–244.
[17]  Wynn, T.A.; Barron, L. Macrophages: Master regulators of inflammation and fibrosis. Semin. Liver Dis. 2010, 30, 245–257.
[18]  Barron, L.; Wynn, T.A. Fibrosis is regulated by Th2 and Th17 responses and by dynamic interactions between fibroblasts and macrophages. Am. J. Physiol. Gastrointest. Liver Physiol. 2011, 300, G723–G728.
[19]  Wong, V.W.; Rustad, K.C.; Akaishi, S.; Sorkin, M.; Glotzbach, J.P.; Januszyk, M.; Nelson, E.R.; Levi, K.; Paterno, J.; Vial, I.N.; et al. Focal adhesion kinase links mechanical force to skin fibrosis via inflammatory signaling. Nat. Med. 2011.
[20]  Oakes, P.W.; Patel, D.C.; Morin, N.A.; Zitterbart, D.P.; Fabry, B.; Reichner, J.S.; Tang, J.X. Neutrophil morphology and migration are affected by substrate elasticity. Blood 2009, 114, 1387–1395.
[21]  Wong, V.W.; Akaishi, S.; Longaker, M.T.; Gurtner, G.C. Pushing back: Wound mechanotransduction in repair and regeneration. J. Investig. Dermatol. 2011, 131, 2186–2196.
[22]  Abraham, D.J.; Eckes, B.; Rajkumar, V.; Krieg, T. New developments in fibroblast and myofibroblast biology: Implications for fibrosis and scleroderma. Curr. Rheumatol. Rep. 2007, 9, 136–143.
[23]  Wong, V.W.; Paterno, J.; Sorkin, M.; Glotzbach, J.P.; Levi, K.; Januszyk, M.; Rustad, K.C.; Longaker, M.T.; Gurtner, G.C. Mechanical force prolongs acute inflammation via T-cell-dependent pathways during scar formation. FASEB J. 2011.
[24]  Grinnell, F. Fibroblast biology in three-dimensional collagen matrices. Trends Cell Biol. 2003, 13, 264–269.
[25]  Churg, A.; Brauer, M. Ambient atmospheric particles in the airways of human lungs. Ultrastruct. Pathol. 2000, 24, 353–361.
[26]  Sasaki, E.; Tanahashi, Y.; Yamasaki, Y.; Oda, N.; Nozawa, Y.; Terakawa, H.; Miyoshi, K.; Muranaka, Y.; Miyake, H.; Matsuura, N. Inhibitory effect of TAS-301, a new synthesized constrictive remodeling regulator, on renarrowing after balloon overstretch injury of porcine coronary artery. J. Pharmacol. Exp. Ther. 2000, 295, 1043–1050.
[27]  Eckes, B.; Nischt, R.; Krieg, T. Cell-matrix interactions in dermal repair and scarring. Fibrogenesis Tissue Repair 2010, 3.
[28]  Strieter, R.M.; Gomperts, B.N.; Keane, M.P. The role of CXC chemokines in pulmonary fibrosis. J. Clin. Investig. 2007, 117, 549–556.
[29]  Wolfram, D.; Tzankov, A.; Pulzl, P.; Piza-Katzer, H. Hypertrophic scars and keloids—A review of their pathophysiology, risk factors, and therapeutic management. Dermatol. Surg. 2009, 35, 171–181, doi:10.1111/j.1524-4725.2008.34406.x.
[30]  Laurent, G.J.; Chambers, R.C.; Hill, M.R.; McAnulty, R.J. Regulation of matrix turnover: Fibroblasts, forces, factors and fibrosis. Biochem. Soc. Trans. 2007, 35, 647–651, doi:10.1042/BST0350647.
[31]  Delavary, B.M.; van der Veer, W.M.; van Egmond, M.; Niessen, F.B.; Beelen, R.H. Macrophages in skin injury and repair. Immunobiology 2011, 216, 753–762.
[32]  Holt, D.J.; Chamberlain, L.M.; Grainger, D.W. Cell-cell signaling in co-cultures of macrophages and fibroblasts. Biomaterials 2010, 31, 9382–9394.
[33]  Long, E.O. ICAM-1: Getting a grip on leukocyte adhesion. J. Immunol. 2011, 186, 5021–5023.
[34]  Kelemen, O.; Kollar, L. Current methods of treatment and prevention of pathologic scars. Magy. Seb. 2007, 60, 63–70.
[35]  Ogawa, R. The most current algorithms for the treatment and prevention of hypertrophic scars and keloids. Plast. Reconstruct. Surg. 2010, 125, 557–568.
[36]  Cheng, K.; Ashby, D.; Smyth, R.L. Oral steroids for long-term use in cystic fibrosis. Cochrane Database Syst. Rev. 2011.
[37]  Hunzelmann, N.; Moinzadeh, P.; Genth, E.; Krieg, T.; Lehmacher, W.; Melchers, I.; Meurer, M.; Müller-Ladner, U.; Olski, T.M.; Pfeiffer, C.; et al. High frequency of corticosteroid and immunosuppressive therapy in patients with systemic sclerosis despite limited evidence for efficacy. Arthritis Res. Ther. 2009, 11.
[38]  Pfaff, A.W.; Georges, S.; Candolfi, E. Different effect of Toxoplasma gondii infection on adhesion capacity of fibroblasts and monocytes. Parasite Immunol. 2008, 30, 487–490.
[39]  Taub, D.D.; Lloyd, A.R.; Conlon, K.; Wang, J.M.; Ortaldo, J.R.; Harada, A.; Matsushima, K.; Kelvin, D.J.; Oppenheim, J.J. Recombinant human interferon-inducible protein 10 is a chemoattractant for human monocytes and T lymphocytes and promotes T cell adhesion to endothelial cells. J. Exp. Med. 1993, 177, 1809–1814.
[40]  Zhang, Z.G.; Bothe, I.; Hirche, F.; Zweers, M.; Gullberg, D.; Pfitzer, G.; Krieg, T.; Eckes, B.; Aumailley, M. Interactions of primary fibroblasts and keratinocytes with extracellular matrix proteins:Contribution of α2β1 integrin. J. Cell Sci. 2006, 119, 1886–1895.
[41]  Gaussian 9, Revision A.02; Gaussian, Inc.: Wallingford, CT, USA, 2009.
[42]  Zhao, Y.; Truhlar, D.G. Density functionals with broad applicability in chemistry. Acc. Chem. Res. 2008, 41, 157–167.
[43]  Marenich, A.V.; Cramer, C.J.; Truhlar, D.G. Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions. J. Phys. Chem. B 2009, 113, 6378–6396.

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