The use of salicylaldehyde derivatives as a nitrogen source for antibiotic production by Streptomyces hygroscopicus CH-7
Main Article Content
Abstract
In the present work, four derivatives of salicylaldehyde (salicylaldehyde-hydrazone, phenylhydrazone, semicarbazone and thiosemicarbazone) were synthesized using both conventional (95% ethanol) and green (crude glycerol from biodiesel production) solvents. The obtained compounds were identified by elemental microanalysis, as well as FTIR, UV/VIS, 1H NMR and X-ray spectroscopic methods. Yields of 93-98% of the compounds in crude glycerol were achieved within 10-25 min. The derivatives of salicylaldehyde and crude glycerol were used as a nitrogen and carbon source, respectively, in the medium for antibiotic (Hexaene H-85 and Azalomycine B) production by Streptomyces hygroscopicus CH-7. The highest concentrations of Hexaene H-85 and Azalomycine B were achieved in the medium containing salicylaldehyde-thiosemicarbazone (198 g/cm3 and 69 µg/cm3, respectively). Derivatives of salicylaldehyde also impacted the strain morphology. In the media with salicylaldehyde-phenylhydrazone and salicylaldehyde-thiosemicarbazone, S. hygroscopicus CH-7 grew like large dispersive pellets with long twisted filaments that produced the highest yield of the antibiotics.
Article Details
Issue
Section
Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
Authors grant to the Publisher the following rights to the manuscript, including any supplemental material, and any parts, extracts or elements thereof:
- the right to reproduce and distribute the Manuscript in printed form, including print-on-demand;
- the right to produce prepublications, reprints, and special editions of the Manuscript;
- the right to translate the Manuscript into other languages;
- the right to reproduce the Manuscript using photomechanical or similar means including, but not limited to photocopy, and the right to distribute these reproductions;
- the right to reproduce and distribute the Manuscript electronically or optically on any and all data carriers or storage media – especially in machine readable/digitalized form on data carriers such as hard drive, CD-Rom, DVD, Blu-ray Disc (BD), Mini-Disk, data tape – and the right to reproduce and distribute the Article via these data carriers;
- the right to store the Manuscript in databases, including online databases, and the right of transmission of the Manuscript in all technical systems and modes;
- the right to make the Manuscript available to the public or to closed user groups on individual demand, for use on monitors or other readers (including e-books), and in printable form for the user, either via the internet, other online services, or via internal or external networks.
How to Cite
References
Wolfson A, Snezhko A, Meyouhas T, Tavor D. Glycerol derivatives as green reaction mediums. Green Chem Lett Rev. 2012; 5: 7-12.
Konstantinović SS, Danilović BR, Ilić SB, Savić DS, Vlada B. Veljković VB. Valorization of crude glycerol from biodiesel production. Chem Ind Chem Eng Q. 2016; 22: 461−489.
Wolfson A, Litvak G, Dlugy C, Shotland Y, Tavor D. Employing crude glycerol from biodiesel production as an alternative green reaction medium. Ind Crops Prod.2009; 30: 78-81.
Valerioa O, Horvath T, Ponda C, Misraa M, Mohantya A. Improved utilization of crude glycerol from biodiesel industries: Synthesis and characterization of sustainable biobased polyesters. Ind Crops Prod.2015; 78: 141–147.
Nanda MR, Yuan Z, Qin W, Ghaziaskar HS, Poirier M, Xu C. Thermodynamic and kinetic studies of a catalytic process to convert glycerol into solketal as an oxygenated fuel additive. Fuel 2014; 117: 470-477.
Wolfson A, Dlugy C. Palladium-catalyzed heck and suzuki coupling in glycerol. Chem Papers. 2001; 61: 228-232.
Gu Y, Barrault J, Jerome F. Glycerol as an efficient promoting medium for organic reactions. Adv Synth Catal. 2008; 350: 2007-2012.
Jovanović MB, Konstantinović SS, Ilić SB, Veljković VB. The synthesis of vanillin-semicarbazone in crude glycerol as a green solvent. Adv Technol. 2013; 2: 38-44.
[9] Arulmurugan S, Kavitha HP, Venkatraman BR. Biological activities of Schiff base and its complexes. Rasayan J Chem. 2010; 3: 385-340.
Ilić SB, Konstantinović SS, Savić DS, Veljković VB, Gojgić-Cvijović G. The impact of Schiff bases on antibiotic production by Streptomyces hygroscopicus. Med Chem Res. 2010; 19: 690-697.
Ilić SB, Konstantinović SS, Gojgić-Cvijović G, Savić DS, Veljković VB. The influence of Schiff base inclusion complexes with beta-cyclodextrine on antibiotic production by Streptomyces hygroscopicus CH-7. Chem Ind. 2015; 69: 9-15.
Ćirić JT, Konstantinović SS, Ilić SB, Gojgić-Cvijović G, Savić DS, Veljković VB. The impact of isatin derivatives on antibiotic production by Streptomyces hygroscopicus CH-7. Hem Ind. 2016; 70:123-128.
Isahak WN, Ismail M, Yarmo MA, Jahim JM, Salimon J. Purification of crude glycerol from transesterification RBD palm oil over homogeneous and heterogeneous catalysts for the biolubricant preparation. J App Sci. 2010; 10: 2590-2595.
Konstantinović SS, Radovanović BC, Cakić Z, Vasić V. Synthesis and characterization of Co(II), Ni(II), Cu(II) and Zn(II) complexes with 3-salycilidenehydrazono-2-indolinone. J Serb Chem Soc. 2003; 68: 641-647.
Karadžić I, Gojgić-Cvijović G, Vučetić J. Hexaene H-85, A Hexaene H-85 macrolide complex. J Antibiot.1991; 12: 1452–1453.
Vučetić I, Karadžić I, Gojgić-Cvijović G, Radovanović E. Improving HexaeneH-85 production by Streptomyces hygroscopicus. J Serb Chem Soc. 1994; 59: 973–980.
Machado I, Fernández S, Beccoc L, Garatc B, Gancheffa JS, Reyb A, Gambino D. New fac-tricarbonyl rhenium(I) semicarbazone complexes: synthesis, characterization, and biological evaluation. J Coord Chem. 2014; 67: 1835-1850.
Baruah D, Saikia UP, Pahari P, Dutta DP, Konwar D. Deprotection of oximes, imines, and azines to the corresponding carbonyls using Cu-nano particles on cellulose template as green reusable catalyst. RSC Adv. 2014; 4: 59338-59343.
Cai P, Kong F, Fink P, Ruppen ME, Williamson RT, Keiko T. Polyene antibiotics from Streptomyces mediocidicus. J Nat Prod. 2007; 70:215–219.
Kaiser H, Keller-Schierlein W, Metabolites of microorganisms. Part 202. Structure elucidation of elaiophylin: spectroscopic studies and degradation. Helv Chim Acta. 1981; 64:407-424.
Zotchev SB. Polyene macrolide antibiotics and their applications in human therapy. Curr Med Chem. 2003; 10:211–23.
Zhang L, Hashimoto T, Qin B, Hashimoto J, Kozone I, Kawahara T, Okada M, Awakawa T, Ito T, Asakawa Y, Ueki M, Takahashi S, Osada H, Wakimoto T, Ikeda H, Shin-ya K, Abe I. Characterization of Giant Modular PKSs Provides Insight into Genetic Mechanism for Structural Diversification of Aminopolyol Polyketides. Angew Chem Int Ed. 2017; 56:1740-45.
Caffrey P, De Poire E, Sheehan J, Sweeney P. Polyene macrolide biosynthesis in streptomycetes and related bacteria: recent advances from genome sequencing and experimental studies. Appl Microbiol Biotechnol. 2016; 100: 3893-3908.
Solovieva SE, Olsufyeva EN, Preobrazhenskaya MN. Chemical modification of antifungal polyene macrolide antibiotics. Russ Chem Rev. 2011; 80:103 – 126.
Domingues FC, Queiroz JA, Cabral JMS, Fonseca LP. The influence of culture conditions on mycelial structure and cellulase production by Trichodermareesei Rut C-30.Enzyme Microb Technol. 2000; 26:394-401.
Yang W, Hartwieg AE, Fang A, Demain A. Effects of carboxymethylcellulose and carboxypolymethylene on morphology of Aspergillus fumigatus NRRL 2346 and fumagillin production. Curr Microbiol.2003; 46: 24-27.
Choi D, Park E, Okabe M. Dependence of apparent viscosity on mycelia morphology of Streptomyces fradiae culture in various nitrogen sources. Biotech Prog. 2000; 16:525-532.
Saurav K, Kannabiran K. Diversity and optimization of process parameters for the growth of Streptomyces VITSVK9 spp. Isolated from Bay and Bengal, India. J Nat Env Sci. 2010; 1: 56-65.
Ilić SB, The effect of composition and rheology of nutrition medium on kinetic of antibiotic production by bacteria Streptomyces hygroscopicus CH-7, Ph.D. Thesis, Faculty of Technology, University of Nis, Leskovac, 2010.