Startseite The mechanism of antibacterial activity of corylifolinin against three clinical bacteria from Psoralen corylifolia L
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The mechanism of antibacterial activity of corylifolinin against three clinical bacteria from Psoralen corylifolia L

  • Nan He , Juan Zhou , Miyun Hu , Changyang Ma EMAIL logo und Wenyi Kang
Veröffentlicht/Copyright: 3. September 2018
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Open Chemistry
Aus der Zeitschrift Open Chemistry Band 16 Heft 1

Abstract

Effective antibacterial activity against Grampositive bacteria isolated in clinical strains was exhibited when corylifolinin was tested using the Disc diffusion method (K-B method). Minimum inhibitory concentration (MIC) of corylifolinin against Staphylococcus aureus (SA), Methcillin-resistant Staphylococcus aureus (MRSA) and extended spectrum β-lactamases Staphylococcus aureus (ESBLs-SA) were 0.078, 0.156 and 0.078 mg/mL, respectively. The minimum bactericide concentrations (MBCs) were 0.156, 0.156 and 0.078 mg/mL respectively. Scanning electron microscopy (SEM), alkaline phosphatase (AKP) and bacterial extracellular protein leakage were used to investigate the antibacterial mechanism of corylifolinin. After adding corylifolinin at the MBC level, there were obvious changes to the Staphylococcus aureus of bacteria cells. Both MIC level and MBC levels of corylifolinin led to the leakage of AKP and bacterial extracellular protein.

Keywords: Corylifolinin; Antibacterial mechanism; Scanning electron micsoscopy; Bacterial membrane and wall permeability

1 Introduction

The history of Traditional Chinese Medicines (TCMs) are thousands of years old. Many researchers in China are interested in studying TCMs because of their significant health-promoting effects. Studies have shown that the compounds from TCMs have an effective antibacterial activity, such as the compounds isolated from the bark of Pterocarya stenoptera C. DC. [1], volatile oil of Pilea aquarum [2], extract of wild mushroom Fomes fomentarius (L.) Fr., Polyporaceae and flowers of Rhanterium adpressum [3,4] etc. The previous study of TCM components conducted by this research group, identified that corylifolinin was effective against the Gram-positive bacteria form Psoralen corylifolia L (P. corylifolia) [5].

P. corylifolia L., one member of the leguminous family, is widely distributed in Henan, Sichuan and Shanxi Provinces in China [6]. Coumarins, flavonoids, monoterpene phenols, coumarones, and steroids were found as the main compounds in P. corylifolia L [7]. Pharmacological investigations revealed that they exhibited anti-inflammatory, anti-hyperglycemic, anti-depressant, anti-microbial, anti-tumor, and anti-dermatophytic effects [8]. The research group isolated Corylifolinin, one of the 12 compounds from the P. corylifolia L. It showed a side chain of isopentenyl with anti-microbial activity [9]. It induced apoptosis in chronic leukemia noted in a previous report [10], and possessed strong anti-bacterial activity against Gram-positive bacteria [5]. Thus, it may be potentially used in common antibiotics. However, there is no report about an antibacterial mechanism of corylifolinin which may warrant further study corylifolinin and explore it as a commonly antibiotics. Therefore, in the present study, we investigated the antibacterial activities and mechanism underlying the effective antibacterial activities of corylifolinin.

2 Materials and Methods

2.1 Clinically isolated strains and chemical reagents

P. corylifolia Linn. was purchased from Le Ren Tang (Kaifeng, Henan, China) and identified by Professor Chang-qin Li of the Institute of Chinese Materia Medica, at Henan University, Kaifeng, Henan, China. The samples were as left at the Institute of Traditional Chinese Medicine, Henan University.

Gram-positive bacteria Staphylococcus aureus, methcillin-resistant Staphylococcus aureus, extended spectrum β-lactamases Staphylococcus aureus were isolated from Huaihe Hospital of Henan University (Zhengzhou, Henan, China). The AKP kit and protein assay kit were purchased from the Institute of Biotechnology (Nanjing Jiancheng, Jiangsu, China). The protein sample buffer 4x,N,N,N’,N’-Tetramethylethylenediamine, Coomassie brilliant blue G-250 and glycine were purchased from SERVA. Other chemicals used in the study were of analytical grade.

2.2 Isolation of corylifolinin

The powdered P. corylifolia (1.5 kg) was extracted with petroleum ether three times for nine days at room temperature, then extracted with 70% aqueous ethanol at 50°C three times for nine hours. The extract was concentrated on a rotary evaporator to gain 150 g, which was subjected to D101 column and eluted successively with 20%, 40%, 60% and 90% aqueous ethanol. Four (4) fractions were obtained. Sixteen grams of a 60% fraction were subjected to a silica gel column by gradient petroleum ether-ethyl acetate (30:1~2:1). Subfractions were subjected to Sephadex LH-20 and eluted with methanol to obtain corylifolinin.

C20H20O4, EI-MS: m/z 325(M+1)+, 1H-NMR(CDCl3): δ 1.78 (3H, s, CH3), δ 1.82 (3H, s, CH3), δ 3.5 (2H, d, CH2), δ 5.3 (1H, t, CH), δ 6.4(1H, d, J=9, 5′-H), δ7.7 (1H, d, J=8.8, 6′-H), δ 7.4 (1H, d, J=15.46, α-H), δ7.8 (1H, d, J=15.46, β-H), δ 6.9(2H, d, J=9.11, 3,5-H), δ7.6 (2H, d, J=9.11, 2,6-H) [5].

2.3 Preparation of bacterial suspension and assays of antimicrobial activity

2.3.1 Preparation of bacterial suspension

Three kinds of strains (SA, MRSA and ESBLs-SA) were expanded culture in petri dishes at 37°C. To obtain strains on logarithmic growth phase, two colonies were picked up from each strain, inoculated into a 100 mL of sterile broth and cultured at 37°C with shaking at 120 r/min. Finally, the concentration of bacteria was diluted with fresh broth to 1×107 CFU/mL [11].

2.3.2 Antibacterial Assay with Disk diffusion method (K-B method)

The Disk diffusion method (K-B method) [12] was used to determine the antimicrobial activity of the corylifolinin. A sterile petri plate (180 mm) was prepared with 45 mL of nutrient broth medium, 200 μL of bacterial suspension (1×107 cfu/ml) spread onto the plates after solidifying and repeated twice. Sterile filter paper (6 mm) containing 20 μg of corylifolinin was placed in the sterile agar plates after five minutes. DMSO was used as a control. Afterwards, the plates were incubated at 37°C for 24 hours. The antibacterial activity of corylifolinin was expressed by measuring the diameter of the inhibition zone (IZ). Values were described as the mean ± SD of assays performed three times.

2.3.3 Determination of minimum inhibitory concentration (MIC) and minimum bactericide concentration (MBC)

MIC was defined as the lowest concentration of corylifolinin at which, there was no visible bacterial growth. MBC was defined as the lowest concentration of corylifolinin at which initial inoculum bacteria were killed.

MIC was determined by the Disk diffusion method (K-B method) according to the previously described method [13]. MBC was determined by the liquid culture method and plate count method [14]. First, the bacterial suspension (90 μL)/well was seeded into 96-well plates. Different concentrations of corylifolinin (MIC, 2×MIC, 3×MIC, 4×MIC, 5×MIC were added to a 96 wells, respectively, and mixed well. The plate was incubated at 37°C for 10 hours. Ten (10) μL of samples from each well were withdrawn and dropped into the agar and incubated at 37°C for 24 hours. The minimum concentration at which there were no more than five bacterial colonies was defined as MBC. Each test was performed three times.

2.3.4 Determination of half (50%) inhibitory concentration (IC50)

Ninety (90) μL of bacterial suspension was mixed with 10 μL of different concentrations of the residual liquid. Each mixture was added to each well with a solvent control, a blank control and a negative control. Each test was performed three times. The 96-well culture plate was incubated at 37°C for 24 hours. The absorbance at 595 nm (OD595) was measured. All operations were performed under sterile conditions. The inhibition rate (%) was calculated according to the formula [15](1-1) as follows:

Inhibitionrate(%)=(solventcontrolwellsOD−supernatantOD)−(liquidOD−supernatantOD)negativecontrolOD−supernatantOD×100%(1-1)

2.4 Elucidation of antibacterial mechanism

2.4.1 Scanning electron microscopy (SEM) analysis

The SA and MRSA ESBLs-SA (approximately 1×107 cfu/ ml) were incubated with different concentrations of corylifolinin (control, MIC and MBC) at 37°C for 2, 6 hours, respectively. The suspensions were centrifuged at 6500 rpm for ten minutes, and the pellet was washed twice with a 0.1 M phosphate buffer solution (PBS). The bacterial cells were fixed with 2.5%v/v glutaraldehyde in 0.1 M PBS for 24 h at 4°C. The samples were dehydrated by sequential graded ethanol, which was replaced by 100% tertiary butyl alcohol.Finally, all the samples were sputter-coated with gold fixed on the freeze dryer for two minutes, followed by examining the ultra-structural changes of bacteria by the scanning electron microscope [16].

2.4.2 AKP assay

Different concentrations of corylifolinin (MIC, MBC, 2×MBC and 3×MIC) were added to the bacterial suspension. Sterile distilled water was placed into the control group. The above culture media were placed in a shaker at 37°C, 120 rpm according to instructions provided in the AKP kit. The supernatant was transferred to 96-well plates and mixed with a microplate reader. OD595 of each well was measured after being incubated for 0, 0.5, 1, 2, 3, 4, 5, 6, 7, 8 and 9 hours, respectively. Samples were measured three times. APK contents were calculated according to the formulas (1-2) [17].

APK=sampleOD−controlODstandardOD−controlOD×concentrationofPhenol×100mL×dilutionratioofsample(1-2)

2.4.3 Extracellular soluble protein assay

The integrity of cell membrane was evaluated by measuring the release of cell components, including nucleic acids and proteins, into cell suspension [18].

A sample was prepared the same way as the AKP assay. The untreated cell culture was fixed with 3.5%v/v propanediol and used as a control. All the samples were incubated at 37° for 0, 0.5, 1, 2, 3, 4, 5, 6, 7, 8 and 9 hours, respectively. Absorbance value at 595 nm was measured after samples were mixed and kept in the dark for 10 minutes. Each test was performed three times. The concentration of bacterial extracellular proteins was calculated according to formulas (1-3) [18] as follows:

proteinconcentration(g/L)=measuringtubeOD−blanktubeODstandardpipeOD−blanktubeOD×concentrationofstandardpipe(0.563 g/L)(1-3)

2.5 Statistical analysis

All the experiments were performed three times. SPSS 20 and GraphPad Prism 5 were used for data analysis. Difference between groups with P <0.05 was regarded as statistically significant.

3 Results and discussion

3.1 Antibacterial activity

As shown in Table 1, corylifolinin exhibited relatively strong antibacterial activity against SA, MRSA and ESBLs-SA with the IZ values of 15.1, 13.1 and 12.0 mm at the concentration of 2.5 mg/mL. The MIC for SA was 0.078 mg/mL; the MBC was 0.156 mg/mL. Both the MIC and MBC for MRSA were 0.156 mg/mL. Both MIC and MBC of corylifolinin against ESBLs-SA were the lowest ones among the three kinds of Staphylococcus aureus. In general, bactericidal activity was defined with the rate of MBC/ MIC less than 4 [19]. And the results showed that the rate of MBC/ MIC of SA, MRSA, ESBLs-SA were 2, 1, 1, respectively.

Table 1

IZ, IC50, MIC and MBC of corylifolinin against the tested bacteria.

Gram-positive bacteriaIZ (mm)[a]IC50 (mg/mL)[b]MIC (mg/mL)[c]MBC (mg/mL)[d]
SA15.1±0.20.031±0.0050.0780.156
MRSA13.1±0.20.107±0.0060.1560.156
ESBLs-SA12.0±0.30.048±0.0010.0780.078

All of above showed that corylifolinin had a relatively strong antibacterial activity against three clinically isolated bacterial strains.

3.2 Changes in the ultrastructure of bacterial strains revealed by Scanning electron microscope (SEM) analysis

The SEM has high magnification, more depth of field and strong stereoscopic perception. The changes in ultrastructure could be observed under SEM. Thus the changes in bacterial ultrastructure after being treated with corylifolinin could be observed clearly and directly by SEM. In Figure 2 (a, c and e), the surface of the bacteria untreated with corylifolinin was smooth and compact. Changes were observed in bacterial morphs and in the intracellular protein leakage to the extracellular when three strains (SA, MRSA and ESBLs-SA) treated with corylifolinin at MBC level for 6 h in Figure 2 (b, d, f).

Figure 1 corylifolinin.
Figure 1

corylifolinin.

Figure 2 The inhibition zone of corylifolinin. (‘’75’’ represents Methcillin-resistant S. Aureus; BL represents Extended spectrum β-Lactamase producing S.aureus;)
Figure 2

The inhibition zone of corylifolinin. (‘’75’’ represents Methcillin-resistant S. Aureus; BL represents Extended spectrum β-Lactamase producing S.aureus;)

The above results showed that the levels of MBC were significantly different in the morphology and protein leakage of the bacteria, indicating that corylifolinin could affect the bacterial morphology as the cellular membrane of bacteria was destroyed and the substance in the cell were leaked.

3.3 Leakage of AKP caused by corylifolinin treatment

AKP mainly exists between the cell wall and cell membrane of the bacteria. AKP will be leaked into the extracellular due to the increasing permeability of the bacterial cell wall. The results of AKP leakage assay can indirectly reflect the integrity of the bacterial cell wall [20,21].

In Figure 3 (A1, B1, and C1), the leakage of AKP in corylifolinin-treated groups at the MIC level was significantly higher than that of the control group. The leakage of AKP was correlated with the corylifolinin concentration. The higher the concentration, the higher the AKP content was detected. In the Figure 3 (A1, B1 and C1), the AKP leakage level was higher than that of the blank control for 3 hours with the MIC level. The results showed that the cell wall’s permeability of three strains could be increased by corylifolinin in a short period of time.

Figure 3 Results of SEM assay. a : SEM of SA; b: SEM of SA treated with corylifolinin at MBC level; c : SEM of MRSA; d:MRSA treated with corylifolinin at MBC level; e : SEM of ESBLs-SA; and d: ESBLs-SA treated with corylifolinin at MBC level.
Figure 3

Results of SEM assay. a : SEM of SA; b: SEM of SA treated with corylifolinin at MBC level; c : SEM of MRSA; d:MRSA treated with corylifolinin at MBC level; e : SEM of ESBLs-SA; and d: ESBLs-SA treated with corylifolinin at MBC level.

In Figure 3 (A2, B2 and C2), when being treated with corylifolinin at the level of MBC, SA exhibited a higher absorbance as compared with the control group from start to finish. For the other two kinds of Staphylococcus aureus, a higher absorbance was detected before a three-hours lapsed.

In general, the results indicated that the cell wall of SA, MRSA and ESBLs-SA could be damaged by corylifolinin at the levels of MIC and MBC.

3.4 Leakage of extracellular protein caused by corylifolinin

Protein plays an important role in the life activity of bacterial cells because the accurate expression of bacterial protein is related to the bacterial growth. The increased permeability of the bacterial cell membrane may result in the leakage of intracellular protein into the extracellular protein. The effects of the Diyu tannin extract on the S. aureus protein leakage was determined by Liu et al. [22], and the results showed that the leakage of the extracellular soluble protein was positively related to the concentrations of the Diyu tannin extract. By detecting the changes of the extracellular protein leakage, the results indirectly reflected the permeability of the bacterial cell membrane.

In Figure 4 (A1, B1 and C1), the treatment with corylifolinin at the MIC level could enhance the leakage of proteins of SA, MRSA and ESBLs-SA. But in time, the amount of the extracellular protein was decreased gradually, which, may be based on the effective decrease in the concentration of corylifolinin and the extracellular protein consumed by the growing bacteria.

The leakage of protein at the level of MBC was shown in Figure 4 (A2, B2 and C2). After three kinds of S. aureus were treated at the MBC level and 2×MBC level of corylifolinin, the leakage soluble protein was higher than that of the control group, especially in 3 hours. Then, the soluble protein was slowly reduced. The results suggested that the sterilization effect gradually reduced given a time extension.

Figure 4 Effects of corylifolinin on leakage of AKP of SA (A), MRSA (B) and ESBLs-SA (C). The activity of AKP extra cellular at the level of MIC (A1, B1, C1); The activity of AKP extcellular at the level of MBC (A2, B2, C2).
Figure 4

Effects of corylifolinin on leakage of AKP of SA (A), MRSA (B) and ESBLs-SA (C). The activity of AKP extra cellular at the level of MIC (A1, B1, C1); The activity of AKP extcellular at the level of MBC (A2, B2, C2).

Figure 5 The leakage of extracellular soluble protein from three bacteria which were treated with different concentrations of corylifolinin. A: SA; B: MRSA; C: ESBLs-SA.; Image A1, B1, C1: The leakage of extracellular soluble protein from three bacteria at MIC.; ImageA2, B2, C2: The leakage of extracellular soluble protein from three bacteria at MBC.
Figure 5

The leakage of extracellular soluble protein from three bacteria which were treated with different concentrations of corylifolinin. A: SA; B: MRSA; C: ESBLs-SA.; Image A1, B1, C1: The leakage of extracellular soluble protein from three bacteria at MIC.; ImageA2, B2, C2: The leakage of extracellular soluble protein from three bacteria at MBC.

As a whole, the leakage of protein indicated that corylifolinin hadcertain effects on the cell membrane of Staphylococcus aureus, methcillin-resistant Staphylococcus aureus and extended spectrum β-lactamases Staphylococcus aureus. There were positive correlations between the leakage of proteins and the concentration of corylifolinin.

4 Conclusions

In general, the antimicrobial activity of corylifolinin against SA, ESBLs-SA at MIC level was stronger than that of MRSA. Results revealed that the MBC of MRSA and ESBLs-SA were equal to their MIC. In addition, the changes of bacterial morphology were observed by SEM, and antibacterial mechanism of corylifolinin were studied by measuring AKP and the extracellular soluble protein content. The mechanism of antibacterial effects mainly included (1) to destroy the cell membrane and bacterial cell wall to affect permeability of bacterial membrane; (2) effect on synthesis of protein and nucleotide; and (3) inhibition of enzymatic activity of bacteria [23]. We primarily explored the mechanism of corylifolinin on antibacteria by studying the effect of corylifolinin on cell wall and cell membrane. Results showed that there was a positive correlation between the changes in bacterial morphology and the concentration of corylifolinin used to treat bacteria. Striking changes in the content of alkaline phosphatase, extracellular soluble protein took place. All of those results indicated that corylifolinin possessed strong antibacterial effect by bacteriolysis. Further studies on the effect of corylifolinin on DNA, RNA and enzymes of bacteria are needed for further study.

Acknowledgements

This work was supported by Henan Province University Science and Technology Innovation Team (16IRTSTHN019), Kaifeng City Science and Technology Innovation Talent (1509010), National Cooperation Project of Henan Province (2015GH12).

  1. Ethics: We declare that the ethical background to this study was approved by National Ethical Committee.

  2. Conflict of Interest: The authors declared no potential conflicts interest with respect to the research, authorship, and publication of this article.

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Received: 2017-12-25
Accepted: 2018-05-31
Published Online: 2018-09-03

© 2018 Nan He et al., published by De Gruyter

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

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  45. Epithelial–Mesenchymal Transition Induced by SMAD4 Activation in Invasive Growth Hormone-Secreting Adenomas
  46. Physicochemical properties of stabilized sewage sludge admixtures by modified steel slag
  47. In Vitro Cytotoxic and Antiproliferative Activity of Cydonia oblonga flower petals, leaf and fruit pellet ethanolic extracts. Docking simulation of the active flavonoids on anti-apoptotic protein Bcl-2
  48. Synthesis and Characterization of Pd exchanged MMT Clay for Mizoroki-Heck Reaction
  49. A new selective, and sensitive method for the determination of lixivaptan, a vasopressin 2 (V2)-receptor antagonist, in mouse plasma and its application in a pharmacokinetic study
  50. Anti-EGFL7 antibodies inhibit rat prolactinoma MMQ cells proliferation and PRL secretion
  51. Density functional theory calculations, vibration spectral analysis and molecular docking of the antimicrobial agent 6-(1,3-benzodioxol-5-ylmethyl)-5-ethyl-2-{[2-(morpholin-4-yl)ethyl] sulfanyl}pyrimidin-4(3H)-one
  52. Effect of Nano Zeolite on the Transformation of Cadmium Speciation and Its Uptake by Tobacco in Cadmium-contaminated Soil
  53. Effects and Mechanisms of Jinniu Capsule on Methamphetamine-Induced Conditioned Place Preference in Rats
  54. Calculating the Degree-based Topological Indices of Dendrimers
  55. Efficient optimization and mineralization of UV absorbers: A comparative investigation with Fenton and UV/H2O2
  56. Metabolites of Tryptophane and Phenylalanine as Markers of Small Bowel Ischemia-Reperfusion Injury
  57. Adsorption and determination of polycyclic aromatic hydrocarbons in water through the aggregation of graphene oxide
  58. The role of NR2C2 in the prolactinomas
  59. Chromium removal from industrial wastewater using Phyllostachys pubescens biomass loaded Cu-S nanospheres
  60. Hydrotalcite Anchored Ruthenium Catalyst for CO2 Hydrogenation Reaction
  61. Preparation of Calcium Fluoride using Phosphogypsum by Orthogonal Experiment
  62. The mechanism of antibacterial activity of corylifolinin against three clinical bacteria from Psoralen corylifolia L
  63. 2-formyl-3,6-bis(hydroxymethyl)phenyl benzoate in Electrochemical Dry Cell
  64. Electro-photocatalytic degradation of amoxicillin using calcium titanate
  65. Effect of Malus halliana Koehne Polysaccharides on Functional Constipation
  66. Structural Properties and Nonlinear Optical Responses of Halogenated Compounds: A DFT Investigation on Molecular Modelling
  67. DMFDMA catalyzed synthesis of 2-((Dimethylamino)methylene)-3,4-dihydro-9-arylacridin-1(2H)-ones and their derivatives: in-vitro antifungal, antibacterial and antioxidant evaluations
  68. Production of Methanol as a Fuel Energy from CO2 Present in Polluted Seawater - A Photocatalytic Outlook
  69. Study of different extraction methods on finger print and fatty acid of raw beef fat using fourier transform infrared and gas chromatography-mass spectrometry
  70. Determination of trace fluoroquinolones in water solutions and in medicinal preparations by conventional and synchronous fluorescence spectrometry
  71. Extraction and determination of flavonoids in Carthamus tinctorius
  72. Therapeutic Application of Zinc and Vanadium Complexes against Diabetes Mellitus a Coronary Disease: A review
  73. Study of calcined eggshell as potential catalyst for biodiesel formation using used cooking oil
  74. Manganese oxalates - structure-based Insights
  75. Topological Indices of H-Naphtalenic Nanosheet
  76. Long-Term Dissolution of Glass Fibers in Water Described by Dissolving Cylinder Zero-Order Kinetic Model: Mass Loss and Radius Reduction
  77. Topological study of the para-line graphs of certain pentacene via topological indices
  78. A brief insight into the prediction of water vapor transmissibility in highly impermeable hybrid nanocomposites based on bromobutyl/epichlorohydrin rubber blends
  79. Comparative sulfite assay by voltammetry using Pt electrodes, photometry and titrimetry: Application to cider, vinegar and sugar analysis
  80. MicroRNA delivery mediated by PEGylated polyethylenimine for prostate cancer therapy
  81. Reversible Fluorescent Turn-on Sensors for Fe3+ based on a Receptor Composed of Tri-oxygen Atoms of Amide Groups in Water
  82. Sonocatalytic degradation of methyl orange in aqueous solution using Fe-doped TiO2 nanoparticles under mechanical agitation
  83. Hydrotalcite Anchored Ruthenium Catalyst for CO2 Hydrogenation Reaction
  84. Production and Analysis of Recycled Ammonium Perrhenate from CMSX-4 superalloys
  85. Topical Issue on Agriculture
  86. New phosphorus biofertilizers from renewable raw materials in the aspect of cadmium and lead contents in soil and plants
  87. Survey of content of cadmium, calcium, chromium, copper, iron, lead, magnesium, manganese, mercury, sodium and zinc in chamomile and green tea leaves by electrothermal or flame atomizer atomic absorption spectrometry
  88. Biogas digestate – benefits and risks for soil fertility and crop quality – an evaluation of grain maize response
  89. A numerical analysis of heat transfer in a cross-current heat exchanger with controlled and newly designed air flows
  90. Freshwater green macroalgae as a biosorbent of Cr(III) ions
  91. The main influencing factors of soil mechanical characteristics of the gravity erosion environment in the dry-hot valley of Jinsha river
  92. Free amino acids in Viola tricolor in relation to different habitat conditions
  93. The influence of filler amount on selected properties of new experimental resin dental composite
  94. Effect of poultry wastewater irrigation on nitrogen, phosphorus and carbon contents in farmland soil
  95. Response of spring wheat to NPK and S fertilization. The content and uptake of macronutrients and the value of ionic ratios
  96. The Effect of Macroalgal Extracts and Near Infrared Radiation on Germination of Soybean Seedlings: Preliminary Research Results
  97. Content of Zn, Cd and Pb in purple moor-grass in soils heavily contaminated with heavy metals around a zinc and lead ore tailing landfill
  98. Topical Issue on Research for Natural Bioactive Products
  99. Synthesis of (±)-3,4-dimethoxybenzyl-4-methyloctanoate as a novel internal standard for capsinoid determination by HPLC-ESI-MS/MS(QTOF)
  100. Repellent activity of monoterpenoid esters with neurotransmitter amino acids against yellow fever mosquito, Aedes aegypti
  101. Effect of Flammulina velutipes (golden needle mushroom, eno-kitake) polysaccharides on constipation
  102. Bioassay-directed fractionation of a blood coagulation factor Xa inhibitor, betulinic acid from Lycopus lucidus
  103. Antifungal and repellent activities of the essential oils from three aromatic herbs from western Himalaya
  104. Chemical composition and microbiological evaluation of essential oil from Hyssopus officinalis L. with white and pink flowers
  105. Bioassay-guided isolation and identification of Aedes aegypti larvicidal and biting deterrent compounds from Veratrum lobelianum
  106. α-Terpineol, a natural monoterpene: A review of its biological properties
  107. Utility of essential oils for development of host-based lures for Xyleborus glabratus (Coleoptera: Curculionidae: Scolytinae), vector of laurel wilt
  108. Phenolic composition and antioxidant potential of different organs of Kazakh Crataegus almaatensis Pojark: A comparison with the European Crataegus oxyacantha L. flowers
  109. Isolation of eudesmane type sesquiterpene ketone from Prangos heyniae H.Duman & M.F.Watson essential oil and mosquitocidal activity of the essential oils
  110. Comparative analysis of the polyphenols profiles and the antioxidant and cytotoxicity properties of various blue honeysuckle varieties
  111. Special Issue on ICCESEN 2017
  112. Modelling world energy security data from multinomial distribution by generalized linear model under different cumulative link functions
  113. Pine Cone and Boron Compounds Effect as Reinforcement on Mechanical and Flammability Properties of Polyester Composites
  114. Artificial Neural Network Modelling for Prediction of SNR Effected by Probe Properties on Ultrasonic Inspection of Austenitic Stainless Steel Weldments
  115. Calculation and 3D analyses of ERR in the band crack front contained in a rectangular plate made of multilayered material
  116. Improvement of fuel properties of biodiesel with bioadditive ethyl levulinate
  117. Properties of AlSi9Cu3 metal matrix micro and nano composites produced via stir casting
  118. Investigation of Antibacterial Properties of Ag Doped TiO2 Nanofibers Prepared by Electrospinning Process
  119. Modeling of Total Phenolic contents in Various Tea samples by Experimental Design Methods
  120. Nickel doping effect on the structural and optical properties of indium sulfide thin films by SILAR
  121. The effect mechanism of Ginnalin A as a homeopathic agent on various cancer cell lines
  122. Excitation functions of proton induced reactions of some radioisotopes used in medicine
  123. Oxide ionic conductivity and microstructures of Pr and Sm co-doped CeO2-based systems
  124. Rapid Synthesis of Metallic Reinforced in Situ Intermetallic Composites in Ti-Al-Nb System via Resistive Sintering
  125. Oxidation Behavior of NiCr/YSZ Thermal Barrier Coatings (TBCs)
  126. Clustering Analysis of Normal Strength Concretes Produced with Different Aggregate Types
  127. Magnetic Nano-Sized Solid Acid Catalyst Bearing Sulfonic Acid Groups for Biodiesel Synthesis
  128. The biological activities of Arabis alpina L. subsp. brevifolia (DC.) Cullen against food pathogens
  129. Humidity properties of Schiff base polymers
  130. Free Vibration Analysis of Fiber Metal Laminated Straight Beam
  131. Comparative study of in vitro antioxidant, acetylcholinesterase and butyrylcholinesterase activity of alfalfa (Medicago sativa L.) collected during different growth stages
  132. Isothermal Oxidation Behavior of Gadolinium Zirconate (Gd2Zr2O7) Thermal Barrier Coatings (TBCs) produced by Electron Beam Physical Vapor Deposition (EB-PVD) technique
  133. Optimization of Adsorption Parameters for Ultra-Fine Calcite Using a Box-Behnken Experimental Design
  134. The Microstructural Investigation of Vermiculite-Infiltrated Electron Beam Physical Vapor Deposition Thermal Barrier Coatings
  135. Modelling Porosity Permeability of Ceramic Tiles using Fuzzy Taguchi Method
  136. Experimental and theoretical study of a novel naphthoquinone Schiff base
  137. Physicochemical properties of heat treated sille stone for ceramic industry
  138. Sand Dune Characterization for Preparing Metallurgical Grade Silicon
  139. Catalytic Applications of Large Pore Sulfonic Acid-Functionalized SBA-15 Mesoporous Silica for Esterification
  140. One-photon Absorption Characterizations, Dipole Polarizabilities and Second Hyperpolarizabilities of Chlorophyll a and Crocin
  141. The Optical and Crystallite Characterization of Bilayer TiO2 Films Coated on Different ITO layers
  142. Topical Issue on Bond Activation
  143. Metal-mediated reactions towards the synthesis of a novel deaminolysed bisurea, dicarbamolyamine
  144. The structure of ortho-(trifluoromethyl)phenol in comparison to its homologues – A combined experimental and theoretical study
  145. Heterogeneous catalysis with encapsulated haem and other synthetic porphyrins: Harnessing the power of porphyrins for oxidation reactions
  146. Recent Advances on Mechanistic Studies on C–H Activation Catalyzed by Base Metals
  147. Reactions of the organoplatinum complex [Pt(cod) (neoSi)Cl] (neoSi = trimethylsilylmethyl) with the non-coordinating anions SbF6– and BPh4–
  148. Erratum
  149. Investigation on Two Compounds of O, O’-dithiophosphate Derivatives as Corrosion Inhibitors for Q235 Steel in Hydrochloric Acid Solution
https://doi.org/10.1515/chem-2018-0091
Schlagwörter für diesen Artikel
Corylifolinin; Antibacterial mechanism; Scanning electron micsoscopy; Bacterial membrane and wall permeability
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Artikel in diesem Heft

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  44. Phytosynthetic Ag doped ZnO nanoparticles: Semiconducting green remediators
  45. Epithelial–Mesenchymal Transition Induced by SMAD4 Activation in Invasive Growth Hormone-Secreting Adenomas
  46. Physicochemical properties of stabilized sewage sludge admixtures by modified steel slag
  47. In Vitro Cytotoxic and Antiproliferative Activity of Cydonia oblonga flower petals, leaf and fruit pellet ethanolic extracts. Docking simulation of the active flavonoids on anti-apoptotic protein Bcl-2
  48. Synthesis and Characterization of Pd exchanged MMT Clay for Mizoroki-Heck Reaction
  49. A new selective, and sensitive method for the determination of lixivaptan, a vasopressin 2 (V2)-receptor antagonist, in mouse plasma and its application in a pharmacokinetic study
  50. Anti-EGFL7 antibodies inhibit rat prolactinoma MMQ cells proliferation and PRL secretion
  51. Density functional theory calculations, vibration spectral analysis and molecular docking of the antimicrobial agent 6-(1,3-benzodioxol-5-ylmethyl)-5-ethyl-2-{[2-(morpholin-4-yl)ethyl] sulfanyl}pyrimidin-4(3H)-one
  52. Effect of Nano Zeolite on the Transformation of Cadmium Speciation and Its Uptake by Tobacco in Cadmium-contaminated Soil
  53. Effects and Mechanisms of Jinniu Capsule on Methamphetamine-Induced Conditioned Place Preference in Rats
  54. Calculating the Degree-based Topological Indices of Dendrimers
  55. Efficient optimization and mineralization of UV absorbers: A comparative investigation with Fenton and UV/H2O2
  56. Metabolites of Tryptophane and Phenylalanine as Markers of Small Bowel Ischemia-Reperfusion Injury
  57. Adsorption and determination of polycyclic aromatic hydrocarbons in water through the aggregation of graphene oxide
  58. The role of NR2C2 in the prolactinomas
  59. Chromium removal from industrial wastewater using Phyllostachys pubescens biomass loaded Cu-S nanospheres
  60. Hydrotalcite Anchored Ruthenium Catalyst for CO2 Hydrogenation Reaction
  61. Preparation of Calcium Fluoride using Phosphogypsum by Orthogonal Experiment
  62. The mechanism of antibacterial activity of corylifolinin against three clinical bacteria from Psoralen corylifolia L
  63. 2-formyl-3,6-bis(hydroxymethyl)phenyl benzoate in Electrochemical Dry Cell
  64. Electro-photocatalytic degradation of amoxicillin using calcium titanate
  65. Effect of Malus halliana Koehne Polysaccharides on Functional Constipation
  66. Structural Properties and Nonlinear Optical Responses of Halogenated Compounds: A DFT Investigation on Molecular Modelling
  67. DMFDMA catalyzed synthesis of 2-((Dimethylamino)methylene)-3,4-dihydro-9-arylacridin-1(2H)-ones and their derivatives: in-vitro antifungal, antibacterial and antioxidant evaluations
  68. Production of Methanol as a Fuel Energy from CO2 Present in Polluted Seawater - A Photocatalytic Outlook
  69. Study of different extraction methods on finger print and fatty acid of raw beef fat using fourier transform infrared and gas chromatography-mass spectrometry
  70. Determination of trace fluoroquinolones in water solutions and in medicinal preparations by conventional and synchronous fluorescence spectrometry
  71. Extraction and determination of flavonoids in Carthamus tinctorius
  72. Therapeutic Application of Zinc and Vanadium Complexes against Diabetes Mellitus a Coronary Disease: A review
  73. Study of calcined eggshell as potential catalyst for biodiesel formation using used cooking oil
  74. Manganese oxalates - structure-based Insights
  75. Topological Indices of H-Naphtalenic Nanosheet
  76. Long-Term Dissolution of Glass Fibers in Water Described by Dissolving Cylinder Zero-Order Kinetic Model: Mass Loss and Radius Reduction
  77. Topological study of the para-line graphs of certain pentacene via topological indices
  78. A brief insight into the prediction of water vapor transmissibility in highly impermeable hybrid nanocomposites based on bromobutyl/epichlorohydrin rubber blends
  79. Comparative sulfite assay by voltammetry using Pt electrodes, photometry and titrimetry: Application to cider, vinegar and sugar analysis
  80. MicroRNA delivery mediated by PEGylated polyethylenimine for prostate cancer therapy
  81. Reversible Fluorescent Turn-on Sensors for Fe3+ based on a Receptor Composed of Tri-oxygen Atoms of Amide Groups in Water
  82. Sonocatalytic degradation of methyl orange in aqueous solution using Fe-doped TiO2 nanoparticles under mechanical agitation
  83. Hydrotalcite Anchored Ruthenium Catalyst for CO2 Hydrogenation Reaction
  84. Production and Analysis of Recycled Ammonium Perrhenate from CMSX-4 superalloys
  85. Topical Issue on Agriculture
  86. New phosphorus biofertilizers from renewable raw materials in the aspect of cadmium and lead contents in soil and plants
  87. Survey of content of cadmium, calcium, chromium, copper, iron, lead, magnesium, manganese, mercury, sodium and zinc in chamomile and green tea leaves by electrothermal or flame atomizer atomic absorption spectrometry
  88. Biogas digestate – benefits and risks for soil fertility and crop quality – an evaluation of grain maize response
  89. A numerical analysis of heat transfer in a cross-current heat exchanger with controlled and newly designed air flows
  90. Freshwater green macroalgae as a biosorbent of Cr(III) ions
  91. The main influencing factors of soil mechanical characteristics of the gravity erosion environment in the dry-hot valley of Jinsha river
  92. Free amino acids in Viola tricolor in relation to different habitat conditions
  93. The influence of filler amount on selected properties of new experimental resin dental composite
  94. Effect of poultry wastewater irrigation on nitrogen, phosphorus and carbon contents in farmland soil
  95. Response of spring wheat to NPK and S fertilization. The content and uptake of macronutrients and the value of ionic ratios
  96. The Effect of Macroalgal Extracts and Near Infrared Radiation on Germination of Soybean Seedlings: Preliminary Research Results
  97. Content of Zn, Cd and Pb in purple moor-grass in soils heavily contaminated with heavy metals around a zinc and lead ore tailing landfill
  98. Topical Issue on Research for Natural Bioactive Products
  99. Synthesis of (±)-3,4-dimethoxybenzyl-4-methyloctanoate as a novel internal standard for capsinoid determination by HPLC-ESI-MS/MS(QTOF)
  100. Repellent activity of monoterpenoid esters with neurotransmitter amino acids against yellow fever mosquito, Aedes aegypti
  101. Effect of Flammulina velutipes (golden needle mushroom, eno-kitake) polysaccharides on constipation
  102. Bioassay-directed fractionation of a blood coagulation factor Xa inhibitor, betulinic acid from Lycopus lucidus
  103. Antifungal and repellent activities of the essential oils from three aromatic herbs from western Himalaya
  104. Chemical composition and microbiological evaluation of essential oil from Hyssopus officinalis L. with white and pink flowers
  105. Bioassay-guided isolation and identification of Aedes aegypti larvicidal and biting deterrent compounds from Veratrum lobelianum
  106. α-Terpineol, a natural monoterpene: A review of its biological properties
  107. Utility of essential oils for development of host-based lures for Xyleborus glabratus (Coleoptera: Curculionidae: Scolytinae), vector of laurel wilt
  108. Phenolic composition and antioxidant potential of different organs of Kazakh Crataegus almaatensis Pojark: A comparison with the European Crataegus oxyacantha L. flowers
  109. Isolation of eudesmane type sesquiterpene ketone from Prangos heyniae H.Duman & M.F.Watson essential oil and mosquitocidal activity of the essential oils
  110. Comparative analysis of the polyphenols profiles and the antioxidant and cytotoxicity properties of various blue honeysuckle varieties
  111. Special Issue on ICCESEN 2017
  112. Modelling world energy security data from multinomial distribution by generalized linear model under different cumulative link functions
  113. Pine Cone and Boron Compounds Effect as Reinforcement on Mechanical and Flammability Properties of Polyester Composites
  114. Artificial Neural Network Modelling for Prediction of SNR Effected by Probe Properties on Ultrasonic Inspection of Austenitic Stainless Steel Weldments
  115. Calculation and 3D analyses of ERR in the band crack front contained in a rectangular plate made of multilayered material
  116. Improvement of fuel properties of biodiesel with bioadditive ethyl levulinate
  117. Properties of AlSi9Cu3 metal matrix micro and nano composites produced via stir casting
  118. Investigation of Antibacterial Properties of Ag Doped TiO2 Nanofibers Prepared by Electrospinning Process
  119. Modeling of Total Phenolic contents in Various Tea samples by Experimental Design Methods
  120. Nickel doping effect on the structural and optical properties of indium sulfide thin films by SILAR
  121. The effect mechanism of Ginnalin A as a homeopathic agent on various cancer cell lines
  122. Excitation functions of proton induced reactions of some radioisotopes used in medicine
  123. Oxide ionic conductivity and microstructures of Pr and Sm co-doped CeO2-based systems
  124. Rapid Synthesis of Metallic Reinforced in Situ Intermetallic Composites in Ti-Al-Nb System via Resistive Sintering
  125. Oxidation Behavior of NiCr/YSZ Thermal Barrier Coatings (TBCs)
  126. Clustering Analysis of Normal Strength Concretes Produced with Different Aggregate Types
  127. Magnetic Nano-Sized Solid Acid Catalyst Bearing Sulfonic Acid Groups for Biodiesel Synthesis
  128. The biological activities of Arabis alpina L. subsp. brevifolia (DC.) Cullen against food pathogens
  129. Humidity properties of Schiff base polymers
  130. Free Vibration Analysis of Fiber Metal Laminated Straight Beam
  131. Comparative study of in vitro antioxidant, acetylcholinesterase and butyrylcholinesterase activity of alfalfa (Medicago sativa L.) collected during different growth stages
  132. Isothermal Oxidation Behavior of Gadolinium Zirconate (Gd2Zr2O7) Thermal Barrier Coatings (TBCs) produced by Electron Beam Physical Vapor Deposition (EB-PVD) technique
  133. Optimization of Adsorption Parameters for Ultra-Fine Calcite Using a Box-Behnken Experimental Design
  134. The Microstructural Investigation of Vermiculite-Infiltrated Electron Beam Physical Vapor Deposition Thermal Barrier Coatings
  135. Modelling Porosity Permeability of Ceramic Tiles using Fuzzy Taguchi Method
  136. Experimental and theoretical study of a novel naphthoquinone Schiff base
  137. Physicochemical properties of heat treated sille stone for ceramic industry
  138. Sand Dune Characterization for Preparing Metallurgical Grade Silicon
  139. Catalytic Applications of Large Pore Sulfonic Acid-Functionalized SBA-15 Mesoporous Silica for Esterification
  140. One-photon Absorption Characterizations, Dipole Polarizabilities and Second Hyperpolarizabilities of Chlorophyll a and Crocin
  141. The Optical and Crystallite Characterization of Bilayer TiO2 Films Coated on Different ITO layers
  142. Topical Issue on Bond Activation
  143. Metal-mediated reactions towards the synthesis of a novel deaminolysed bisurea, dicarbamolyamine
  144. The structure of ortho-(trifluoromethyl)phenol in comparison to its homologues – A combined experimental and theoretical study
  145. Heterogeneous catalysis with encapsulated haem and other synthetic porphyrins: Harnessing the power of porphyrins for oxidation reactions
  146. Recent Advances on Mechanistic Studies on C–H Activation Catalyzed by Base Metals
  147. Reactions of the organoplatinum complex [Pt(cod) (neoSi)Cl] (neoSi = trimethylsilylmethyl) with the non-coordinating anions SbF6– and BPh4–
  148. Erratum
  149. Investigation on Two Compounds of O, O’-dithiophosphate Derivatives as Corrosion Inhibitors for Q235 Steel in Hydrochloric Acid Solution
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