Dayun Zhao

As the focus on green chemistry intensifies, researchers are progressively looking to incorporate biodegradable and environmentally friendly solvents. Given the prevalent use of inorganic solvents in conventional methods for detecting selenium content, this study utilized a mixture design approach to create four deep eutectic solvents (DESs). The elements of the DESs consisted of six different compounds: guanidine hydrochloride, fructose, glycerol, citric acid, proline, and choline chloride. The synthesized deep eutectic solvents (DESs) exhibited a uniform and transparent appearance. The ideal ratios for each DES were established based on their density and viscosity measurements, leading to the formulations of DES1 (34% guanidine hydrochloride, 21% fructose, 45% water), DES2 (23% guanidine hydrochloride, 32% glycerol, 45% water), DES3 (27.5% citric acid, 27.5% proline, 45% water), and DES4 (30% choline chloride, 25% citric acid, 45% water). The characterization of the deep eutectic solvents (DESs) was performed using nuclear magnetic resonance (NMR) spectroscopy and infrared (IR) spectroscopy, which confirmed the molecular formation of each DES. Following this, the DESs were applied as extraction solvents in a process involving ultrasonic-assisted microextraction (UAE) combined with inductively coupled plasma mass spectrometry (ICP-MS) to assess the selenium levels in selenium-rich rice. The results were benchmarked against traditional microwave-assisted acid digestion (TM-AD), revealing selenium recovery rates ranging from 85.5% to 106.7%. These results indicate that UAE is an effective method for extracting selenium from selenium-rich rice, thereby establishing a solid data foundation for the environmentally friendly analysis of selenium content in rice.

Research suggests that soyasaponins are poorly absorbed in the GI tract and that soyasaponin aglycones or soyasapogenols are absorbed faster and in greater amounts than the corresponding soyasaponins. Therefore, it is important to understand the bioavailability of these compounds for the potential development of functional foods containing their components. In this paper, to investigate the metabolic characteristics of soyasapogenols A and B, the pharmacokinetic parameters in rats were determined via oral and intravenous administration. The liver metabolites of soyasapogenols were identified using UPLC–/Q-TOF–MS/MS, and their metabolic pathways were also speculated. The results show that, after oral administration, there was a bimodal phenomenon in the absorption process. T_max was about 2 h, and soyasapogenol was completely metabolized 24 h later. The bioavailability of soyasapogenol was superior, reaching more than 60%. There were sixteen metabolites of soyasapogenol A and fifteen metabolites of soyasapogenol B detected in rat bile. Both phase I and II metabolic transformation types of soyasapogenols, including oxidation, dehydrogenation, hydrolysis, dehydration, deoxidization, phosphorylation, sulfation, glucoaldehyde acidification, and conjugation with cysteine, were identified. In addition, soyasapogenol A could be converted into soyasapogenols B and E in the metabolic process. These results suggest that it is feasible to use soyasapogenols as functional ingredients in nutraceuticals or food formulations.

Soyasapogenols derived from soyasaponins, which abundantly occur in soy hypocotyls, are of great importance as bioactive compounds due to their physiological activities. However, there is a lack of a high-efficiency and scalable preparation and isolation procedure. This work extends research on applying and comparing high-speed countercurrent chromatography (HSCCC) and preparative high-performance liquid chromatography (prep-HPLC) either singly and/or combinedly in preparative isolation of soyasapogenol A and B. The comparison reveals that the yield of 0.24 and 0.21% of soyasapogenol A and B with the purity of 98.09 and 98.90%, respectively, were obtained from the starting material of soy hypocotyls in two-steps HSCCC separation procedure. In contrast, prep-HPLC allowed isolation and purification of these two target compounds with significantly lower productivity and higher solvent consumption. An optimal two-phase solvent system of n-hexane–ethyl acetate–methanol–water (3:6:4:2, v/v/v/v) was selected to separate soyasapogenols in HSCCC procedure. The present investigation indicates that two-steps HSCCC can potentially provide a fast, high yielding, and more environmentally friendly tool for the preparative separation and purification of soyasapogenol A and B starting from the materials of soy hypocotyls. Graphical Abstract

Summary: Previous studies have demonstrated that the undigested or insoluble high molecular fraction of soy protein exerts a lowering effect on serum cholesterol by inhibiting the absorption of cholesterol in the intestinal tract. The aim of this study was to investigate the interaction between the soluble fraction of soy protein peptic hydrolysate and dietary mixed micelles (DMMs) for cholesterol micellar solubility and uptake. The collected soluble tofu peptic hydrolysate (STPH) components, generated from hard and lactone tofu were evaluated by two in vitro models and a Caco‐2 cell model after tofu soy protein was digested, thus simulating the gastrointestinal tract. The results showed that the administration of STPH effectively decreased the cholesterol solubility and uptake by 37.6% and 18.99%, respectively, as detected by the in vitro models and the Caco‐2 cell model. Current findings demonstrated the potential hypocholesterolaemic benefit of the STPH.

Molecular imprinting technology (MIT) offers an effective technique for efficient separation and enrichment of specific analytes from complicated matrices and has been used for illicit veterinary drug detectionin recent years due to its high selectivity, good chemical stability, and simple preparation. The development of in silico-based approaches has enabled the simulation of molecularly imprinted polymers (MIPs) to facilitate the selection of imprinting conditions such as template, functional monomer, and the best suitable solvent. In this work, using density functional theory (DFT), the molecularly imprinted polymers of clenbuterol and its metabolites were designed by computer-aided at B3LYP/6-31 + G (d, p) level. Screening molecular imprinting components such as functional monomers, cross-linkers, and solvents has been achieved in the computational simulation considerations. The simulation results showed that methacrylic acid (MAA) is the best functional monomer; the optimal imprinting ratio for both clenbuterol (CLB) and its dummy template molecule of phenylephrine (PE) to functional monomer is 1:3, while the optimal imprinting ratio for the two dummy template molecules of CLB’s metabolites is 1:5. Choosin gethyleneglycol dimethacrylate (EDGMA) as a crosslinker and aprotic solvents could increase the selectivity of the molecularly imprinted system. Atoms in Molecules (AIM) topology analysis was applied to investigate the template-monomer complexes bonding situation and helped to explain the nature of the reaction in the imprinting process. These theoretical predictions were also verified by the experimental results and found to be in good agreement with the computational results. The computer-simulated imprinting process compensates for the lack of clarity in the mechanism of the molecular imprinting process, and provides an important reference and direction for developing better recognition pattern towards CLB and its metabolite analytes in swine urine samples at the same time.

Soyasaponins are naturally occurring triterpenoid glycosides associated with many biological activities. The aim of the present study was to develop an effective method for isolation and purification of differently glycosylated, acetylated, and 2,3‐dihydro‐2,5‐dihydroxy‐6‐methyl‐4H‐pyran‐4‐one (DDMP)‐conjugated soyasaponins from soy hypocotyls. Both gel filtration using Sephadex LH‐20 chromatography (Amersham Pharmacia Biotech AB; elution phase: methanol, flow rate: 3.0 mL/min, sample loading: 60 mg) and high‐speed countercurrent chromatography (stationary phase: n‐butanol–acetic acid (5.0%, v/v), mobile phase: water flow rate: 3.0 mL/min, sample loading: 100 mg) could effectively fractionate isoflavones and soyasaponins from the crude extract with yield of soyasaponin complexes 20.5 mg and 22.3 mg, respectively. After fractionation, the soyasaponin complexes could be purified further using preparative HPLC to separate individuals. A total of nine soyasaponins, triacetyl soyasaponin Ab (yield 1.55%, HPLC purity >98%), Aa (2.68%, >99%), Ab (18.53%, >98%), Ae (0.85%, >98%), Ba (0.63%, >91%), Af (1.12%, >85%), Bb (3.45%, >98%) and Be (0.59%, >76.8%) were obtained. DDMP‐conjugated groups, αg (2.06%, >85%), βg (7.59%, >85%), and γg (0.29%, >85%) that were very labile even in mild conditions, were also collected. The method described here can be used as an effective protocol to separate different soyasaponins occurring in the original sample.

A new molecularly imprinted polymer (MIP) has been prepared on silica beads using the radical “grafting from” polymerization method for selective extraction of minor contaminant mycotoxin of patulin (PTL). After the introduction of amino groups onto the silica surface with 3-aminopropyltriethoxysilane, azo initiator onto the silica surface was achieved by the reaction of surface amino groups with 4,4′-azobis(4-cyanopentanoic acid). The scale-up synthesis of MIP was then carried out in the presence of 6-hydroxynicotinic acid as template substitute, functional, and cross-linking monomers. The prepared sorbent was characterized using FT-IR spectroscopy, scanning electron microscopy, elemental analysis, and the adsorption–desorption selectivity, and the capacity characteristic of the polymer was investigated by a conventional batch adsorption test and Scatchard plot analysis. The results indicated that coated polymers had specific adsorption to PTL as compared with its co-occurring 5-hydroxymethyl-2-furaldehyde (hydroxymethylfurfural (HMF)), at the same bulk concentration for solution of PTL and HMF, the maximum absorbance in the solid-phase extraction (SPE) method to PTL were 93.97% or 0.654 μg/mg while to HMF they were 76.89% or 0.496 μg/mg. Scatchard analysis revealed that two classes of binding sites were formed in PTL-MIP with dissociation constants of 3.2 × 10⁻² and 5.0 × 10⁻³ mg/mL and the affinity binding sites of 8.029 and 1.364 mg/g, respectively. The recoveries of PTL were more than 90% for the developed MISPE and around 75% for the traditional liquid–liquid extraction in spiked apple juice samples. It was concluded that the method is suitable for the scale-up synthesis of PTL-MIP grafted on silica, and the polymer can be effectively applied as SPE coupled with high-performance liquid chromatography (HPLC) for the determination of PTL in apple juice or other related products. HPLC chromatograms of loading, washing, and eluting fractions of PTL and HMF from the MIP cartridge. Test samples in each chromatogram from top to bottom: mixed standard of HMF and PTL (10 mg/L), residue solution through the cartridge, first elution and second elution washed with 1 mL of 1% (w/v) HAc aqueous solution.