10.1007/s40097-020-00385-3

Isolation of antimicrobial Tridecanoic acid from Bacillus sp. LBF-01 and its potentialization through silver nanoparticles synthesis: a combined experimental and theoretical studies

  1. Department of Botany, Plant and Microbial Physiology and Biochemistry Laboratory, University of Gour Banga, Malda, West Bengal, 732 103, IN Department of Botany, Balurghat College, Balurghat, West Bengal, 733101, IN Department of Botany, Balurghat College, Balurghat, West Bengal, 733101, IN
  2. Department of Chemistry, JIS College of Engineering, Kalyani, West Bengal, 741235, IN
  3. Department of Chemistry, University of Kalyani, Kalyani, 741235, IN
  4. Department of Chemistry, University of Gour Banga, Malda, West Bengal, 732 103, IN
  5. Department of Botany, Plant and Microbial Physiology and Biochemistry Laboratory, University of Gour Banga, Malda, West Bengal, 732 103, IN

Published in Issue 20-01-2021

How to Cite

Chowdhury, S. K., Dutta, T., Chattopadhyay, A. P., Ghosh, N. N., Chowdhury, S., & Mandal, V. (2021). Isolation of antimicrobial Tridecanoic acid from Bacillus sp. LBF-01 and its potentialization through silver nanoparticles synthesis: a combined experimental and theoretical studies. Journal of Nanostructure in Chemistry, 11(4 (December 2021). https://doi.org/10.1007/s40097-020-00385-3

Abstract

Abstract Tridecanoic acid (TDA), an antimicrobial compound, was isolated from Bacillus sp. LBF-01 and purified with the help of column and multidimensional liquid chromatography (MDLC), and characterized by Thin-layer chromatography (TLC), Electrospray Ionisation Mass Spectrometry (ESI–MS), Ultraviolet–Visible (UV–Vis), Fourier Transform Infrared Spectroscopy (FTIR), and Nuclear Magnetic Resonance (NMR) spectroscopic studies. Isolated TDA was potentialized through the synthesis of silver nanoparticles (AgNPs). UV–Vis, FTIR, and TEM analysis showed that synthesized AgNPs were stable, monodispersed, and spherical shape of average 19 nm diameter. Theoretical simulation using Density Functional Theory revealed that AgNPs were stabilized by the tridecanoate form of TDA with a binding energy of 59.9 kJ/mol. Both TDA and AgNPs showed strong antifungal and antibacterial activities against the plant and human pathogenic organisms, however, AgNPs showed higher antimicrobial efficacy than TDA. Synergistic activity of TDA and AgNPs with a fungicide (Bavistin) and antibiotics (Streptomycin and Ciprofloxacin) showed enhanced antimicrobial potency in the range of 20–32%. TDA and AgNPs cause severe morphological abnormalities in Fusarium oxysporum as observed under the light microscope. Hence, the study reveals that the antimicrobial TDA produced by Bacillus sp. LBF-01 have disease control potentiality, and also the TDA stabilized AgNPs have much higher antimicrobial efficacy against the target pathogens that could be utilized in plant and human diseases control. Graphic abstract

Keywords

  • Antimicrobial,
  • Bacillus sp. LBF-01,
  • Density functional theory,
  • Silver nanoparticles,
  • Synergistic,
  • Tridecanoic acid

References

  1. Müller et al. (2008) Some insights in the effect of growing bio-energy demand on global food security and natural resources 10(S1) (pp. 83-94)
  2. Avery et al. (2019) The fungal threat to global food security 123(8) (pp. 555-557)
  3. Savary and Willocquet (2020) Modeling the impact of crop diseases on global food security https://doi.org/10.1146/annurev-phyto-010820-012856
  4. Prema et al. (2010) Production and characterization of an antifungal compound (3-phenyllactic acid) produced by Lactobacillus plantarum strain 3(3) (pp. 379-386)
  5. Ibrahim et al. (2020) Green-synthesization of silver nanoparticles using endophytic bacteria isolated from garlic and its antifungal activity against wheat Fusarium head blight pathogen Fusarium graminearum 10(2)
  6. Mohamed et al. (2020) Eco-friendly mycogenic synthesis of ZnO and CuO nanoparticles for in vitro antibacterial, antibiofilm, and antifungal applications https://doi.org/10.1007/s12011-020-02369-4
  7. El Abd El Aty and Zohair (2020) Green-synthesis and optimization of an eco-friendly nanobiofungicide from Bacillus amyloliquefaciens MH046937 with antimicrobial potential against phytopathogens
  8. Dutta et al. (2020) Green synthesis of antibacterial and antifungal silver nanoparticles using Citrus limetta peel extract: experimental and theoretical studies
  9. Gourama and Bullerman (1995) Aspergillus flavus and Aspergillus parasiticus: Aflatoxigenic fungi of concern in foods and feeds: a review 58(12) (pp. 1395-1404)
  10. Yang et al. (2008) Antifungal substances produced by Penicillium oxalicum strain PY-1—potential antibiotics against plant pathogenic fungi 24(7) (pp. 909-915)
  11. Diekema et al. (2004) Rapid detection of antimicrobial-resistant organism carriage: an unmet clinical need 42(7) (pp. 2879-2883)
  12. Roy et al. (2019) Green synthesis of silver nanoparticles: biomolecule-nanoparticle organizations targeting antimicrobial activity 9(5) (pp. 2673-2702)
  13. Amini (2019) Preparation of antimicrobial metallic nanoparticles with bioactive compounds
  14. Bhat et al. (2011) Photo-irradiated biosynthesis of silver nanoparticles using edible mushroom Pleurotus florida and their antibacterial activity studies
  15. Silver (2003) Bacterial silver resistance: molecular biology and uses and misuses of silver compounds 27(2–3) (pp. 341-353)
  16. Atiyeh et al. (2007) Effect of silver on burn wound infection control and healing: review of the literature 33(2) (pp. 139-148)
  17. Dutta et al. (2019) Chitosan encapsulated water-soluble silver bionanocomposite for size-dependent antibacterial activity
  18. Dutta et al. (2020) Facile green synthesis of silver bionanocomposite with size dependent antibacterial and synergistic effects: a combined experimental and theoretical studies 30(5) (pp. 1839-1851)
  19. Abid et al. (2002) Preparation of silver nanoparticles in solution from a silver salt by laser irradiation (pp. 792-793)
  20. Gasaymeh et al. (2010) Synthesis and characterization of silver/polyvinilpirrolidone (Ag/PVP) nanoparticles using gamma irradiation techniques https://doi.org/10.3844/ajassp.2010.892.901
  21. Soroushian et al. (2005) Radiolysis of silver ion solutions in ethylene glycol: solvated electron and radical scavenging yields 72(2–3) (pp. 111-118)
  22. Rai et al. (2015) Three Phoma spp. synthesised novel silver nanoparticles that possess excellent antimicrobial efficacy 9(5) (pp. 280-287)
  23. Sastry et al. (2003) Biosynthesis of metal nanoparticles using fungi and actinomycete 85(2) (pp. 162-170)
  24. Ramanathan et al. (2011) Bacterial kinetics-controlled shape-directed biosynthesis of silver nanoplates using Morganella psychrotolerans 27(2) (pp. 714-719)
  25. Rajamanickam, U., Mylsamy, P., Viswanathan, S., Muthusamy, P.: Biosynthesis of zinc nanoparticles using actinomycetes for antibacterial food packaging. In: International Conference on Nutrition and Food Sciences IPCBEE, vol. 39 (2012).
  26. Merin et al. (2010) Antibacterial screening of silver nanoparticles synthesized by marine micro algae 3(10) (pp. 797-799)
  27. Tsibakhashvili et al. (2011) Microbial synthesis of silver nanoparticles by Streptomyces glaucus and Spirulina platensis 4(11–12) (pp. 3408-3417)
  28. Gade et al. (2010) Biofabrication of silver nanoparticles by Opuntia ficus-indica: in vitro antibacterial activity and study of the mechanism involved in the synthesis 6(4) (pp. 370-375)
  29. Iravani (2011) Green synthesis of metal nanoparticles using plants 13(10) (pp. 2638-2650)
  30. Fira et al. (2018) Biological control of plant pathogens by Bacillus species (pp. 44-55)
  31. Gajbhiye et al. (2010) Biotechnology: isolation, evaluation and characterization of Bacillus subtilis from cotton rhizospheric soil with biocontrol activity against Fusarium oxysporum 26(7) (pp. 1187-1194)
  32. Prajakta et al. (2019) Potential biocontrol and superlative plant growth promoting activity of indigenous Bacillus mojavensis PB-35 (R11) of soybean (Glycine max) rhizosphere 1(10)
  33. Agoramoorthy et al. (2007) Antibacterial and antifungal activities of fatty acid methyl esters of the blind-your-eye mangrove from India 38(4) (pp. 739-742)
  34. Kavitha and Uduman (2017) Identification of bioactive components and its biological activities of Abelmoschas moschatus flower extrtact-a GC-MS study (pp. 19-22)
  35. Moussa and Almaghrabi (2016) Fatty acid constituents of Peganum harmala plant using Gas Chromatography-Mass Spectroscopy 23(3) (pp. 397-403)
  36. Chowdhury et al. (2020) Application of Bacillus sp. LBF-01 in Capsicum annuum plant reduces the fungicide use against Fusarium oxysporum
  37. Chowdhury et al. (2020) Biocontrol potential and growth promotion capability of Bacillus sp. LBF-1 for management of wilt disease of Solanum lycopersicum caused by Fusarium sp. (pp. 139-147)
  38. Fernández-Garayzábal et al. (1992) Role of potassium tellurite and brain heart infusion in expression of the hemolytic phenotype of Listeria spp. on agar plates 58(1) (pp. 434-438)
  39. Dong et al. (2009) One-step synthesis of uniform silver nanoparticles capped by saturated decanoate: direct spray printing ink to form metallic silver films 11(29) (pp. 6269-6275)
  40. Giannozzi et al. (2009) QUANTUM ESPRESSO: a modular and open-source software project for quantum simulations of materials 21(39)
  41. Perdew et al. (1996) Generalized gradient approximation made simple 77(18)
  42. Perdew et al. (1993) Erratum: atoms, molecules, solids, and surfaces: applications of the generalized gradient approximation for exchange and correlation 48(7)
  43. Vanderbilt (1990) Soft self-consistent pseudopotentials in a generalized eigenvalue formalism 41(11)
  44. Kokalj (1999) XCrySDen—a new program for displaying crystalline structures and electron densities 17(3–4) (pp. 176-179)
  45. Dutta et al. (2020) Materials: Facile green synthesis of silver bionanocomposite with size dependent antibacterial and synergistic effects: a combined experimental and theoretical studies 30(5) (pp. 1839-1851)
  46. Iscla et al. (2015) A new antibiotic with potent activity targets MscL 68(7) (pp. 453-462)
  47. Dutta et al. (2020) Biogenic silver nanoparticle synthesis and stabilization for apoptotic activity; insights from experimental and theoretical studies https://doi.org/10.1007/s11696-020-01216-z
  48. Gwatidzo et al. (2017) Fatty acid profile of Manketti (Schinziophyton rautanenii) nut oil: Influence of extraction method and experimental evidence on the existence of α-eleostearic acid 8(5) (pp. 33-44)
  49. Rioux et al. (1999) High performance liquid chromatography of fatty acids as naphthacyl derivatives 27(2) (pp. 186-193)
  50. Hill and Levin (1979) Vibrational spectra and carbon–hydrogen stretching mode assignments for a series of n-alkyl carboxylic acids 70(2) (pp. 842-851)
  51. Dong et al. (2009) One-step synthesis of uniform silver nanoparticles capped by saturated decanoate: direct spray printing ink to form metallic silver films 11(29) (pp. 6269-6275)
  52. Tanna et al. (2016) Alumina Nanoparticle: A new and reusable catalyst for synthesis of dihydropyrimidinone derivatives 7(8) (pp. 100-150)
  53. Han et al. (2011) Lipase-catalyzed synthesis of 6-O-d-glucosyldecanoate in tert-butanol: reaction optimization and effect of mixing power input 25(4) (pp. 2642-2651)
  54. Abad et al. (2000) Synthesis of dideuterated and enantiomers of monodeuterated tridecanoic acids at C-9 and C-10 positions 65(25) (pp. 8582-8588)
  55. Chowdhury et al. (2020) Application of Bacillus sp. LBF-01 in Capsicum annuum plant reduces the fungicide use against Fusarium oxysporum
  56. Hildebrandt and Stockburger (1984) Surface-enhanced resonance Raman spectroscopy of Rhodamine 6G adsorbed on colloidal silver 88(24) (pp. 5935-5944)
  57. Link et al. (1999) Alloy formation of gold− silver nanoparticles and the dependence of the plasmon absorption on their composition 103(18) (pp. 3529-3533)
  58. Geetha et al. (2016) DFT and SERS study of adsorption of 1, 4-dimethoxy-2-nitro-3-methylanthracene-9, 10-dione onto silver nanoparticles 69(1) (pp. 76-84)
  59. Mulfinger et al. (2007) Synthesis and study of silver nanoparticles 84(2)
  60. Mavani and Shah (2013) Technology: synthesis of silver nanoparticles by using sodium borohydride as a reducing agent 2(3) (pp. 1-5)
  61. Biswal and Misra (2020) Biosynthesis and characterization of silver nanoparticles for prospective application in food packaging and biomedical applications
  62. Prasad et al. (2002) Digestive ripening of thiolated gold nanoparticles: the effect of alkyl chain length 18(20) (pp. 7515-7520)
  63. Shim et al. (2008) Physics: an organometallic route to highly monodispersed silver nanoparticles and their application to ink-jet printing 110(2–3) (pp. 316-321)
  64. Misra et al. (2009) Effect of organized assemblies, part vii: adsorption behavior of polyoxyethylated nonyl phenol at silica− cyclohexane interface and its efficiency in stabilizing the silica—cyclohexane dispersion 48(7) (pp. 3403-3409)
  65. Das et al. (2008) Effect of organized assemblies Part 4 Formulation of highly concentrated coal—water slurry using a natural surfactant 22(3) (pp. 1865-1872)
  66. Mei et al. (2013) Bioconjugated nanoparticles for attachment and penetration into pathogenic bacteria 34(38) (pp. 10328-10337)
  67. Griffith et al. (2015) (pp. 127-146) Springer
  68. Shrivastava et al. (2007) Characterization of enhanced antibacterial effects of novel silver nanoparticles 18(22)
  69. Kadurugamuwa et al. (1993) Surface action of gentamicin on Pseudomonas aeruginosa 175(18) (pp. 5798-5805)
  70. Carlson et al. (2008) Unique cellular interaction of silver nanoparticles: size-dependent generation of reactive oxygen species 112(43) (pp. 13608-13619)
  71. Zhao et al. (2015) In vitro antibacterial activities and mechanism of sugar fatty acid esters against five food-related bacteria (pp. 370-377)
  72. Tundis et al. (2019) An ancient remedial repurposing: synthesis of new pinocembrin fatty acid acyl derivatives as potential antimicrobial/anti-inflammatory agents 33(2) (pp. 162-168)
  73. Lateef et al. (2016) Anti-candida, anti-coagulant and thrombolytic activities of biosynthesized silver nanoparticles using cell-free extract of Bacillus safensis LAU 13 51(10) (pp. 1406-1412)
  74. Chang et al. (2019) Nanodiamond-supported silver nanoparticles as potent and safe antibacterial agents 9(1) (pp. 1-11)
  75. Batarseh (2004) Anomaly and correlation of killing in the therapeutic properties of silver (I) chelation with glutamic and tartaric acids 54(2) (pp. 546-548)
  76. Chitarra et al. (2003) An antifungal compound produced by Bacillus subtilis YM 10–20 inhibits germination of Penicillium roqueforti conidiospores 94(2) (pp. 159-166)
  77. Li et al. (2007) Compounds inhibitory to nematophagous fungi produced by Bacillus sp. strain H6 isolated from fungistatic soil 117(4) (pp. 329-340)