Fengycin

Manufactured by Merck Group

Sourced in United States, Germany

Fengycin is a lipopeptide produced by Bacillus subtilis. It functions as an antifungal agent.

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Lab products found in correlation

9 protocols using fengycin

Characterization of Fengycin Lipopeptides

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Lipids were purchased from Avanti Polar Lipids, Inc. (Pelham, AL): 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC), 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoethanolamine (POPE), 1-palmitoyl-2-oleoyl-sn-glycero-3-phospho-(1’-rac-glycerol) (POPG), 1,1′,2,2′-tetraoleoyl cardiolipin[4-(dipyrrometheneboron difluoride)butanoyl] (ammonium salt) (TOCL), 1-oleoyl-rac-glycerol (GMO), 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC), and ergosterol (ERG) Phloretin, myricetin, 3,3′,5-triiodo-L-thyronine (T₃), 4-{4-[4-(dipentylamino)phenyl]-1,3-butadienyl}-1-(4-sulfobutyl)pyridinium hydroxide (RH 421), tetracaine hydrochloride (TTC), Triton X-100 (TX-100), caffeine, nonactin, KCl, CHES, HEPES, KOH, and hexadecane were purchased from Sigma Chemical (St. Louis, MO).
Fengycin, purchased from Sigma Chemical, is a lipopeptide mixture synthesized by the Bacillus subtilis strain F-29-3. It is composed of two components, FE A and FE B (Fig. 1S, Supplementary Information).

Zakharova A.A., Efimova S.S., Malev V.V, & Ostroumova O.S. (2019). Fengycin induces ion channels in lipid bilayers mimicking target fungal cell membranes. Scientific Reports, 9, 16034.

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Identification of Antifungal Cyclic Lipopeptides

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The antifungal active compound and the two CLP fractions, fraction 1 and fraction 2, isolated from JCK-12 were analyzed by HPLC using the following conditions. A C₁₈ column (Atlantis T3, 5 μm, OBD 19 × 250 mm; Waters, Wexford, Ireland) was used, and the antifungal compound and fraction 1 were detected at 230 nm, whereas fraction 2 was detected at 215 nm. The mobile phases were as follows: solvent A, water with 0.1% trifluoroacetic acid (TFA); and solvent B, acetonitrile with 0.1% TFA. The compound was eluted with a linear gradient of solvent A increasing from 10 to 100% at a flow rate of 1 ml/min for 60 min. Iturin A (Sigma–Aldrich), fengycin (Sigma–Aldrich), and surfactin (Sigma–Aldrich) were used as standard chemicals. The retention times and UV spectra of the three CLPs were compared with those of the standard chemicals. To clearly confirm the identities of the CLPs isolated by prep TLC, electrospray ionization tandem mass spectrometry (ESI-MS/MS) analysis was performed on a SYNAPT G2 time-of-flight (TOF) mass spectrometry system (Waters, Manchester, United Kingdom) at a mass range of m/z 100–2,000.

Kim K., Lee Y., Ha A., Kim J.I., Park A.R., Yu N.H., Son H., Choi G.J., Park H.W., Lee C.W., Lee T., Lee Y.W, & Kim J.C. (2017). Chemosensitization of Fusarium graminearum to Chemical Fungicides Using Cyclic Lipopeptides Produced by Bacillus amyloliquefaciens Strain JCK-12. Frontiers in Plant Science, 8, 2010.

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Quantification of Lipopeptides by UHPLC

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The extracted and purified mixtures of lipopeptides were dissolved in acetonitrile and then filtered using a 0.22 μm membrane filter. For analyses, the UHPLC Dionex UltiMate 3000 system with DAD detector at a wavelength of 214 nm was used. For separations, the reverse-phase column YMC Meteoric Core C18 Bio (150 × 4.6 mm) with a particle size of 2.7 μm was utilized. The injection volumes were 20 μL. All the standard lipopeptides (iturin A, fengycin, surfactin) were purchased from Sigma Aldrich, Germany. The concentration of standards was 0.5 mg/mL. The eluent A consisted of 0.025% TFA in acetonitrile and eluent B was 0.025% water solution of TFA. The separation strategy was optimalized using gradient elution and at the 0–5 min mark 100% of eluent B was used with the flow rate of 0.5 mL/min; the linear gradient followed from 5 to 10 min, using 0–10% of eluent A with the flow rate of 0.8 mL/min, and finally, from 10 to 75 min, 10–90% of eluent A with the flow rate of 1.5 mL/min was performed.

Englerová K., Bedlovičová Z., Nemcová R., Király J., Maďar M., Hajdučková V., Styková E., Mucha R, & Reiffová K. (2021). Bacillus amyloliquefaciens—Derived Lipopeptide Biosurfactants Inhibit Biofilm Formation and Expression of Biofilm-Related Genes of Staphylococcus aureus. Antibiotics, 10(10), 1252.

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Virus Inactivation by Bacterial Components

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CoVs were diluted 10% (vol/vol) in solutions with final concentrations of 1 mg/ml (PG and LPS) or 100 μg/μl (CLPs) unless otherwise specified in the text. For alcohol wash experiments, samples were instead diluted 5% (vol/vol). Treated samples were then incubated for 2 h at 37°C, after which they titer was determined. The following bacterial components were purchased from Sigma-Aldrich: lipopolysaccharides from Escherichia coli (catalog no. L4130), peptidoglycan Bacillus subtilis (catalog no. 69554), Staphylococcus aureus (catalog no. 77140), Streptomyces species (catalog no. 79682), and Micrococcus luteus (catalog no. 53243). Peptidoglycan from Escherichia coli (PGN-EB) was purchased from InvivoGen. For each surface component, stock solutions were created by suspending the component in PBS and then stored at –20°C. The cyclic lipopeptides surfactin (catalog no. S3523), iturin A (catalog no. I1774), fengycin (catalog no. SMB00292), polymyxin B (catalog no. P1004), colistin (catalog no. C4461), ramoplanin (catalog no. R1781), and daptomycin (catalog no. D2446) were also purchased from Sigma-Aldrich. PBS was selected as a vehicle based on solubility data from previous studies, which established that surfactin is soluble in PBS at levels well above the concentrations used here (57 (link)– (link)59 (link)).

Johnson B.A., Hage A., Kalveram B., Mears M., Plante J.A., Rodriguez S.E., Ding Z., Luo X., Bente D., Bradrick S.S., Freiberg A.N., Popov V., Rajsbaum R., Rossi S., Russell W.K, & Menachery V.D. (2019). Peptidoglycan-Associated Cyclic Lipopeptide Disrupts Viral Infectivity. Journal of Virology, 93(22), e01282-19.

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Analytical Grade Chemicals for Iturin A and Fengycin

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Solvents used in this study were LC–MS grade, and all other chemicals were analytical grade. Iturin A, fengycin and solvents as well were from Sigma-Aldrich (Steinheim, Germany) unless otherwise stated. Water was purified using a Milli-Q system (Millipore, Bedford, MA). ESI–TOF tune mix was purchased from Agilent Technologies (Torrance, CA, USA).

Devi S., Kiesewalter H.T., Kovács R., Frisvad J.C., Weber T., Larsen T.O., Kovács Á.T, & Ding L. (2019). Depiction of secondary metabolites and antifungal activity of Bacillus velezensis DTU001. Synthetic and Systems Biotechnology, 4(3), 142-149.

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HPLC Separation and Identification of Lipopeptides

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The powder of Anti-JFL21 and Anti-LQG17 was dissolved in an aqueous solution of 40% methanol at 1 mg/mL and filtered using a 0.22 μm pore filter (Millipore, United States). A 20 μL aliquot was injected into an Inertsil ODS-SP C18 column (4.6 mm ID × 25 cm L, 5 μm particle diameter) in the HPLC system (Shimadzu, Japan) to separate and identify the isoforms, according to published methods with some modifications (Yang et al., 2015 (link)). In brief, the equal volumes of 1 mg/mL standard surfactin, fengycin and iturin (purity of 90% or greater, Sigma-Aldrich, United States) were fully mixed and used to confirm the RP-HPLC fraction groups of three lipopeptide families. The mobile phases consisted of water (A) and acetonitrile (B), and all of them contained 0.1% trifluoroacetic acid (TFA). The detailed gradient strategy for the acetonitrile-water mobile phase system was as follows: 0–3 min, 45% acetonitrile to 50% acetonitrile; 3–8 min, 50% acetonitrile to 80% acetonitrile; 8–25 min, 80% acetonitrile to 100% acetonitrile; 25–30 min, 100% acetonitrile. The total flow rate of the mobile phases was kept at 0.8 mL/min, and the products were monitored by absorbance at 215 nm. All HPLC solvents were prepared fresh daily and filtered under vacuum before use.

Lin L.Z., Zheng Q.W., Wei T., Zhang Z.Q., Zhao C.F., Zhong H., Xu Q.Y., Lin J.F, & Guo L.Q. (2020). Isolation and Characterization of Fengycins Produced by Bacillus amyloliquefaciens JFL21 and Its Broad-Spectrum Antimicrobial Potential Against Multidrug-Resistant Foodborne Pathogens. Frontiers in Microbiology, 11, 579621.

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Antimicrobial Compounds Characterization

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PVA (M_w = 13,000–23,000 g/mol,
99% hydrolysis), glucose,
surfactin, and fengycin were purchased from Sigma Aldrich (Sigma Chemicals,
St. Louis, MO). Dulbecco’s modified Eagle’s medium (DMEM)
and fetal bovine serum were purchased from Gibco-Invitrogen Corp.
(Grand Island, NY). Also used were Bacto Tryptone, Bacto Yeast extract,
Bacto Agar, Bacto peptone (Becton Dickenson, NJ, USA), NaCl (Bio-Lab
Chemicals, Jerusalem), MgSO₄ (Spectrum Chemical, CA, USA),
KH₂PO₄ (Riedel-de Haën, Munich), HCl
37% (Daejung Chemicals, Korea), and acetonitrile (J.T. Baker, NJ,
USA). B. subtilis 3610 was generously
provided by Prof. Ilana Kolodkin-Gal’s lab,^{42 (link)} Weizmann Institute of Science, Israel. Bacterial cultures
were American Type Culture Collection (ATCC) strains: S. aureus 25923 and methicillin-resistant 43300.

Ben David N., Mafi M., Nyska A., Gross A., Greiner A, & Mizrahi B. (2021). Bacillus subtilis in PVA Microparticles for Treating Open Wounds. ACS Omega, 6(21), 13647-13653.

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Biosurfactant Procurement for Research

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The biosurfactants (bacitracin, fengycin, iturin A, and rhamnolipids) used in this study were purchased from Sigma Aldrich (St. Louis, MO, USA) (Table 1). All the biosurfactants were in powder form.

Edosa T.T., Jo Y.H., Keshavarz M., Kim I.S, & Han Y.S. (2020). Biosurfactants Induce Antimicrobial Peptide Production through the Activation of TmSpatzles in Tenebrio molitor. International Journal of Molecular Sciences, 21(17), 6090.

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Antibacterial Compound Screening Against Xcc

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Several antibacterial compounds were detected by metabolome and transcriptome analysis. Several compounds such as fengycin and surfactin (purchased from Sigma-Aldrich, St. Louis, MO, USA) and macrolactin isolated from Bv-25 (purified and identified by Dr. Sanghee Shim from Seoul National University, Seoul, Republic of Korea) were tested for antagonistic effects against Xcc based on the procedure described in Section 2.2.

Rabbee M.F, & Baek K.H. (2023). Detection of Antagonistic Compounds Synthesized by Bacillus velezensis against Xanthomonas citri subsp. citri by Metabolome and RNA Sequencing. Microorganisms, 11(6), 1523.

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