Synthesis, characterization, biological potency, and molecular docking of Co2+, Ni2+ and Cu2+ complexes of a benzoyl isothiocyanate based ligand.

The primary objective of the present study was to produce metal complexes of H4DAP ligand (N,N'-((pyridine-2,6-diylbis(azanediyl))bis(carbonothioyl))dibenzamide) derived from 2,6-diaminopyridine and benzoyl isothiocyanate with either ML or M2L stoichiometry. There are three distinct coordination complexes obtained with the formulas [Co(H2DAP)]·H2O, [Ni2(H2DAP)Cl2(H2O)2]·H2O, and [Cu(H4DAP)Cl2]·3H2O. The confirmation of the structures of all derivatives was achieved through the utilization of several analytical techniques, including FT-IR, UV-Vis, NMR, GC-MS, PXRD, SEM, TEM analysis, and QM calculations. Aiming to analyze various noncovalent interactions, topological methods such as QTAIM, NCI, ELF, and LOL were performed. Furthermore, the capacity of metal-ligand binding was examined by fluorescence emission spectroscopy. An in vitro investigation showed that the viability of MDA-MB-231 and HepG-2 cells was lower when exposed to the manufactured Cu2+ complex, in comparison to the normal cis-platin medication. The compounds were further evaluated for their in vitro antibacterial activity. The Ni2+ complex has shown promising activity against all tested pathogens, comparable to the reference drugs Gentamycin and Ketoconazole. Furthermore, a computational docking investigation was conducted to further examine the orientation, interaction, and conformation of the recently created compounds on the active site of the Bcl-2 protein.

Antimalarial Activity of Aqueous Extracts of Nasturtium (Tropaeolum majus L.) and Benzyl Isothiocyanate.

Malaria remains an important and challenging infectious disease, and novel antimalarials are required. Benzyl isothiocyanate (BITC), the main breakdown product of benzyl glucosinolate, is present in all parts of Tropaeolum majus L. (T. majus) and has antibacterial and antiparasitic activities. To our knowledge, there is no information on the effects of BITC against malaria. The present study evaluates the antimalarial activity of aqueous extracts of BITC and T. majus seeds, leaves, and stems. We used flow cytometry to calculate the growth inhibition (GI) percentage of the extracts and BITC against unsynchronized cultures of the chloroquine-susceptible Plasmodium falciparum 3D7 - GFP strain. Extracts and/or compounds with at least 70% GI were validated by IC50 estimation against P. falciparum 3D7 - GFP and Dd2 (chloroquine-resistant strain) unsynchronized cultures by flow cytometry, and the resistance index (RI) was determined. T. majus aqueous extracts showed some antimalarial activity that was higher in seeds than in leaves or stems. BITC's GI was comparable to chloroquine's. BITC's IC50 was similar in both strains; thus, a cross-resistance absence with aminoquinolines was found (RI < 1). BITC presented features that could open new avenues for malaria drug discovery.

Computer-driven Evolution of Myrosinase from the Cabbage Aphid for Efficient Production of (R)-Sulforaphane.

Myrosinase (Myr) catalyzes the hydrolysis of glucosinolates, yielding biologically active metabolites. In this study, glucoraphanin (GRA) extracted from broccoli seeds was effectively hydrolyzed using a Myr-obtained cabbage aphid (Brevicoryne brassicae) (BbMyr) to produce (R)-sulforaphane (SFN). The gene encoding BbMyr was successfully heterologously expressed in Escherichia coli, resulting in the production of 1.6 g/L (R)-SFN, with a remarkable yield of 20.8 mg/gbroccoli seeds, achieved using recombination E. coli whole-cell catalysis under optimal conditions (pH 4.5, 45 °C). Subsequently, BbMyr underwent combinatorial simulation-driven mutagenesis, yielding a mutant, DE9 (N321D/Y426S), showing a remarkable 2.91-fold increase in the catalytic efficiency (kcat/KM) compared with the original enzyme. Molecular dynamics simulations demonstrated that the N321D mutation in loopA of mutant DE9 enhanced loopA stability by inducing favorable alterations in hydrogen bonds, while the Y426S mutation in loopB decreased spatial resistance. This research lays a foundation for the environmentally sustainable enzymatic (R)-SFN synthesis.

Synthetic access to diverse thiazetidines via a one-pot microwave assisted telescopic approach and their interaction with biomolecules.

A one-pot microwave assisted telescopic approach is reported for the chemo-selective synthesis of substituted 1,3-thiazetidines using readily available 2-aminopyridines/pyrazines/pyrimidine, substituted isothiocyanates and 1,2-dihalomethanes. The procedure involves thiourea formation from 2-aminopyridines/pyrazines/pyrimidine with the substituted isothiocyanates followed by a base catalysed nucleophilic attack of the CS bond on the 1,2-dihalomethane. Subsequently, a cyclization reaction occurs to yield substituted 1,3-thiazetidines. These four membered strained ring systems are reported to possess broad substrate scope with high functional group tolerance. The above synthetic sequence for the formation of four membered heterocycles is proven to be a modular and straightforward approach. Further the mechanistic pathway for the formation of 1,3-thiazetidines was supported by computational evaluations and X-ray crystallography analyses. The relevance of these thiazetidines in biological applications is evaluated by studying their ability to bind bio-macromolecules like proteins and nucleic acids.

Non-enzymatic degradation of aliphatic Brassicaceae isothiocyanates during aqueous heat treatment.

Glucosinolate-derived isothiocyanates are valuable for human health as they exert health promoting effects. As thermal food processing could affect their levels in a structure dependent way, the stability and reactivity of 12 Brassicaceae isothiocyanates during aqueous heating at 100 °C and pH 5-8 were investigated. The formation of their corresponding amines and N,N'-dialk(en)yl thioureas was quantified. Further, the potential to form odor active compounds was investigated by HRGC-MS-olfactometry. A strong structure-reactivity relationship was found and shorter side chains and electron withdrawing groups increase the reactivity of isothiocyanates. 3-(Methylsulfonyl)-propyl isothiocyanate was least stable. The main products are the corresponding amines (up to 69% recovery) and formation of N,N'-dialk(en)yl thioureas is only relevant at neutral to basic pH values. Apart from allyl isothiocyanate also 3-(methylthio)propyl isothiocyanate is precursor to many sulfur-containing odor active compounds. Thus, the isothiocyanate-structure affects their levels but also contributes to the flavor of boiled Brassicaceae vegetables.

Moving Beyond Isothiocyanates: A Look at the Stability of Conjugation Links Toward Radiolysis in 89Zr-Labeled Immunoconjugates.

Zirconium-89 is the most widely used radioisotope for immunoPET because its physical half-life (78.2 h) suits the one of antibodies. Desferrioxamine B (DFO) is the standard chelator for the complexation of zirconium(IV), and its bifunctional version, containing a phenylisothiocyanate function, is the most commonly used for the conjugation of DFO to proteins. However, preliminary results have shown that the thiourea link obtained from the conjugation of isothiocyanate and lysines is sensitive to the ionizing radiation generated by the radioisotope, leading to the rupture of the link and the release of the chelator/radiometal complex. This radiolysis phenomenon could produce nonspecific signal and prevent the detection of bone metastasis, as free zirconium accumulates into the bones. The aim of this work was to study the stability of a selection of conjugation linkers in 89Zr-labeled immunoconjugates. We have synthesized several DFO-based bifunctional chelators appended with an isothiocyanate moiety, a bicyclononyne, or a squaramate ester. Two antibodies (trastuzumab and rituximab) were conjugated and radiolabeled with zirconium-89. The effect of increasing activities of zirconium-89 on the integrity of the bioconjugate bearing thiourea links was evaluated as well as the impact of the presence of a radioprotectant. The stability of the radiolabeled antibodies was studied over 7 days in PBS and human plasma. Radioconjugates' integrity was evaluated using iTLC and size-exclusion chromatography. This study shows that the nature of the linker between the chelator and biomolecule can have a strong impact on the stability of the 89Zr-labeled conjugates, as well as on the aggregation of the conjugates.

14C-Isotope Use to Quantify Covalent Reactions between Flavor Compounds and ß-Lactoglobulin.

A 14C-based method was developed to study the rate and extent of covalent bond formation between ß-lactoglobulin and three model flavor compounds: a ketone (2-undecanone UDO), an aldehyde (decanal DAL), an isothiocyanate (2-phenylethyl isothiocyanate PEITC), and an unreactive "methods blank" (decane DEC). Aqueous protein solutions with one of the 14C-labeled model flavor compounds were placed in water baths at 25, 45, and 65 °C for 4 weeks measuring the amount of flavor: protein reaction at 1, 3, 7, 14, 21, and 28 days. UDO showed lowest reactivity (max of 0.9% of added compound reacted), DAL (max of 16.4% reacted), and PEITC (max of 71.8% reacted). All compounds showed a rapid initial reaction rate which slowed after ca. 7 days. It appears that only PEITC (at 65 °C) saturated all potential protein-reactive sites over the storage period.

Characterization of unique EDTA-insensitive methylthioalkylmalate synthase from Eutrema japonicum and its potential application in synthetic biology.

6-(Methylsulfinyl)hexyl isothiocyanate (6-MSITC), a derivative of glucosinolate with a six-carbon chain, is a compound found in wasabi and has diverse health-promoting properties. The biosynthesis of glucosinolates from methionine depends on a crucial step catalyzed methylthioalkylmalate synthases (MAMs), which are responsible for the generation of glucosinolates with varying chain lengths. In this study, our primary focus was the characterization of two methylthioalkyl malate synthases, MAM1-1 and MAM1-2, derived from Eutrema japonicum, commonly referred to as Japanese wasabi. Eutremajaponicum MAMs (EjMAMs) were expressed in an Escherichiacoli expression system, subsequently purified, and in vitro enzymatic activity was assayed. We explored the kinetic properties, optimal pH conditions, and cofactor preferences of EjMAMs and compared them with those of previously documented MAMs. Surprisingly, EjMAM1-2, categorized as a metallolyase family enzyme, displayed 20% of its maximum activity even in the absence of divalent metal cofactors or under high concentrations of EDTA. Additionally, we utilized AlphaFold2 to generate structural homology models of EjMAMs, and used in silico analysis and mutagenesis studies to investigate the key residues participating in catalytic activity. Moreover, we examined in vivo biosynthesis in E. coli containing Arabidopsis thaliana branched-chain amino acid transferase 3 (AtBCAT3) along with AtMAMs or EjMAMs and demonstrated that EjMAM1-2 exhibited the highest conversion rate among those MAMs, converting l-methionine to 2-(2-methylthio) ethyl malate (2-(2-MT)EM). EjMAM1-2 shows a unique property in vitro and highest activity on converting l-methionine to 2-(2-MT)EM in vivo which displays high potential for isothiocyanate biosynthesis in E. coli platform.

The synthesis of broccoli sprout extract-loaded silk fibroin nanoparticles as efficient drug delivery vehicles: development and characterization.

Targeted drug delivery of biological molecules using the development of biocompatible, non-toxic and biodegradable nanocarriers can be a promising method for cancer therapy. In this study, silk fibroin protein nanoparticles (SFPNPs) were synthesized as a targeted delivery system for sulforaphane-rich broccoli sprout extract (BSE). The BSE-loaded SFPNPs were conjugated with polyethylene glycol and folic acid, and then their physicochemical properties were characterized via UV-Vis, XRD, FTIR, DLS, FE-SEM and EDX analyses. In vitro, the release profile, antioxidant and anticancer activities of NPs were also studied. The FE-SEM and DLS analyses indicated stable NPs with an average size of 88.5 nm and high zeta potential (-32 mV). The sulforaphane release profile from NPs was pH-dependent, with the maximum release value (70%) observed in simulated intestinal fluid (pH = 7.4). Encapsulation of BSE also decreased the release rate of sulforaphane from the capsules compared to free BSE. In vitro cytotoxicity of BSE and NPs on breast cancer cell lines (MCF-7) was concentration-dependent, and the IC50 for BSE and NPs were 54 and 210 µg ml-1, respectively. Moreover, the NPs demonstrated no appreciable cytotoxicity in normal mouse fibroblast (L929) cell lines. These results indicated that biocompatible NPs synthesized as controlled and long-term targeted drug delivery systems can be a potential candidate for breast cancer therapy.

Phytochemical Profiling by UHPLC-Q-TOF/MS and Chemopreventive Effect of Aqueous Extract of Moringa oleifera Leaves and Benzyl Isothiocyanate on Murine Mammary Carcinogenesis.

Moringa oleifera Lam, commonly known as moringa, is a plant widely used both as a human food and for medicinal purposes around the world. This research aimed to evaluate the efficacy of the aqueous extract of Moringa oleifera leaves (MoAE) and benzyl isothiocyanate (BIT) in rats with induced breast cancer. Cancer was induced with 7,12-dimethylbenz[a]anthracene (DMBA) at a dose of 60 mg/kg by orogastric gavage once only. Forty-eight rats were randomly assigned to eight groups, each consisting of six individuals. The control group (healthy) was called Group I. Group II received DMBA plus saline. In addition to DMBA, Groups III, IV, and V received MoAE at 100, 250, and 500 mg/kg/day, respectively, while Groups VI, VII, and VIII received BIT at 5, 10, and 20 mg/kg/day, respectively. Treatment was carried out for 13 weeks. Secondary metabolite analysis results identified predominantly quercetin, caffeoylquinic acid, neochlorogenic acid, vitexin, and kaempferol, as well as tropone, betaine, loliolide, and vitexin. The administration of MoAE at a dose of 500 mg/kg and BIT at 20 mg/kg exhibited a notable decrease in both the total tumor count and the cumulative tumor weight, along with a delay in their onset. Furthermore, they improved the histological grade. A significant decrease in serum levels of VEGF and IL-1ß levels was observed (p < 0.001) with a better effect demonstrated with MoAE at 500 mg/kg and BIT at 20 mg/kg. In conclusion, this study suggests that both the aqueous extract of Moringa oleifera leaves and the benzyl isothiocyanate possess antitumor properties against mammary carcinogenesis, and this effect could be due, at least in part, to the flavonoids and isothiocyanates present in the extract.

Optimization of cultivar, germination time and extraction for radish sprout extract with high sulforaphene content.

BACKGROUND: Cruciferous vegetable sprout has been highlighted as a promising functional material rich in bioactive compounds called isothiocyanates (ITCs) and it can be grown in very short periods in controlled indoor farms. However, because ITCs content depends on multiple factors such as cultivar, germination time and myrosinase activity, those variables need to be controlled during germination or extraction to produce functional materials enriched in ITCs. Sulforaphene (SFEN), an ITC found primarily in radishes (Raphanus sativus L.), exerts beneficial effects on obesity. However, the optimal germination and extraction conditions for radish sprout (RSP) to increase SFEN content remain unascertained, and the extract's anti-obesity effect has yet to be evaluated. RESULTS: The present study found that the SFEN content was highest in purple radish sprout (PRSP) among the six cultivars investigated. Optimal SFEN content occurred after 2 days of PRSP germination (2 days PRSP). To maximize the dry matter yield, total ITCs and SFEN contents in RSP extract, we found the optimal conditions for extracting PRSP [27.5 °C, 60 min, 1:75.52 solute/solvent (w/v), no ascorbic acid] using response surface methodology. Consistent with high SFEN content, 2 days PRSP extract significantly outperformed 3 days or 4 days PRSP extract in inhibiting lipid accumulation in 3T3-L1 cells. Moreover, 2 days PRSP extract suppressed adipogenesis and lipogenesis-related protein expression. CONCLUSION: Regarding the cultivar, germination time and extraction conditions, optimally produced PRSP extract contains high SFEN content and exerts anti-obesity effects. Thus, we suggest PRSP extract as a potent functional material for obesity prevention. © 2024 Society of Chemical Industry.

Comparative Studies of Extracts Obtained from Brassica oleracea L. Plants at Different Stages of Growth by Isolation and Determination of Isothiocyanates: An Assessment of Chemopreventive Properties of Broccoli.

The main goal of this work was to develop analytical procedures for the isolation and determination of selected isothiocyanates. As an example, particularly sulforaphane from plants of the Brassicaceae Burnett or Cruciferae Juss family. The applied methodology was mainly based on classical extraction methods and high-performance liquid chromatography coupled with tandem mass spectrometry. Moreover, the effect of temperature on the release of isothiocyanates from plant cells was considered. The cytotoxic activity of the obtained plant extracts against a selected cancer cell line has also been included. The results allow evaluating the usefulness of obtained plant extracts and raw sprouts regarding their content of isothiocyanates-bioactive compounds with chemopreventive properties.

Isothiocyanates as potential antifungal agents: a mini-review.

Cruciferous vegetables and mustard oil are rich in the glucosinolate group of molecules. Isothiocyanates are an important group of glucosinolate derivatives. These derivatives have various bioactive properties, including antioxidant, antibacterial, anticarcinogenic, antifungal, antiparasitic, herbicidal and antimutagenic activity. Previous studies indicate that regular intake of such vegetables may considerably reduce the incidence of various types of cancer. These studies have inspired studies where the bioactive agents of these plants have been isolated and explored for their therapeutic applications. The use of these bioactive compounds as antifungals could be a new therapeutic approach against human pathogenic fungi. Isothiocyanates have been studied for their antifungal activity and have the potential to be used for antifungal therapy.

Vegetables like cabbage, cauliflower and broccoli have a distinct flavor because of chemicals called glucosinolates. Whenever we cut and eat these vegetables, glucosinolates are broken down into isothiocyanates. Glucosinolates and isothiocyanates have health benefits because they stop the growth of bacteria, parasites and fungi that cause disease, such as Candida albicans. They may also prevent cancer, as regularly eating these vegetables has been shown to reduce the development of some types of cancer in humans. Investigation is needed to explore how glucosinolates and isothiocyanates could be used to treat fungal infections.

Construction of benzyl isothiocyanate-loaded fish skin gelatin-luteolin compound emulsion delivery system, and its digestion and absorption characteristics.

BACKGROUND: Fish skin gelatin (FSG) and luteolin (LUT) were used as composite emulsifiers, and benzyl isothiocyanate (BITC) was used as a model of nutrient delivery to construct a stable emulsion. The storage stability of the FSG-LUT emulsion and its effect on BITC release were investigated both in vitro and ex vivo. RESULTS: LUT can quench FSG fluorophores statically and form a stable complex through hydrogen bonding and hydrophobic interactions. The FSG-LUT emulsion storage stability and embedding rate were higher than those of the FSG emulsion. The FSG-LUT emulsion microstructure was resistant to oral and gastric digestion, and the BITC retention rate and bioaccessibility were much higher than those of the FSG emulsion. Lastly, the ex vivo everted gut sac of rat intestine study demonstrated that BITC showed the highest absorption in the ileum, and the FSG-LUT emulsion absorbed BITC and sustained a controlled release in a specific position. CONCLUSION: LUT could form stable complexes with FSG, which improved the stability and bioavailability of BITC in the FSG-LUT emulsion delivery system, and promoted further intestinal BITC absorption. © 2022 Society of Chemical Industry.

Dynamics of the glucosinolate-myrosinase system in tuber mustard (Brassica juncea var. tumida) during pickling and its relationship with bacterial communities and fermentation characteristics.

Pickled tuber mustard is a traditional fermented pickle widely consumed in China, and it is characterized by the presence of glucosinolates (GSLs). To understand the biotransformation of GSLs in tuber mustard during pickling, the dynamics of the glucosinolate-myrosinase (GSL-MYR) system and its potential associations with bacterial communities and fermentation characteristics (i.e., salinity, titratable acidity [TAA], and pH) were investigated. In total, 18 GSLs were identified in fresh tuber mustard; 12 were aliphatic, 4 were indolic, and 2 were aromatic, with aliphatic sinigrin and aromatic gluconasturtiin being the dominating components. The pickling process resulted in complete degradation of GSLs, with isothiocyanates (ITCs) and nitriles being the main breakdown products. Total ITCs reached maximum concentrations on day 21-28, while total nitriles peaked at the end of pickling. Based on Spearman's correlation analysis, our study showed that lactic acid bacteria (LAB) species might contribute to GSL transformation in pickled tuber mustard. Specifically, Weissella paramesenteroides, Pediococcus pentosaceus, and unclassified Lactococcus exhibited positive correlations with GSL contents (p < 0.01), suggesting that they might contribute to the increasing amounts of GSLs in the initial pickling, while the Lactobacillus-related populations that dominated in the later stages (i.e., Companilactobacillus alimentarius and Lactiplantibacillus Plantarum) were positively correlated with nitrile product concentrations. Moreover, redundancy analysis showed that pH and TAA had strong effect on myrosinase activity during tuber mustard pickling, which was dictated via the organic acids produced by microorganisms. This study provided a perspective for understanding the effect of fermentation on the transformation of tuber mustard GSLs.

Formation and stability of isothiocyanate protein conjugates at different pH values and bread types enriched with nasturtium (Tropaeolum majus L.).

Brassicaceae vegetables are rich in glucosinolates (GLS), which degrade into various breakdown products, including isothiocyanates (ITC), during food processing. ITC are associated with health-promoting properties; therefore, producing food products enriched with a high content of these compounds is of interest for improving and maintaining human health. The present study aimed at evaluating a potential increase in ITC formation in Brassicaceae-enriched bread while minimizing ITC-protein conjugates. The influence of pH on GLS degradation was evaluated in different bread types and pH-adjusted model breads. In all samples, ITC, nitriles, and ITC-amino acid conjugates were analyzed by GC-MS and LC-ESI-MS/MS, respectively. The highest ITC-Lys levels with 33.9 µmol BITC-Lys/g bread could be found in a (more alkaline soda) bread with a pH of 7.2, while "free" BITC content was the lowest. However, this finding could not be directly correlated to pH value, because in model breads no significant relation between the pH and the BITC content could be identified. Especially the baking process impacted the ITC content as it was reduced from dough to the bread by 98%. Therefore, a heated food product is not suitable for an enrichment with GLS-rich vegetables to achieve a high content on BITC. Nevertheless, in the bread matrix itself the degradation products and BITC-Lys conjugates were stable during storage.

Novel transformation products from glucosinolate-derived thioglucose and isothiocyanates formed during cooking.

Glucosinolates are plant secondary metabolites occurring in Brassicaceae plants. Upon tissue disruption, these compounds can be enzymatically hydrolyzed into isothiocyanates, which are very reactive and can react with nucleophiles during thermal processes such as boiling. Here, a novel type of glucosinolate degradation product was identified resulting from the reaction of thioglucose with the isothiocyanates sulforaphane or allyl isothiocyanate during aqueous heating. The two heterocyclic compounds 4-hydroxy-3-(4-(methylsulfinyl)butyl)thiazolidine-2-thione and 3-allyl-4-hydroxythiazolidine-2-thione were isolated and their structure elucidated by NMR spectroscopy and high-resolution mass spectrometry. Based on a set of chemical experiments, a reaction mechanism was proposed. Finally, the formation of the two 3-alk(en)yl-4-hydroxythiazolidine-2-thiones was quantified in boiled cabbage samples using a standard addition method in which 92 pmol/g and 19 pmol/g fresh weight of the sulforaphane and allyl isothiocyanate derivatives were found, respectively.

Untargeted Metabolomic Analysis of Nonvolatile and Volatile Glucosinolates in Brassicaceae.

Glucosinolates (GLSs) are a group of plant secondary metabolites mainly found in Cruciferous plants. The main hydrolysis products of GLSs, isothiocyanates (ITCs), are the bioactive metabolites that have shown plant defense and human cancer prevention properties. Untargeted metabolomic analysis of plant metabolites can uncover the profiles of these bioactive phytochemicals in specific plants and discover potential human health promoting products. We have developed an integrated metabolomic analysis method for plant samples, with specific focus on nonvolatile GLSs and volatile ITCs. In this chapter, we describe in detail the protocols, including metabolite extraction, high resolution LC-MS and GC-MS analysis, and data processing. The method is readily applicable to untargeted analysis of other nonvolatile and volatile metabolites in plants.

Synthesis and Evaluation of Functionalized Aryl and Biaryl Isothiocyanates against Human MCF-7 Cells.

Organic isothiocyanates (ITCs) are a class of anticancer agents which naturally result from the enzymatic degradation of glucosinolates produced by Brassica vegetables. Previous studies have demonstrated that the structure of an ITC impacts its potency and mode(s) of anticancer properties, opening the way to preparation and evaluation of synthetic, non-natural ITC analogues. This study describes the preparation of a library of 79 non-natural ITC analogues intended to probe further structure-activity relationships for aryl ITCs and second-generation, functionalized biaryl ITC variants. ITC candidates were subjected to bifurcated evaluation of antiproliferative and antioxidant response element (ARE)-induction capacity against human MCF-7 cells. The results of this study led to the identification of (1) several key structure-activity relationships and (2) lead ITCs demonstrating potent antiproliferative properties.

Influence of fish skin gelatin-sodium alginate complex stabilized emulsion on benzyl isothiocyanate stability and digestibility in vitro and in vivo.

BACKGROUND: An emulsion delivery system for benzyl isothiocyanate (BITC) was prepared using fish skin gelatin (FSG) and sodium alginate (Alg). The effects of the FSG-Alg complex on the emulsion stability and BITC release pattern from the emulsion were investigated in vitro and in vivo. RESULTS: The storage stability and embedding rate of the 10 g kg-1 FSG and 2.5 g kg-1 Alg (FSG-Alg) emulsion were the highest among all samples. The FSG-Alg complex provided BITC a better protection during in vitro digestion. The microstructure of the FSG-Alg emulsions was more stable during in vitro digestion, and the bioaccessibility and retention rate of BITC were much higher compared to those of the FSG emulsion. The results of the ex vivo everted gut sac of rat intestine study showed that the FSG-Alg emulsion significantly increased the BITC absorption rate in the duodenum. CONCLUSION: The FSG-Alg emulsion delivery system is a highly stable system for the delivery of BITC that improves the bioaccessibility of BITC and promotes its absorption in the duodenum. © 2022 Society of Chemical Industry.