Startseite Naturwissenschaften Influence of Production Parameters on the Content of Polyphenolic Compounds in Extruded Porridge Enriched with Chokeberry Fruit (Aronia melanocarpa (Michx.) Elliott)
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Influence of Production Parameters on the Content of Polyphenolic Compounds in Extruded Porridge Enriched with Chokeberry Fruit (Aronia melanocarpa (Michx.) Elliott)

  • Tomasz Oniszczuk , Gabriela Widelska , Anna Oniszczuk EMAIL logo , Kamila Kasprzak , Agnieszka Wójtowicz , Marta Olech , Renata Nowak , Karolina Wojtunik- Kulesza , Grzegorz Jóźwiak und Monika Waksmundzka- Hajnos
Veröffentlicht/Copyright: 22. März 2019
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Open Chemistry
Aus der Zeitschrift Open Chemistry Band 17 Heft 1

Abstract

Chokeberry fruit (Aronia melanocarpa (Michx.) Elliott) is known for its antioxidant properties and generally beneficial impact on human health. The aim of the research was to produce innovative corn porridge with a different content of chokeberry fruit percentage-wise and to test it to determine the content of polyphenolic compounds, including flavonoids and individual free phenolic acids, and determine the antioxidant properties of analysed extracts. One of the objectives was also to identify the optimum porridge production parameters, including, among other things, the rotational speed of the extruder screw during the extrusion process.

Obtained results showed that an increased content of chokeberry fruit in porridge enhances its antioxidant properties, as well the content of polyphenols, flavonoids, and free phenolic acids. The greatest free radicals scavenging activity by all extracts was reported after 10 minutes of the process. The results of the above study demonstrate that extruded porridge enriched with chokeberry fruit have a potential for becoming a good source of natural antioxidants, and the extrusion process at 80 rpm does not degrade the tested active compounds.

Keywords: LC-MS; antioxidant tests; chokeberry fruit; phenolic compounds; functional food

1 Introduction

In the times of more and more common diseases of affluence, to a large extent attributable to a busy and unhealthy lifestyle marked by stress, environmental pollution and improper nutrition, consumers are looking for foodstuffs that replace synthetic ingredients with the natural ones. The goal of any balanced diet is to supply enough nutrients to meet person’s nutritional needs. However, there is increasing scientific evidence to confirm the hypothesis that some food can offer other beneficial effects on top of supplying the most essential nutrients. A shift towards a healthy lifestyle and focus on the prevention of diseases, just to mention cancer, diabetes, or neurodegenerative and cardiovascular conditions, contribute to the emergence of new dietary trends. Given the above, we are seeking to develop food that can bring more health benefits than mere good taste. Looking at the existing socio-economic developments and demographic trends, functional food (FF) seems to be exactly what is needed to improve the quality of life [1]. Functional food can be classified both by product ranges (snacks, pastas, porridge, breakfast cereals, etc.) and by the technological process used during production. For example, such processes may involve the addition of a bioactive ingredient or a modification of the concentration of natural ingredients to enhance the desired action [2]. Moreover, specific functional food products can be designed and targeted at the whole population or specific groups, for example, age groups or consumers suffering from specific diseases [3].

In order to exert a beneficial effect on human health, functional food can be enriched with biologically active secondary metabolites of plant-origin. In this context, many scientists highlight the highly positive effects of polyphenols. It is a diverse group of compounds with at least two hydroxyl groups bound to one or more aromatic rings. Structure-wise, they can be divided into flavonoids, lignans, stilbenes, coumarins, and phenolic acids [4].

Polyphenols exhibit a high antioxidant activity and a number of other pharmacological properties; besides, they reveal anti-inflammatory [5], cardioptotically, neuroprotectively, antineoplastic, antiviral [6], immunomodulatory [7,8] antimicrobial [9], antiallergic, anti-oedematous, and antiatherosclerotic characteristics [10,11]. In addition, they works as a natural and effective food preservative [12].

The antioxidant activity of polyphenols comes from the inhibition of enzymes responsible for the formation of reactive forms of oxygen, among them: xanthine oxidase, NADPH (Nicotinamide Adenine Dinucleotide Phosphate), but they can also bind existing free radicals. Such properties are due to the presence of hydroxyl groups in the structure, and such groups reduce free radicals.

A plant known for its antioxidant properties and generally beneficial effects on human health is the chokeberry (Aronia melanocarpa), or, to be precise, its fruit. Chokeberry fruit contains a wide range of nutrients and health-improving substances, such as: sugars (glucose, fructose), pectins, tannins, calcium and iron compounds, vitamins (A, C, E, PP and others from the B group), flavonoids (hyperoside, quercetin, rutin), anthocyanins (cyanidin derivatives), phenolic acids (ferulic, p-coumaric, protocatech). Chokeberry extracts have proven effective in the prevention of stomach ulcers; besides, they help seal blood vessels, improve vessel flexibility, and reduce permeability. They are administered for colds and in periods of reduced immunity [13].

The aim of the research was to produce innovative corn porridge with a different content of chokeberry fruit percentage-wise and to test it to determine the content of polyphenolic compounds, including flavonoids and individual free phenolic acids, and determine the antioxidant properties of analysed extracts. One of the objectives was also to identify the optimum porridge production parameters, including, among other things, the rotational speed of the extruder screw during the extrusion process.

Extrusion-cooking is a process of processing starchy materials under specific thermal (120-200ºC), moisture, and high pressure (20 MPa) conditions. The intense processing of mechanical shearing results in a deep transformation of individual components. This highly effective technology brings to the market new product ranges featuring attractive sensory features and texture. The outcome is microbiologically clean and durable products. Owing to the use of techniques, such as microencapsulation and on-surface application of vitamins, condiments, and colourants, the nutritional value of such products can be almost freely shaped [14,15].

2 Materials and methods

2.1 Reagents

Standards of caffeic, gallic, ferulic, isoferulic, protocatechuic, 3-OH-benzoic, 4-OH-benzoic, rosmarinic, 3,4-dihydroxyphenylacetic, vanillic, syringic, m-coumaric, o-coumaric, p-coumaric, salicylic, 3-OH-cinnamic, 3,4-dimethoxycinnamic acid and LC grade acetonitrile were purchased from Sigma–Aldrich Fine Chemicals (St. Louis, MO, USA). Gentisic, sinapic, veratric acids were from ChromaDex (Irvine, USA). LC grade water was prepared using a Millipore Direct-Q3 purification system (Bedford, MA, USA). Ethanol and methanol (reagent grade purity) used for the preparation of extracts, Folin-Ciocalteu reagents and all analytical grade reagents were obtained from Avantor Performance Materials (Center Valley, PA, USA).

2.2 Porridge production

Chokeberry fruits purchased from a local farmer (Lublin Voivodeship located in southeastern Poland) were dried in an air oven at 40°C for 12 hours. The raw material mixes used for the tests were made from corn porridge (DASCA, distributor: Awiko, Lublin, Poland) with an addition of 0, 5, 10, 15 and 20% of dried chokeberry fruit. The mixes were moistened up to 14%. The extrudates were prepared on the single-screw extruder TS-45 (ZMCh Metalchem, Gliwice, Poland) equipped with a modified plasticising system L/D = 12:1. The extrusion was carried out at a varied screw speed of the extruder plasticizing system: 80 and 120 rpm. A single-opening die of 3 mm in diameter was used. During the extrusion process, temperature changes were recorded in the individual extruder sections at different temperature profiles: 132-142°C. The obtained extrudates were milled in the laboratory mill LMN10 (TestChem, Radlin, Poland) to obtain material of less than 1 mm in granularity.

2.3 Preparation of extracts

2 gram-samples of porridge were transferred to ground-necked flasks, and 40 mL of ethanol was added. An ultrasonic bath with a thermostat was used for extraction (Bandelin Electronic, Sonorex RK 100H, Germany). The extraction protocol was previously optimized in terms of temperature, time, type of solvent and ultrasound power. The extraction process took 40 minutes at the temperature of 60°C, the ultrasound frequency of 33kHz and the power of 320W. The extracts were filtered into beakers; 40 mL of ethanol was added to the reminder, and the extraction was repeated. The obtained extracts were combined and put aside in beakers under a hood until the solvent evaporated. The dry residues were quantitatively transferred to volumetric flasks and supplemented with methanol up to 5 mL [11].

2.4 Determination of the total content of polyphenolic compounds

The total content of polyphenolic compounds in the studied extracts was determined with the Folin-Ciocalteu (FC) method designed earlier [16,17]. 100 μL of the tested extracts were placed in 5 mL volumetric flasks. Next, 900 μL of distilled water and 100 μL of Folin-Ciocalteu reagent were added. The solutions were mixed and put aside. After 4 minutes, 1mL of 7.7% sodium bicarbonate and 400 μL of distilled water were added. The content was mixed and placed in a 40°C water bath for 50 minutes. After that, the absorbance of the solutions was measured using a UV spectrometer (Genesys 10S VIS, Thermo Scientific, Waltham, MA, US) at a wavelength of 765 nm.

Next, a calibration curve of gallic acid (0.05, 0.15, 0.25, 0.35, 0.5, 1.0 mg/mL) was plotted. 100 μL of each of the calibration solutions were collected, 900 μL of distilled water and 100 μL of Folin-Ciocalteu reagent were added to them and processed as in the case of the extracts above. A solution without gallic acid was used for a blank experiment. Basedon obtained results, a calibration curve of gallic acid (y = 3.7995x + 0.0986) was plotted. It was used to calculate the total polyphenol content in the analysed extracts, expressed as the equivalents of gallic acid.

2.5 Determination of the total flavonoid content

The total flavonoid content was determined by the colorimetric method with the use of aluminium chloride. 0.5 mL of the extract were put in 10 mL volumetric flasks; next, the following were added: 0.5 mL of methanol, 4 mL of distilled water and 0.3 mL of 5% NaNO2. The flasks were sealed and put aside for 5 minutes. After 5 minutes, 0.3 mL of 10% AlCl3 solution was added; the content was mixed and left for 6 minutes. Then, 2 mL of 1 mol NaOH solution was added and topped up with 10 mL of distilled water. The mixture was stirred and left for 10 minutes; after this time, absorbance was measured at the wave length of 510 nm.

Next, a calibration curve of quercetin (0.08, 0.40, 0.80, 1.6, 3.2, 4.8, 6.4, 8.0 and 9.6 mg/mL) was plotted. 1mL of each solution was collected, mixed with 4 mL of distilled water; 0.3 mL of 5% NaNO2 solution was added; the entire sample was put aside for 6 minutes and then processed as in the case of the extracts discussed above. Based on the obtained quercetin calibration curve (y = 0.1989x + 0.0908), the total flavonoid content in the extracts was calculated (as per quercetin). For a blank experiment, a solution was prepared in which aluminium chloride was replaced with distilled water; the remainder of the process remained unchanged [18].

2.6 TLC-DPPH Tests of obtained extracts

The antioxidant properties of obtained extracts were also examined by the TLC-DPPH test. For the stationary phase, 10x10 cm silica gel plates were used while for the mobile phase, a mixture of ethyl acetate, toluene, and formic acid at the ratio of 10:10:0.5 v/v/v. A standard solution of 0.1mg/mL quercetin was prepared. 10 μL aliquots of extracts were applied with the automatic TLC applicator Desaga AS -30. The plates were developed in one direction in horizontal chambers (DS II, Chromdes, Lublin, Poland). After drying, they were sprayed with a 0.1% DPPH solution. Next, the plates were scanned with a flat-bed scanner (Lide 50, Canon) after 0, 10, and 30 minutes. The results of TLC–DPPH tests were recorded in the form of JPG documents. For further analysis, the computer software Sorbfil TLC Videodensitometr (Sorbpolymer, Russia) [11,19] was used.

2.7 LC-ESI-MS/MS analysis of phenolic acids

Phenolic acids content was determined according to modified method described by Oniszczuk et al. [11]. Experiments were carried out using an Agilent 1200 Series HPLC system (Agilent Technologies, USA) connected to 3200 QTRAP Mass spectrometer (AB Sciex, USA) equipped with electrospray ionisation source (ESI). Both were controlled with Analyst 1.5 software (AB Sciex, USA), which was also used for data interpretation. Separations were carried out on a Zorbax SB-C18 column (2.1 x 100 mm, 1.8-mm particle size; Agilent Technologies, USA) at 20ºC. Gradient method was used with mobile phases: water with 0.1% HCOOH (A) and acetonitrile with 0.1% HCOOH (B). Injection volume was 3 μL, the flow rate was 250 ml/min and the gradient was as follows: 0-2 min – 25%B, 3-6 min – 35%B, 8-10 min – 55%B, 12-16 min - 75%B, 19-25 min - 25%B.

ESI operated in the negative-ion mode worked at the following conditions: capillary temperature 400 °C, curtain gas at 30 psi, nebulizer gas at 50 psi, negative ionisation mode source voltage −4500 V. Triplicate injections were made for each standard solution and sample. The analytes were identified by comparing retention time and m/z values obtained by MS and MS2 (Table 1) with the mass spectra from corresponding standards tested under the same conditions. The calibration curves obtained in MRM mode were used for quantification of all analytes. The identified phenolic acids were quantified on the basis of their peak areas and comparison with a calibration curve obtained with the corresponding standards. Linearity ranges for calibration curves were specified. The limits of detection (LOD) and quantification (LOQ) for phenolic compounds were determined at a signal-to-noise ratio of 3:1 and 10:1, respectively, by injecting a series of dilute solutions with known concentrations. Samples were purified and concentrated before LC-MS analysis using SPE technique.

Table 1

LC-ESI-MS/MS analytical results of phenolic acids investigated in samples. Compounds confirmed by comparison with authentic standards.

CompoundTR (min)[M-H]- (m/z)Fragment ions (m/z)Colision energy (eV)
Protocatechuic acid5.9152.9108- 38
81- 26
trans-Caffeic acid6.9178.7134.9- 16
88.9- 46
cis-Caffeic acid7.4178.7134.9- 16
88.9- 46
4-OH-benzoic acid7.29136.893- 18
75- 48
Gentisic acid7.75152.8108- 36
81- 30
p-Coumaric acid9.28162.7119- 14
93- 44
Ferulic acid9.9192.8177.9- 12
133.9- 16
Isoferulic acid10.5192.8177.9- 12
133.9- 16
Salicylic acid14.16136.893- 16
75- 48

2.8 Solid Phase Extraction (SPE)

Solid phase extraction was carried out using SPE system (Baker spe-12G™, J.T. Baker, Deventer,Netherlands) and columns with a chemically bonded octadecyl phase (Bakerbond C18, 500 mg). 2 ml of the extract in 50% methanol was applied to each of the conditioned columns. The desired fraction was eluted with 5 mL of 50% methanol and then with 5 mL of 80% methanol. The extracts obtained were concentrated and subjected to the LC-ESI-MS/MS analysis [11].

2.9 Statistical evaluation

Statistical analysis of data was made using the MSExcel 2013 and Statistica 12 program (StatSoft Inc., USA). All analytical measurements were repeated six times for each sample and reference compounds. The obtained results were expressed as the mean values ± SD. The significance of the obtained results was determined at p<0.05 performing t-test for the applied methods.

Ethical approval: The conducted research is not related to either human or animal use.

3 Results and Discussion

3.1 Determination of the total content of polyphenolic compounds

Extrusion-cooking is a food processing procedure that arouses a keen interest in the food industry. The action of temperature, pressure and shear forces on moist raw material induces profound changes in the processed matter in a very short time, among them: enhanced digestibility of nutrients, inactivation of anti-nutritive factors, modified sensory characteristics. The intensity of these changes depends both on the properties of raw material and on the settings of the extrusion-cooking proper, involving the temperature or rotational speed of the extruder screw. A high degree of mixing and homogenisation leads to a decrease in diffusion barriers and the breaking down of chemical bonds, which results in a heightened reactivity of the components. As a result, this is a source of both beneficial and non-beneficial changes in the processed material [20]. Therefore, to avoid undesirable degradation of active ingredients, including one that could occur during this process, it is important to select appropriate production parameters, among which the rotational speed of the extruder screw is key.

In the opening phase of the study, the authors compared the total content of polyphenols in porridge with the different content of chokeberry fruit (0, 5, 10, 15 and 20%) obtained at 80 and 120 rpm of the extruder screw. Polyphenol compounds are popular secondary metabolites. As mentioned above, many favourable biological effects are achieved owing to their presence in functional food products. Obtained results demonstrated that the screw speed of 80 rpm results, for all the chokeberry contents used, in a higher content of polyphenols (as per gallic acid) than the speed of 120 rpm (Table 2).

Table 2

Total polyphenols and total flavonoids content.

Chokeberry contentTotal polyphenols (mg GAE/mL)Total flavonoids (mg QE/mL)
80 rpm screw speed120 rpm screw speed80 rpm screw speed120 rpm screw speed
00.199 ± 0.005a0.198 ± 0.0041.159 ± 0.0111.157 ± 0.023
50.362 ± 0.0180.346 ± 0.0051.339 ± 0. 0261.321 ± 0.065
100.489 ± 0.0070.481 ± 0.0103.372 ± 0.0334.100 ± 0.021
150.752 ± 0.0080.725 ± 0.0025.899 ± 0.1085.872 ± 0.132
200.957 ± 0.0010. 893 ± 0.0038.695 ± 0.0896.935 ± 0.074

  1. aSD - standard deviation (n=6)

The broadest group of phenolic compounds are flavonoids. They have a key role in protecting the human body against various diseases, mainly due to their high antioxidant activity. Therefore, the following stage of the research focused on the influence of screw rotational speed on the total content of flavonoids (as per quercetin). It was demonstrated that, in this case, 80 rpm showed superior results compared with 120 rpm in all other examined cases (Table 2).

According to research done by Alonso et al. [21], the main factors stimulating the transformation of input material during the extrusion-cooking process are high temperatures and mechanical aspects related to shear forces that rise along with the increase of screw rotational speed. It is possible that production at 120 rpm is too extreme and lead to the decomposition of some phenolic compounds, including flavonoids [20]. Obtained results may be interesting for consumers as the selection of appropriate extrusion-cooking parameters helps maintain adequate nutritional, sensory and, above all, health-improving properties of the tested samples. The results of the tests clearly show that a higher level of chokeberry fruit in porridge means a higher content of polyphenols and flavonoids in the samples. The highest total content of polyphenols and flavonoids was reported in porridge a 20% addition of the chokeberry while the lowest in a sample without such functional additives.

3.2 TLC-DPPH test of obtained extracts and interpretation of results using the Sorbfil TLC Videodensitometer program

Having obtained the results discussed above, the authors decided to look at the antioxidant properties of porridge produced at the speed of 80 rpm of the extruder screw. For this purpose, a TLC was performed using a stable DPPH radical. The extracts were applied to successive plates; finally, a standard quercetin solution was added and left for development. After drying, the plates were sprayed with a DPPH solution and scanned after 0, 10, 30 minutes. Next, the obtained image was converted into numerical data in the Sorbfil TLC Videodensitometer program. For this purpose, on each scan of the chromatographic plate with the visualised area of bright spots, tacks were made corresponding to the area of development of each polyphenol extract. The function of result analysis permitted a precise assessment of the colour intensity of the spots and the size of the areas under peaks (and their conversion into numerical data). The area of a standard solution of quercetin at the concentration of 0.1 mg/mL was adopted as a reference point. Its activity was marked ‘1’ [22].

The TLC-DPPH test confirmed an increase in antioxidant properties of porridge along with the growing content of chokeberry fruit (Table 3, Figure 1). Thus, a well visible trend is that a higher amount of functional raw material causes an increase in the content of polyphenols and flavonoids and an increase in antioxidant properties. Extracts with the largest, i.e. 20%, addition of chokeberry fruit exhibited superior antioxidant properties. The top free radicals scavenging activity by all extracts was reported at the beginning after 10 minutes of the process. According to Brand et al. [13], chokeberry fruits have a tremendous effect on the human body, largely due to their antioxidant properties attributable to the presence of polyphenol compounds, which, as demonstrated by the research results, remained active after the extrusion-cooking process. Such porridge are a good source of natural antioxidants, thus being capable of preventing certain diseases and improving the quality of health and life.

Figure 1 TLC–DPPH test results for the extracts of corn porridge of the varied chokeberry content; plate scanned after 30 min. Mobile phase: ethyl acetate, toluene, and formic acid at the ratio of 10:10:0.5 v/v/. Stationary phase: plates with silica gel 10 × 10 cm. 1- a standard solution of 0.1mg/mL quercetin; 2, 3, 4, 5, 6 - extract of porridge with 20%, 15%, 10%, 5%, 0% addition of chokeberry fruit, respectively.
Figure 1

TLC–DPPH test results for the extracts of corn porridge of the varied chokeberry content; plate scanned after 30 min. Mobile phase: ethyl acetate, toluene, and formic acid at the ratio of 10:10:0.5 v/v/. Stationary phase: plates with silica gel 10 × 10 cm. 1- a standard solution of 0.1mg/mL quercetin; 2, 3, 4, 5, 6 - extract of porridge with 20%, 15%, 10%, 5%, 0% addition of chokeberry fruit, respectively.

Table 3

Results of TLC-DPPH assay showing the antiradical activity of analysed extracts in relation to the activity of 0.1 mg/mL quercetin solution (activity of quercetin solution equal to “1”).

TimeActivity in relation to quercetin (Ʃ of areas under the common peak/area under quercetin peak) ± SDa
Corn porridge without additionCorn porridge with 5% addition of chokeberryCorn porridge with 10% addition of chokeberryCorn porridge with 15% addition of chokeberryCorn porridge with 20% addition of chokeberry
after 0 min2.2532.3353.1933.7974.199
± 0.003a± 0.023± 0.062± 0.120± 0.088
after 10 min2.6743.0834.2234.9955.605
± 0.091± 0.111± 0.106± 0.092± 0.120
after 30 min1.1691.2762.2953.5263.685
± 0.022± 0.008± 0.077± 0.041± 0.043

  1. aSD - standard deviation (n=6)

3.3 LC-ESI-MS/MS analysis of phenolic acids

At the next stage of the research, the authors performed a quantitative analysis of free phenolic acids in porridge with a 0, 5, 10, 15 and 20% addition of chokeberry fruit; the porridge were produced at the optimum rotational speed of the extruder, i.e. 80 rpm. Prior to determination, all crude extracts were purified using the SPE method. In order to assess the accuracy of the SPE method, a recovery test was held. Crude extracts were enriched with known amounts of the standard solution having three different concentrations. Next, a solid phase extraction was performed with the same methods as used for the quantification of phenolic compounds in the samples. The recovered amounts ranged from 93.7% for isoferulic acid to 102.4% for 4-hydroxybenzoic acid, which means that using the SPE for extract purification proved most effective.

The LC-MS analysis exposed a wide variety of phenolic acids present in the tested samples. In the sample with the 20% content of chokeberry fruit, nine acids were identified (Table 4, Figure 2) . They derived from benzoic acid and included: protocatecholic acid, 4-OH-benzoic acid, gentiic acid, salicylic acid, and cinnamic acid derivatives: trans-and cis-caffeic, p-coumaric, ferulic, and isoferulic. This was the only extract where gentisic acid was determined. In the porridge without any functional additive, only five free phenolic acids were detected: protocatechuic acid, 4-OH-benzoic acid, salicylic acid, ferulic acid, and isoferulic acid. The total content of these compounds grew along with the increasing amount of chokeberry fruit in the samples and reached 18.184 μg, 35.101 μg, 39.938 μg, 41.497 μg and 45.074 μg/g of dry matter, respectively, for samples enriched with 0, 5, 10, 15 and 20% of this fruit. Also, the content of individual acids increased as more chokeberry fruit was added. We observed that porridge enriched with this functional additive become an important source of free phenolic acids, especially protocatechuic acid. Its content in samples with the addition of chokeberry fruits is very high and grows even more as more of this fruit is added. This acid plays a vital role in disease prevention, especially when we speak about diseases of affluence. Recent research have shown that it has a potential as a prevention factor in cardiovascular diseases. In the 1990s, based on the results of research on chemically induced carcinogenesis, some chemopreventive properties of this compound were reported in experimental animals. Its action is based on antioxidant properties, i.e. inhibited generation of free radicals, the ability to scavenge them and enhance the catalytic activity of endogenous enzymes taking part in the neutralisation of free radicals. Of significance is also the

Figure 2 Extracted LC-MS-MRM chromatogram of phenolic acids found in sample with 20% addition of chokeberry fruit; MRM transition are given in brackets: 1 - protocatechuic (m/z 152.9 > 107.8); 2 – trans-caffeic (m/z 178.7 > 134.9); 3 –cis-caffeic (m/z 178.7 > 134.9); 4 - 4-hydroxy-benzoic (m/z 136.9 > 93); 5 - salicylic (m/z 136.9 > 93); 6 - gentisic (m/z 152.8 > 107.9); 7 - p-coumaric (m/z 162.8 > 119); 8 - ferulic (m/z 192.8 > 133.9); 9 - isoferulic acid (m/z m/z 192.8 > 133.9).
Figure 2

Extracted LC-MS-MRM chromatogram of phenolic acids found in sample with 20% addition of chokeberry fruit; MRM transition are given in brackets: 1 - protocatechuic (m/z 152.9 > 107.8); 2 – trans-caffeic (m/z 178.7 > 134.9); 3 –cis-caffeic (m/z 178.7 > 134.9); 4 - 4-hydroxy-benzoic (m/z 136.9 > 93); 5 - salicylic (m/z 136.9 > 93); 6 - gentisic (m/z 152.8 > 107.9); 7 - p-coumaric (m/z 162.8 > 119); 8 - ferulic (m/z 192.8 > 133.9); 9 - isoferulic acid (m/z m/z 192.8 > 133.9).

Table 4

Content of phenolic acids .

Phenolic acidYield of phenolic acids (μg/g of dry weight)
Corn porridge without additionCorn porridge with 5% addition of chokeberryCorn porridge with 10% addition of chokeberryCorn porridge with 15% addition of chokeberryCorn porridge with 20% addition of chokeberry
Protocatechuic0.10013.96124.32129.04032.646
SD*0.00130.26110.38200.21430.5212
trans-CaffeicND0.5800.8241.0681.304
SD-0.00050.01510.02130.0862
cis-CaffeicBQLBQLBQLBQLBQL
SD-----
4-OH-benzoic0.2900.3200.3440.3640.520
SD0.00420.00120.00210.00450.0093
GentisicNDNDNDBQL0.036
SD-----
p-CoumaricND3.4363.4723.5013.520
SD-0.04520.00870.07600.0242
Ferulic1.1501.3521.4721.5321.668
SD0.00120.00080.03710.05210.0065
Isoferulic18.43015.1209.1205.5604.920
SD0.03240.42370.23910.16720.0883
Salicylic0.2140.3320.3850.4320.460
SD0.00430.00620.00880.02100.0189

  1. * aSD - standard deviation (n=3), BQL - peak detected, concentration lower than the LOQ but higher than the LOD, ND – not detected

influence of enzymes involved in the first and the second stage of carcinogen biotransformation and, most probably, the direct blocking of the locations of specific bonds of metabolised carcinogens with a DNA molecule [23,24].

A drop in the content of isoferulic acid as more of the fruit is added to porridge is interesting. It can be explained by the fact that the matrix itself, i.e. the corn porridge free of any additives, contained more of this compound that the chokeberry.

Obtained results showed that the antioxidant activity measured in the TLC-DPPH test was positively correlated with the content of all groups of compounds identified in porridge, including with free phenolic acids. Pearson’s coefficients between the addition of chokeberry fruit, the content of polyphenols, flavonoids, free phenolic acids and the antioxidant activity (measured after 10 minutes) are shown in Table 5. Very high and positive correlations were reported between the addition of chokeberry fruit and antioxidant properties (r = 0.991), between the addition of chokeberry fruit and polyphenol content (r = 0.981) and between antioxidant properties and the content of polyphenols (r = 0.967). These correlations indicate that the measured antioxidant activity of the tested porridge was mainly due to the addition of polyphenol-rich chokeberry fruit. Antioxidant properties were also closely associated with the level of flavonoids (r = 0.970) and free phenolic acids (r = 0.866). Our results are aligned with those of Madhujith et al. [25,26]. They reported that it was the level of free and not bonded and conjugated phenolic acids that significantly contributed to the antioxidant properties of the tested plant samples.

Table 5

Pearson correlation coefficient; p <0,05.

Chokeberry contentTotal polyphenolsTotal flavonoidsFree phenolic acidTLC-DPPH radical scavenging capacity
Chokeberry content10.9810.9640.9000.991
Total polyphenols10.9770.8310.967
Total flavonoids10.7540.970
Free phenolic acids10.866
TLC-DPPH radical scavenging capacity1

The content of free phenolic acids in the examined extracts was determined by means of calibration curves designed for each model. The limit of detection (LOD) and the limit of quantification (LOQ) were determined at the signal to noise ratio (S/N) of 3 and 10, respectively. All the tested compounds showed positive linearity. The correlation coefficients for all calibration curves were r2 > 0.998. The values of LOD and LOQ as well as the linear range for all analysed compounds are shown in Table 6.

Table 6

Limit of detection (LOD), limit of quantification (LOQ) and calibration curve parameters for all analytes.

CompoundLOD [ng/μL]LOQ [ng/μL]r2Linearity range [ng/μL]
Protocatechuic acid0.0170.0340.99970.034-3.47
trans-Caffeic acid0.060.160.99900.175-3.5
cis-Caffeic acid0.060.160.99900.175-3.5
4-OH-benzoic acid0.01740.03470.99930.0694-3.47
Gentisic acid0.00170.00330.99970.0033-0.33
p-Coumaric acid0.00730.01810.99960.0181-1.82
Ferulic acid0.01740.03470.99940.0694-11.6
Isoferulic acid0.01720.6860.99970.343-11.4
Salicylic acid0.00330.01650.99890.0165-1.65

Our research has demonstrated that innovative porridge with the addition of chokeberry fruit can become a source of antioxidants that are so important for the human body. For this reason, they can prospectively make their way into the product range known as functional foods.

4 Conclusions

The research demonstrated that porridge manufactured in the extrusion-cooking process with the addition of chokeberry fruit, especially at the level of 20%, have a potential for becoming an important source of antioxidant polyphenolic compounds. The extrusion-cooking process at 80 rpm of the extruder screw does not degrade the tested active compounds, whose content increases along with the addition of the chokeberry to samples. Very high and positive correlations are reported between the addition of fruit and antioxidant properties (r = 0.991), between the addition of fruit and and polyphenol content (r = 0.981) and between antioxidant properties and the content of polyphenolic compounds (r = 0.967). Antioxidant properties are also closely associated with the level of flavonoids (r = 0.970) and free phenolic acids (r = 0.866).

The presented results prove to be a major step towards making the extruded porridge obtained in our experiments a much-demanded product ranked among functional foods.

  1. Conflict of interest: Authors declare no conflict of interest.

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Received: 2018-10-12
Accepted: 2018-11-15
Published Online: 2019-03-22

© 2019 Tomasz Oniszczuk et al., published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 Public License.

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https://doi.org/10.1515/chem-2019-0019
Schlagwörter für diesen Artikel
LC-MS; antioxidant tests; chokeberry fruit; phenolic compounds; functional food
Creative Commons
BY 4.0

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  27. Phytochemical screening and estrogenic activity of total glycosides of Cistanche deserticola
  28. Biological evaluation of a series of benzothiazole derivatives as mosquitocidal agents
  29. Chemical pretreatments of Trapa bispinosa's peel (TBP) biosorbent to enhance adsorption capacity for Pb(ll)
  30. Dynamic Changes in MMP1 and TIMP1 in the Antifibrotic Process of Dahuang Zhechong Pill in Rats with Liver Fibrosis
  31. The Optimization and Production of Ginkgolide B Lipid Microemulsion
  32. Photodynamic Therapy Enhanced the Antitumor Effects of Berberine on HeLa Cells
  33. Chiral and Achiral Enantiomeric Separation of (±)-Alprenolol
  34. Correlation of Water Fluoride with Body Fluids, Dental Fluorosis and FT4, FT3 –TSH Disruption among Children in an Endemic Fluorosis area in Pakistan
  35. A one-step incubation ELISA kit for rapid determination of dibutyl phthalate in water, beverage and liquor
  36. Free Radical Scavenging Activity of Essential Oil of Eugenia caryophylata from Amboina Island and Derivatives of Eugenol
  37. Effects of Blue and Red Light On Growth And Nitrate Metabolism In Pakchoi
  38. miRNA-199a-5p functions as a tumor suppressor in prolactinomas
  39. Solar photodegradation of carbamazepine from aqueous solutions using a compound parabolic concentrator equipped with a sun tracking system
  40. Influence of sub-inhibitory concentration of selected plant essential oils on the physical and biochemical properties of Pseudomonas orientalis
  41. Preparation and spectroscopic studies of Fe(II), Ru(II), Pd(II) and Zn(II) complexes of Schiff base containing terephthalaldehyde and their transfer hydrogenation and Suzuki-Miyaura coupling reaction
  42. Complex formation in a liquid-liquid extraction-chromogenic system for vanadium(IV)
  43. Synthesis, characterization (IR, 1H, 13C & 31P NMR), fungicidal, herbicidal and molecular docking evaluation of steroid phosphorus compounds
  44. Analysis and Biological Evaluation of Arisaema Amuremse Maxim Essential Oil
  45. A preliminary assessment of potential ecological risk and soil contamination by heavy metals around a cement factory, western Saudi Arabia
  46. Anti- inflammatory effect of Prunus tomentosa Thunb total flavones in LPS-induced RAW264.7 cells
  47. Collaborative Influence of Elevated CO2 Concentration and High Temperature on Potato Biomass Accumulation and Characteristics
  48. Methods of extraction, physicochemical properties of alginates and their applications in biomedical field – a review
  49. Characteristics of liposomes derived from egg yolk
  50. Preparation of ternary ZnO/Ag/cellulose and its enhanced photocatalytic degradation property on phenol and benzene in VOCs
  51. Influence of Human Serum Albumin Glycation on the Binding Affinities for Natural Flavonoids
  52. Synthesis and antioxidant activity of 2-methylthio-pyrido[3,2-e][1,2,4] triazolo[1,5-a]pyrimidines
  53. Comparative study on the antioxidant activities of ten common flower teas from China
  54. Molecular Properties of Symmetrical Networks Using Topological Polynomials
  55. Synthesis of Co3O4 Nano Aggregates by Co-precipitation Method and its Catalytic and Fuel Additive Applications
  56. Phytochemical analysis, Antioxidant and Antiprotoscolices potential of ethanol extracts of selected plants species against Echinococcus granulosus: In-vitro study
  57. Silver nanoparticles enhanced fluorescence for sensitive determination of fluoroquinolones in water solutions
  58. Simultaneous Quantification of the New Psychoactive Substances 3-FMC, 3-FPM, 4-CEC, and 4-BMC in Human Blood using GC-MS
  59. Biodiesel Production by Lipids From Indonesian strain of Microalgae Chlorella vulgaris
  60. Miscibility studies of polystyrene/polyvinyl chloride blend in presence of organoclay
  61. Antibacterial Activities of Transition Metal complexes of Mesocyclic Amidine 1,4-diazacycloheptane (DACH)
  62. Novel 1,8-Naphthyridine Derivatives: Design, Synthesis and in vitro screening of their cytotoxic activity against MCF7 cell line
  63. Investigation of Stress Corrosion Cracking Behaviour of Mg-Al-Zn Alloys in Different pH Environments by SSRT Method
  64. Various Combinations of Flame Retardants for Poly (vinyl chloride)
  65. Phenolic compounds and biological activities of rye (Secale cereale L.) grains
  66. Oxidative degradation of gentamicin present in water by an electro-Fenton process and biodegradability improvement
  67. Optimizing Suitable Conditions for the Removal of Ammonium Nitrogen by a Microbe Isolated from Chicken Manure
  68. Anti-inflammatory, antipyretic, analgesic, and antioxidant activities of Haloxylon salicornicum aqueous fraction
  69. The anti-corrosion behaviour of Satureja montana L. extract on iron in NaCl solution
  70. Interleukin-4, hemopexin, and lipoprotein-associated phospholipase A2 are significantly increased in patients with unstable carotid plaque
  71. A comparative study of the crystal structures of 2-(4-(2-(4-(3-chlorophenyl)pipera -zinyl)ethyl) benzyl)isoindoline-1,3-dione by synchrotron radiation X-ray powder diffraction and single-crystal X-ray diffraction
  72. Conceptual DFT as a Novel Chemoinformatics Tool for Studying the Chemical Reactivity Properties of the Amatoxin Family of Fungal Peptides
  73. Occurrence of Aflatoxin M1 in Milk-based Mithae samples from Pakistan
  74. Kinetics of Iron Removal From Ti-Extraction Blast Furnace Slag by Chlorination Calcination
  75. Increasing the activity of DNAzyme based on the telomeric sequence: 2’-OMe-RNA and LNA modifications
  76. Exploring the optoelectronic properties of a chromene-appended pyrimidone derivative for photovoltaic applications
  77. Effect of He Qi San on DNA Methylation in Type 2 Diabetes Mellitus Patients with Phlegm-blood Stasis Syndrome
  78. Cyclodextrin potentiometric sensors based on selective recognition sites for procainamide: Comparative and theoretical study
  79. Greener synthesis of dimethyl carbonate from carbon dioxide and methanol using a tunable ionic liquid catalyst
  80. Nonisothermal Cold Crystallization Kinetics of Poly(lactic acid)/Bacterial Poly(hydroxyoctanoate) (PHO)/Talc
  81. Enhanced adsorption of sulfonamide antibiotics in water by modified biochar derived from bagasse
  82. Study on the Mechanism of Shugan Xiaozhi Fang on Cells with Non-alcoholic Fatty Liver Disease
  83. Comparative Effects of Salt and Alkali Stress on Antioxidant System in Cotton (Gossypium Hirsutum L.) Leaves
  84. Optimization of chromatographic systems for analysis of selected psychotropic drugs and their metabolites in serum and saliva by HPLC in order to monitor therapeutic drugs
  85. Electrocatalytic Properties of Ni-Doped BaFe12O19 for Oxygen Evolution in Alkaline Solution
  86. Study on the removal of high contents of ammonium from piggery wastewater by clinoptilolite and the corresponding mechanisms
  87. Phytochemistry and toxicological assessment of Bryonia dioica roots used in north-African alternative medicine
  88. The essential oil composition of selected Hemerocallis cultivars and their biological activity
  89. Mechanical Properties of Carbon Fiber Reinforced Nanocrystalline Nickel Composite Electroforming Deposit
  90. Anti-c-myc efficacy block EGFL7 induced prolactinoma tumorigenesis
  91. Topical Issue on Applications of Mathematics in Chemistry
  92. Zagreb Connection Number Index of Nanotubes and Regular Hexagonal Lattice
  93. The Sanskruti index of trees and unicyclic graphs
  94. Valency-based molecular descriptors of Bakelite network BNmn
  95. Computing Topological Indices for Para-Line Graphs of Anthracene
  96. Zagreb Polynomials and redefined Zagreb indices of Dendrimers and Polyomino Chains
  97. Topological Descriptor of 2-Dimensional Silicon Carbons and Their Applications
  98. Topological invariants for the line graphs of some classes of graphs
  99. Words for maximal Subgroups of Fi24‘
  100. Generators of Maximal Subgroups of Harada-Norton and some Linear Groups
  101. Special Issue on POKOCHA 2018
  102. Influence of Production Parameters on the Content of Polyphenolic Compounds in Extruded Porridge Enriched with Chokeberry Fruit (Aronia melanocarpa (Michx.) Elliott)
  103. Effects of Supercritical Carbon Dioxide Extraction (SC-CO2) on the content of tiliroside in the extracts from Tilia L. flowers
  104. Impact of xanthan gum addition on phenolic acids composition and selected properties of new gluten-free maize-field bean pasta
  105. Impact of storage temperature and time on Moldavian dragonhead oil – spectroscopic and chemometric analysis
  106. The effect of selected substances on the stability of standard solutions in voltammetric analysis of ascorbic acid in fruit juices
  107. Determination of the content of Pb, Cd, Cu, Zn in dairy products from various regions of Poland
  108. Special Issue on IC3PE 2018 Conference
  109. The Photocatalytic Activity of Zns-TiO2 on a Carbon Fiber Prepared by Chemical Bath Deposition
  110. N-octyl chitosan derivatives as amphiphilic carrier agents for herbicide formulations
  111. Kinetics and Mechanistic Study of Hydrolysis of Adenosine Monophosphate Disodium Salt (AMPNa2) in Acidic and Alkaline Media
  112. Antimalarial Activity of Andrographis Paniculata Ness‘s N-hexane Extract and Its Major Compounds
  113. Special Issue on ABB2018 Conference
  114. Special Issue on ICCESEN 2017
  115. Theoretical Diagnostics of Second and Third-order Hyperpolarizabilities of Several Acid Derivatives
  116. Determination of Gamma Rays Efficiency Against Rhizoctonia solani in Potatoes
  117. Studies On Compatibilization Of Recycled Polyethylene/Thermoplastic Starch Blends By Using Different Compatibilizer
  118. Liquid−Liquid Extraction of Linalool from Methyl Eugenol with 1-Ethyl-3-methylimidazolium Hydrogen Sulfate [EMIM][HSO4] Ionic Liquid
  119. Synthesis of Graphene Oxide Through Ultrasonic Assisted Electrochemical Exfoliation
  120. Special Issue on ISCMP 2018
  121. Synthesis and antiproliferative evaluation of some 1,4-naphthoquinone derivatives against human cervical cancer cells
  122. The influence of the grafted aryl groups on the solvation properties of the graphyne and graphdiyne - a MD study
  123. Electrochemical modification of platinum and glassy carbon surfaces with pyridine layers and their use as complexing agents for copper (II) ions
  124. Effect of Electrospinning Process on Total Antioxidant Activity of Electrospun Nanofibers Containing Grape Seed Extract
  125. Effect Of Thermal Treatment Of Trepel At Temperature Range 800-1200˚C
  126. Topical Issue on Agriculture
  127. The effect of Cladophora glomerata exudates on the amino acid composition of Cladophora fracta and Rhizoclonium sp.
  128. Influence of the Static Magnetic Field and Algal Extract on the Germination of Soybean Seeds
  129. The use of UV-induced fluorescence for the assessment of homogeneity of granular mixtures
  130. The use of microorganisms as bio-fertilizers in the cultivation of white lupine
  131. Lyophilized apples on flax oil and ethyl esters of flax oil - stability and antioxidant evaluation
  132. Production of phosphorus biofertilizer based on the renewable materials in large laboratory scale
  133. Human health risk assessment of potential toxic elements in paddy soil and rice (Oryza sativa) from Ugbawka fields, Enugu, Nigeria
  134. Recovery of phosphates(V) from wastewaters of different chemical composition
  135. Special Issue on the 4th Green Chemistry 2018
  136. Dead zone for hydrogenation of propylene reaction carried out on commercial catalyst pellets
  137. Improved thermally stable oligoetherols from 6-aminouracil, ethylene carbonate and boric acid
  138. The role of a chemical loop in removal of hazardous contaminants from coke oven wastewater during its treatment
  139. Combating paraben pollution in surface waters with a variety of photocatalyzed systems: Looking for the most efficient technology
  140. Special Issue on Chemistry Today for Tomorrow 2019
  141. Applying Discriminant and Cluster Analyses to Separate Allergenic from Non-allergenic Proteins
  142. Chemometric Expertise Of Clinical Monitoring Data Of Prolactinoma Patients
  143. Chemomertic Risk Assessment of Soil Pollution
  144. New composite sorbent for speciation analysis of soluble chromium in textiles
  145. Photocatalytic activity of NiFe2O4 and Zn0.5Ni0.5Fe2O4 modified by Eu(III) and Tb(III) for decomposition of Malachite Green
  146. Photophysical and antibacterial activity of light-activated quaternary eosin Y
  147. Spectral properties and biological activity of La(III) and Nd(III) Monensinates
  148. Special Issue on Monitoring, Risk Assessment and Sustainable Management for the Exposure to Environmental Toxins
  149. Soil organic carbon mineralization in relation to microbial dynamics in subtropical red soils dominated by differently sized aggregates
  150. A potential reusable fluorescent aptasensor based on magnetic nanoparticles for ochratoxin A analysis
  151. Special Issue on 13th JCC 2018
  152. Fluorescence study of 5-nitroisatin Schiff base immobilized on SBA-15 for sensing Fe3+
  153. Thermal and Morphology Properties of Cellulose Nanofiber from TEMPO-oxidized Lower part of Empty Fruit Bunches (LEFB)
  154. Encapsulation of Vitamin C in Sesame Liposomes: Computational and Experimental Studies
  155. A comparative study of the utilization of synthetic foaming agent and aluminum powder as pore-forming agents in lightweight geopolymer synthesis
  156. Synthesis of high surface area mesoporous silica SBA-15 by adjusting hydrothermal treatment time and the amount of polyvinyl alcohol
  157. Review of large-pore mesostructured cellular foam (MCF) silica and its applications
  158. Ion Exchange of Benzoate in Ni-Al-Benzoate Layered Double Hydroxide by Amoxicillin
  159. Synthesis And Characterization Of CoMo/Mordenite Catalyst For Hydrotreatment Of Lignin Compound Models
  160. Production of Biodiesel from Nyamplung (Calophyllum inophyllum L.) using Microwave with CaO Catalyst from Eggshell Waste: Optimization of Transesterification Process Parameters
  161. The Study of the Optical Properties of C60 Fullerene in Different Organic Solvents
  162. Composite Material Consisting of HKUST-1 and Indonesian Activated Natural Zeolite and its Application in CO2 Capture
  163. Topical Issue on Environmental Chemistry
  164. Ionic liquids modified cobalt/ZSM-5 as a highly efficient catalyst for enhancing the selectivity towards KA oil in the aerobic oxidation of cyclohexane
  165. Application of Thermal Resistant Gemini Surfactants in Highly Thixotropic Water-in-oil Drilling Fluid System
  166. Screening Study on Rheological Behavior and Phase Transition Point of Polymer-containing Fluids produced under the Oil Freezing Point Temperature
  167. The Chemical Softening Effect and Mechanism of Low Rank Coal Soaked in Alkaline Solution
  168. The Influence Of NO/O2 On The NOx Storage Properties Over A Pt-Ba-Ce/γ-Al2O3 Catalyst
  169. Special Issue on the International conference CosCI 2018
  170. Design of SiO2/TiO2 that Synergistically Increases The Hydrophobicity of Methyltrimethoxysilane Coated Glass
  171. Antidiabetes and Antioxidant agents from Clausena excavata root as medicinal plant of Myanmar
  172. Development of a Gold Immunochromatographic Assay Method Using Candida Biofilm Antigen as a Bioreceptor for Candidiasis in Rats
  173. Special Issue on Applied Biochemistry and Biotechnology 2019
  174. Adsorption of copper ions on Magnolia officinalis residues after solid-phase fermentation with Phanerochaete chrysosporium
  175. Erratum
  176. Erratum to: Sand Dune Characterization For Preparing Metallurgical Grade Silicon
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Heruntergeladen am 16.1.2026 von https://www.degruyterbrill.com/document/doi/10.1515/chem-2019-0019/html
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