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Qianchun Zhang School of Biology and Chemistry, Key Laboratory for Analytical Science of Food and Environment Pollution of Qian Xi Nan, Xingyi Normal University for Nationalities, Xingyi, 562400, PR China

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Yan Chen School of Biology and Chemistry, Key Laboratory for Analytical Science of Food and Environment Pollution of Qian Xi Nan, Xingyi Normal University for Nationalities, Xingyi, 562400, PR China

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Yanqun Yang School of Biology and Chemistry, Key Laboratory for Analytical Science of Food and Environment Pollution of Qian Xi Nan, Xingyi Normal University for Nationalities, Xingyi, 562400, PR China
Guangxi Colleges and Universities Key Laboratory of Food Safety and Detection, College of Chemistry and Bioengineering, Guilin University of Technology, Guangxi, 541004, PR China

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Yulan Liu School of Biology and Chemistry, Key Laboratory for Analytical Science of Food and Environment Pollution of Qian Xi Nan, Xingyi Normal University for Nationalities, Xingyi, 562400, PR China

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Ming Wen School of Biology and Chemistry, Key Laboratory for Analytical Science of Food and Environment Pollution of Qian Xi Nan, Xingyi Normal University for Nationalities, Xingyi, 562400, PR China

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Xingyi Wang School of Biology and Chemistry, Key Laboratory for Analytical Science of Food and Environment Pollution of Qian Xi Nan, Xingyi Normal University for Nationalities, Xingyi, 562400, PR China

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Abstract

A novel method was established for analysing trace four acidic phytohormones, namely, indole-3-acetic acid, 3-indolebutyric acid, abscisic acid, and 1-naphthylacetic acid, using magnetic ordered mesoporous carbon (MOMC). MOMC was facilely synthesised via self-assembly strategy with a direct carbonisation process. The properties of MOMC were characterised using various instruments. MOMC exhibited excellent adsorption capacity towards the analytes. Various critical parameters which may influence the enrichment efficiency were evaluated, including amount of MOMC, extraction conditions, and desorption conditions. An efficient method based on MOMC magnetic solid-phase extraction coupled with ultra-high-performance liquid chromatography–tandem mass spectrometry (UHPLC–MS/MS) was developed to analyse the trace four acidic phytohormones, with good correlation coefficients (R2 = 0.9965–0.9998) and low limits of detection (0.13–9.7 ng L−1, S/N = 3). Trace acidic phytohormones in Agaricus bisporus and Hypsizygus marmoreus samples were determined with satisfactory recoveries (91.8–108%) and reproducibility (2.6–6.3%). The features indicated that MOMC provides an efficient platform for mushroom sampling; the developed method is convenient, promising, and sensitive for the detection of trace phytohormones in complicated mushroom samples.

Abstract

A novel method was established for analysing trace four acidic phytohormones, namely, indole-3-acetic acid, 3-indolebutyric acid, abscisic acid, and 1-naphthylacetic acid, using magnetic ordered mesoporous carbon (MOMC). MOMC was facilely synthesised via self-assembly strategy with a direct carbonisation process. The properties of MOMC were characterised using various instruments. MOMC exhibited excellent adsorption capacity towards the analytes. Various critical parameters which may influence the enrichment efficiency were evaluated, including amount of MOMC, extraction conditions, and desorption conditions. An efficient method based on MOMC magnetic solid-phase extraction coupled with ultra-high-performance liquid chromatography–tandem mass spectrometry (UHPLC–MS/MS) was developed to analyse the trace four acidic phytohormones, with good correlation coefficients (R2 = 0.9965–0.9998) and low limits of detection (0.13–9.7 ng L−1, S/N = 3). Trace acidic phytohormones in Agaricus bisporus and Hypsizygus marmoreus samples were determined with satisfactory recoveries (91.8–108%) and reproducibility (2.6–6.3%). The features indicated that MOMC provides an efficient platform for mushroom sampling; the developed method is convenient, promising, and sensitive for the detection of trace phytohormones in complicated mushroom samples.

Introduction

Plant hormones are small organic molecules that are important in regulating plant growth [1]. They are involved in facilitating various processes that affect plant growth and development, such as cell division, elongation and differentiation, germination, rooting, flowering, fruiting, sex determination, dormancy, and organ shedding [2]. Moreover, plant hormones play a vital role in the stress response of plants, such as the stress resistance growth process of plants under high temperature, drought, saline-alkali soil, and cold environments [3–5]. For example, the plant hormone abscisic acid (ABA) mediates seed dormancy, controls seedling development, and induces tolerance to abiotic stressors [6]. In addition, studies have shown that ABA, an endogenous immune modulator, plays a role in mammalian physiology and influences various biological activities [7]. It is worth noting that the physiological functions of hormones in plants are affected by their concentrations [8]. The interaction of plant hormones is important for normal plant development, and in recent years, there has been more attention in the accurate quantification of plant hormones. Research studies range in size from only one plant hormone [9, 10] to the simultaneous investigation of many plant hormones [11–13]. However, plant hormones are difficult to accurately analyse because of complex matrix interference, as well as low hormone concentrations (ng g−1 fresh weight) [14]. Therefore, an efficient sample pretreatment and an accurate, reliable, and sensitive analytical method should be developed to determine plant hormones.

Various methods are used to detect the content of plant hormones, such as enzyme-linked immunosorbent assays [15], gas chromatography–mass spectrometry [16], high-performance liquid chromatography with ultraviolet or fluorometric [17, 18], and liquid chromatography–mass spectrometry (LC–MS) [19] has rapidly developed, exhibiting high separation efficiency, high specificity, and high sensitivity detection. Although these approaches contribute greatly to the analysis of plant hormones, there are still some limitations to their applications. Owing to the low content of plant hormones and the complexity of the sample matrix, it is still challenging to completely isolate and quantitatively analyse plant hormones.

Therefore, sample concentration and purification techniques are necessary prior to chromatographic analysis. To date, there have been a variety of enrichment and purification methods for preparing plant hormone samples, such as immunoaffinity purification [20], liquid-liquid extraction [21], solid-phase microextraction [22], solid-phase extraction [11], micro-solid-phase extraction [18], and magnetic solid-phase extraction (MSPE) [23]. MSPE is a convenient solid-phase extraction method based on magnetic or magnetisable adsorbents that exhibits many advantages in the field of separation science [24]. A variety of materials have been applied for the extraction of plant hormones, such as polymer [18, 22], MOF-199 [25], hydrophilic molecularly imprinted resin [26], Graphene oxide-SiO2 nanocomposite [27], UiO-66/PAN [28], polyaniline [29], C18 [30], and polyacrylonitrile [31]. Magnetic ordered mesoporous carbon (MOMC) has the characteristics of a high specific surface area, high stability, and uniform pore structure. Furthermore, the pore structure is easy to control, which has important application potential in pretreatment.

In this study, MOMC was simple synthesised via self-assembly strategy with a direct carbonisation process. Subsequently, an efficient and novel analytical methodology based on MOMC and MSPE, coupled with UHPLC-MS/MS, was applied to the trace analysis of four acid phytohormones, indole-3-acetic acid, 3-indolebutyric acid, abscisic acid, and 1-naphthylacetic acid in Agaricus bisporus and Hypsizygus marmoreus samples.

Experimental

Chemicals and materials

Hydrogen peroxide (H2O2, 30 wt%), ironic citrate, phenol, and formaldehyde solution (37 wt%) were obtained from Shanghai Chemical Corporation (Shanghai, China). The poly (ethylene glycol)-block-poly(propylene glycol)-block-poly-(ethylene glycol) triblock copolymer Pluronic F127 (Mw = 14,600), sodium hydrate (NaOH), hydrochloric acid (HCl, 37 wt%), and anhydrous ethyl alcohol were obtained from Aladdin (Shanghai, China). Indole-3-acetic acid (IAA, >98%), 3-indolebutyric acid (IBA, >98%), abscisic acid (ABA, >98%), and 1-naphthylacetic acid (NAA, >98%), were obtained from J&K Scientific, Inc. (Beijing, China). The structures and log KOW of the four phytohormones are listed in Table S1. Stock standard solutions of the phytohormones (400 mg L−1) were dissolved in methanol. Naphthalene, fluorene, pyrene, benzo(b)fluoranthene, 2-hydroxynaphthalene, 2-hydroxyfluorene, 1-hydroxypyrene, methylbenzene, phenol, and phenylamine were also purchased from J&K Scientific, Inc. (Beijing, China). HPLC-grade formic acid and acetic acid were gained from the Beijing Dikma Company (Beijing, China). HPLC-grade acetonitrile and methanol were gained from Tedia (Fairfield, OH, USA). Primary secondary amine (PSA) was purchased from the Shanghai Anpu Company (Shanghai, China). High pure water used throughout the experiments was purified using a Milli-Q gradient A10 system (Millipore, UK).

Instruments

Fourier-transform infrared (FT-IR) spectroscopy was performed using a Nicolet Avatar 330 spectrometer. X-Ray diffraction (XRD) analysis was performed using a Rigaku diffractometer. Magnetic properties were measured with a squid-based magnetometer (San Diego, CA, USA). The size and morphology of the MOMC were characterized by a 4,300 scanning electron microscopy (SEM, Hitachi, Japan) and a JEOL-1011 transmission electron microscopy (TEM, JEOL, Tokyo, Japan). The specific surface area of MOMC was gained using an analyser (Micrometrics, TriStar II 3020). All mass spectrometric experiments of phytohormones were performed on a UHPLC–MS/MS 8050 with a Shim-pack XR-ODS-III C18 column (length = 75 mm, internal diameter = 2.0 mm, and particle size = 1.6 μm, Shimadzu, Kyoto, Japan). Further details of the chromatographic and mass spectrometric analyses (Table S2) are provided in Supporting Information Section 1.

Preparation of resol precursors

Phenol and formaldehyde were used to prepare resol precursors using a base-catalysed method according to a previous report with minor modifications [32]. For a typical preparation, 5.00 g of phenol was melted at 40–45 °C; subsequently, 1.06 mL of 20 wt% NaOH solution was added slowly by injector pump (Kunshan, Suzhou, America) at 100 μL min−1 under stirring. Then, 8.85 mL of formaldehyde (37 wt%) was added guttatim using an injector pump at 300 μL min−1, and then, the mixture was stirred continuously at 72 °C for 60 min and cooled at 25–35 °C, the pH was adjusted to approximately 6.5–7.5 using 1.0 mol L−1 HCl solution. subsequently water from the previous mixture was eliminated under vacuum below 45 °C. The resol precursors were redissolved in 20 wt% ethanol and separated using sodium chloride.

Synthesis of magnetic ordered mesoporous carbon

MOMC was synthesised according to previously reports with modification [33]. MOMC was synthesised from the co-assembly of triblock copolymers F127 with soluble resol precursors, and ferric citrate, in which F127 was used as the template and resol precursors by an evaporation induced self-assembly strategy in an ethanol solution. Carbonisation was then carried out under inert gas at 600 °C. In a typical synthesis, 1.0 g of F127 was added in 20.0 g of ethanol. 5.0 g of 20 wt% ethanolic solution of resol precursors was then added. After stirring for 10 min, 0.12 g of ferric citrate was dissolved in water (20 mL). The solution was finally added into above the mixture. After further stirring for 30 min, the solution was poured into a culture dish (I. D. 12 cm) and kept at 28 ± 4 °C for 6–8 h to evaporate the ethanol solution. The culture dish was then placed in an oven at 100 °C for the thermopolymerisation for 24 h. The as-prepared products were stripped and pyrolysed in a quartz tube furnace under nitrogen atmosphere, and the temperature of the quartz tube furnace was increased from 30 °C to 600 °C for 570 min and maintained at 600 °C for 180 min. The as-prepared carbonised materials were oxidised by H2O2 treatment to improve their hydrophilic performance. The as-made carbonised material (0.15 g) was added to a 30 wt% H2O2 solution (8.00 mL) at ambient temperatures, and the reaction solution was maintained at 60 °C with 30 min. The magnetic ordered mesoporous materials were isolated from the solution by an external magnet, washed with ethanol and dried at 100 °C in an oven for 6 h. The resulting magnetically ordered mesoporous carbon was denoted as MOMC (Fig. S1).

Sample preparation and magnetic solid-phase extraction procedure

A. bisporus and H. marmoreus were obtained from Yikelai supermarket (Xingyi, China). A. bisporus and H. marmoreus were cleaned, cut into small pieces, and homogenised. A homogenised sample (50 mg) was used. The sample was extracted using an ultrasonic instrument (Kunshan, Suzhou, China) for 5 min in 5.0 mg PSA and 2.0 mL acetonitrile containing 2% acetic acid(v/v). The extraction process was repeated and the extraction solutions were combined and centrifuged for 5 min at 10,000 rpm. Afterwards, the centrifuged solutions were dried with rotary evaporators at 45 °C, and then redissolved in 15 mL ultrapure water for MOMC sorptive extraction. MSPE was performed on MOMC particles as sorbents. Typically, 30.0 mg of MOMC adsorbent was added for 30 min of mixed extraction. The analytes of the four acidic phytohormones were then desorbed from the MOMC using 800 μL of methanol/formic acid (95/5, v/v) to desorb the analytes with 10 min, and the supernatant was isolated from the MOMC using a magnet. The eluents were concentrated to desiccation at 40 °C under a nitrogen stream and then redissolved in 100 μL of methanol/water (1/1, v/v). Next, 2,000 µL of redissolved solution was injected and analysed using the UHPLC-MS/MS system. With regard to the spiked samples, specific amount of phytohormones were added to the blank A. bisporus and H. marmoreus samples and then prepared as described above.

Results and discussion

Characterisation of magnetic ordered mesoporous carbon

FT-IR, XRD, VSM magnetisation curves, SEM, and TEM were used to investigate the MOMC. FT-IR spectra were first used to detect the functional groups of MOMC (Fig. S2). The results revealed the chemical characteristics of MOMC, showing a strong and broad band at 3,425 cm−1, which was caused by vibrational stretching of the –OH groups, while the characteristic peaks of the C=O vibrational stretching of the –COOH groups were seen at around 1,646 cm−1. Furthermore, the XRD patterns of the ordered mesoporous carbon and the MOMC materials are shown in Fig. 1A. The wide-angle XRD patterns of the mesoporous carbon nanocomposites pyrolysed at 600 °C presented six diffraction peaks, the main diffraction peaks at low angles, 2θ = 35.2°, 41.5°, 49.7°, 50.4°,67.4°, and 74.4° were attributed to (220), (311), (400), (422), (511), and (440), respectively, and assigned to the maghemite phase, according to JCPDS Card Number 89-5892. To investigate the magnetic properties of MOMC, the VSM magnetisation curves were obtained at room temperature. The saturation magnetisation intensity of MOMC was 5.01 emu/g, indicating that MOMC showed excellent superparamagnetic performance (Fig. 1B).

Fig. 1.
Fig. 1.

Characterisation of the MOMC. (A) XRD of (a) MOMC, (b) ordered mesoporous carbon; (B) VSM magnetisation curves of MOMC; (C) TEM images and (D) SEM images of MOMC

Citation: Acta Chromatographica 35, 1; 10.1556/1326.2022.01022

The morphology of the MOMC were obtained by TEM and SEM. TEM images (Fig. 1C) of the nanocomposite MOMC show the pore structure of the ordered mesostructure in a large area, and the magnetic particles were slightly decentralized in the ordered mesoporous carbon matrix. The SEM images (Fig. 1D) reveal that the morphology of MOMC was loose and microporous; therefore, it is important to improve the mass transport properties, which are favourable for increasing the enrichment performance. As shown in Fig. 2 and Table S3, the textural properties of the pores were measured by N2 adsorption-desorption isotherms, which were verified to be type V isotherms without hysteresis. The surface areas, pore volume, and pore sizes of MOMC were 575.9739 m2 g−1, 0.407837 cm³ g−1, and 3.3023 nm, respectively. The exceptional surface area of the MOMC suggested it was potentially applicable as an adsorbent for pretreatment and capturing of phytohormones.

Fig. 2.
Fig. 2.

(A) N2 adsorption-desorption isotherms, and (B) pore size distribution of MOMC

Citation: Acta Chromatographica 35, 1; 10.1556/1326.2022.01022

Optimisation of the extraction efficiency

To determine the optimal extraction conditions, several key factors, including the amount of MOMC, extraction time, sample solution pH, and desorption conditions were evaluated. The extraction volume (15.00 mL) and sample solution concentration (5.00 μg L−1) were adopted for all enrichment experiments in triplicate.

Enrichment conditions

In order to acquire the optimum dosages of MOMC for the adsorption of phytohormones (IAA, ABA, IBA, and NAA), the amount of MOMC (20.0–40.0 mg) was investigated. As shown in Fig. 3A, the adsorption amount increased gradually from 20.0 to 30.0 mg, and the excellent recovery rate was obtained with 30.0 mg of MOMC. From an economical standpoint, 30.0 mg was considered the optimal amount of adsorbent. The contact time plays a crucial role in ensuring adsorption equilibrium. Extraction time affected the adsorption efficiency of acidic phytohormones. To study the extent of its impact a time range of 15–40 min was used (Fig. 3B). The results showed that when the sample solutions were extracted for 30 min, the best recovery rates of all acidic phytohormones were achieved and maintained for prolonged extraction times. It was clear that adsorption equilibrium was reached. Therefore, The optimal extraction time was 30 min. Ultrapure water was regarded as the extraction solvent, and to evaluate the effect of the pH of the solution on the recovery rate of acidic phytohormones, the pH of the water was changed from 5.0 to 9.0, while keeping the other parameters constant. The recovery rate of all acidic phytohormones was the greatest at pH 7.0; therefore, the water pH of 7.0 was selected for subsequent experiments (Fig. 3C).

Fig. 3.
Fig. 3.

Extraction conditions of phytohormones with MOMC-based MSPE treatment with (A) amount of sorbent, (B) extraction time, (C) pH, (D) desorption solvent, (E) desorption time, and (F) desorption volume

Citation: Acta Chromatographica 35, 1; 10.1556/1326.2022.01022

Desorption conditions

Acidic phytohormones must be desorbed from the MOMC materials as completely as possible before UHPLC-MS/MS analysis. The π-π interactions between acidic phytohormones and MOMC materials must be disrupted. Therefore, in this work, a series of desorption solvents were investigated, including acetonitrile, acetonitrile containing 5% formic acid, methanol, methanol/formic acid (95/5, v/v), methanol/acetic acid (95/5, v/v). The results are shown in Fig. 3D. The best desorption efficiency can be achieved in methanol/formic acid (95/5, v/v) solvent. Moreover, the desorption time usually plays a key role in the extraction performance, and desorption equilibrium was obtained after approximately 10 min (Fig. 3E). Therefore, 10 min was used for the subsequent experiments. Under the above optimised conditions, the acidic phytohormones were desorbed with 0.60–1.20 mL of desorption solvent (Fig. 3F). The desorption amount increased with the desorption volume prior to 0.80 mL. After adsorption equilibrium was reached, no significant change was observed, the mass of acidic phytohormones was almost completely transferred from MOMC to solution. Therefore, 0.80 mL of methanol/formic acid (95/5, v/v) was selected as the preferred desorption volume.

Adsorption performance of magnetic ordered mesoporous carbon

Extraction capacity of magnetic ordered mesoporous carbon

The maximum amount of the four acidic phytohormones extracted by MOMC was considered to be the extraction capacity of MOMC. The extraction capacity of MOMC was detected by increasing the concentration of phytohormones (0.050–35.0 mg L−1), as shown in Fig. S3(A). The MOMC can efficiently extract up to 25.0 mg L−1 of phytohormones, and the maximum amount of extracted phytohormones achieved equilibrium at higher levels. The extraction amount increased with increasing concentration, and the amazing capacities of MOMC for IAA, ABA, IBA, and NAA were 2,169, 654, 3,289, and 3,204 ng mg−1 MOMC sorbent, respectively.

Investigation of reproducibility

Reproducibility is a crucial factor in assessing the stability and long-term efficiency of an MOMC. To explore the reproducibility of MOMC, multiple extraction and desorption tests with four acidic phytohormones were performed based on MOMC enrichment. After each experiment, the MOMC was cleaned with 2.00 mL of methanol/formic acid (95/5, v/v) and 2.00 mL of ultrapure water, respectively. The results are shown in Fig. S3(B). The results indicated that the MOMC could be reused 30 times without an apparent decrease in adsorption ability; hence, the enrichment capacity of the MOMC was stable, and the MOMC could be used for reduplication.

Adsorption characteristics of the magnetic ordered mesoporous carbon

Adsorption mechanism

To estimate the selectivity of MOMC materials, a competitive experiment was conducted. A succession of aromatic compounds endowed with different structural features and physicochemical properties (π electron conjugation strength, hydrophobicity, and substituent groups) were selected as model analytes. Non-polar analytes such as naphthalene, fluorene, pyrene, and benzo(b)fluoranthene and aromatic compounds are endowed with different functional groups (2-hydroxynaphthalene, 2-hydroxyfluorene, 1-hydroxypyrene, toluene, phenol, and aniline). The extraction amount was used to estimate the adsorption affinity of the compounds on the MOMC, as shown in Table 1. The hydrophobicity (log KOW) of the ten compounds was different; the adsorption amount of polycyclic aromatic hydrocarbons (PAHs), such as naphthalene, fluorene, pyrene, and benzo(b)fluoranthene, increased with the increase of the number of their condensed rings and log KOW values. The hydrophobicity of 1-hydroxypyrene, 2-hydroxyfluorene, and 2-hydroxynaphthalene, which were bonded to the hydrophilic group (–OH), was slightly lower than that of the corresponding polyaromatic hydrocarbons not linked with –OH. Simultaneously, the adsorption capacity of MOMC also decreased. Although polar analytes (methylbenzene, phenol, and phenylamine) were endowed with low log KOW values and exhibited lower adsorption ability on the MOMC material than PAHs, hydrogen bonding interactions should be considered between the model analytes and the MOMC material. Therefore, analytes endowed with polyaromatic ring structures, strong hydrophobicity (benzo(b)fluoranthene, pyrene, fluorene), and hydrogen bond donors (1-hydroxypyrene, 2-hydroxyfluorene) easily bound to MOMC. Research on the adsorption mechanism of materials is key for selecting suitable target analytes. Studying the adsorption mechanism can guide the selection of target compounds, based on the strong enrichment ability of MOMC for PAHs. Judging from the adsorption characteristics of the MOMC, MOMC was an efficient adsorbent for the determination of phytohormones in A. bisporus and H. marmoreus samples.

Table 1.

Adsorption capacity of MOMC MSPE for the different compounds

CompoundsStructureLog KOW aExtraction amount(ng) (Mean ± SD)
Naphthalene3.2959.8 ± 1.3
Fluorene4.0966.3 ± 1.2
Pyrene5.1569.8 ± 1.4
Benzo(b)fluoranthene6.4176.6 ± 2.1
2-Hydroxynaphthalene2.8854.8 ± 1.6
2-Hydroxyfluorene3.561.7 ± 2.4
1-Hydroxypyrene4.7464.1 ± 3.5
Methylbenzene2.4653.3 ± 3.4
Phenol1.6250.4 ± 2.4
Phenylamine1.2148.2 ± 1.8

aKOW: n-octanol/water partition coefficients. Data taken from https://www.reaxys.com/#/institution.

Isotherm analysis

The Langmuir and Freundlich adsorption models are most conventional models for investigating adsorption isotherm, they were applied to fit experimental data of the adsorption behaviour. The Langmuir isotherm model assumes a monomolecular layer adsorption process, it can be expressed as follows [34]:
qe=qmaxKLCe1+KLCe
The Langmuir adsorption isotherm can be represented in terms of a dimensionless constant called the separation factor or equilibrium parameter (RL), which is defined as follows equation (2)
RL=11+KLC0
where qmax(mg·g1) is the maximum monolayer adsorption capacity of MOMC, KL(Lmg1) is the Langmuir adsorption free energy constant, C0 (mg·g1) and Ce (mg·g1) are the initial and equilibrium concentrations, respectively, and RL is the equilibrium parameter from which the isotherms can be described as favourable (0 < RL < 1), linear (RL = 1), or unfavourable (RL > 1). All values of RL were positive. Thus, the adsorption of IAA, ABA, IBA, and NAA on MOMC was favourable and agreed well with the Langmuir isotherm model.
Moreover, the Freundlich isotherm describes adsorption on a heterogeneous surface through a multilayer adsorption mechanism, and the sites on the surface have different binding energies, it can be expressed as follows [34]:
qe=KFCe1/n
where qe(mg·g1) is the adsorption capacity at equilibrium concentration and KF (mg·g1) is the Freundlich adsorption constant.

The fitting results of the isotherms of the adsorption of IAA, ABA, IBA, and NAA on the MOMC are shown in Fig. 4. The results are listed in Table 2. From the results, the Langmuir model could better fit to the empirical data due to the higher correlation coefficient values compared with the Freundlich model, confirming the homogeneous adsorption of IAA, ABA, IBA, and NAA on MOMC. It was also revealed that the adsorbed IAA, ABA, IBA, and NAA formed a monomolecular layer on the surface of MOMC.

Fig. 4.
Fig. 4.

(A) Freundlich models for the adsorption of four acidic phytohormones; (B) Langmuir models for the adsorption of four acidic phytohormones

Citation: Acta Chromatographica 35, 1; 10.1556/1326.2022.01022

Table 2.

Langmuir and Freundlich parameters for the adsorption of IAA, ABA, IBA, and NAA onto MOMC. Experimental conditions: 30 mg of MOMC, extraction time: 30 min, extraction solution: ultrapure water at pH 7.0

AnalytesFreundlichLangmuir
KF (mg·g1)nR2qm (mg·g1)KL (L·mg1)R2
IAA0.598612.650.9743.209140.069570.981
ABA0.407367.150.9980.739150.264490.999
IBA1.252183.530.9834.325870.106410.988
NAA1.667295.100.9863.890880.171380.989

Development of the quantitative method

Method validation

Optimum extraction and UHPLC-MS/MS conditions. A MSPE method based on MOMC coupled with UHPLC-MS/MS was developed. The results are presented in Table 3. The linear range was detected to be 0.00200–5.00 μg L−1 for IAA, ABA, and IBA, while the concentration range of NAA was 0.0500–50.0 μg L−1. The excellent correlation coefficients were found to be 0.9965–0.9998, low limits of detection (LODs) were obtained as 0.13–9.7 ng L−1 (LODs were measured based on 3:1 signal-to-noise) with intraday RSDs of 2.2–6.6% and interday RSDs 3.3–7.8%.

Table 3.

Analytical performance of MOMC MSPE-UHPLC-MS/MS method for the determination of phytohormones (n = 5)

AnalytesEquation of linearityR2Range (μg L−1)LOD (ng L−1)LOQa (ng L−1)RSDb (%)RSDb (%)
IntradayInterday
IAAY = 1.690 × 106 X + 2.89 × 1030.99650.00200–5.000.130.456.67.8
ABAY = 3.260 × 105 X + 3.84 × 1030.99980.00200–5.000.411.45.25.8
IBAY = 5.317 × 105 X + 2.45 × 1030.99790.00200–5.000.190.654.24.7
NAAY = 1.230 × 104 X + 4.35 × 1020.99960.0500–50.09.7322.23.3

a LOQ was estimated based on 10:1 signal-to-noise ratios, and LOD was estimated on the basis of 3:1 signal-to-noise ratios.

b The RSD was calculated with a 0.50 μg L−1.

Evaluation of the matrix effect

The matrix effect in UHPLC–MS/MS analysis must be investigated to explore any possible ion suppression or enhancement. The matrix effect was evaluated using blank A. bisporus and H. marmoreus samples spiked with IAA, ABA, and IBA at concentrations of 0.0200 and 0.200 μg L−1, and spiked with NAA at concentrations of 0.0500 and 0.500 μg L−1. The recoveries were found to be 92.5–109%; these results proved that the matrix effects of A. bisporus and H. marmoreus are negligible and did not interfere significantly, thereby demonstrating that the proposed MSPE method based on MOMC is fit for analyses of A. bisporus and H. marmoreus phytohormones.

Sample analysis

The developed MSPE-UHPLC-MS/MS method was applied to monitor two plant samples, A. bisporus and H. marmoreus. The results are presented in Table 4 and Fig. 5. The amounts of IAA in A. bisporus and H. marmoreus samples were found to be 29.9 and 414 ng g−1, respectively; meanwhile, ABA was monitored and quantified to be 0.174 ng g−1 in H. marmoreus samples. IBA and NAA were also detected in A. bisporus and H. marmoreus samples, but they were not quantified. To assess the matrix influence, the A. bisporus and H. marmoreus samples were spiked at different levels (Table 4). Satisfactory recoveries ranging from 91.8% to 108% were obtained with good precision (RSDs of 2.6%–6.3%) for the A. bisporus and H. marmoreus samples, the results proved that the established method was suitable for simultaneously detecting trace phytohormones in complex mushroom samples.

Table 4.

Determination of four phytohormones in mushroom samples by MOMC MSPE combined with UHPLC-MS/MS (n = 5)

SamplesAnalytesOriginal amount (ng g−1)RSD (%)Spiked concentration (ng g−1)Recovery (%)RSD (%)
Agaricus bisporusIAA29.97.330.093.15.8
ABAN. Q.-0.2501084.8
IBAN. Q.-0.2501074.9
NAAN. Q.-25.01086.3
Hypsizygus marmoreusIAA4143.340096.35.3
ABA0.1744.80.2501024.7
IBAN. Q.-0.25091.82.6
NAAN. Q.-25.091.83.9

Note. N. Q.: not quantified.

Fig. 5.
Fig. 5.

Typical chromatograms for IAA and ABA in Agaricus bisporus and Hypsizygus marmoreus samples using MSPE-UHPLC-MS/MS detection: (a) the IAA and ABA of direction injection standard solution at 50.0 μg L−1 and 5.00 μg L−1, respectively; (b) the enrichment of sample; (c) the spiked sample each analyte

Citation: Acta Chromatographica 35, 1; 10.1556/1326.2022.01022

Conclusion

In conclusion, MOMC was facilely synthesised by a block-copolymer self-assembly process. MOMC was used for MSPE and exhibited a high enrichment performance for trace phytohormones. The developed method was highly efficient for the preconcentration of trace phytohormones in A. bisporus and H. marmoreus samples. A MSPE-UHPLC-MS/MS method based on MOMC for the determination of phytohormones in A. bisporus and H. marmoreus samples was successfully applied. MOMCs are believed to be potential adsorbents for sample pretreatment and can also be used to enrich trace phytohormones in plants.

Conflicts of interest

The authors declare no competing financial interest.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (21505115), the Top Scientific and Technological Talents in Universities of Guizhou Province (KY2018078), the Science and Technology for Youth Talent Growth Project of the Guizhou Provincial Education Department (KY2020216), and the Key Laboratory for Analytical Science of Food and Environment Pollution of Qian Xi Nan (2021-2-31).

Supplementary data

Supplementary data to this article can be found online at https://doi.org/10.1556/1326.2022.01022.

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    Li, X.; Cao, W. C.; Liu, Y. G.; Zeng, G. M.; Zeng, W.; Qin, L.; Li, T. T. Property variation of magnetic mesoporous carbon modified by aminated hollow magnetic nanospheres: synthesis, characterization, and sorption. ACS Sustain. Chem. Eng. 2017, 5, 179188.

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Supplementary Materials

  • 1.

    Jiang, K.; Asami, T. Chemical regulators of plant hormones and their applications in basic research and agriculture. Biosci. Biotech. Bioch. 2018, 82, 12651300.

    • Search Google Scholar
    • Export Citation
  • 2.

    Zhao, B. Q.; Liu, Q. Y.; Wang, B. S.; Yuan, F. Roles of phytohormones and their signaling pathways in leaf development and stress responses. J. Agric. Food Chem. 2021, 69, 35663584.

    • Search Google Scholar
    • Export Citation
  • 3.

    Sharma, L.; Dalal, M.; Verma, R. K.; Kumar, S. V. V.; Yadav, S. K.; Pushkar, S.; Kushwaha, S. R.; Bhowmik, A.; Chinnusamy, V. Auxin protects spikelet fertility and grain yield under drought and heat stresses in rice. Environ. Exp. Bot. 2018, 150, 924.

    • Search Google Scholar
    • Export Citation
  • 4.

    Zhu, Y. C.; Wang, Q. Y.; Gao, Z. W.; Wang, Y.; Liu, Y. J.; Ma, Z. P.; Chen, Y. W.; Zhang, Y. C.; Yan, F.; Li, J. W. Analysis of phytohormone signal transduction in sophora alopecuroides under salt stress. Int. J. Mol. Sci. 2021, 22, 73137335.

    • Search Google Scholar
    • Export Citation
  • 5.

    Luo, D.-L.; Ba, L. J.; Shan, W.; Kuang, J. F.; Lu, W. J.; Chen, J. Y. Involvement of WRKY transcription factors in abscisic-acid-induced cold tolerance of banana fruit. J. Agr. Food Chem. 2017, 65, 36273635.

    • Search Google Scholar
    • Export Citation
  • 6.

    Hauser, F.; Waadt, R.; Schroeder, J. I. Evolution of abscisic acid synthesis and signaling mechanisms. Curr. Biol. 2011, 21, 346355.

  • 7.

    Liu, J. J.; Gu, X. Z.; Zou, R. X.; Nan, W. P.; Yang, S. H.; Wang, H. L.; Chen, X. T. Phytohormone abscisic acid improves spatial memory and synaptogenesis involving NDR1/2 kinase in rats. Front. Pharmacol. 2018, 9, 11411150.

    • Search Google Scholar
    • Export Citation
  • 8.

    Zhang, X.-F.; Tong, J. H.; Bai, A. N.; Liu, C. M.; Xiao, L. T.; Xue, H. W. Phytohormone dynamics in developing endosperm influence rice grain shape and quality. J. Integr. Plant Biol. 2020, 62, 16251637.

    • Search Google Scholar
    • Export Citation
  • 9.

    Hou, S. H.; Song, X.; Li, L. L.; Wang, R. Y.; Wang, X.; Ji, W. H. Boronic acid-functionalized scholl-coupling mesoporous polymers for online solid-phase extraction of brassinosteroids from plant-derived foodstuffs. J. Agr. Food Chem. 2021, 69, 48834893.

    • Search Google Scholar
    • Export Citation
  • 10.

    Li, Y. X.; Deng, T.; Duan, C. F.; Ni, L. X.; Wang, N.; Guan, Y. F. Dispersive matrix solid-phase extraction method coupled with high performance liquid chromatography-tandem mass spectrometry for ultrasensitive quantification of endogenous brassinosteroids in minute plants and its application for geographical distribution study. J. Agr. Food Chem. 2019, 67, 30373045.

    • Search Google Scholar
    • Export Citation
  • 11.

    Jiang, C. L.; Dai, J. X.; Han, H. L.; Wang, C.; Zhu, L.; Lu, C. Y.; Chen, H. P. Determination of thirteen acidic phytohormones and their analogues in tea (camellia sinensis) leaves using ultra high performance liquid chromatography tandem mass spectrometry. J. Chromatogr. B 2020, 1149, 122144122152.

    • Search Google Scholar
    • Export Citation
  • 12.

    Wang, H. X.; Wang, M. L.; Wang, X. Z.; Ding, Y. L. Detection of seven phytohormones in peanut tissues by ultra-high-performance liquid chromatography-triple quadrupole tandem mass spectrometry. J. Integr. Agr. 2020, 19, 700708.

    • Search Google Scholar
    • Export Citation
  • 13.

    Jin, L. M.; Guo, B. J.; Bo, J.; Hua, J.; Shan, J. Y. Determination of four kinds of endogenous hormones in poplar dialyzate by HPLC with microdialysis. Acta Chromatogr. 2013, 25, 627637.

    • Search Google Scholar
    • Export Citation
  • 14.

    Zeng, Q. L.; Ruan, Y. J.; Sun, L. S.; Du, F. Y.; Guo, L.; Cheng, Z. F.; Ruan, G. H.; Li, J. P. Development of graphene oxide functionalized cotton fiber based solid phase extraction combined with liquid chromatography-fluorescence detection for determination of trace auxins in plant samples. Chromatographia 2018, 81, 861869.

    • Search Google Scholar
    • Export Citation
  • 15.

    Jiraskova, D.; Poulickova, A.; Novak, O.; Sedlakova, K.; Hradecka, V.; Strnad, M. High-throughput screening technology for monitoring phytohormone production in microalgae. J. Phycol. 2009, 45, 108118.

    • Search Google Scholar
    • Export Citation
  • 16.

    Huang, Z. H.; Wang, Z. L.; Shi, B. L.; Wei, D.; Chen, J. X.; Wang, S. L.; Gao, B. J. Simultaneous determination of salicylic acid, jasmonic acid, methyl salicylate, and methyl jasmonate from ulmus pumila leaves by GC-MS. Int. J. Anal. Chem. 2015, 2015, 698630698636.

    • Search Google Scholar
    • Export Citation
  • 17.

    Bosco, R.; Caser, M.; Vanara, F.; Scariot, V. Development of a rapid LC-DAD/FLD method for the simultaneous determination of auxins and abscisic acid in plant extracts. J. Agr. Food Chem. 2013, 61, 1094010947.

    • Search Google Scholar
    • Export Citation
  • 18.

    Cai, W.-J.; Yu, L.; Wang, W.; Sun, M. X.; Feng, Y. Q. Simultaneous determination of multiclass phytohormones in submilligram plant samples by One-Pot multifunctional derivatization-assisted liquid chromatography-tandem mass spectrometry. Anal. Chem. 2019, 91, 34923499.

    • Search Google Scholar
    • Export Citation
  • 19.

    Aihebaier, S.; Muhammad, T.; Wei, A.; Mamat, A.; Abuduaini, M.; Pataer, P.; Yigaimu, A.; Yimit, A. Membrane-protected molecularly imprinted polymer for the microextraction of indole-3-butyric acid in mung bean sprouts. ACS Omega 2019, 4, 1678916793.

    • Search Google Scholar
    • Export Citation
  • 20.

    Liang, Y.; Zhu, X. C.; Zhao, M. P.; Liu, H. W. Sensitive quantification of isoprenoid cytokinins in plants by selective immunoaffinity purification and high performance liquid chromatography-quadrupole-time of flight mass spectrometry. Methods 2012, 56, 174179.

    • Search Google Scholar
    • Export Citation
  • 21.

    Wang, Q.; Cai, W. J.; Yu, L.; Ding, J.; Feng, Y. Q. Comprehensive profiling of phytohormones in honey by sequential liquid-liquid extraction coupled with liquid chromatography-mass spectrometry. J. Agr. Food Chem. 2017, 65, 575585.

    • Search Google Scholar
    • Export Citation
  • 22.

    Liu, Z.; Wei, F.; Feng, Y. Q. Determination of cytokinins in plant samples by polymer monolith microextraction coupled with hydrophilic interaction chromatography-tandem mass spectrometry. Anal. Methods 2010, 2, 16761685.

    • Search Google Scholar
    • Export Citation
  • 23.

    Luo, X. T.; Cai, B. D.; Chen, X.; Feng, Y. Q. Improved methodology for analysis of multiple phytohormones using sequential magnetic solid-phase extraction coupled with liquid chromatography-tandem mass spectrometry. Anal. Chim. Acta 2017, 983, 112120.

    • Search Google Scholar
    • Export Citation
  • 24.

    Ding, J.; Gao, Q.; Luo, D.; Shi, Z. G.; Feng, Y. Q. N-octadecylphosphonic acid grafted mesoporous magnetic nanoparticle: preparation, characterization, and application in magnetic solid-phase extraction. J. Chromatogr. A. 2010, 1217, 73517358.

    • Search Google Scholar
    • Export Citation
  • 25.

    Zhang, Z. M.; Huang, Y. C.; Ding, W. W.; Li, G. K. Multilayer interparticle linking hybrid MOF-199 for noninvasive enrichment and analysis of plant hormone ethylene. Anal. Chem. 2014, 86, 35333540.

    • Search Google Scholar
    • Export Citation
  • 26.

    Wang, M. W.; Liang, S.; Bai, L. G.; Qiao, F. X.; Yan, H. Y. Green protocol for the preparation of hydrophilic molecularly imprinted resin in water for the efficient selective extraction and determination of plant hormones from bean sprouts. Anal. Chim. Acta 2019, 1064, 4755.

    • Search Google Scholar
    • Export Citation
  • 27.

    Zhang, X. N.; Niu, J. H.; Zhang, X. T; Xiao, R.; Lu, M. H.; Cai, Z. W. Graphene oxide-SiO2 nanocomposite as the adsorbent for extraction and preconcentration of plant hormones for HPLC analysis. J. Chromatogr. B 2017, 1046, 5864.

    • Search Google Scholar
    • Export Citation
  • 28.

    Yan, Z. M.; Wu, M.; Hu, B. Q.; Yao, M. N.; Zhang, L.; Lu, Q. M.; Pang, J. Electrospun UiO-66/polyacrylonitrile nanofibers as efficient sorbent for pipette tip solid phase extraction of phytohormones in vegetable samples. J. Chromatogr. A. 2018, 1542, 1927.

    • Search Google Scholar
    • Export Citation
  • 29.

    Wu, Q.; Wu, D. P.; Guan, Y. F. Polyaniline sheathed electrospun nanofiber bar for in vivo extraction of trace acidic phytohormones in plant tissue. J. Chromatogr. A. 2014, 1342, 1623.

    • Search Google Scholar
    • Export Citation
  • 30.

    Wang, W.; He, M.; Chen, B. B.; Hu, B. Simultaneous determination of acidic phytohormones in cucumbers and green bean sprouts by ion-pair stir bar sorptive extraction-high performance liquid chromatography. Talanta 2017, 170, 128136.

    • Search Google Scholar
    • Export Citation
  • 31.

    Cao, J. K.; Li, R. X.; Liang, S. H.; Li, J.; Xu, Q.; Wang, C. M. Simultaneous extraction of four plant growth regulators residues in vegetable samples using solid phase extraction based on thiol-functionalized nanofibers mat. Food Chem. 2020, 310, 125859125866.

    • Search Google Scholar
    • Export Citation
  • 32.

    Meng, Y.; Gu, D.; Zhang, F. Q.; Shi, Y. F.; Yang, H. F.; Li, Z.; Yu, C. Z.; Tu, B.; Zhao, D. Y. Ordered mesoporous polymers and homologous carbon frameworks: amphiphilic surfactant templating and direct transformation. Angew. Chem. Int. Ed. 2005, 44, 70537059.

    • Search Google Scholar
    • Export Citation
  • 33.

    Zhai, Y. P.; Dou, Y. Q.; Liu, X. X.; Tu, B.; Zhao, D. Y. One-pot synthesis of magnetically separable ordered mesoporous carbon. J. Mater. Chem. 2009, 19, 32923300.

    • Search Google Scholar
    • Export Citation
  • 34.

    Li, X.; Cao, W. C.; Liu, Y. G.; Zeng, G. M.; Zeng, W.; Qin, L.; Li, T. T. Property variation of magnetic mesoporous carbon modified by aminated hollow magnetic nanospheres: synthesis, characterization, and sorption. ACS Sustain. Chem. Eng. 2017, 5, 179188.

    • Search Google Scholar
    • Export Citation
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Senior editors

Editor(s)-in-Chief: Kowalska, Teresa (1946-2023)

Editor(s)-in-Chief: Sajewicz, Mieczyslaw

Editors(s)

  • Danica Agbaba (University of Belgrade, Belgrade, Serbia)
  • Łukasz Komsta (Medical University of Lublin, Lublin, Poland)
  • Ivana Stanimirova-Daszykowska (University of Silesia, Katowice, Poland)
  • Monika Waksmundzka-Hajnos (Medical University of Lublin, Lublin, Poland)

Editorial Board

  • R. Bhushan (The Indian Institute of Technology, Roorkee, India)
  • J. Bojarski (Jagiellonian University, Kraków, Poland)
  • B. Chankvetadze (State University of Tbilisi, Tbilisi, Georgia)
  • M. Daszykowski (University of Silesia, Katowice, Poland)
  • T.H. Dzido (Medical University of Lublin, Lublin, Poland)
  • A. Felinger (University of Pécs, Pécs, Hungary)
  • K. Glowniak (Medical University of Lublin, Lublin, Poland)
  • B. Glód (Siedlce University of Natural Sciences and Humanities, Siedlce, Poland)
  • A. Gumieniczek (Medical University of Lublin, Lublin, Poland)
  • U. Hubicka (Jagiellonian University, Kraków, Poland)
  • K. Kaczmarski (Rzeszow University of Technology, Rzeszów, Poland)
  • H. Kalász (Semmelweis University, Budapest, Hungary)
  • K. Karljiković Rajić (University of Belgrade, Belgrade, Serbia)
  • I. Klebovich (Semmelweis University, Budapest, Hungary)
  • A. Koch (Private Pharmacy, Hamburg, Germany)
  • P. Kus (Univerity of Silesia, Katowice, Poland)
  • D. Mangelings (Free University of Brussels, Brussels, Belgium)
  • E. Mincsovics (Corvinus University of Budapest, Budapest, Hungary)
  • Á. M. Móricz (Centre for Agricultural Research, Budapest, Hungary)
  • G. Morlock (Giessen University, Giessen, Germany)
  • A. Petruczynik (Medical University of Lublin, Lublin, Poland)
  • R. Skibiński (Medical University of Lublin, Lublin, Poland)
  • B. Spangenberg (Offenburg University of Applied Sciences, Germany)
  • T. Tuzimski (Medical University of Lublin, Lublin, Poland)
  • Y. Vander Heyden (Free University of Brussels, Brussels, Belgium)
  • A. Voelkel (Poznań University of Technology, Poznań, Poland)
  • B. Walczak (University of Silesia, Katowice, Poland)
  • W. Wasiak (Adam Mickiewicz University, Poznań, Poland)
  • I.G. Zenkevich (St. Petersburg State University, St. Petersburg, Russian Federation)

 

KOWALSKA, TERESA (1946-2023)
E-mail: kowalska@us.edu.pl

SAJEWICZ, MIECZYSLAW
E-mail:msajewic@us.edu.pl

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Impact Factor
without
Journal Self Cites
1.9
5 Year
Impact Factor
1.4
Journal Citation Indicator 0.41
Rank by Journal Citation Indicator

Chemistry, Analytical (Q3)

Scimago  
Scimago
H-index
29
Scimago
Journal Rank
0.28
Scimago Quartile Score

Chemistry (miscellaneous) (Q3)

Scopus  
Scopus
Cite Score
3.1
Scopus
CIte Score Rank
General Chemistry 211/407 (48th PCTL)
Scopus
SNIP
0.549

2021  
Web of Science  
Total Cites
WoS
652
Journal Impact Factor 2,011
Rank by Impact Factor Chemistry, Analytical 66/87
Impact Factor
without
Journal Self Cites
1,789
5 Year
Impact Factor
1,350
Journal Citation Indicator 0,40
Rank by Journal Citation Indicator Chemistry, Analytical 72/99
Scimago  
Scimago
H-index
29
Scimago
Journal Rank
0,27
Scimago Quartile Score Chemistry (miscellaneous) (Q3)
Scopus  
Scopus
Cite Score
2,8
Scopus
CIte Score Rank
General Chemistry 210/409 (Q3)
Scopus
SNIP
0,586

2020
 
Total Cites
650
WoS
Journal
Impact Factor
1,639
Rank by
Chemistry, Analytical 71/83 (Q4)
Impact Factor
 
Impact Factor
1,412
without
Journal Self Cites
5 Year
1,301
Impact Factor
Journal
0,34
Citation Indicator
 
Rank by Journal
Chemistry, Analytical 75/93 (Q4)
Citation Indicator
 
Citable
45
Items
Total
43
Articles
Total
2
Reviews
Scimago
28
H-index
Scimago
0,316
Journal Rank
Scimago
Chemistry (miscellaneous) Q3
Quartile Score
 
Scopus
393/181=2,2
Scite Score
 
Scopus
General Chemistry 215/398 (Q3)
Scite Score Rank
 
Scopus
0,560
SNIP
 
Days from
58
submission
 
to acceptance
 
Days from
68
acceptance
 
to publication
 
Acceptance
51%
Rate

2019  
Total Cites
WoS
495
Impact Factor 1,418
Impact Factor
without
Journal Self Cites
1,374
5 Year
Impact Factor
0,936
Immediacy
Index
0,460
Citable
Items
50
Total
Articles
50
Total
Reviews
0
Cited
Half-Life
6,2
Citing
Half-Life
8,3
Eigenfactor
Score
0,00048
Article Influence
Score
0,164
% Articles
in
Citable Items
100,00
Normalized
Eigenfactor
0,05895
Average
IF
Percentile
20,349
Scimago
H-index
26
Scimago
Journal Rank
0,255
Scopus
Scite Score
226/167=1,4
Scopus
Scite Score Rank
Chemistry (miscellaneous) 240/398 (Q3)
Scopus
SNIP
0,494
Acceptance
Rate
41%

 

Acta Chromatographica
Publication Model Online only
Gold Open Access
Submission Fee none
Article Processing Charge 400 EUR/article
Regional discounts on country of the funding agency World Bank Lower-middle-income economies: 50%
World Bank Low-income economies: 100%
Further Discounts Editorial Board / Advisory Board members: 50%
Corresponding authors, affiliated to an EISZ member institution subscribing to the journal package of Akadémiai Kiadó: 100%
Subscription Information Gold Open Access
Purchase per Title  

Acta Chromatographica
Language English
Size A4
Year of
Foundation
1988
Volumes
per Year
1
Issues
per Year
4
Founder Institute of Chemistry, University of Silesia
Founder's
Address
PL-40-007 Katowice, Poland, Bankowa 12
Publisher Akadémiai Kiadó
Publisher's
Address
H-1117 Budapest, Hungary 1516 Budapest, PO Box 245.
Responsible
Publisher
Chief Executive Officer, Akadémiai Kiadó
ISSN 2083-5736 (Online)

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