Search Results (69)

In this study, using 70% anhydrous ethanol as the extraction solvent, Moringa oleifera Lam. seed powder was extracted with the microwave-assisted extraction method, followed by purification using macroporous adsorbent resin NKA-9. The purified glucosinolate was subsequently hydrolyzed with myrosinase. The glucosinolate and its enzymatic product were identified as 4-(α-L-rhamnopyranosyloxy) benzyl glucosinolate (4-RBMG) and benzyl isothiocyanate (BITC) by UV–Vis, FT-IR, NMR, and MS. The bioactivities, including anti-oxidation, anti-inflammation, and anti-tumor activities of 4-RBMG and BITC, were systematically evaluated and compared. The results show that at 5–20 mg/mL, the anti-oxidation effects of 4-RBMG on DPPH and ABTS free radicals are superior to those of BITC. However, at the same concentrations, BITC has stronger anti-inflammatory and anti-tumor activities compared to 4-RBMG. Notably, at a concentration of 6.25 μmol/L, BITC significantly inhibited NO production with an inhibitory rate of 96.67% without cytotoxicity. Additionally, at a concentration of 40 μmol/L, BITC exhibited excellent inhibitory effects on five tumor cell lines, with the cell inhibitory rates of leukemia HL-60, lung cancer A549, and hepatocellular carcinoma HepG2 exceeding 90%. This study provides some evidence that the enzymatic product, BITC, shows promise as a therapeutic agent for tumor suppression and inflammation reduction. Full article

The garden Nasturtium (Tropaeolum majus L.) is increasingly consumed worldwide due to its culinary appeal and perceived health benefits. However, the chemical markers underlying its functional properties remain insufficiently characterized. Building on evidence from a recent human pilot study confirming both high acceptability and dietary safety, we conducted a comprehensive volatilomic and phytochemical analysis of T. majus flowers and their juice. Headspace solid-phase microextraction coupled with gas chromatography–mass spectrometry (HS-SPME/GC-MS) was employed to establish the volatilomic fingerprint of floral tissues and juice. Our analysis revealed a striking dominance of benzyl isothiocyanate and benzonitrile, which together accounted for 88% of the total volatile organic metabolites (VOMs) in the juice, 67% and 21%, respectively. In the floral tissues, benzyl isothiocyanate was even more prevalent, representing 95% of the total volatile profile. Complementary in vitro assays confirmed a substantial total phenolic content and strong antioxidant activity in the flowers. These findings provide a robust chemical rationale for the potential health-promoting attributes of T. majus, while identifying key volatilomic markers that could support future functional and safety claims. In parallel, a benefit–risk assessment framework is discussed in accordance with the European Food Safety Authority (EFSA) guidelines for the Qualified Presumption of Safety (QPS) of edible flowers. Given that both benzyl isothiocyanate and benzonitrile are classified as Cramer Class III substances, a conservative intake threshold of 1.5 μg/kg body weight per day is proposed. To enable quantitative exposure modeling and support the derivation of a tolerable daily intake (TDI), future studies should integrate organic solvent-based extraction methodologies to estimate the total volatile load per gram of floral biomass. This would align risk–benefit assessments with the EFSA’s evolving framework for novel foods and functional ingredients. Full article

This study aims to elucidate the synergistic antibacterial mechanism of benzyl isothiocyanate (BITC) and resveratrol (RES) on Staphylococcus aureus (S. aureus) at the transcriptional level. Compared with the individuals, the combination of BITC and RES (BITC_RES) reduced S. aureus growth, inhibited biofilm formation, and increased cell membrane disruption. The transcriptomic results showed that the BITC_RES group presented 245 and 1150 more DEGs than the BITC group and the RES group, respectively. In addition, some other key genes in the BITC_RES group, including serine protease (splA, splE), Sae regulatory system (saeR, saeS, tsaE, sau300), accessory gene regulator protein C (agrC), cysteine protease (sspB), glutamyl endopeptidase (sspA), and hemolysin toxin family-related genes (hly, lukDv, lukEv), and the relative expression of these 12 genes was downregulated by 2.2–259.8-fold, 0.8–259.8-fold and 1.2–158.2-fold greater than those in the BITC group and the RES group, respectively. Finally, a synergistic antimicrobial effect of this combination was also observed in fresh lean beef at 4 °C and 25 °C. These findings provide information for future studies on the synergistic antimicrobial effects of BITC and RES on S. aureus. Full article

Isothiocyanates (ITCs), found in edible plants such as cruciferous vegetables, are a group of reactive organo-sulfur phytochemicals produced by the hydrolysis of precursors known as glucosinolates. ITCs have been studied extensively both in vivo and in vitro to define their therapeutic potential for the treatment of chronic health conditions. Therapeutically, they have shown an intrinsic ability to inhibit oxidative and inflammatory phenotypes to support enhanced health. This review summarizes the current evidence supporting the observation that the antioxidant and anti-inflammatory activities of ITCs temper the pathogenic effects of a group of reactive metabolites called advanced glycation end products (AGEs). AGE exposure has significantly increased across the lifespan due to health risk factors that include dietary intake, a sedentary lifestyle, and comorbid conditions. By contributing to a chronic cycle of inflammatory stress through the aberrant activation of the transmembrane receptor for AGE (RAGE), increased AGE bioavailability is associated with chronic disease onset, progression, and severity. This review debates the potential molecular mechanisms by which ITCs may inhibit AGE bioavailability to reduce RAGE-mediated pro-oxidant and pro-inflammatory phenotypes. Bringing to light the molecular impact that ITCs may have on AGE biogenesis may stimulate novel intervention strategies for reversing or preventing the impact of lifestyle factors on chronic disease risk. Full article

Isothiocyanates (ITCs) are naturally occurring sulfur-containing compounds with diverse biological effects. This study investigated the effects of sulforaphane (SFN, an aliphatic ITC) and benzyl isothiocyanate (BITC, an aromatic ITC) on human acute myeloid leukemia SKM-1 cells, focusing on cell proliferation, cell death, and drug resistance. Both drug-sensitive SKM-1 cells and their drug-resistant SKM/VCR variant, which overexpresses the drug transporter P-glycoprotein, were used. SFN and BITC reduced cell viability in a dose-dependent manner, with BITC showing greater potency. IC50 values ranged from 7.0–8.0 µM for SFN and 4.0–5.0 µM for BITC in both cell types, with only slight differences between the variants. Both ITCs induced autophagy as evidenced by increased LC3-II production and caused a significant increase in the sub-G0/G1 cell population, especially with BITC. Apoptosis was more pronounced after BITC treatment, whereas SFN had a weaker effect. These results suggest that autophagy may act as a defense mechanism in response to ITC-induced apoptosis in human AML cells. Full article

Carica papaya Linn. is one of the most common plants in almost all tropical countries. Its fruit is widely used as food or an ointment in traditional medicine. It is one of the few tropical fruits to contain glucotropaeolin (benzyl glucosinolate) detected in great quantity, mainly in the seeds of papaya. When cells in plant tissue are damaged, glucotropaeolin is hydrolysed by the enzyme myrosinase to benzyl isothiocyanate. The anticancer activity of this latter compound has been widely evidenced, but the metabolic profile of the papaya seed extracts is not reported in the literature. The objective of this study is to investigate the seed extracts of C. papaya L. by UHPLC-PDA ESI/MS, with and without the inactivation of myrosinase, and compare the recovery of some main components using two different inactivation procedures. The extracts (methanol/water, 60:40, v/v) were studied in negative and positive ionisation modes. Separations were carried out on an Acquity BEH C18 (50 × 2.1 mm i.d.) 1.7 μm analytical column, and 0.02% formic acid in water and acetonitrile was used as the mobile phase at a flow rate of 0.6 mL min⁻¹. Beyond the amino acids and glucotropaeolin already detected in papaya seeds, 4-hydroxybenzoic acid, which has never been detected in papaya seeds with this technique before, was identified. Moreover, mono-, di- and tri-glycosides of 4-hydroxybenzoic acid were putatively assigned. Glucotropaeolin, 4-hydroxybenzoic and tryptophan were quantified in seeds extracted after myrosinase deactivation. These three components were more effectively recovered using an oven than microwave myrosinase inactivation. Full article

The aim of our study was to investigate whether the combination of benzyl isothiocyanate (BITC) and resveratrol (RES) has a synergistic effect on the inhibition of inflammation in colitis. The results revealed that the BITC and RES combination (BITC_RES) was more effective than either substance alone at significantly alleviating the symptoms of dextran sodium sulfate (DSS)-induced colitis in mice, including the prevention of colon shortening and loss of body weight, a reduction in the disease activity index, and prevention of colon damage. Similarly, compared with the DSS group, BITC_RES reduced myeloperoxidase (MPO) and inducible nitric oxide synthase (iNOS) levels in the mouse colon by 1.4–3.0-fold and 1.4-fold, respectively. In addition, the combination of BITC and RES upregulated the inflammatory factor IL-10 by 1.3- and 107.4-fold, respectively, compared to the individual BITC and RES groups, whereas the proinflammatory factors, including TNF-α, IL-1β, and IL-6, were downregulated by 1.1–7.4-, 0.7–3.6-, and 0.6–2.6-fold, respectively, in the BITC_RES group compared with the individual groups. Gut microbiome analysis indicated that BITC_RES remodeled the structure of gut bacteria at the phylum, family, and genus levels, upregulating the abundance of the phylum Bacteroidetes and the family Muribaculaceae and the genus norank_f_Muribaculaceae and downregulating the abundance of the phylum Firmicutes. Significant correlations between the relative levels of these proinflammatory cytokines and changes in the gut microbiota were found using Pearson’s correlation analysis. BITC and RES exhibited synergistic effects by reshaping the gut microbiota and modulating the level of serum cellular inflammatory factors, thus exerting a protective effect against colitis. Full article

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. Full article

Triple-negative breast cancer (TNBC) presents a therapeutic challenge due to its complex pathology and limited treatment options. Addressing this challenge, our study focuses on the effectiveness of combination therapy, which has recently become a critical strategy in cancer treatment, improving therapeutic outcomes and combating drug resistance and metastasis. We explored a novel combination therapy employing Benzyl isothiocyanate (BITC) and Sorafenib (SOR) and their nanoformulation, aiming to enhance therapeutic outcomes against TNBC. Through a series of in vitro assays, we assessed the cytotoxic effects of BITC and SOR, both free and encapsulated. The BITC–SOR-loaded nanoparticles (NPs) were synthesized using an amphiphilic copolymer, which demonstrated a uniform spherical morphology and favorable size distribution. The encapsulation efficiencies, as well as the sustained release profiles at varied pH levels, were quantified, revealing distinct kinetics that were well-modeled by the Korsmeyer–Peppas equation. The NP delivery system showed a marked dose-dependent cytotoxicity towards TNBC cells, with an IC50 of 7.8 μM for MDA-MB-231 cells, indicating improved efficacy over free drugs, while exhibiting minimal toxicity toward normal breast cells. Furthermore, the NPs significantly inhibited cell migration and invasion in TNBC models, surpassing the effects of free drugs. These findings underscore the potential of BITC–SOR-NPs as a promising therapeutic approach for TNBC, offering targeted delivery while minimizing systemic toxicity. Full article

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-1β 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. Full article

Isothiocyanates are biologically active products resulting from the hydrolysis of glucosinolates predominantly present in cruciferous vegetables belonging to the Brassicaceae family. Numerous studies have demonstrated the diverse bioactivities of various isothiocyanates, encompassing anticarcinogenic, anti-inflammatory, and antioxidative properties. Nature harbors distinct isothiocyanate precursors, glucosinolates such as glucoraphanin and gluconastrin, each characterized by unique structures, physical properties, and pharmacological potentials. This comprehensive review aims to consolidate the current understanding of Moringa isothiocyanates, mainly 4-[(α-L-rhamnosyloxy) benzyl] isothiocyanate), comparing this compound with other well-studied isothiocyanates such as sulforaphane and phenyl ethyl isothiocyanates. The focus is directed toward elucidating differences and similarities in the efficacy of these compounds as agents with anticancer, anti-inflammatory, and antioxidative properties. Full article

Despite substantial heterogeneity of studies, there is evidence that antibiotics commonly used in primary care influence the composition of the gastrointestinal microbiota in terms of changing their composition and/or diversity. Benzyl isothiocyanate (BITC) from the food and medicinal plant nasturtium (Tropaeolum majus) is known for its antimicrobial activity and is used for the treatment of infections of the draining urinary tract and upper respiratory tract. Against this background, we raised the question of whether a 14 d nasturtium intervention (3 g daily, N = 30 healthy females) could also impact the normal gut microbiota composition. Spot urinary BITC excretion highly correlated with a weak but significant antibacterial effect against Escherichia coli. A significant increase in human beta defensin 1 as a parameter for host defense was seen in urine and exhaled breath condensate (EBC) upon verum intervention. Pre-to-post analysis revealed that mean gut microbiome composition did not significantly differ between groups, nor did the circulating serum metabolome. On an individual level, some large changes were observed between sampling points, however. Explorative Spearman rank correlation analysis in subgroups revealed associations between gut microbiota and the circulating metabolome, as well as between changes in blood markers and bacterial gut species. Full article

The search for new antifungal substances is increasingly relevant due to growing antifungal resistance. Candida albicans is the most common pathogen yeast in humans, primarily in immuno-compromised individuals. Isothiocyanates, derived from glucosinolates, are compounds with an antimicrobial effect at low concentrations. The purpose of this study was to analyse the ultrastructural changes in three C. albicans isolates after exposure to benzyl isothiocyanate (BITC) at different lengths of exposure time (2.5, 5 and 24 h). Before exposure to BITC, cells presented a regular round or oval shape, with a uniform cell wall. After exposure to BITC, cell wall damage and loss occurred in the three strains. The cells developed extensive indentations, and a band of electrodense material was formed in the cortical cytoplasm. Although, for one isolate, no intact cells were detected, at the highest exposure time, two of the isolates showed a relevant response, regaining almost normal cell shape with nearly complete cell wall recovery. Cell lysis led to the deposition of a melted and unmixed mass with two apparently distinct fractions, the cell wall fraction and the cytoplasmic fraction. The present work demonstrates that, through targeting the C. albicans cell wall, BITC may prove to be a promising antifungal compound. Full article

Tropaeolum majus L. is a traditional medicinal plant with a wide range of biological activities due to the degradation products of the glucosinolate glucotropaeolin. Therefore, the goals of this study were to identify volatiles using gas chromatography–mass spectrometry analysis (GC-MS) of the hydrosols (HYs) isolated using microwave-assisted extraction (MAE) and microwave hydrodiffusion and gravity (MHG). Cytotoxic activity was tested against a cervical cancer cell line (HeLa), human colon cancer cell line (HCT116), human osteosarcoma cell line (U2OS), and healthy cell line (RPE1). The effect on wound healing was investigated using human keratinocyte cells (HaCaT), while the antibacterial activity of the HYs was tested against growth and adhesion to a polystyrene surface of Staphylococcus aureus and Escherichia coli. Antiphytoviral activity against tobacco mosaic virus (TMV) was determined. The GC-MS analysis showed that the two main compounds in the HYs of T. majus are benzyl isothiocyanate (BITC) and benzyl cyanide (BCN) using the MAE (62.29% BITC and 15.02% BCN) and MHG (17.89% BITC and 65.33% BCN) extraction techniques. The HYs obtained using MAE showed better cytotoxic activity against the tested cancer cell lines (IC₅₀ value of 472.61–637.07 µg/mL) compared to the HYs obtained using MHG (IC₅₀ value of 719.01–1307.03 μg/mL). Both concentrations (5 and 20 µg/mL) of T. majus HYs using MAE showed a mild but statistically non-significant effect in promoting gap closure compared with untreated cells, whereas the T. majus HY isolated using MHG at a concentration of 15 µg/mL showed a statistically significant negative effect on wound healing. The test showed that the MIC concentration was above 0.5 mg/mL for the HY isolated using MAE, and 2 mg/mL for the HY isolated using MHG. The HY isolated using MHG reduced the adhesion of E. coli at a concentration of 2 mg/mL, while it also reduced the adhesion of S. aureus at a concentration of 1 mg/mL. Both hydrosols showed excellent antiphytoviral activity against TMV, achieving100% inhibition of local lesions on the leaves of infected plants, which is the first time such a result was obtained with a hydrosol treatment. Due to the antiphytoviral activity results, hydrosols of T. majus have a promising future for use in agricultural production. Full article