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. 2020 Dec 9;5(50):32632–32640. doi: 10.1021/acsomega.0c05002

Green and Facile Synthesis and Antioxidant and Antibacterial Evaluation of Dietary Myricetin-Mediated Silver Nanoparticles

Zhao Li †, Wenya Ma †,‡, Iftikhar Ali †,§, Huanzhu Zhao †, Daijie Wang †,*, Jiying Qiu ∥,*
PMCID: PMC7758972  PMID: 33376900

Abstract

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Myricetin (MY) is a dietary flavonoid which exhibits a wide spectrum of biological properties, viz., antibacterial, antioxidant, anticancer, and so forth. The lower solubility in aqueous medium and hence lesser bioavailability of MY limits the use of such dietary flavonoids in further in vivo research. To overcome bioavailability limitations, a number of drug-delivery systems are being investigated. Herein, MY-mediated silver nanoparticles (MY-AgNPs) were synthesized by a green approach to improve the therapeutic efficacy of MY. MY-AgNPs were characterized by ultraviolet–visible spectroscopy (UV–Vis), scanning electron microscopy (SEM), transmission electron microscopy (TEM), Fourier transform infrared (FTIR) spectroscopy, and X-ray powder diffraction (XRD). The results showed that the dispersion of AgNPs had the maximum UV–vis absorption at about 410 nm. The synthesized nanoparticles were almost spherical. MY-AgNPs were further investigated against human pathogenic bacteria, and their antioxidant potential was also determined. The free radical scavenging rate was about 60–87%. MY-AgNPs had good antibacterial activity against Escherichia coli and Salmonella at room temperature with minimum inhibitory concentrations of 10–4 and 10–5 g/L, respectively.

1. Introduction

Recently, many natural products have shown promising antibiotic and antiviral properties,1,2 including the flavonoids,3 alkaloids,4 organic acids, volatile oil, polysaccharide, saponins, anthraquinones, terpenoids, and others. Among them, flavonoids are a kind of important natural organic compounds and secondary metabolites with extensive biological activities and pharmacological effects5 and antiviral properties.6

Myricetin (MY) or 3,3,4,5,5,7-hexahydroxy-flavone belongs to a class of natural dietary flavonoids that can be extracted from the bark and leaves of bayberry, beyond that, it is also widely found in vegetables, fruit, tea, and medicinal herbs.7 MY has a variety of biological functions including antibacterial,8 antiviral and antioxidant,9−11 anti-inflammatory and anticancer,12 inhibition of urease,13 and so forth. At present, MY has been widely used in medicine, food, healthcare products, cosmetics, and other fields.

Nanoparticles (NPs) have versatile uses in biological, medical, electrical, and chemical sciences.14 The size and shape are the main factors that determine the performance of NPs.15 Silver nanoparticles (AgNPs) possess at least one dimension ranging from 1 to 100 nm. AgNPs are a very versatile nanomaterial with antimicrobial properties.16 AgNPs are reported to possess antibacterial, antifungal, and antiinflammatory potential. AgNPs, in antibacterial activity, get attached to the cell membrane and are released in the bacterial cells, which make them possess good activity.17

Although there are many ways to synthesize nanoparticles, their green synthesis has been highlighted in recent years.18,19 Green synthesis uses a variety of reductants, including biomass, plant extracts,17,20 microorganisms,21 and many other sources.22 Among these methods, biomass especially flavonoids are reported for the reduction of Ag+ ions to AgNPs. Flavonoids possess important application values because of their wide sources and high synthetic efficiency.

The present study provides a new method for green synthesis of AgNPs, which uses MY to reduce silver ions into nanoparticles without adding any toxic chemicals. Compared with the traditional method, this method is easy-to-operate, cost-effective, and environmentally friendly, hence green. The antibacterial and antioxidant activities of MY-mediated AgNPs (MY-AgNPs) were studied. This study will contribute to the research and application of natural biomass in nanoscience and nanotechnology.

2. Results and Discussion

2.1. Visible Observation of AgNP Synthesis

AgNPs were synthesized using MY. In the mixing process, the Ag+ ions were reduced to AgNPs, which were observed through naked eyes by color change. As shown in Figure 1a–d, the change in color from yellow to purplish red was observed because of the mixing of Ag+ ions with MY. As the reaction went on, the solution changed from purplish red to yellowish green, and the formation of black nanoparticles was observed.

Figure 1.

Figure 1

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(a) MY. (b) MY after the addition of alkali. (c) MY initially mixed with silver nitrate. (d) MY reacted with silver nitrate for 3 h.

2.2. UV–Visible Spectroscopy Analysis

Figure 2a,b shows the effects of different molar ratios of MY and silver nitrate on AgNP synthesis. The molar ratios 2:1, 1:1, 2:3, 1:2, and 1:4 (MY/AgNO3) were studied. When the molar ratios were 2:1, 1:1, and 2:3, although the silver ion conversion rate was 99.93, 99.88, and 99.74%, respectively, the absorption peak was observed to be lower. This suggests that MY overdose affects the size of nanoparticles. In the case of more MY concentration, the silver ion transformation was relatively complete, but the excessive amount of MY affected the size of nanoparticles, making the peak deformation shorter and wider. When the molar ratio was 1:4, silver nitrate was not completely transformed and the silver ion conversion rate was only 71.18%. When the molar ratio was 1:2, the absorption peak was higher and the peak shape was narrower and more stable, so it was the optimal molar ratio. Under this condition, the silver ion conversion rate was 98.34%.

Figure 2.

Figure 2

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(a) UV–vis spectra of MY-mediated AgNPs at different AgNO3 concentrations. (b) Silver ion conversion rate of MY-mediated AgNPs at different AgNO3 concentrations. (c) UV–vis spectra of MY-mediated AgNPs at different pH values. (d) Silver ion conversion rate of MY-mediated AgNPs at different pH values. (e) UV–vis spectra of MY-mediated AgNPs at different temperatures. (f) Silver ion conversion rate of MY-mediated AgNPs at different temperatures.

Figure 2c,d shows the absorption spectra at different pH values. The acidic reaction mixture caused decrease in the reaction rate with the decrease in the pH value. The MY reduction was affected under strong acidic conditions. Therefore, the absorption peaks were relatively wider and the binding rate was lower. When the pH was 2 and 4, the silver ion conversion rate was only 62.73 and 71.53%, respectively. Under alkaline conditions, the absorption peaks of the solution became higher and narrower. However, at pH 11 and 12, although the peak shape was good, the silver ion conversion rate was very low, indicating that the strongly alkaline environment was not conducive for the AgNP formation. When the pH was 8, the peak shape was the best and the silver ion conversion rate was 96.44%, so it was the optimal pH for the reaction.

As shown in Figure 2e,f, the effect of different temperature ranges (40, 50, 60, and 70 °C) on AgNP synthesis was studied. The lower temperature was directly linked with the lesser AgNP formation. It was observed that at 40 °C, the silver ion conversion rate was 93.91%, which yielded lower AgNPs. Similarly, too high temperature such as 60 and 70 °C resulted in a too fast reaction. Previously, a non-Arrhenius behavior has been reported for the Ag-reduction rate with temperature. Because of the increase in coil diameter, a sudden agglomeration of individual micelles has been reported to form bigger network structures, while at the highest temperature, bunch-like particle structures have been found in a previous study.23 In the present study, at higher temperatures, the agglomeration was observed, showing bigger structures. Taking the temperature as a factor, a narrow and stable adsorption peak was observed that proved the best reaction temperature (50 °C).

To sum up, the optimum reaction conditions for the AgNP synthesis were the molar ratio of MY and silver nitrate (1:2), the pH (8), and the reaction temperature (50 °C).

2.3. Characterization

The morphology, size, and shape of MY-AgNPs were determined by transmission electron microscopy (TEM). The TEM images of AgNPs synthesized under optimized conditions are shown in Figure 3a, and the synthesized AgNPs were found mostly spherical. Scanning electron microscopy (SEM) analysis (Figure 3b) shows the size and morphology of the MY-AgNPs at different magnifications. The circular dot-shaped particles ranged from 20 to 50 nm. The maximum point and the minimum point were selected and measured with the ruler in the electron microscope to obtain a range, thus the size was determined.

Figure 3.

Figure 3

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(a) Transmission electron microscopy (TEM) image of MY-mediated AgNPs. (b) Scanning electron microscopy (SEM) image of MY-mediated AgNPs. (c) Fourier transform infrared (FTIR) spectroscopy image of MY-mediated AgNPs. (d) X-ray powder diffraction (XRD) pattern of MY-mediated AgNPs.

Fourier transform infrared (FTIR) spectroscopy (Figure 3c) was performed to identify the bond linkages and functional groups associated with MY and Ag+. These groups are important to understand their participation in the reduction process. The results revealed four peaks at 3410, 1610, 1390, and 1090 cm–1. The absorption band at 3410 cm–1 was assigned to the stretching vibration of υ (O–H).24 The absorption band at 1610 cm–1 was attributed to the stretching vibration of υ (C=C).25 The absorption band at 1390 cm–1 was the in-plane bending vibration of δ (O–H). Moreover, the band at 1090 cm–1 was contributed by the skeletal C–O bond of glycosidic linkage.26 It showed the presence of the residual flavonoids on the surface of MY-AgNPs.

The X-ray powder diffraction (XRD) pattern of MY-AgNPs is shown in Figure 3d. The narrow peaks indicated the crystalline properties of the nanoparticles.27−29 The XRD pattern showed four intense peaks corresponding to 2θ values 38.1923, 44.3907, 64.5384, and 77.4049° that represented the face-centered cubic (fcc) lattice of silver corresponding to Miller indices of (111), (200), (220), and (311), which were similar to the Bragg reflection of silver nanocrystals. According to the intensity ratio of (111) to other diffraction peaks, it was deduced that the (111) plane was the principal orientation in the silver crystal structure of MY-AgNPs.

Recently, certain suitable MY delivery systems have been reported. MY-loaded bovine serum albumin NPs were designed to increase the anticancer potential of MY.30 Similarly, MY lipid NPs have been reported as efficient skin-applicable antiperspirants.31 In addition, MY-mediated polymeric NP carrier,32 MY-mediated ternary platinum NPs,33 MY-mediated gold NPs,34 and MY-mediated chitosan NPs35,36 have also been investigated.

2.4. Antioxidant Activity

The free radical-scavenging activity of MY-AgNPs was determined by the DPPH method, and the results are shown in Figure 4. The free radical-scavenging capacity of MY-AgNPs was increased steadily with the continuous increase in concentration. Compared with MY, they had a similar effect as the reference antioxidant BHT. At different concentrations of synthetic silver nanoparticles (0.01–0.1 mg/mL), the free radical-scavenging rate was about 60–87%. As reported recently, MY significantly scavenged DPPH (91%) and ABTS+ (97%) radicals at a concentration of 16 μM.37 MY has been reported to inhibit reactive oxygen species generation38 and enhance antioxidant potential.39 MY-AgNPs, in the present study, also exhibited better antioxidant potential.

Figure 4.

Figure 4

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Comparison of free radical DPPH-scavenging rate between MY-AgNPs, MY, and BHT.

2.5. Antibacterial Activity

Biosynthetic AgNPs significantly inhibited bacterial growth. The minimum inhibitory concentrations (MICs) of AgNPs on Escherichia coli and Salmonella were 10–4 and 10–5 g/L, respectively, indicating that AgNPs had good inhibitory effects on these two bacteria. E. coli and Salmonella are common pathogenic bacteria, so the selection of two representative strains can better show the antibacterial effect of silver nanoparticles. Under the premise of the same concentration of the bacterial solution and sample, the inhibition effect of AgNPs on the number of viable bacterial colonies can be seen in Figure 5a–h, which also has a relatively obvious advantage over tetracycline.

Figure 5.

Figure 5

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Number of viable bacteria of culture medium. (a) E. coli. (b) E. coli treated with 0.1 mg/mL MY. (c) E. coli treated with 0.1 mg/mL MY-AgNPs. (d) E. coli treated with 0.1 mg/mL tetracycline. (e) Salmonella. (f) Salmonella treated with 0.1 mg/mL MY. (g) Salmonella treated with 0.1 mg/mL MY-AgNPs. (h) Salmonella treated with 0.1 mg/mL tetracycline.

The determination of the premise of bacterial liquid concentration by changing the concentration of the samples, get the samples on the inhibition rate of E. coli and Salmonella curve, can be seen in Figure 6a,b. The bacteriostatic rate increased with the increase in the concentration of the sample; eventually, the inhibition rate reached 100%. Compared with MY and tetracycline, better effect of AgNPs and significant, under low concentration had the obvious bacteriostatic effect.

Figure 6.

Figure 6

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Inhibition rate curves of different samples to bacteria. (a) E. coli. (b) Salmonella.

Through the observation of bacteria through electron microscopy (Figure 7a–h), we can basically see the principle of inhibiting bacteria in the samples. AgNPs were evenly coated on the surface of the bacterial cell membrane, destroying the structure and morphology of the bacteria to a certain extent, thus preventing the growth and reproduction of the bacteria.

Figure 7.

Figure 7

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SEM images of bacterial morphology. (a) E. coli. (b) E. coli with MY. (c) E. coli with MY-AgNPs. (d) E. coli with tetracycline. (e) Salmonella. (f) Salmonella with MY. (g) Salmonella with MY-AgNPs. (h) Salmonella with tetracycline.

MY has recently been reported for its antibacterial potential against Staphylococcus aureus.40 The sulfonamide moiety41 and 1,2,4-triazole Schiff base42 containing MY have exhibited antibacterial properties against Xanthomonas axonopodis pv. citri. MY has been reported for its antimicrobial properties (MIC 31 μg/mL) against E. coli.43

The AgNPs from some other plant crude such as Caralluma tuberculata,44 onion peel,45 durian-rind extract,46Cornus officinalis,47Rhodotorula mucilaginosa,48 and so forth have been recently reported for antibacterial and some other properties. The present study findings also imply that the MY-mediated AgNPs following a green approach were of interest for their antibacterial and antioxidant properties and could further be investigated for other properties.

3. Materials and Methods

3.1. Materials

MY was obtained from Chengdu Desite Co., Ltd. (Chengdu, China). 2,2-Diphenyl-1-picrylhydrazyl (DPPH), butylated hydroxytoluene (BHT), silver nitrate, and anhydrous alcohol were obtained from Sinopharm Chemical Reagent Co., Ltd (Shanghai, China). Trifluoroacetic acid and triethylamine were of analytical grade. The deionized water, used to make aqueous solutions, was dispensed by an osmosis Milli-Q system.

3.2. Apparatus

A Nicolet 710 FTIR spectrometer (Thermo Nicolet, USA) was used to check and analyze the FTIR results. An IRIS Advantage OPTIMA 7000DV inductively coupled plasma-atomic emission spectrometer (Thermo Perkin-Elmer) was employed to determine the metal element content and inductively coupled plasma (ICP). The surface morphology observation, particle size measurement analysis, and scanning electron microscope images of the NPs were determined using a SUPRA 55 Thermal field emission scanning electron microscope (Carl Zeiss, Germany). The transmission electron microscope images of NPs were determined using a JEM-2100F transmission electron microscope (JEOL, Japan). X-ray diffraction studies were carried out on an EMPYREAN X-ray diffractometer (PANalytical, Netherlands). A Genesys 10S UV–vis spectrometer (Thermo Flsher) was used for the ultraviolet and visible spectral analysis.

3.3. Synthesis of Silver Nanoparticles

The standard sample of MY (2 mM) was prepared using 50% ethanol. Silver nitrate was separately dissolved in deionized water. Then, 8 mL of MY solution (2 mM) was taken in a 25 mL round-bottom flask, and 2 mL of silver nitrate solution was added to the MY solution, making the MY/AgNO3 (1:1) final molar ratio. The mixture was heated at a set temperature (50 °C) on the oil bath. The mulberry-colored solution, appeared in 15 min, gradually changed to a grass green, and visible black particles were found suspended in the solution. This preliminary test predicted the AgNP formation. The heating was continued for 3 h and later on, a suspension was found and poured in a centrifuge tube. Previously, silver nanoparticles have been obtained at different centrifugation speeds such as 14,000,49 10,000,50 4000,51 and 350052 rpm and so forth. Herein, the supernatant was removed after centrifugation at a speed of 8000 rpm for 30 min. The supernatant was retained for the determination of ICP. The AgNPs were washed with deionized water 2–3 times to remove the excess organic matter. After drying at 70 °C in an oven, AgNPs were evenly distributed in water and kept in the refrigerator for later use. The reported protocols49,50,53,54 were consulted for experiments.

3.4. Reaction Condition Optimization for Biosynthesis

The optimum conditions for biosynthesis of AgNPs were found by changing the concentration of silver nitrate, pH, and temperature. In order to understand the effect of silver nitrate concentration, 2 mL of different concentrations was added to 8 mL of MY solution. Different molar ratios of MY and silver nitrate were studied, that is, 2:1, 1:1, 2:3, 1:2, and 1:4. In order to explore the possible influence of pH on the synthesis, the mixed solutions of trifluoroacetic acid and triethylamine were adjusted with different pH values such as 2, 4, 6, 7, 8, 9, 10, 11, and 12. Similarly, different temperatures were investigated such as 40, 50, 60, and 70 °C.

3.5. Characterization of AgNPs

3.5.1. Ultraviolet–Visible Spectroscopy

To determine the development of AgNPs and exploit their optical properties, the surface plasmon resonance (SPR) peaks were monitored using an ultraviolet–visible spectrophotometer (UV–vis spectra). The sampling of aliquots (AgNPs diluted with distilled water) was poured into a 1.0 cm cuvette. The UV–vis spectra were recorded in a wavelength range of 330–800 nm at room temperature.

3.5.2. SEM, TEM, FTIR, and XRD Analysis

SEM analysis was carried out at 50,000 magnifications. Prior to observation, the xerogel was sputter-coated with a thin layer of gold. Thin films of MY-AgNPs were prepared by dropping a very small amount of the sample on the carbon-coated copper grid. Then, the morphology and size of MY-AgNPs were analyzed under a mercury lamp for 5 min.

TEM images of the AgNPs were recorded at 120,000 magnifications, and the acceleration voltage was adjusted to 150 kv.

FTIR spectroscopy was performed in the wavelength range between 4000 and 400 cm–1 to find the functional groups present around the synthesized AgNPs. The AgNPs were dried and grinded with KBr pellets and analyzed.

XRD was carried out by dipping a glass plate loaded with a thin film of the AgNPs in a solution.

3.5.3. Conversion of Ag+ Ions

The MY-AgNP suspensions were centrifuged at a high speed of 8000 rpm for 30 min, and the remaining Ag+ ions were separated from the generated AgNPs. The concentration of Ag+ ions in the supernatant represents the residual or unreacted concentration of Ag+ ions. The reacted Ag+ ions were determined by deducting the remaining Ag+ ions, and the Ag+ value after the reaction was determined by ICP. The conversion rate of Ag+ ions was determined by comparing the mass of Ag+ with that of initial Ag+.

3.6. Antioxidant Activity of AgNPs

The antioxidant activity of synthesized nanoparticles was determined by 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging.37,55 DPPH was weighed and dissolved in anhydrous ethanol to produce 0.015 μg/mL solution. Samples of different concentrations were mixed with DPPH to obtain the final concentrations of 0.01, 0.25, 0.5, 0.75, and 0.1 mg/mL, respectively. BHT was adopted as a control, and the sample concentration was kept similar to that of the study samples. The mixture was reacted at 30 °C for 30 min, and the absorbance of each test tube was determined at 517 nm using an ultraviolet spectrometer. The blank group only contained DPPH. The DPPH free radical-scavenging activity was calculated using the following equation.

3.6.

A0 is the absorbance of the control and At is the absorbance of the sample.

3.7. Antibacterial Activity of AgNPs

The antibacterial activity of AgNPs against human pathogenic bacteria such as E. coli and Salmonella was studied.56−58 The MIC was obtained by 96-well plate gradient dilution. Under aseptic conditions, AgNPs were mixed in proportion with different bacterial fluids, after adding normal saline to the culture for one day, a certain amount of liquid was absorbed from the mixture and evenly coated on the AGAR plate containing nutritious broth. After another day of culture at 37° C, counting was carried out after taking out the plate, and finally, an intuitive curve of the bacterial inhibition rate was obtained.

4. Conclusions

The development of AgNPs with high efficiency, environmental protection, and low cost is an important direction of current nanotechnology research and application. Recently, biomass has been used as an effective reducing agent and stabilizer for the synthesis of AgNPs. In this study, the dietary MY-mediated AgNPs were successfully synthesized. Compared with previous synthesis methods, the present study provides a simple, nontoxic, cost-effective, and environmentally friendly green approach for the synthesis of AgNPs of MY. The MY-AgNPs possessing spherical and moderate size showed obvious antibacterial activity against E. coli and Salmonella. These results indicated that the MY-mediated AgNPs could be used as alternate good bacterial inhibitors. Furthermore, the green approach may be employed on other dietary flavonoids and other skeletons.

Acknowledgments

We gratefully acknowledge the financial support from the Talented Young Scientist Program for I.A., Shandong Province “Double-Hundred Talent Plan” Program, and Shandong Province Major Scientific and Technological Innovation Project (2017CXGC1301 and 2017CXGC1308). The authors also thank International Cooperation Project (2019GHPY01) of Qilu University of Technology (Shandong Academy of Sciences).

The authors declare no competing financial interest.

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