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Future Journal of Pharmaceutical Sciences
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Evaluation of antioxidant activity in different Egyptian barley cultivars: an in vitro and in silico study

Future Journal of Pharmaceutical Sciences volume 10, Article number: 69 (2024) Cite this article

Abstract

Background

Cereals have historically played a crucial role in the human diet, serving as a significant natural source of energy and offering various health benefits. Barley (Hordeum vulgare L.) has been given significant attention in recent years due to its exceptional nutritional value, surpassing that of other cereals. The objective of this research is to evaluate the antioxidant activity of various solvent extracts obtained from three different barley cultivars.

Results

The G.136 variety's acetone extract exhibited the highest level of antioxidant activity in both the DPPH assay, with an IC50 of 55.62 µg/ml, and the FRAP assay, with 447 μM trolox/mg extract. The dominant compounds identified before in the acetone fraction were subjected to an evaluation of their docking scores, along with an assessment of ADMET (Absorption, Distribution, Metabolism, Excretion, and Toxicity) and TOPKAT (Toxicity Prediction by Komputer Assisted Technology) studies. Notably, hordatine A1, prodelphinidin B3, hordatine B1, procyanidin B2, and isovitexin 7-O-glucoside were the major compounds with the highest LipDock scores compared to trolox the reference drug with polyphenol oxidase.

Conclusions

The findings indicate that the acetone extract from all three cultivars demonstrates noteworthy results, surpassing the efficacy of other solvent extracts against the antioxidant activity.

Background

Cereals have long been closely linked to food and drink, acting as a major natural energy source and providing numerous benefits for human health [1]. Barley is one of the oldest cereal crops that are grown. 10,500 years ago, the ancient Egyptians utilized it for the first time near the Nile River [2]. Barley can be classified according to its grain content into several categories, including normal, waxy (characterized by high-amylose starch content), high-glucan, and proanthocyanidin-free varieties [1]. Among the grains, barley has the highest quantities of β-glucan, followed by rye, wheat, and oats in decreasing order [3]. Oxidative stress, which is associated with the development of several diseases such as cancer, anemia, ischemia, diabetes, and cardiovascular diseases, is known to have a significant impact on the body's cellular processes [4]. Studies have demonstrated that barley grains contain phytochemical substances that have significant antioxidant qualities when evaluated in vitro [5]. The type of solvent employed during the extraction process has been discovered to affect the nature and quantity of secondary metabolites recovered from medicinal plants [6]. The structural dissimilarities of phenolic compounds influence their solubility in liquids of variable polarity. As a result, the solvent used for extraction and separation processes can have a substantial impact on the yield of phytochemicals derived from plant sources [7]. The primary objective of this study was to examine the principal phytochemical constituents within the most potent barley plant extract. The extraction process encompassed the use of various solvents, including 70% ethanol, methanol, water, 80% methanol, and acetone. Additionally, the research evaluated the antioxidant capabilities of the barley extracts, and in silico investigations were conducted to assess the potential binding modes of various phytochemicals as ligands with polyphenol oxidases (PPOs) receptor proteins.

Methods

Plant materials collection and extraction

In August 2019, whole barley grains (Hordeum vulgare L.) from three distinct cultivars were gathered from the Agriculture Research Center in Egypt, sourced from different geographic locations. The three commonly cultivated H. vulgare varieties in Egypt, namely Giza 136 (G.136), Giza 127 (G.127), and Giza 131 (G.131), were utilized. Fifty grams of powdered plant material from each of the three cultivars underwent extraction using five distinct solvents: 100% methanol, 80% methanol in water, 70% ethanol in water, 80% acetone in water, and distilled water. The yield from cultivar G.136 was 5.9% with methanol, 6.12% with ethanol in water, 11.43% with 70% ethanol in water, 8.23% with 80% acetone in water, and 3.8% with distilled water. Meanwhile, for cultivar G.127, the yields were 4.42% with methanol, 7.23% with 80% methanol in water, 8.39%, 8.38% with 70% ethanol in water, 8.45% with 80% acetone in water, and 12.44% with distilled water. As for cultivar G.131, the yields were 3.19% with methanol, 8.52% with 80% methanol in water, 7.42% with 70% ethanol in water, 6.5% with 80% acetone in water, and 5.5% with distilled water. This process resulted in a total of 15 samples (three cultivars in five different solvents). To extract the compounds, all of the samples underwent sonication for 30 min, three times using 500 mL each time [8].

Ultra high-performance liquid chromatography-mass spectrometry analysis (UHLPC-MS)

The combined extracts were concentrated under reduced pressure. Ten milligrams of each extract was accurately weighed and then subjected to UHPLC-MS/MS analysis and measured their antioxidant activity.

Antioxidant activity measurements

DPPH radical scavenging activity

The three varieties of barley with different solvents were evaluated for their antioxidant capacity using the DPPH as mentioned by Boly et al. [9]. Briefly, in a 96-well plate (n = 6), 100 μL of freshly made DPPH reagent (0.1% in methanol) was together with 100 μL of the sample. The reaction was allowed to proceed for 30 min in the dark at room temperature. The subsequent decrease in DPPH color intensity was measured at 540 nm after the incubation period. FluoStar Omega, a microplate reader, was used to record the results. The following equation describes how data are expressed as means ± standard deviation, compared to torolox the standard drug.

$${\text{Percentage\,inhibition}} = \frac{{{\text{Average\,absorbance\,of\,blank}} - {\text{Average\,absorbance\,of\,the\,test}}}}{{{\text{Average\,absorbance\,of\,blank}}}} \times 100$$

Microsoft Excel® was used to analyze the data, and Graph Pad Prism 5® was used to get the IC50 value by converting the concentrations to their logarithmic value and choosing a nonlinear inhibitor regression equation. (log (inhibitor) vs. normalized response−variable slope equation) [10].

Ferric reducing antioxidant power assay (FRAP)

With a few minor adjustments to be performed in microplates, the Benzi et al. [11] method for the ferric reducing ability assay was used. In summary, a freshly made TPTZ reagent (300 mM acetate buffer (pH 3.6), 10 mM TPTZ in 40 mM HCl, and 20 mMFeCl3, respectively) was used. In a 96-well plate (n = 3), 190 uL of freshly made TPTZ reagent was combined with 10 uL of the sample. The reaction was then allowed to sit at room temperature for 30 min while kept in the dark. The final measurement of the blue color after incubation was made at 593 nm. Data are displayed as means ± SD. FluoStar Omega, a microplate reader, was used to record the results. The ferric reducing ability of the samples is presented as μM TE/mg sample using the linear regression equation extracted from the calibration curve, compared to torolox the standard drug.

Molecular docking studies

A molecular docking study was conducted using the Discovery Studio 4.1 program and the LIPDOCKER methodology. The isolated component was docked against the active site of antioxidant, PDB (ID: 2Y9X). Heavy atoms were created, superfluous chains were eliminated, hydrogens were added, and the protein was purified. The CHARMm forcefield and MMFF94 as a partial charge were used in the simulation. Fixed constraints and protein minimization were applied. The receptor binding site was located using the complicated ligand interaction site.

ADMET/TOPKAT prediction

The in silico ADMET (Absorption, Distribution, Metabolism, Excretion, and Toxicity) investigations were conducted using the Discovery Studio 4.1 program. These analyses aimed to predict the pharmacokinetic properties of the drug under examination, offering insights into its potential behavior within the body. The outcomes also yielded crucial structural information guiding the assessment of potential antioxidant activity. Graphical representations and numerical data were generated and presented. Additionally, the toxicity protocol TOPKAT was applied to the same set of compounds, evaluating various criteria including Ames Prediction, Carcinogenicity, and Rat Oral LD50 g/kg body weight.

Results

DPPH radical scavenging activity

In this experiment, the presence of hydrogen or electrons supplied by the antioxidant constituents in the samples resulted in the initial purple color of the DPPH radical changing to yellow. Figure 1 demonstrates that the antioxidant capacity of various sample extracts varies according to the polarity of the utilized solvents. As IC50 values decrease, the degree of antioxidative activity increases [12].

Fig. 1
figure 1

DPPH activity of the three barley varieties in different solvents. Significant differences among means of different treatments were determined using Bonferroni posttests at P < 0.001 (n = 3) with all solvent extracts compared to each other. a, b, c, d significant difference compared to methanol, water, acetone, and 80% methanol of G.136, a′, b′, c′, d′ significant difference compared to methanol, water, acetone, and 80% methanol of G.127, a″, b″, c″, d″ significant difference compared to methanol, water, acetone, and 80% methanol of G.131, *corresponding to P < 0.05, **corresponding to P < 0.01, and the significance difference with P < 0.001

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All tested varieties exhibited a significant difference with a P value less than 0.0001. However, variety G.131 methanol extract besides varieties G.127 and G.136 acetone extracts did not exhibit a significant difference with P > 0.05 in comparison with the standard drug, trolox, in terms of their antioxidant activity. This implies that they possess antioxidant properties. Besides, among all the varieties, variety G.136 acetone extract had the highest antioxidant activity (IC50: 55.62 µg/ml), whereas variety G.127 acetone extract had the second-highest antioxidant activity (IC50: 58.77 µg/ml). However, the methanolic extract of variety G.136 did not show any measurable DPPH activity.

Ferric reducing antioxidant power assay (FRAP)

A significant difference was found between the tested cultivars at a significance level of P < 0.0001, as illustrated by the antioxidant capacity of various sample extracts in Fig. 2. After comparing the acetone extracts of different varieties, the G.136 variety showed the highest antioxidant activity (447 μM trolox/mg extract), while the G.127 variety showed the subsequent highest antioxidant activity (426 μM trolox/mg extract). As expected from the results of DPPH, the ethanolic extracts of cultivars G.136 and G.127 showed the lowest levels of antioxidant activity (132.1 and 91.2 μM trolox/mg extract, respectively).

Fig. 2
figure 2

FRAP activity of the three barley varieties in different solvents. Significant differences among means of different treatments were determined using Bonferroni posttests at P < 0.001 (n = 3) with all solvent extracts compared to each other. a, b, c, d, e significant difference compared to methanol, ethanol, water, acetone, and 80% methanol of G.136, a′, b′, c′, d′, e′ significant difference compared to methanol, ethanol, water, acetone, and 80% methanol of G.127, a″, b″, c″, d″, e″ significant difference compared to methanol, ethanol, water, acetone and 80% methanol of G.131, *corresponding to P < 0.05, **corresponding to P < 0.01, and the significance difference with P < 0.001

Full size image

Ultra high-performance liquid chromatography-mass spectrometry analysis (UHLPC-MS)

Previously, sixty-four compounds using various solvents were discovered from all extracts (under publication). Because the acetone fraction has the highest activity in the previously mentioned antioxidant activity, we shed light on its prominent components. In the acetone fraction of the three cultivars, the major identified 18 compounds are shown in Table 1 and Fig. 3. Proanthocyanidin was the most prevalent chemical class among the identified phytochemicals in the three cultivars, followed by flavonoids and hordatines in the acetone fraction. Proanthocyanidin and flavonoid abundance were highest in G.131 of all the cultivars. However, cultivars, G.127, displayed the greatest quantity of hortatines (Fig. 4).

Table 1 Metabolites using ultra high-performance liquid chromatography (UHPLC)-MS/MS of the acetone fraction in the three cultivars and their height
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Fig. 3
figure 3

Acetone fraction chromatogram of the three barley cultivars

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Fig. 4
figure 4

Chemical classes among the three varieties

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Based on a comparison of the detected component amounts in the three cultivars, quercetin 3-O-glucoside had the highest abundance among the three cultivars, with the G.131 cultivar exhibiting the highest concentration of the other varieties in addition to iso-orientin and hordatine B1; iso-orientin was also prominent in G.127 cultivar as well as prodelphinidin B3. Moreover, the main compounds in variety G.136 were tricin and procyanadin B2 as shown in Fig. 5.

Fig. 5
figure 5

Dominant compounds in the three barley cultivars (G.131, G.127 and G.136)

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Molecular docking studies

Molecular docking

The polyphenol oxidase enzyme PPO, which was obtained from the Protein Data Bank (PDB ID: 2Y9X), was docked to the identified phytochemicals and trolox, as reference antioxidant standard, to determine their potential binding mechanisms and virtual binding affinities. Docking of the 18 major detected compounds using the LIPDOCKER protocol after ligand preparation showed a LipDock score ranging from (− 61.3546 to − 143.402) (Table 2). Trolox showed hydrogen bond interaction with the essential amino acids (His85, Glu322, and Asn81) and hydrophobic interaction with (His 244).

Table 2 LipDock score of the dominant compounds beside their amino acid interactions along with the reference trolox and the ligand drug
Full size table

Hordatine A1, prodelphinidin B3, hordatine B1, and procyanadin B2 showed the highest LipDock interaction energy score relative to trolox (Fig. 6), in addition to their highest abundance in the LCMS/MS results. Moreover, hordatine A1 and prodelphinidin B3 shared the same binding interaction with the essential amino acids as trolox (His85, Glu322, Asn81, and Val283) that showed a better stability along with the LipDock score.

Fig. 6
figure 6figure 6figure 6

2D binding mode of A: hordatine A1, B: prodelphinidin B3, C: hordatine B1, D: procyanadin B2, E: isovitexin 7-O-glucoside along with reference compound, F: trolox and the ligand drug, G: 2Y9X

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In vitro predictive Absorption, Distribution, Metabolism, Excretion, and Toxicity (ADMET) study

The ADMET investigation, carried out using Discovery Studio 4.1 Software, focused on the molecular composition of the compound and included the computation of various parameters [30]. These parameters included: ADMET solubility level, Blood Brain Barrier Level (BBB LEV), and CYP2D6. Most of the compounds in the ADMET plot exhibited BBB levels ranging between 3 and 4. In the HIA plot, a significant portion of the compounds were located outside the 99% ellipse. Furthermore, many of these compounds had an ADME aqueous solubility rating falling between 3 and 4. The CYP2D6 score serves as an indicator of whether a specific chemical structure is inhibitory or non-inhibitory to the cytochrome P450 2D6 enzyme.

The key property, PSA (polar surface area), is a factor associated with drug bioavailability. Generally, molecules with a PSA greater than 240 are assumed to have limited bioavailability when passively absorbed (Fig. 7; Table 3).

Fig. 7
figure 7

ADMET Plot of the 2D polar surface area (PSA_2D) against calculated ALogP98 for examined compounds

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Table 3 Computer-aided ADMET screening and TOPKAT Ames Toxicity study results of the identified compounds
Full size table

TOPKAT toxicity studies

The compounds that were previously prepared underwent (TOPKAT) toxicity protocol [31], which involved evaluating them based on specific criteria, including Ames Prediction, Hepatotoxic Prediction, Rat Oral LD50, and Carcinogenic Potency. This methodology was designed to gauge the potential toxicity of newly developed substances (Table 3).

Discussion

Natural antioxidants are significantly more beneficial and efficient in combating oxidative stress when compared to their synthetic counterparts. Medications derived from plant products are considered safer for consumption [32].

The DPPH radical dot assay is commonly employed to evaluate the free radical scavenging capabilities of an antioxidant molecule. It is recognized as a standard and straightforward colorimetric method for assessing antioxidant properties [33].

It is noteworthy that the acetone extract from variety G.136 exhibited the most substantial antioxidant activity. Following closely, the acetone extract derived from variety G.127 demonstrated the second-highest antioxidant potency. Conversely, it is essential to highlight that the methanolic extract obtained from variety G.131 did not manifest any detectable DPPH activity.

The FRAP assay stands out as a straightforward, rapid, and cost-effective direct technique for gauging the total antioxidant activity of reductive antioxidants present in a test sample [34].

In line with the findings from the DPPH assay, it was observed that the G.136 variety exhibited the highest antioxidant activity, followed by the G.127 variety with a slightly lower but still significant antioxidant activity. Interestingly, in contrast with the acetone extracts discussed earlier, the ethanolic extracts of cultivars G.136 and G.127 displayed the lowest levels of antioxidant activity.

Numerous studies have suggested that pure water is not an efficient solvent for extracting polyphenols due to their higher solubility in solvents that are less polar than water [35]. Comparable findings were published by Zhu et al. [36] concerning the significant antioxidant activity of the Chinese-grown barley acetone extract.

Among the identified phytochemical classes in the three cultivars, proanthocyanidins were the most prevalent, followed by flavonoids and hordatines in the acetone fraction. Specifically, proanthocyanidins and flavonoids were most abundant in G.131, while G.127 exhibited the highest quantity of hordatines. Quercetin 3-O-glucoside was the most abundant component across all cultivars, with G.131 having the highest concentration of this compound compared to the other varieties.

A docking study was applied on the most prominent compounds in the acetone fractions, hordatine A1, prodelphinidin B3, hordatine B1, and procyanidin B2 exhibited the highest LipDock interaction energy scores compared to trolox.

Furthermore, these compounds also demonstrated the highest abundance in the LCMS/MS results. Likewise, these compounds previously revealed antioxidant activity [37, 38].

After making ADMET and TOPKAT studies of the dominant compounds in the acetone fractions, the compounds' Absorption, Distribution, Metabolism, and Excretion Toxicity could be determined.

This suggests that they are unlikely to permeate the blood–brain barrier and, consequently, are unlikely to cause adverse effects in the central nervous system (CNS) adverse effects. They are likely to have limited absorption in the intestines suggesting that they possess good aqueous solubility; the expected values for these compounds indicate good passive oral absorption for most of them, which is a positive attribute for their pharmacological effectiveness.

In this context, since these compounds are classified as non-inhibitors of CYP2D6, it suggests that their usage is not likely to lead to adverse effects such as liver impairment.

The results of all TOPKAT Ames probabilities, applications, and scores indicated that these compounds are non-mutagenic and non-carcinogenic, and they fell within the anticipated ranges.

Conclusion

The present study offers valuable insights into the antioxidant applications of different solvents extracts of three different cultivars. The acetone extracts of the three cultivars showed the best results compared to other solvents. G.136 variety showed the highest level of antioxidant activity in both the DPPH and FRAP assays. A docking study was conducted for the 18 major compounds in the acetone fractions of the three varieties followed by ADMET and TOPKAT studies. Hordatine A1, prodelphinidin B3, hordatine B1, procyanidin B2, and isovitexin 7-O-glucoside demonstrated the highest LipDock scores when compared to the reference standard drug. Additionally, these compounds exhibited the highest areas among other constituents in the three cultivars. The results of the current study could offer valuable insights for defining new research avenues regarding the utilization and applications of the examined extracts with specific solvents as pharmaceutical and nutraceutical agents.

Availability of data and materials

The data that support the findings of this study are available from the corresponding author, upon reasonable request.

Abbreviations

DPPH:

2,2-Diphenyl-1-picrylhydrazyl

FRAP:

Ferric reducing antioxidant power assay

ADMET:

Absorption, Distribution, Metabolism, Excretion, and Toxicity

TOPKAT:

Toxicity Prediction by Komputer Assisted Technology

PPOs:

Polyphenol oxidases

PDB:

Protein Data Bank

(UHPLC)-MS/MS:

Ultra high-performance liquid chromatography

PSA:

Polar surface area

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Acknowledgements

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Funding

This research received no external funding

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Authors and Affiliations

  1. Department of Pharmacognosy and Medicinal Plants, Faculty of Pharmacy, Future University in Egypt, Cairo, 12311, Egypt

    Omneya Eid & Wafaa M. Elkady

  2. Pharmacognosy Department, Faculty of Pharmacy, Cairo University, Kasr el Aini St., Cairo, 11562, Egypt

    Shahira Ezzat, Abeer El Sayed & Essam Abd el-sattar

  3. Department of Pharmacognosy, Faculty of Pharmacy, October University for Modern Sciences and Arts (MSA), Giza, 12451, Egypt

    Shahira Ezzat

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  1. Omneya Eid
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Contributions

Conceptualization was performed by O.E.; S.E.; and W.E.; data curation by O.E.; investigation by O.E.; methodology by O.E.; supervision by S.E.; W.E.; A.E.; and E.A.; visualization by O.E.; S.E.; and W.E.; writing—original draft by O.E. and W.E.; writing—review & editing by O.E.; S.E.; W.E.; and E.A. All authors read and approved the final manuscript.

Corresponding author

Correspondence to Shahira Ezzat.

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Ethics approval and consent to participate

Ethical approval was obtained from the research ethics committee, Faculty of Pharmacy, Cairo University, serial number MP (2413).

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Not applicable.

Competing interests

The authors declare that they have no competing interests.

Plant authentication

The Whole barley grains (Hordeum vulgare L.) from three distinct cultivars were gathered from the Agriculture Research Center in Egypt and sourced from different geographic locations in Egypt. The three commonly cultivated H. vulgare varieties in Egypt, namely Giza 136 (G.136), Giza 127 (G.127), and Giza 131 (G.131) were utilized.

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Eid, O., Ezzat, S., Elkady, W.M. et al. Evaluation of antioxidant activity in different Egyptian barley cultivars: an in vitro and in silico study. Futur J Pharm Sci 10, 69 (2024). https://doi.org/10.1186/s43094-024-00642-0

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