Startseite Naturwissenschaften Phytochemical screening and antioxidant activity of Vitex agnus-castus L.
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Phytochemical screening and antioxidant activity of Vitex agnus-castus L.

  • Soufiane Drioua , Hanane Azalmad , Otman El-Guourrami , Mouna Ameggouz , Fatima Zahra Benkhouili , Amine Assouguem EMAIL logo , Mohammed Kara , Riaz Ullah , Essam A. Ali , Sezai Ercisli , Hafize Fidan , Hanane Benzeid und Anass Doukkali
Veröffentlicht/Copyright: 19. Januar 2024
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Open Chemistry
Aus der Zeitschrift Open Chemistry Band 22 Heft 1

Abstract

This research is dedicated to investigating the antioxidant potential and phytochemical composition of three distinct extracts derived from Vitex agnus-castus L. These extracts, prepared through aqueous (EXA), ethanolic (EXE), and methanolic (EXM) maceration, were chosen based on prior assessments of total polyphenol content in extracts obtained from five solvents with differing polarities: water, methanol, ethanol, acetone, and butanol. The study initiated with a comprehensive phytochemical analysis focusing on the determination of total polyphenols and flavonoids. The quantification of total polyphenols was carried out using the Folin–Ciocalteu method, while the AlCl3 method was employed to assess flavonoids. In evaluating the in vitro antioxidant activity, we employed two well-established methods, 2,2-diphenyl-1-picrylhydrazyl (DPPH) and ferric-reducing antioxidant power (FRAP). The preliminary tests, gauging the efficacy of solvents, demonstrated that the order of optimal solvent selection was as follows: aqueous, methanolic, ethanolic, butanolic, and acetone. Consequently, the first three solvents were chosen for the preparation of the extracts. The phytochemical analysis unveiled that EXA exhibited the highest total polyphenol content, with an impressive value of 126.84 ± 1.24 mg EAG/g extract, whereas EXE exhibited the lowest concentration of total polyphenols, measuring at 117.26 ± 0.18 mg EAG/g extract. In contrast, EXM showcased a notably high flavonoid content, registering at 33.65 ± 1.04 mg EQ/g extract, while EXA displayed a comparatively lower flavonoid content at 14.93 ± 0.14 mg EQ/g extract. When assessing antioxidant properties, EXA emerged as the most potent against both DPPH and FRAP, recording values of 78.94 ± 1.84 and 203.27 ± 0.17 μg/ml, respectively. In contrast, the ethanolic extract exhibited relatively lower antioxidant activity, with values of 204.16 ± 1.87 μg/ml for DPPH and 307.10 ± 1.15 μg/ml for FRAP.

Keywords: Vitex agnus-castus ; polyphenols; antioxidant activity; phytochemical screening

1 Introduction

Using plants for healing is a universal practice known for thousands of years and was the primary source of remedies in the past. Today, this practice is referred to as “phytotherapy,” which signifies medicine based on the natural active principles of plants. This designation originates from the Greek words “phuton,” which translates to “plant,” and “therapia,” meaning “treatment.” With the development of medical chemistry in the early nineteenth century, plants became the first essential source of medicine. Today, despite significant advancements in synthetic pharmaceutical chemistry and microbial fermentation, 25% of prescribed drugs in industrialized countries have a plant origin [1].

The World Health Organization considers this therapy as part of traditional medicine. It can be applied either on its own or as a complementary approach alongside other forms of medicine, whether traditional or allopathic. Caution and proper guidelines must be followed when using it. Due to its history and scope, this therapy encompasses all specialties that exist in the medical world. It is recommended for premenstrual syndrome (PMS), which includes the physical and psychological symptoms that women may experience before or during their menstruation.

Today, herbal treatments are coming to the forefront because the effectiveness of drugs such as antibiotics is declining. The use of medicinal plants in phytotherapy has garnered significant interest in biomedical research and is becoming as important as chemotherapy. This renewed interest arises from the fact that medicinal plants offer an endless source of bioactive natural substances and compounds and the need for gentler therapy with fewer side effects in the quest for improved medication [2].

Morocco has a long history in traditional medicine. It is a country with highly diverse geography and boasts a rich and varied flora, including approximately 4,200 plant species, of which 800 are recognized in traditional medicine [3].

Vitex agnus-castus L., commonly known as chaste tree or monk’s pepper, has been extensively studied across diverse scientific domains owing to its historical medicinal significance. Research studies encompass a spectrum of investigations, from its traditional application in hormonal regulation, particularly in addressing menstrual irregularities and PMS, to modern pharmacological explorations elucidating its bioactive compounds, including flavonoids, iridoids, and essential oils. Studies delve into its impact on hormonal balance, notably dopamine and prolactin levels, suggesting potential effects on the endocrine system. Clinical trials and observational studies have examined its efficacy in managing PMS symptoms, irregular menstruation, breast pain, and even its role in fertility support. Additionally, investigations into its neurological effects on mood regulation and anxiety, pharmacokinetics, receptor interactions, toxicological assessments, and safety profiles contribute significantly to understanding its pharmacological actions and potential therapeutic applications. Collectively, these multidisciplinary studies bridge traditional knowledge with contemporary scientific insights, enriching our comprehension of Vitex agnus-castus and its plausible roles in women’s health, hormonal balance, and beyond [4].

Vitex agnus castus L. is a plant that has been used for hundreds of years and may have certain efficacy. Its potential mechanisms of action are still not fully understood, but there is ongoing research partially investigating its effects.

The plant has been used for various health benefits, including the treatment of menstrual disorders, acne, and fertility issues. It has been found to contain chemicals that affect many hormones involved in the female reproductive cycle [5]. Some of the key prior works involving Vitex agnus-castus include studies on the effects of Vitex agnus-castus on hormone levels and menstrual cycle symptoms. These studies have shown that Vitex agnus-castus may help reduce symptoms of PMS and menopause, as well as improve fertility [6].

The aim of our work is to study the chemical composition of chaste tree seeds, characterize the different chemical groups, and assess their antioxidant activity. The interest in selecting this plant is due to the richness of our country in aromatic and medicinal plants, particularly this plant, while also highlighting that very few studies have been conducted on the seeds of the chosen plant. Therefore, this study on the chaste tree was initiated in the first instance to determine its main characteristics and more precisely, to evaluate the polyphenolic and flavonoid constituents of various extracts from (Vitex agnus castus L.) and assess the in vitro potential of these extracts to inhibit or protect against oxidative damage.

2 Materials and methods

2.1 Plant materials

The chaste tree seeds used in this study were purchased from an herbalist in the Beni Mellal-Azilal region. The plant material was ground into a fine powder using a blender to prepare extracts.

2.2 Extraction procedure

2.2.1 Solvent screening test

The objective of this experiment is to determine the solvents that have demonstrated the best extraction of total polyphenols from dry plant material. To carry out this test, 50 mg of the dry plant material was placed in five test tubes, to which 1 ml of the following solvents (ethanol, methanol, acetone, distilled water, and butanol) was added, respectively. These mixtures were macerated for 24 h in the dark at room temperature. After maceration, we filtered the extracts and then proceeded with quantification using the Folin–Ciocalteu method. The measurements were taken using a spectrophotometer at a wavelength of 765 nm.

2.2.2 Preparation of extracts

A method called maceration was employed, which involves extracting the maximum amount of active compounds contained in the plant. A quantity of 50 g of the finely ground dry plant material is macerated in 1,000 mL of three solvents, namely distilled water, ethanol, and methanol, for 24 h at room temperature. The extracts obtained in this manner are vacuum-filtered, evaporated at a temperature of 40°C using a rotary evaporator to remove most of the solvent, and concentrated the extract. The remaining filtrate is subsequently placed in brown bottles.

2.3 Yield calculation

The yield is calculated using the following formula:

Yield ( % ) = ( M ex / M th ) × 100 ,

where M ex, experimental mass (in g), is the mass of the dry extract and M th, the theoretical mass (in g), is the mass of the dry plant material.

This formula expresses the yield as a percentage, indicating fraction of the theoretical mass actually obtained in the experiment.

2.4 Phytochemical screening

The obtained fractions were utilized in a preliminary phytochemical screening, a series of procedures and techniques aimed at detecting secondary metabolites present in plants. This process is qualitative in nature and relies on coloration and/or precipitation reactions to identify major chemical compound categories. Various reagents were applied for this purpose, using the analytical methods described in previous studies [7,8].

2.5 Phytochemical analysis

2.5.1 Determination of total polyphenols

The total polyphenol content of the various extracts is determined using the Folin–Ciocalteu method. The Folin–Ciocalteu reagent is a yellow-colored acid composed of a mixture of phosphotungstic acid (H3PW12O40) and phosphomolybdic acid (H3PMo12O40). This reagent is reduced through oxidation by phenolic compounds, resulting in a mixture of tungsten blue (W8O23) and molybdenum blue (Mo8O3) with a blue coloration. The intensity of this coloration is directly proportional to the levels of oxidized phenolic compounds. To do this, 2.5 mL of the Folin–Ciocalteu reagent solution (diluted ten times in distilled water) is added to 0.5 mL of the extracts in test tubes. The mixture is then vortexed to ensure thorough mixing. Next, 4 mL of 7.5% (m/v) sodium carbonate (Na2CO3) is added to create an alkaline environment, initiating the redox reaction. The mixture is then incubated in a water bath at 45°C for 30 min. The intensity of the blue coloration produced is measured using a spectrophotometer at a wavelength of 765 nm [9].

The study utilized a UV-visible spectrophotometer, an instrumental tool pivotal in measuring the absorption characteristics of substances across the ultraviolet and visible spectrum. The spectrophotometer employed an optical system (single or double beam) along with a light source, like deuterium and tungsten lamps, for precise wavelength illumination. Its operational range covered wavelengths from the ultraviolet (around 190 nm) to the visible range (extending up to 800 nm or beyond), ensuring comprehensive analysis. The instrument exhibited a high degree of accuracy in wavelength readings, which is vital for meticulous spectral analyses. Additionally, it offered adjustable spectral bandwidth or resolution, allowing for tailored measurement settings. Equipped with mentioned detector type, such as photodiode arrays or photomultiplier tubes, the spectrophotometer provided reliable detection and quantification of absorption values. Further details encompassed the cell holder configuration accommodating various cell sizes for sample containment during measurements. The study’s spectrophotometer was complemented by sophisticated software for data acquisition and analysis, providing a user-friendly interface for control and facilitating precise interpretation of results [10].

2.5.2 Dosage of flavonoids

The quantification of flavonoids is carried out using the Dewanto colorimetric method, employing aluminum trichloride (AlCl3) and sodium hydroxide (NaOH) as reagents. AlCl3 forms a yellow complex with flavonoids, and NaOH forms a pink complex that absorbs in the visible spectrum at 510 nm. In test tubes, 1 mL of each extract (1 mg/mL) and 6.4 mL of distilled water were successively introduced. Then, 0.3 mL of 5% (m/v) sodium nitrite solution (NaNO2) was added. After 5 min, 0.3 mL of 10% (m/v) AlCl3 was added, and the mixture was allowed to stand for 6 min. Subsequently, 2 mL of 1 M NaOH was added, and the solution was thoroughly mixed. The entire mixture was incubated in the shade at room temperature for 30 min. Absorbance was immediately measured at a wavelength of 510 nm. The total flavonoid contents in each extract were calculated by referring to the calibration curve equation, established using quercetin as the standard reference at various concentrations under the same conditions and steps of the assay [11].

2.6 Antioxidant activities

2.6.1 DPPH free radical scavenging activity

The evaluation of the antioxidant activity of various extracts against the 2,2-diphenyl-1-picrylhydrazyl (DPPH°) radical is based on the method described by Şahin et al. [12]. This method relies on measuring the ability of antioxidants to scavenge the DPPH° radical. This radical, initially violet in color, is reduced to 2,2-diphenyl-1-picrylhydrazine, which is yellow, upon accepting a hydrogen radical. The results are expressed in milligrams of quercetin equivalents per gram of extract (mg EQ/g extract).

In test tubes, 2.5 mL of different concentrations of each extract and 0.5 mL of freshly prepared methanolic DPPH solution were introduced. The mixture was vigorously vortexed and then placed in the dark at room temperature for 30 min. After vortexing, the change in the color was measured by recording the absorbance at a wavelength of 517 nm. The antioxidant activity of the extracts is expressed as IC50 (inhibitory concentration 50), a parameter defined as the concentration of the antioxidant that causes a 50% loss of DPPH activity.

The percentage of DPPH radical reduction (PR) is calculated using the following formula:

Antiradical activity ( % ) = ( ( A control – A sample ) / A control ) × 100 .

where “A control” is the absorbance of the control and “A sample” is the absorbance of the tested samples. The measurement is performed at 517 nm, and the results are compared to a standard containing quercetin at various concentrations.

2.6.2 Ferric-reducing antioxidant power (FRAP) test

This test is based on the reduction of ferric iron (Fe3+) to ferrous iron (Fe2+). The ability of our extracts to transfer electrons to the ferric iron ion was determined following the protocol established by Oyaizu et al. [13]. Concentrations of our samples and the positive control (catechin) were prepared. In each test tube, 0.2 mL of each sample, 2.5 mL of a phosphate buffer (0.2 M, pH = 6.6), and 2.5 mL of 1% potassium ferricyanide complex (K3Fe(CN)6) were added. The mixture was incubated in a water bath at 50°C for 20 min. After incubation, 2.5 mL of 10% trichloroacetic acid was added to stop the reaction. Subsequently, 2.5 mL of each tube was mixed with 2.5 mL of distilled water and 0.5 mL of 0.1% iron chloride (FeCl3).

Absorbance was measured at a wavelength of 700 nm with calibration of the spectrophotometer using the mixture without the extract. The test was conducted in triplicate, and the concentration that converts 50% of Fe3+ to Fe2+ was calculated.

2.7 Statistical analysis

Statistical analysis was carried out using GraphPad Prism version 8 software. Data were expressed as mean ± standard deviation.

3 Results and discussion

3.1 Solvent screening test

The results of this test, expressed in milligrams equivalent gallic acid per gram of dry plant material (mg EAG/g dry matter), are shown in Table 1.

Table 1

Dosage of total polyphenols

Extract Total polyphenols (mg EAG/g extract)
Ethanol 32.09 ± 1.2
Butanol 24.91 ± 0.180
Acetone 18.97 ± 0.03
Methanol 38.22 ± 1.89
Water 50.91 ± 0.13

The solvent screening test conducted in this study aimed to determine the total polyphenol content of different extracts obtained from the plant material. The results, expressed in mg EAG/g dry matter, are presented in Table 1. This test assessed the effectiveness of various solvents in extracting polyphenolic compounds from the plant material and provided valuable insights into the choice of solvent for subsequent extraction processes.

The results indicate varying levels of total polyphenols in the different extracts, with significant differences among the solvents used. Notably, water extraction (50.91 mg EAG/g extract) yielded the highest concentration of polyphenols. This result underscores the efficiency of water as an extracting solvent for polyphenolic compounds, indicating its potential as an excellent choice for the extraction of these valuable phytochemicals.

Methanol extraction (38.22 mg EAG/g extract) also demonstrated a high polyphenol content, making it a suitable option for extracting polyphenols from the plant material. Ethanol extraction (32.09 mg EAG/g extract) provided a moderate but notable level of polyphenols, indicating its effectiveness in capturing these compounds.

Butanol (24.91 mg EAG/g extract) and acetone (18.97 mg EAG/g extract) extractions resulted in relatively lower levels of polyphenols compared to the other solvents. These solvents may be less efficient at extracting polyphenolic compounds from the plant material.

In summary, the solvent screening test highlights the critical role of the choice of solvent in extracting polyphenolic compounds from the plant material. Water and methanol emerge as the most effective solvents for extracting polyphenols, with water being particularly efficient in this regard. These results have practical implications for the design of extraction processes for polyphenols, emphasizing the importance of selecting an appropriate solvent to maximize the yield of these valuable compounds.

3.2 Yield calculation

The extraction yield is the ratio of the quantity of substances extracted by the extracting action of a solvent to the quantity of plant material. It depends on several parameters, such as the solvent used, temperature, extraction time, and the composition of the sample. The yields of the aqueous, ethanolic, and butanolic extracts of chaste tree seeds are provided in Table 2.

Table 2

Yield of different extracts of Vitex agnus castus L.

Plant extracts Color Yield (%)
Aqueous extract Verdate brown 5.8
Methanolic extract Dark green 4.9
Ethanolic extract Dark green 6.62

The result of the extraction yields for the chaste tree (Vitex agnus castus L.) extracts show that the ethanolic extract has a yield of approximately 6.62%, which is the highest yield, followed by the aqueous extract at 5.8%, and finally, the methanolic extract has the lowest yield at 4.9%. Extraction yield depends on several factors that can influence the extraction performance, such as the solubilization capacity of compounds, temperature, and extraction time.

3.3 Phytochemical screening

The identification of various classes of secondary metabolites present in plants provides insight into their pharmacological activities. We conducted phytochemical tests on the aqueous, ethanolic, and butanolic extracts of chaste tree seeds. These tests are related to the intensity of precipitation and coloration, which are proportional to the quantity of the sought-after substance. The results of the phytochemical screening of chaste trees are presented in Table 3.

Table 3

Phytochemical characterization of different chaste tree seed extracts

Compounds Plant
Alkaloids Mayer reagent +
Dragendorff reagent ++
Polyphenols +++
Flavonoids Flavonols −
Flavones ++
Flavonones −
Tannins Catechins −
Gallic and ellagic −
Terpenoids +++
Sterols and triterpenes +++

The presence of chemical compounds is indicated as follows: (+++) significant, (++) moderate, (+) slight, and (−) absent.

Table 3 offers a detailed insight into the phytochemical composition of Vitex agnus-castus L., presenting a diverse array of compounds within the plant. Alkaloids, indicated by positive reactions with Mayer and Dragendorff reagents, suggest their presence, aligning with their known medicinal significance.

The substantial presence of polyphenols underscores the plant’s antioxidant potential, which is crucial for its possible health benefits. Within the flavonoid category, while flavones and flavonols exhibit varied intensities, the absence of flavonones suggests their limited presence. Tannins, particularly catechins, gallic, and ellagic types, appear to be relatively low or absent.

Conversely, terpenoids and sterols/triterpenes demonstrate considerable abundance, indicating their potential pharmacological significance. This comprehensive profile of compounds in Vitex agnus-castus underscores their complex chemical composition, hinting at their potential therapeutic and medicinal applications that deserve further exploration and research.

3.4 Phytochemical analysis

3.4.1 Determination of total polyphenols

The quantification of total polyphenols was performed through extrapolation based on a calibration curve generated using a standard (gallic acid) at various concentrations, following the same conditions as the extracts. The results are expressed in milligrams of gallic acid equivalent per gram of dry plant material (mg EAG/g extract), utilizing the linear regression equation of the gallic acid calibration curve.

The total polyphenol content, expressed in milligrams equivalent gallic acid per gram of extract (mg EAG/g extract), is presented in Table 4.

Table 4

Total polyphenol assay results of Vitex agnus castus L.

Plant extracts Total polyphenol content (mg EAG/g extract)
Aqueous extract 126.84 ± 1.24
Methanolic extract 121.64 ± 2.10
Ethanolic extract 117.26 ± 0.18

Table 4 provides insight into the total polyphenol content of the aqueous extract, methanolic extract, and ethanolic extract of Vitex agnus-castus, expressed in milligrams equivalent gallic acid per gram of extract (mg EAG/g extract). Polyphenols are renowned for their antioxidant properties and potential health benefits. This analysis allows us to understand the polyphenolic composition of these extracts and their potential as sources of antioxidants.

The aqueous extract exhibited the highest total polyphenol content among the three extracts, with a value of 126.84 mg EAG/g extract. This result indicates a substantial concentration of polyphenolic compounds within the aqueous extract.

The methanolic extract also displayed a considerable total polyphenol content, measured at 121.64 mg EAG/g extract. This value underscores the presence of polyphenolic compounds within the methanolic extract, which contributes to its antioxidant potential.

Similarly, the ethanolic extract showed a substantial total polyphenol content, with a value of 117.26 mg EAG/g extract. This result indicates that the ethanolic extract also contains a significant amount of polyphenolic compounds, reinforcing its potential as an antioxidant source.

In summary, the total polyphenol content analysis reveals that all three extracts of Vitex agnus-castus are rich in polyphenolic compounds. The aqueous extract exhibits the highest concentration, followed closely by the methanolic and ethanolic extracts. These polyphenols are essential contributors to the antioxidant potential of these extracts.

The variations in total polyphenol content highlight the diverse composition of bioactive compounds present in Vitex agnus-castus, depending on the extraction method employed. These differences play a role in the varying levels of antioxidant potential observed in previous assays.

3.4.2 Dosage of flavonoids

The concentration of flavonoids in chaste tree (Vitex agnus castus L.) extracts is determined using a spectrophotometric method with aluminum chloride. The content of flavonoids is expressed in milligrams of quercetin equivalent per gram of extract (mg EQ/g extract).

The total polyphenol content, expressed in milligrams equivalent quercetin per gram of extract (mg EQ/g extract), is presented in Table 5.

Table 5

Contents of flavonoids of Vitex agnus castus L.

Plant extracts Contents of flavonoids (mg EQ/g extract)
Aqueous extract 14.93 ± 0.14
Methanolic extract 33.65 ± 1.04
Ethanolic extract 25.775 ± 0.84

Table 5 presents the contents of flavonoids in the aqueous extract, methanolic extract, and ethanolic extract of Vitex agnus-castus, expressed in milligrams equivalent quercetin per gram of extract (mg EQ/g extract). Flavonoids are a subgroup of polyphenolic compounds known for their antioxidant properties and various health benefits. Comparing the flavonoid content of these extracts provides insights into their potential antioxidant capabilities.

The aqueous extract exhibited a flavonoid content of 14.93 mg EQ/g extract. While this value indicates the presence of flavonoids in the extract, it is essential to recognize that this is a lower concentration compared to the other extracts. Flavonoids are key contributors to antioxidant activity, and their presence suggests potential free radical-scavenging capabilities within the aqueous extract.

In contrast, the methanolic extract contained a notably higher flavonoid content of 33.65 mg EQ/g extract. This finding suggests that the methanolic extract is rich in flavonoids, which are likely responsible for a significant portion of its antioxidant potential.

The ethanolic extract also contained a substantial flavonoid content, measured at 25.775 mg EQ/g extract. While slightly lower than the methanolic extract, this value indicates a considerable presence of flavonoids in the ethanolic extract, emphasizing its potential as an antioxidant source.

In summary, the flavonoid content analysis demonstrates that both the methanolic and ethanolic extracts of Vitex agnus-castus contain a substantial amount of flavonoids, which are well-documented for their antioxidant properties. The aqueous extract, while showing a lower flavonoid content, still exhibits the presence of these important compounds.

The variation in flavonoid content among the extracts underscores the diverse composition of bioactive compounds within Vitex agnus-castus, depending on the extraction method. These differences contribute to the varying levels of antioxidant potential observed in previous assays.

3.5 Antioxidant activities

3.5.1 DPPH free radical scavenging activity

In this study, antioxidant activity is defined based on the percentage of scavenging (or inhibition) of the free radical DPPH. Since there is no absolute measure of the antioxidant capacity of a compound, the results are expressed relative to quercetin as a reference antioxidant and are presented in Table 6.

Table 6

Antioxidant activity of extracts of Vitex agnus castus L. using DPPH

Plant extracts DPPH IC50 (µg/ml)
Aqueous extract 78.94 ± 1.84
Methanolic extract 207.89 ± 0.67
Ethanolic extract 204.16 ± 1.87
Quercetin 5.49 ± 0.02

The results of the antioxidant activity evaluation for the methanolic extract, ethanolic extract, and aqueous extract of Vitex agnus-castus, in comparison to the reference compound quercetin [14], provide valuable insights into the potential use of these extracts as sources of natural antioxidants.

Quercetin, a well-known flavonoid with potent antioxidant properties, served as the reference standard in this study. It exhibited a remarkably low IC50 value of 5.49 µg/ml, highlighting its strong antioxidant activity. This result validates the sensitivity and reliability of the DPPH assay used in the study and serves as a benchmark for assessing the extracts’ antioxidant potential.

In contrast, the methanolic extract, with an IC50 value of 207.89 µg/ml, and the ethanolic extract, with an IC50 value of 204.16 µg/ml, displayed moderately higher IC50 values when compared to quercetin. These values suggest that both the methanolic and ethanolic extracts possess moderate antioxidant activity. While not as potent as quercetin, their ability to neutralize free radicals indicates that they can contribute to reducing oxidative stress and related damage.

The aqueous extract of Vitex agnus-castus demonstrated the strongest antioxidant activity among the tested extracts, with an IC50 value of 78.94 µg/ml. Although its IC50 value is higher than that of quercetin, it is important to note that natural extracts often contain a complex mixture of compounds, each with its own antioxidant properties. This diversity of antioxidants can have a cumulative effect, potentially enhancing their overall capacity to combat oxidative stress and protect cells from damage.

In summary, the methanolic and ethanolic extracts, while not as potent as quercetin, display moderate antioxidant activity, which is promising for their potential use as natural antioxidants. The aqueous extract, while exhibiting the strongest antioxidant activity among the tested extracts, also shows potential as a source of antioxidants. These findings underscore the diversity of antioxidant compounds present in Vitex agnus-castus through different extraction methods.

3.5.2 FRAP test

The evaluation of the antioxidant activity of chaste tree seed extracts using the FRAP method is based on the reduction of ferric ions Fe3+ to ferrous ions Fe2+. The presence of ferrous ions can be assessed by measuring and monitoring the increase in absorbance of the reaction medium at 700 nm. Catechin is used as the reference antioxidant. Table 7 presents the values of IC50 concentrations (the concentration equivalent to an absorbance of 0.5) obtained for catechin and for each chaste tree extract.

Table 7

Antioxidant activity of extracts of Vitex agnus castus L. using FRAP

Plant extracts FRAP EC50 (µg/ml)
Aqueous extract 203.27 ± 0.17
Methanolic extract 307.10 ± 1.15
Ethanolic extract 211.98 ± 0.74
Catechin 19.54 ± 0.25

Catechin, a well-known and widely studied flavonoid, serves as the reference compound in this study. It displayed a notably low FRAP EC50 value of 19.54 µg/ml, indicating its strong antioxidant activity. This result underscores the reliability of the FRAP assay in assessing antioxidant potential and sets a high benchmark for the extracts’ performance.

In comparison, the methanolic extract exhibited an FRAP EC50 value of 307.10 µg/ml, indicating relatively lower antioxidant activity when compared to catechin [14]. Similarly, the ethanolic extract displayed an FRAP EC50 value of 211.98 µg/ml, suggesting moderate antioxidant potential. While both extracts show higher EC50 values compared to catechin, these values are still within a range that implies antioxidant capacity.

The aqueous extract, with an FRAP EC50 value of 203.27 µg/ml, also demonstrated moderate antioxidant activity. While its EC50 value is higher than that of catechin, it is important to consider that natural extracts often contain a mixture of antioxidants, which, when combined, can contribute to a cumulative antioxidant effect.

These findings highlight that the aqueous extract, methanolic extract, and ethanolic extract all possess antioxidant potential, albeit at different levels when compared to the reference compound catechin. These variations in the antioxidant activity may be attributed to differences in the composition of bioactive compounds within each extract, as well as the efficiency of the extraction methods employed.

In conclusion, the results of the FRAP assay suggest that while the methanolic, ethanolic, and aqueous extracts of Vitex agnus-castus may not match the exceptional antioxidant activity of catechin, they still exhibit moderate to low antioxidant potential. This is an encouraging finding, as it implies that these extracts can contribute to reducing oxidative stress and its associated health risks.

The results reported by Hajdú et al. [15], l’extrait d’acétate d'éthyle des fruits de Vitex agnus-castus a été examiné. Cet extrait contient des composants flavonoïdes, en particulier la casticine, la vitexine et l’orientine. Les flavonoïdes sont une classe de composés polyphénoliques naturels connus pour leurs puissants effets antioxydants. Ces composés ont la capacité de neutraliser les radicaux libres nocifs et de réduire le stress oxydatif dans l’organisme. La présence de ces flavonoïdes dans l’extrait d’acétate d'éthyle suggère que cette fraction de Vitex agnus-castus possède un potentiel antioxydant.

According to Sağlam et al. [16], a porté sur les extraits d'éthanol, de n-hexane et d’eau des feuilles et des fruits de la plante. Ces extraits contiennent des flavonoïdes et des tanins, tous deux reconnus pour leurs propriétés antioxydantes. Les flavonoïdes sont connus pour leur capacité à piéger les radicaux libres, tandis que les tanins peuvent chélater efficacement les ions métalliques qui contribuent aux dommages oxydatifs. La diversité des composés antioxydants présents dans les différentes parties de la plante souligne le potentiel du Vitex agnus-castus à fournir des effets antioxydants complets.

Selon Sarikurkcu et al. [17], divers extraits, dont l’huile essentielle, l’eau, l’hexane, le dichlorométhane, l’acétate d'éthyle et les extraits de méthanol des fruits de Vitex agnus-castus, ont été analysés pour leur teneur en composés phénoliques et en flavonoïdes. Les composés phénoliques, en particulier les acides phénoliques et les flavonoïdes, jouent un rôle clé dans la capacité antioxydante de nombreuses plantes. La présence de composés phénoliques et flavonoïdes dans ces extraits indique leur potentiel d’atténuation du stress oxydatif.

L’étude de Mesaik et al. [18], s’est concentrée sur l’extrait méthanolique des feuilles et a révélé la présence de flavonoïdes et de composés phénoliques totaux. Cette découverte suggère que les feuilles de Vitex agnus-castus contiennent également des constituants antioxydants précieux, élargissant ainsi les applications potentielles de la plante au-delà de ses fruits.

The findings from these studies emphasize the varied chemical composition of Vitex agnus-castus and its promising role as a natural antioxidant source. These antioxidants are crucial in shielding against oxidative damage, a factor implicated in various health issues, including aging, inflammatory diseases, and chronic conditions.

4 Conclusion

Vitex agnus-castus, commonly known as chaste tree, is recognized as a medicinal and aromatic plant owing to its abundant secondary metabolites. It serves as a significant reservoir of diverse bioactive molecules renowned for their antioxidant, antimicrobial, and pharmacological properties. Our study pursued a dual objective: initially, to identify the most effective solvent for extraction and determine the yields of fixed extracts from Vitex agnus-castus seeds using maceration; subsequently, to conduct a qualitative and quantitative analysis of secondary metabolites and assess their in vitro antioxidant potential within these fixed extracts. Phytochemical examinations of the extracts derived from Vitex agnus-castus seeds unveiled substantial levels of polyphenols, flavonoids, and terpenoids. Evaluation of the antioxidant prowess of these extracts through the ferric reduction assay (FRAP) accentuated their ability to reduce ferric iron, notably showcasing the aqueous extract with the highest antioxidant potency. Assessment of the seed extracts’ antioxidant capabilities via the DPPH test across varying concentrations revealed robust antioxidant activity across most extracts, with the aqueous extract displaying the lowest IC50 value of 78.94 ± 1.84 compared to others. These findings underscore the inherent antioxidant capacity of the studied plant as established through the DPPH and FRAP assessments.

Future investigations in subsequent years should focus on exploring the antidiabetic, anti-inflammatory, and antimicrobial attributes of the bioactive compounds sourced from this plant. Moreover, efforts to determine their therapeutic dosage and elucidate their cellular mechanisms of action are imperative. Such advancements hold promise for the development of pharmaceutical products showing significant therapeutic potential. Additionally, the presence of phenolic compounds in our plant imparts diverse biological properties, prompting the need for employing complementary methods, like HPLC-MS, to comprehensively describe and identify specific metabolites.

Acknowledgement

The authors wish to thank Researchers Supporting Project Number (RSP2024R110) at King Saud University, Riyadh, Saudi Arabia, for financial support.

  1. Funding information: This research was funded by Researchers Supporting Project number (RSP2024R110) King Saud University, Riyadh, Saudi Arabia.

  2. Author contributions: Conceptualization: Soufiane Drioua, Hanane Azalmad, Otman El-Guourrami, Mouna Ameggouz, Fatima Zahra Benkhouili, formal analysis: Mohammed Kara, Amine Assouguem Writing—original draft preparation Soufiane Drioua, Hanane Azalmad, Otman El-Guourrami writing—review and editing, Riaz Ullah, Essam A. Ali, Sezai Ercisli, Hafize Fidan, Hanane Benzeid, Anass Doukkali, Funding acquisition; Riaz Ullah, Essam A. Ali. All authors have read and agreed to the published version of the manuscript.

  3. Conflict of interest: All authors declare no competing interests.

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

  5. Data availability statement: The datasets generated during and/or analyzed during the current study are available from the corresponding author on reasonable request.

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Received: 2023-11-08
Revised: 2023-12-11
Accepted: 2024-01-04
Published Online: 2024-01-19

© 2024 the author(s), published by De Gruyter

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

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https://doi.org/10.1515/chem-2023-0190
Schlagwörter für diesen Artikel
Vitex agnus-castus; polyphenols; antioxidant activity; phytochemical screening
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Artikel in diesem Heft

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  29. Metformin inhibits knee osteoarthritis induced by type 2 diabetes mellitus in rats: S100A8/9 and S100A12 as players and therapeutic targets
  30. Effect of silver nanoparticles formulated by Silybum marianum on menopausal urinary incontinence in ovariectomized rats
  31. Synthesis of new analogs of N-substituted(benzoylamino)-1,2,3,6-tetrahydropyridines
  32. Response of yield and quality of Japonica rice to different gradients of moisture deficit at grain-filling stage in cold regions
  33. Preparation of an inclusion complex of nickel-based β-cyclodextrin: Characterization and accelerating the osteoarthritis articular cartilage repair
  34. Empagliflozin-loaded nanomicelles responsive to reactive oxygen species for renal ischemia/reperfusion injury protection
  35. Preparation and pharmacodynamic evaluation of sodium aescinate solid lipid nanoparticles
  36. Assessment of potentially toxic elements and health risks of agricultural soil in Southwest Riyadh, Saudi Arabia
  37. Theoretical investigation of hydrogen-rich fuel production through ammonia decomposition
  38. Biosynthesis and screening of cobalt nanoparticles using citrus species for antimicrobial activity
  39. Investigating the interplay of genetic variations, MCP-1 polymorphism, and docking with phytochemical inhibitors for combatting dengue virus pathogenicity through in silico analysis
  40. Ultrasound induced biosynthesis of silver nanoparticles embedded into chitosan polymers: Investigation of its anti-cutaneous squamous cell carcinoma effects
  41. Copper oxide nanoparticles-mediated Heliotropium bacciferum leaf extract: Antifungal activity and molecular docking assays against strawberry pathogens
  42. Sprouted wheat flour for improving physical, chemical, rheological, microbial load, and quality properties of fino bread
  43. Comparative toxicity assessment of fisetin-aided artificial intelligence-assisted drug design targeting epibulbar dermoid through phytochemicals
  44. Acute toxicity and anti-inflammatory activity of bis-thiourea derivatives
  45. Anti-diabetic activity-guided isolation of α-amylase and α-glucosidase inhibitory terpenes from Capsella bursa-pastoris Linn.
  46. GC–MS analysis of Lactobacillus plantarum YW11 metabolites and its computational analysis on familial pulmonary fibrosis hub genes
  47. Green formulation of copper nanoparticles by Pistacia khinjuk leaf aqueous extract: Introducing a novel chemotherapeutic drug for the treatment of prostate cancer
  48. Improved photocatalytic properties of WO3 nanoparticles for Malachite green dye degradation under visible light irradiation: An effect of La doping
  49. One-pot synthesis of a network of Mn2O3–MnO2–poly(m-methylaniline) composite nanorods on a polypyrrole film presents a promising and efficient optoelectronic and solar cell device
  50. Groundwater quality and health risk assessment of nitrate and fluoride in Al Qaseem area, Saudi Arabia
  51. A comparative study of the antifungal efficacy and phytochemical composition of date palm leaflet extracts
  52. Processing of alcohol pomelo beverage (Citrus grandis (L.) Osbeck) using saccharomyces yeast: Optimization, physicochemical quality, and sensory characteristics
  53. Specialized compounds of four Cameroonian spices: Isolation, characterization, and in silico evaluation as prospective SARS-CoV-2 inhibitors
  54. Identification of a novel drug target in Porphyromonas gingivalis by a computational genome analysis approach
  55. Physico-chemical properties and durability of a fly-ash-based geopolymer
  56. FMS-like tyrosine kinase 3 inhibitory potentials of some phytochemicals from anti-leukemic plants using computational chemical methodologies
  57. Wild Thymus zygis L. ssp. gracilis and Eucalyptus camaldulensis Dehnh.: Chemical composition, antioxidant and antibacterial activities of essential oils
  58. 3D-QSAR, molecular docking, ADMET, simulation dynamic, and retrosynthesis studies on new styrylquinolines derivatives against breast cancer
  59. Deciphering the influenza neuraminidase inhibitory potential of naturally occurring biflavonoids: An in silico approach
  60. Determination of heavy elements in agricultural regions, Saudi Arabia
  61. Synthesis and characterization of antioxidant-enriched Moringa oil-based edible oleogel
  62. Ameliorative effects of thistle and thyme honeys on cyclophosphamide-induced toxicity in mice
  63. Study of phytochemical compound and antipyretic activity of Chenopodium ambrosioides L. fractions
  64. Investigating the adsorption mechanism of zinc chloride-modified porous carbon for sulfadiazine removal from water
  65. Performance repair of building materials using alumina and silica composite nanomaterials with electrodynamic properties
  66. Effects of nanoparticles on the activity and resistance genes of anaerobic digestion enzymes in livestock and poultry manure containing the antibiotic tetracycline
  67. Effect of copper nanoparticles green-synthesized using Ocimum basilicum against Pseudomonas aeruginosa in mice lung infection model
  68. Cardioprotective effects of nanoparticles green formulated by Spinacia oleracea extract on isoproterenol-induced myocardial infarction in mice by the determination of PPAR-γ/NF-κB pathway
  69. Anti-OTC antibody-conjugated fluorescent magnetic/silica and fluorescent hybrid silica nanoparticles for oxytetracycline detection
  70. Curcumin conjugated zinc nanoparticles for the treatment of myocardial infarction
  71. Identification and in silico screening of natural phloroglucinols as potential PI3Kα inhibitors: A computational approach for drug discovery
  72. Exploring the phytochemical profile and antioxidant evaluation: Molecular docking and ADMET analysis of main compounds from three Solanum species in Saudi Arabia
  73. Unveiling the molecular composition and biological properties of essential oil derived from the leaves of wild Mentha aquatica L.: A comprehensive in vitro and in silico exploration
  74. Analysis of bioactive compounds present in Boerhavia elegans seeds by GC-MS
  75. Homology modeling and molecular docking study of corticotrophin-releasing hormone: An approach to treat stress-related diseases
  76. LncRNA MIR17HG alleviates heart failure via targeting MIR17HG/miR-153-3p/SIRT1 axis in in vitro model
  77. Development and validation of a stability indicating UPLC-DAD method coupled with MS-TQD for ramipril and thymoquinone in bioactive SNEDDS with in silico toxicity analysis of ramipril degradation products
  78. Biosynthesis of Ag/Cu nanocomposite mediated by Curcuma longa: Evaluation of its antibacterial properties against oral pathogens
  79. Development of AMBER-compliant transferable force field parameters for polytetrafluoroethylene
  80. Treatment of gestational diabetes by Acroptilon repens leaf aqueous extract green-formulated iron nanoparticles in rats
  81. Development and characterization of new ecological adsorbents based on cardoon wastes: Application to brilliant green adsorption
  82. A fast, sensitive, greener, and stability-indicating HPLC method for the standardization and quantitative determination of chlorhexidine acetate in commercial products
  83. Assessment of Se, As, Cd, Cr, Hg, and Pb content status in Ankang tea plantations of China
  84. Effect of transition metal chloride (ZnCl2) on low-temperature pyrolysis of high ash bituminous coal
  85. Evaluating polyphenol and ascorbic acid contents, tannin removal ability, and physical properties during hydrolysis and convective hot-air drying of cashew apple powder
  86. Development and characterization of functional low-fat frozen dairy dessert enhanced with dried lemongrass powder
  87. Scrutinizing the effect of additive and synergistic antibiotics against carbapenem-resistant Pseudomonas aeruginosa
  88. Preparation, characterization, and determination of the therapeutic effects of copper nanoparticles green-formulated by Pistacia atlantica in diabetes-induced cardiac dysfunction in rat
  89. Antioxidant and antidiabetic potentials of methoxy-substituted Schiff bases using in vitro, in vivo, and molecular simulation approaches
  90. Anti-melanoma cancer activity and chemical profile of the essential oil of Seseli yunnanense Franch
  91. Molecular docking analysis of subtilisin-like alkaline serine protease (SLASP) and laccase with natural biopolymers
  92. Overcoming methicillin resistance by methicillin-resistant Staphylococcus aureus: Computational evaluation of napthyridine and oxadiazoles compounds for potential dual inhibition of PBP-2a and FemA proteins
  93. Exploring novel antitubercular agents: Innovative design of 2,3-diaryl-quinoxalines targeting DprE1 for effective tuberculosis treatment
  94. Drimia maritima flowers as a source of biologically potent components: Optimization of bioactive compound extractions, isolation, UPLC–ESI–MS/MS, and pharmacological properties
  95. Estimating molecular properties, drug-likeness, cardiotoxic risk, liability profile, and molecular docking study to characterize binding process of key phyto-compounds against serotonin 5-HT2A receptor
  96. Fabrication of β-cyclodextrin-based microgels for enhancing solubility of Terbinafine: An in-vitro and in-vivo toxicological evaluation
  97. Phyto-mediated synthesis of ZnO nanoparticles and their sunlight-driven photocatalytic degradation of cationic and anionic dyes
  98. Monosodium glutamate induces hypothalamic–pituitary–adrenal axis hyperactivation, glucocorticoid receptors down-regulation, and systemic inflammatory response in young male rats: Impact on miR-155 and miR-218
  99. Quality control analyses of selected honey samples from Serbia based on their mineral and flavonoid profiles, and the invertase activity
  100. Eco-friendly synthesis of silver nanoparticles using Phyllanthus niruri leaf extract: Assessment of antimicrobial activity, effectiveness on tropical neglected mosquito vector control, and biocompatibility using a fibroblast cell line model
  101. Green synthesis of silver nanoparticles containing Cichorium intybus to treat the sepsis-induced DNA damage in the liver of Wistar albino rats
  102. Quality changes of durian pulp (Durio ziberhinus Murr.) in cold storage
  103. Study on recrystallization process of nitroguanidine by directly adding cold water to control temperature
  104. Determination of heavy metals and health risk assessment in drinking water in Bukayriyah City, Saudi Arabia
  105. Larvicidal properties of essential oils of three Artemisia species against the chemically insecticide-resistant Nile fever vector Culex pipiens (L.) (Diptera: Culicidae): In vitro and in silico studies
  106. Design, synthesis, characterization, and theoretical calculations, along with in silico and in vitro antimicrobial proprieties of new isoxazole-amide conjugates
  107. The impact of drying and extraction methods on total lipid, fatty acid profile, and cytotoxicity of Tenebrio molitor larvae
  108. A zinc oxide–tin oxide–nerolidol hybrid nanomaterial: Efficacy against esophageal squamous cell carcinoma
  109. Research on technological process for production of muskmelon juice (Cucumis melo L.)
  110. Physicochemical components, antioxidant activity, and predictive models for quality of soursop tea (Annona muricata L.) during heat pump drying
  111. Characterization and application of Fe1−xCoxFe2O4 nanoparticles in Direct Red 79 adsorption
  112. Torilis arvensis ethanolic extract: Phytochemical analysis, antifungal efficacy, and cytotoxicity properties
  113. Magnetite–poly-1H pyrrole dendritic nanocomposite seeded on poly-1H pyrrole: A promising photocathode for green hydrogen generation from sanitation water without using external sacrificing agent
  114. HPLC and GC–MS analyses of phytochemical compounds in Haloxylon salicornicum extract: Antibacterial and antifungal activity assessment of phytopathogens
  115. Efficient and stable to coking catalysts of ethanol steam reforming comprised of Ni + Ru loaded on MgAl2O4 + LnFe0.7Ni0.3O3 (Ln = La, Pr) nanocomposites prepared via cost-effective procedure with Pluronic P123 copolymer
  116. Nitrogen and boron co-doped carbon dots probe for selectively detecting Hg2+ in water samples and the detection mechanism
  117. Heavy metals in road dust from typical old industrial areas of Wuhan: Seasonal distribution and bioaccessibility-based health risk assessment
  118. Phytochemical profiling and bioactivity evaluation of CBD- and THC-enriched Cannabis sativa extracts: In vitro and in silico investigation of antioxidant and anti-inflammatory effects
  119. Investigating dye adsorption: The role of surface-modified montmorillonite nanoclay in kinetics, isotherms, and thermodynamics
  120. Antimicrobial activity, induction of ROS generation in HepG2 liver cancer cells, and chemical composition of Pterospermum heterophyllum
  121. Study on the performance of nanoparticle-modified PVDF membrane in delaying membrane aging
  122. Impact of cholesterol in encapsulated vitamin E acetate within cocoliposomes
  123. Review Articles
  124. Structural aspects of Pt(η3-X1N1X2)(PL) (X1,2 = O, C, or Se) and Pt(η3-N1N2X1)(PL) (X1 = C, S, or Se) derivatives
  125. Biosurfactants in biocorrosion and corrosion mitigation of metals: An overview
  126. Stimulus-responsive MOF–hydrogel composites: Classification, preparation, characterization, and their advancement in medical treatments
  127. Electrochemical dissolution of titanium under alternating current polarization to obtain its dioxide
  128. Special Issue on Recent Trends in Green Chemistry
  129. Phytochemical screening and antioxidant activity of Vitex agnus-castus L.
  130. Phytochemical study, antioxidant activity, and dermoprotective activity of Chenopodium ambrosioides (L.)
  131. Exploitation of mangliculous marine fungi, Amarenographium solium, for the green synthesis of silver nanoparticles and their activity against multiple drug-resistant bacteria
  132. Study of the phytotoxicity of margines on Pistia stratiotes L.
  133. Special Issue on Advanced Nanomaterials for Energy, Environmental and Biological Applications - Part III
  134. Impact of biogenic zinc oxide nanoparticles on growth, development, and antioxidant system of high protein content crop (Lablab purpureus L.) sweet
  135. Green synthesis, characterization, and application of iron and molybdenum nanoparticles and their composites for enhancing the growth of Solanum lycopersicum
  136. Green synthesis of silver nanoparticles from Olea europaea L. extracted polysaccharides, characterization, and its assessment as an antimicrobial agent against multiple pathogenic microbes
  137. Photocatalytic treatment of organic dyes using metal oxides and nanocomposites: A quantitative study
  138. Antifungal, antioxidant, and photocatalytic activities of greenly synthesized iron oxide nanoparticles
  139. Special Issue on Phytochemical and Pharmacological Scrutinization of Medicinal Plants
  140. Hepatoprotective effects of safranal on acetaminophen-induced hepatotoxicity in rats
  141. Chemical composition and biological properties of Thymus capitatus plants from Algerian high plains: A comparative and analytical study
  142. Chemical composition and bioactivities of the methanol root extracts of Saussurea costus
  143. In vivo protective effects of vitamin C against cyto-genotoxicity induced by Dysphania ambrosioides aqueous extract
  144. Insights about the deleterious impact of a carbamate pesticide on some metabolic immune and antioxidant functions and a focus on the protective ability of a Saharan shrub and its anti-edematous property
  145. A comprehensive review uncovering the anticancerous potential of genkwanin (plant-derived compound) in several human carcinomas
  146. A study to investigate the anticancer potential of carvacrol via targeting Notch signaling in breast cancer
  147. Assessment of anti-diabetic properties of Ziziphus oenopolia (L.) wild edible fruit extract: In vitro and in silico investigations through molecular docking analysis
  148. Optimization of polyphenol extraction, phenolic profile by LC-ESI-MS/MS, antioxidant, anti-enzymatic, and cytotoxic activities of Physalis acutifolia
  149. Phytochemical screening, antioxidant properties, and photo-protective activities of Salvia balansae de Noé ex Coss
  150. Antihyperglycemic, antiglycation, anti-hypercholesteremic, and toxicity evaluation with gas chromatography mass spectrometry profiling for Aloe armatissima leaves
  151. Phyto-fabrication and characterization of gold nanoparticles by using Timur (Zanthoxylum armatum DC) and their effect on wound healing
  152. Does Erodium trifolium (Cav.) Guitt exhibit medicinal properties? Response elements from phytochemical profiling, enzyme-inhibiting, and antioxidant and antimicrobial activities
  153. Integrative in silico evaluation of the antiviral potential of terpenoids and its metal complexes derived from Homalomena aromatica based on main protease of SARS-CoV-2
  154. 6-Methoxyflavone improves anxiety, depression, and memory by increasing monoamines in mice brain: HPLC analysis and in silico studies
  155. Simultaneous extraction and quantification of hydrophilic and lipophilic antioxidants in Solanum lycopersicum L. varieties marketed in Saudi Arabia
  156. Biological evaluation of CH3OH and C2H5OH of Berberis vulgaris for in vivo antileishmanial potential against Leishmania tropica in murine models
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Heruntergeladen am 6.12.2025 von https://www.degruyterbrill.com/document/doi/10.1515/chem-2023-0190/html?lang=de
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