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Here we report the development of a concise and efficient synthetic protocol for the preparation of 1H-perimidin-2-amine derivatives that contain an N-(2,2,2-trichloroethyl)carboxamide substituent near the amino group. These compounds' synthesis method is based on the interaction of naphthalene-1,8-diamine with N-(2,2,2-trichloro-1-isothiocyanatoethyl)carboxamides under reflux in acetonitrile medium for 15 minutes. This transformation is likely to pass through the stage of formation of the intermediate thiourea, which further eliminates hydrogen sulfide, which is accompanied by the closure of the perimidine cycle. Using the developed protocol, we synthesized nine new 1H-perimidin-2-amine derivatives. The yield of synthesized compounds was 67-82%. IR,1H NMR,13C NMR, 1H-1H COSY, 1H-13C HSQC, and 1H-13C HMBC spectroscopy data proved their structures. [ABSTRACT FROM AUTHOR]

Lunaria annua L. (Brassicaceae) is an ornamental plant newly identified in Europe as a promising industrial oilseed crop for its valuable very-long-chain monounsaturated fatty acids (MUFAs), especially erucic acid (EA) and nervonic acid (NA). L. annua seeds were obtained from annual winter-type plants selected and cultivated in Northern France. Using a systematic multiple-method approach, we set out to determine the profile and content of glucosinolates (GSLs), which are the relevant chemical tag of Brassicaceae. Intact GSLs were analyzed through a well-established LC-MS method. Identification and quantification were performed by HPLC-PDA of desulfo-GSLs (dGLs) according to the official EU ISO method. Moreover, GSL structures were confirmed by GC-MS analysis of the related isothiocyanates (ITCs). Seven GSLs were identified, directly or indirectly, as follows: 1-methylethyl GSL, (1S)-1-methylpropyl GSL, (Rs)-5-(methylsulfinyl)pentyl GSL, (Rs)-6-(methylsulfinyl)hexyl GSL, (2S)-2-hydroxy-4-pentenyl GSL, 2-phenylethyl GSL, and 1-methoxyindol-3-ylmethyl GSL. In other respects, the FA composition of the seed oil was determined. Results revealed cultivated L. annua seed to be a source of NA-rich oil, and presscake as a valuable coproduct. This presscake is indeed rich in GSLs (4.3% w/w), precursors of promising bioactive molecules for agricultural and nutraceutical applications. [ABSTRACT FROM AUTHOR]

Oxidative stress is a common feature of neurodegenerative diseases. Different natural compounds mediate neuroprotective effects by activating the Nrf2 antioxidant response. Some isothiocyanates are Nrf2 activators, including Moringin (MOR). In this study, the transcriptional profile of differentiated NSC-34 motor neurons was evaluated after treatment for 48 h and 96 h with concentrations of 0.5, 5, and 10 µM of a new MOR formulation obtained with α-cyclodextrin (α-CD). All the concentrations increased gene expression and cytoplasmic protein levels of Nrf2 at 96 h. However, the highest dose also increased nuclear Nrf2 levels at 96 h. Then, Nrf2 interactors were selected using STRING, and common biological process (BP) terms between the groups were evaluated. α-CD/MOR was able to modulate BP related to responses to oxidative stress, proteostasis, and autophagy. Specifically, the treatment with 10 µM of α-CD/MOR for 96 h induced genes involved in glutathione synthesis and proteasome subunits and reduced the expression of genes related to endoplasmic reticulum stress. Moreover, this group showed the lowest levels of the apoptotic markers Bax, cleaved caspase 9, and cleaved caspase 3. These results indicate the beneficial effects of prolonged α-CD/MOR supplementation that are mediated, at least in part, by Nrf2 activation. Then, α-CD/MOR could be a valuable treatment against neurodegenerative diseases, in particular motor neuron degeneration. [ABSTRACT FROM AUTHOR]

A simple synthetic strategy to construction of novel 4-oxo-2-phenyl-4H-chromene-3-carbothioamides (2–6) was achieved. The synthetic strategy depended on the treatment of 1-(2-hydroxyphenyl)-3-phenylpropane-1,3-dione (1) with some examples of aryl, aralkyl, aroyl and phosphorus isothiocyanates with promotion of DBU. The interesting 4,6-diphenyl-5-(2-hydroxy-benzoyl)-2-thioxo-3,4-dihydro-2H-1,3,4-oxazaphosphinine (8) as a highly regioselective product was obtained through treatment of the substrate 1 with phenyl phosphonisothiocyanatidous chloride whereas the other novel 2-phenyl-3-(2-thioxo-2H-1,3,5,4-thiadiazaphosphinin-6-yl)-4-oxo-4H-chromenes (9 and 10) were formed by using phosphorous diisothiocyanate and triisothiocyanate, respectively, under the same basic reaction conditions. All the reaction mechanisms were discussed. Structures of all the synthesized products were established by elemental analysis and available spectral tools. [ABSTRACT FROM AUTHOR]

Breast cancer is the most common tumor in women. Chemotherapy is the gold standard for cancer treatment; however, severe side effects and tumor resistance are the major obstacles to chemotherapy success. Numerous dietary components and phytochemicals have been found to inhibit the molecular and signaling pathways associated with different stages of breast cancer development. In particular, this review is focused on the antitumor effects of PUFAs, dietary enzymes, and glucosinolates against breast cancer. The major databases were consulted to search in vitro and preclinical studies; only those with solid scientific evidence and reporting protective effects on breast cancer treatment were included. A consistent number of studies highlighted that dietary components and phytochemicals can have remarkable therapeutic effects as single agents or in combination with other anticancer agents, administered at different concentrations and via different routes of administration. These provide a natural strategy for chemoprevention, reduce the risk of breast cancer recurrence, impair cell proliferation and viability, and induce apoptosis. Some of these bioactive compounds of dietary origin, however, show poor solubility and low bioavailability; hence, encapsulation in nanoformulations are promising tools able to increase clinical efficiency. [ABSTRACT FROM AUTHOR]

In this work we synthesized imidazolidine derivatives in excellent yields using multicomponent reactions of phthalaldehyde or its derivatives, primary amines, isothiocyanate, 2,4-dihydroxyacetophenone and isopropenylacetylene in the presence of catalytic amount of Ag/KF/CP@MWCNTs NCs in water at room temperature. Also, the catalytic activity of the green synthesized Ag/KF/CP@MWCNTs NCs was evaluated in the reduction of organic pollutants such as 4-nitrophenol (4-NP) in water at mild conditions. The results indicated that the biosynthesized NCs have very high and effective catalytic activity for organic pollutants within few seconds. As well the antioxidant activity of some synthesized imidazolidine was studied using trapping of radical by DPPH and ferric reduction activity potential (FRAP) experiment. Also, the antimicrobial activity of some synthesized compounds proved by employing the disk diffusion test on Gram-positive and Gram-negative bacteria. Also, to better understanding reaction mechanism density functional theory (DFT) based quantum chemical methods have been applied. The short time of reaction, high yields of product, easy separation of catalyst and products are some benefits of this procedure. Green chemistry is the use of a set of principles to reduce or eliminate the use or generation of unsafe materials in the design, fabrication and applications of chemical products. Among solvents, water is a green solvents and very suitable for performing organic reaction. The present procedure avoids the use of toxic solvent. Heterocyclic compounds hold a prominent position in medicinal chemistry owing to their wide spectrum of biological activities such as antimalarial, antimicrobial, antitumor, anticancer, antidepressant, antiviral, antidiabetic, anti-inflammatory and anti-HIV. Imidazolidine-2-one moiety found in variety of biologically active compounds, for example, aplysinopsin is exhibiting cytotoxicity toward cancer cells, nilutamide use for the treatment of advanced prostate cancer. [ABSTRACT FROM AUTHOR]

The compound 1-(3-chlorophenyl)-3-(6-((1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)amino)hexyl)thiourea was synthesized for the first time from 6-((1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)amino)hexan-1-amine and 3-chlorophenylisothiocyanate in DMF with a 60% yield. It was characterized by 1H, 13C{1H} NMR, FT-IR, MS, and elemental analysis. [ABSTRACT FROM AUTHOR]

Insufficient vessel maintenance adversely impacts patients in terms of tissue reperfusion following stroke or myocardial infarction, as well as during wound healing. Angiogenesis impairment is a feature typical of metabolic disorders acting at the cardiovascular level, such as diabetes. Therapeutic angiogenesis regulation offers promising clinical implications, and natural compounds as pro‐angiogenic nutraceuticals hold valuable applications in regenerative medicine. By using cultured endothelial cells from human umbilical veins (HUVEC) we studied functional and molecular responses following exposure to erucin, a natural isothiocyanate derived from Brassicaceae plants and extracted from the seeds of rocket. Erucin (at nanomolar concentrations) promotes cell migration and tube formation, similar to vascular endothelial growth factor (VEGF), through mobilizing paxillin at endothelial edges. At the molecular level, erucin induces signaling pathways typical of angiogenesis activation, namely Ras, PI3K/AKT, and ERK1/2, leading to VEGF expression and triggering its autocrine production, as pharmacological inhibition of soluble VEGF and VEGFR2 dampens endothelial functions. Furthermore, erucin, alone and together with VEGF, preserves endothelial angiogenic functions under pathological conditions, such as those induced in HUVEC by high glucose (HG) exposure. Erucin emerges as a compelling candidate for therapeutic revascularization applications, showcasing promising prospects for natural compounds in regenerative medicine, particularly in addressing angiogenesis‐related disorders. [ABSTRACT FROM AUTHOR]

The experiments were conducted in tomato fields and greenhouses in 2019 and 2020 to evaluate the allelopathic effects of white and red cabbage with and without mulch to control johnsongrass. The effect of these methods on Johnsongrass life cycle durations, density, length, fresh and dry weight of stems, and rhizomes were determined. Also, the effect of the treatments on the quantity and quality of tomato production was evaluated. In the greenhouse experiment, tomato seedlings were planted with johnsongrass seeds and rhizomes and were treated with plants' aqueous extracts at concentrations of 2, 5, and 10%. The germination and dry weight reduction percentage of johnsongrass were calculated. Isothiocyanates contained in white and red cabbage were identified by GC-MS. White and red cabbage with mulch reduced johnsongrass density by 69.1 and 65.9%, while the dry weight of stems and rhizomes were reduced by 78.2-74.2% and 71.3-68.0%, respectively. White and red cabbage with mulch treatments achieved an increase in tomato production by 632.1 and 621.8%. According to GC-MS analysis, the predominant isothiocyanate in white cabbage was 3-(methylsulfinyl) propyl (23.43%) and 4-(methylsulfonyl)butyl (10.79%) in red cabbage. The results of these experiments confirm that both white and red cabbage have allelopathic potential that can be used in weed control. [ABSTRACT FROM AUTHOR]

This work represents an overview of the current investigations involving organosulfur compounds and colorectal cancer. The molecules discussed in this review have been investigated regarding their impact on colorectal cancer directly, at the in vitro, in vivo, and clinical stages. Organosulfur compounds may have indirect effects on colorectal cancer, such as due to their modulating effects on the intestinal microbiota or their positive effects on intestinal mucosal health. Here, we focus on their direct effects via the repression of multidrug resistance proteins, triggering of apoptosis (via the inhibition of histone deacetylases, increases in reactive oxygen species, p53 activation, β-catenin inhibition, damage in the mitochondrial membrane, etc.), activation of TGF-β, binding to tubulin, inhibition of angiogenesis and metastasis mechanisms, and inhibition of cancer stem cells, among others. In general, the interesting positive effects of these nutraceuticals in in vitro tests must be further analyzed with more in vivo models before conducting clinical trials. [ABSTRACT FROM AUTHOR]

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. [ABSTRACT FROM AUTHOR]

N,N′-Disubstituted ureas and thioureas containing a 1,1,7-trimethylbicyclo[2.2.1]heptan-2-yl sub-stit-uent were synthesized in up to 99% yields by the reaction of exo-(R or S)-1,1,7-trimethylbicyclo[2.2.1]-heptan-2-amine with aromatic isocyanates and isothiocyanates with the goal of comprehensive estimation of enantiomeric stereospecificity of human soluble epoxide hydrolase (hsEH). The synthesized compounds are promising hsEH inhibitors. [ABSTRACT FROM AUTHOR]

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The compound 1-(3-chlorophenyl)-3-(6-((1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)amino)hexyl)thiourea was synthesized for the first time from 6-((1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene)amino)hexan-1-amine and 3-chlorophenylisothiocyanate in DMF with a 60% yield. It was characterized by 1H, 13C{1H} NMR, FT-IR, MS, and elemental analysis.

This study included the preparation and characterization of the new guanine derivative (N-((6-oxo-6,9-dihydro-1H-purin-2-yl)carbamothioyl)propionamide), with an exciting chemical structure. The guanine part is a bicyclic heterocyclic base that is connected to a carbamothioyl group by a propionamide linker. This nitrogenous base derivative is prepared in two steps: The first step involves the synthesis of propionyl isothiocyanate from the reaction of propionyl chloride with ammonium thiocyanate in acetone. In contrast, the second step consists of the reaction of ammonium thiocyanate with guanine to obtain the ligand. The study also includes the preparation of new complexes of metal ions (Mn+2, Co+2, Ni+2, Cu+2, Zn+2, Cd+2, and Pd+2) with a prepared guanine derivative. The ligand and complexes were characterized by using infrared spectra, ultraviolet-visible spectra, 1H-N.M.R., 13C-N.M.R. spectra, and elemental analysis (C.H.N.S.): molar conductivity measurement, magnetic susceptibility, atomic absorption, and melting point. The results of these studies showed that general formulas for these complexes were given [MCl2(O.P.P.)2], M = (Mn+2, Co+2, Ni+2, Cu+2, Zn+2, Cd+2, and Pd+2). It was found that the geometric shape of all the prepared complexes was an octahedron.

This study introduces a series of novel Alkyl thio-1,2,4-triazole (4a-p) and mercapto-1,2,4-triazole (3a-d) compounds derived from nalidixic acid. The synthesis was streamlined, involving interactions between nalidixic acid hydrazide and various isothiocyanates to yield cyclic and alkyl(aryl) sulfide compounds, characterized using 1H NMR, 13C NMR, IR, and elemental analysis. Antioxidant capabilities were quantified through DPPH and ABTS assays, highlighting significant potential, especially for compound 3d, which demonstrated an ABTS IC50 value of 0.397 μM, on par with ascorbic acid (IC50 = 0.87 μM). Antibacterial efficacy was established through MIC assessments against a broad spectrum of Gram-positive and Gram-negative bacteria, including Candida albicans. Compounds 3b, 4e, 4h, 4j, 4i, 4m, and 4o showed broad-spectrum activity, with 4k and 4m exhibiting pronounced potency against E. coli. Molecular docking studies validated the antibacterial potential, with compounds 4f and 4h showing high binding affinities (docking scores of −9.8 and −9.6 kcal/mol, respectively), indicating robust interactions with the bacterial enzyme targets. These scores underscore the compounds' mechanistic basis for their antibacterial action and support their therapeutic promise. Furthermore, compounds 3b, 4i, and 4m, identified through drug-likeness and toxicity predictions, were highlighted for their favorable profiles, suggesting their suitability for oral antibiotic therapies. This comprehensive study, blending synthetic, in vitro, and in silico approaches, emphasizes the triazole derivatives' potential as future candidates for antibiotic and antioxidant applications, particularly spotlighting compounds 3b, 4i, and 4m due to their promising efficacy and safety profiles.

The phased array antennas based on highly anisotropic nematic liuquid crystals have achieved rapid develepment in recent years. In this paper, super high birefringence liquid crystal compounds with bistolane core were synthesized and their properties were investigated. The bistolane compounds show high bifringence above 0.6 and high clearing points above 200°C. Based on these new liquid crystal compounds, a liquid crystal mixture with nematic temperature range of 5~164 ºC and birefringence of 0.5 was developed. At 19 GHz, the new liquid crystal mixture shows excellent dielectric properties, with dielectric anisotropy of 1.57, which is the highest value reported in known literature. The new liquid crystal mixture also has relatively low dielectric loss of 0.0089 and low viscoelastic coefficient of 17.6 ms/μm2. [ABSTRACT FROM AUTHOR]

Lunaria annua L. (Brassicaceae) is an ornamental plant newly identified in Europe as a promising industrial oilseed crop for its valuable very-long-chain monounsaturated fatty acids (MUFAs), especially erucic acid (EA) and nervonic acid (NA). L. annua seeds were obtained from annual winter-type plants selected and cultivated in Northern France. Using a systematic multiple-method approach, we set out to determine the profile and content of glucosinolates (GSLs), which are the relevant chemical tag of Brassicaceae. Intact GSLs were analyzed through a well-established LC-MS method. Identification and quantification were performed by HPLC-PDA of desulfo-GSLs (dGLs) according to the official EU ISO method. Moreover, GSL structures were confirmed by GC-MS analysis of the related isothiocyanates (ITCs). Seven GSLs were identified, directly or indirectly, as follows: 1-methylethyl GSL, (1S)-1-methylpropyl GSL, (Rs)-5-(methylsulfinyl)pentyl GSL, (Rs)-6-(methylsulfinyl)hexyl GSL, (2S)-2-hydroxy-4-pentenyl GSL, 2-phenylethyl GSL, and 1-methoxyindol-3-ylmethyl GSL. In other respects, the FA composition of the seed oil was determined. Results revealed cultivated L. annua seed to be a source of NA-rich oil, and presscake as a valuable coproduct. This presscake is indeed rich in GSLs (4.3% w/w), precursors of promising bioactive molecules for agricultural and nutraceutical applications.

Oxidative stress is a common feature of neurodegenerative diseases. Different natural compounds mediate neuroprotective effects by activating the Nrf2 antioxidant response. Some isothiocyanates are Nrf2 activators, including Moringin (MOR). In this study, the transcriptional profile of differentiated NSC-34 motor neurons was evaluated after treatment for 48 h and 96 h with concentrations of 0.5, 5, and 10 µM of a new MOR formulation obtained with α-cyclodextrin (α-CD). All the concentrations increased gene expression and cytoplasmic protein levels of Nrf2 at 96 h. However, the highest dose also increased nuclear Nrf2 levels at 96 h. Then, Nrf2 interactors were selected using STRING, and common biological process (BP) terms between the groups were evaluated. α-CD/MOR was able to modulate BP related to responses to oxidative stress, proteostasis, and autophagy. Specifically, the treatment with 10 µM of α-CD/MOR for 96 h induced genes involved in glutathione synthesis and proteasome subunits and reduced the expression of genes related to endoplasmic reticulum stress. Moreover, this group showed the lowest levels of the apoptotic markers Bax, cleaved caspase 9, and cleaved caspase 3. These results indicate the beneficial effects of prolonged α-CD/MOR supplementation that are mediated, at least in part, by Nrf2 activation. Then, α-CD/MOR could be a valuable treatment against neurodegenerative diseases, in particular motor neuron degeneration.

2‐Iminothiazolidin‐4‐one, 5‐ethylidenethiazolidin‐4‐one, and thiazolidine‐4‐thione are all medicinally relevant structures. In this work, a NaSO2CF3‐promoted [2+2+1] cascade annulation reaction of CF3‐imidoyl sulfoxonium ylides and isothiocyanates was reported to synthesize a variety of decorated thiazolidine‐4‐thiones in 35–91% yields with exclusive stereoselectivity. The gram‐scale reaction and further chemoselective S‐alkylations demonstrated the synthetic utilities of this transformation. [ABSTRACT FROM AUTHOR]

An efficient and facile protocol for the synthesis of pyrimidine, pyridine and pyrazole ring systems was reported, Reaction of isothiocyanate with enaminone to give pyrimidinthione 4, the reactions of pyrimidinthione 4 with several active species such as ethyliodide, benzaldehyde, p-anisidine, acetylacetone were studied, the reactions of isothiocyanate 1 with active species such as ethyl cyanoacetate to form thioamide then oxazine, thiourea togivethiosemicarbazide, hydrazine, and phenylhydrazine resulted in pyrimidines. Novel compounds were tested for biological activity against Gram+ bacteria (Bacillus subtilis and Staphylococcus aureus) and Gram– bacteria (E. Coli and Klebsiella pneumonia) using Gentamycin as reference standard drug, Results showed novel compounds as potent antibacterial agents against all bacterial strains except (Klebsiella pneumonia bacteria). [ABSTRACT FROM AUTHOR]

In the present study, we report a facile synthesis of a new series of 3-subtituted-2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives via the cascade reaction of various isothiocyanate derivatives and anthranilic acid. The reaction was assisted by microwave irradiation and finished after 1 h affording the target products with the yield within the range 40–72%. The synthetic compounds were characterized by spectroscopic methods including IR, NMR (1H, 2D, and 13C), and mass spectrometry. All spectral data indicated good accordance with expected structures. In addition, the complex of quinazoline derivatives with Candida albicans dihydrofolate reductase (C. albicans DHFR) were studied in silico. The results showed that all quinazoline compounds (2a–f) have a greater ability to inhibit C. albicans DHFR than 5-(phenylsulfanyl)-2,4-quinazolinediamine. Therefore, they are promising candidates for further studies in finding the lead structure for antimicrobial activity. [ABSTRACT FROM AUTHOR]

Natural products are recognized as potential analgesics since many of them are part of modern medicine to relieve pain without serious adverse effects. The aim of this study was to investigate the antinociceptive and anti-inflammatory activities of an aqueous extract of Brassica oleracea var. italica sprouts (AEBS) and one of its main reported bioactive metabolites sulforaphane (SFN). Antinociceptive activity of the AEBS (30, 100, and 300 mg/kg, i.p. or 1000 and 2000 mg/kg, p.o.) and SFN (0.1 mg/kg, i.p.) was evaluated in the plantar test in rats to reinforce its analgesic-like activity at central level using the reference drug tramadol (TR, 50 mg/kg, i.p.). The anti-inflammatory-like response was determined in the carrageenan-induced oedema at the same dosages for comparison with ketorolac (KET, 20 mg/kg, i.p.) or indomethacin (INDO, 20 mg/kg, p.o.). A histological analysis of the swollen paw was included to complement the anti-inflammatory response. Additionally, acute toxicity observed in clinical analgesics as the most common adverse effects, such as sedation and/or gastric damage, was also explored. As a result, central and peripheral action of the AEBS was confirmed using enteral and parenteral administration, in which significant reduction of the nociceptive and inflammatory responses resembled the effects of TR, KET, or INDO, respectively, involving the presence of SFN. No adverse or toxic effects were observed in the presence of the AEBS or SFN. In conclusion, this study supports that Brassica oleracea var. italica sprouts are a potential source of antinociceptive natural products such as SFN for therapy of pain alone and associated to an inflammation condition. [ABSTRACT FROM AUTHOR]

Glucosinolates are naturally occurring β-d-thioglucosides that mainly exist in the Brassicaceae family. The enzyme myrosinase hydrolyzes glucosinolates to form isothiocyanates, which are chemical protectors. Phenethyl isothiocyanate, sulforaphane, and benzyl isothiocyanate are potential isothiocyanate with efficient anti-cancer effects as a protective or treatment agent. Glucosinolate metabolites exert the cancer-preventive activity through different mechanisms, including induction of the Nrf2 transcription factor, inhibition of expression of tumor necrosis factor-α (TNFα) and interleukin-1β (IL-1β), induction of apoptosis through inhibiting phase I enzymes and inducting phase II enzymes, interruption of caspase pathways, STAT1/STAT2, inhibition of sulfotransferases. Moreover, glucosinolates and their metabolites are effective in cancer treatment by inhibiting angiogenesis, upregulating natural killers, increasing expression of p53, p21, caspase 3 and 9, and modulating NF-κB. Despite the mentioned cancer-preventing effects, some isothiocyanates can increase the risk of tumors. So, further studies are needed to obtain an accurate and effective dose for each glucosinolates to treat different types of tumors. [ABSTRACT FROM AUTHOR]

Metformin (Met) is the first-line therapy in type 2 diabetes mellitus but, in last few years, it has also been evaluated as anti-cancer agent. Several pathways, such as AMPK or PI3K/Akt/mTOR, are likely to be involved in the anti-cancer Met activity. In addition, hydrogen sulfide (H2S) and H2S donors have been described as anti-cancer agents affecting cell-cycle and inducing apoptosis. Among H2S donors, isothiocyanates are endowed with a further anti-cancer mechanism: the inhibition of the histone deacetylase enzymes. On this basis, a hybrid molecule (Met-ITC) obtained through the addition of an isothiocyanate moiety to the Met molecule was designed and its ability to release Met has been demonstrated. Met-ITC exhibited more efficacy and potency than Met in inhibiting cancer cells (AsPC-1, MIA PaCa-2, MCF-7) viability and it was less effective on non-tumorigenic cells (MCF 10-A). The ability of Met-ITC to release H2S has been recorded both in cell-free and in cancer cells assays. Finally, its ability to affect the cell cycle and to induce both early and late apoptosis has been demonstrated on the most sensitive cell line (MCF-7). These results confirmed that Met-ITC is a new hybrid molecule endowed with potential anti-cancer properties derived both from Met and H2S. [ABSTRACT FROM AUTHOR]

A series of triazinethiones was successfully synthesized through cycloaddition reaction between guanidine hydrochloride with isothiocyanate intermediates and further analyzed through in silico analysis employing molecular docking simulations and ADMET prediction to investigate their potential anti-inflammatory activity. The ADMET profile of the synthesized triazinethione derivatives were found to possess favorable drug-like properties with good solubility (0.58–1.89 mg/mL) and oral bioavailability (0.55). The molecular docking analysis showed that among the synthesized triazinethione, 6-amino-4-(4-nitrophenyl)-1,3,5-triazine-2(1H)-thione exhibited a higher binding affinity with anti-inflammatory related enzymes, COX-2 (–7.8 kcal/mol) and iNOS (–6.1 kcal/mol) in comparison to standard drugs of salicylic acid (–6.2 kcal/mol) and Imidazopyridines (–5.9 kcal/mol), respectively owing to the hydrogen bond and hydrophobic interaction. The findings imply that triazinethione derivatives could make excellent possibilities for the development of new anti-inflammatory drugs. [ABSTRACT FROM AUTHOR]

Thioureas containing halogen- and dihalogen-substituted phenyl fragments were obtained based on adamantan-1-ylcarbonyl isothiocyanate in up to 76–94% yields. The effect of the carbonyl group on the melting point, lipophilicity, and water solubility of the thioureas was established. A computational screening of biological activity was carried out, which showed that 1-(adamantan-1-ylcarbonyl)-3-(aryl)thioureas can have antiviral activity and nootropic effect. Purinoceptors, along with epoxide hydrolase, were found to be the most likely targets. [ABSTRACT FROM AUTHOR]

Background: Cognitive functions decline with age. Declined cognitive functions negatively affect daily behaviors. Previous studies showed the positive effect of spices and herbs on cognition. In this study, we investigated the positive impact of wasabi, which is a traditional Japanese spice, on cognitive functions. The main bioactive compound of wasabi is 6-MSITC (6 methylsulfinyl hexyl isothiocyanate), which has anti-oxidant and anti-inflammatory functions. Anti-oxidants and anti-inflammatories have an important role in cognitive health. Therefore, 6-MSITC is expected to have positive effects on cognitive function. Previous studies showed the beneficial effects on cognitive functions in middle-aged adults. However, it is unclear that 6-MSITC has a positive effect on cognitive functions in healthy older adults aged 60 years and over. Here, we investigated whether 12 weeks' 6-MSITC intervention enhances cognitive performance in older adults using a double-blinded randomized controlled trial (RCT). Methods: Seventy-two older adults were randomly assigned to 6-MSITC or placebo groups. Participants were asked to take a supplement (6-MSITC or a placebo) for 12 weeks. We checked a wide range of cognitive performances (e.g., executive function, episodic memory, processing speed, working memory, and attention) at the pre- and post-intervention periods. Results: The 6-MSITC group showed a significant improvement in working and episodic memory performances compared to the placebo group. However, we did not find any significant improvements in other cognitive domains. Discussion: This study firstly demonstrates scientific evidence that 6-MSITC may enhance working memory and episodic memory in older adults. We discuss the potential mechanism for improving cognitive functions after 6-MSITC intake. [ABSTRACT FROM AUTHOR]

Leaf mustard (Brassica juncea) is a kind of cruciferous vegetable that is commonly consumed in Okinawa prefecture. Cruciferous vegetables are known to contain glucosinolate, which is hydrolyzed to isothiocyanate by the enzyme myrosinase; this enzyme derives from the plants themselves or from human intestinal microorganisms. Furthermore, leaf mustard is expected to have some useful functions on human health due to its ingredients, such as sinigrin (a characteristic glucosinolate in leaf mustard), allyl isothiocyanate (AITC), and γ-aminobutyric acid (GABA). The purpose of this study is to clarify the effects of moist heat cooking methods on functional components (sinigrin, AITC, and GABA) contained in leaf mustard. Leaf mustards (grown at the Okinawa Prefectural Agricultural Research Center) were cooked by steaming or boiling with different heating times. Quantitative measurements of sinigrin, AITC, and GABA were carried out by reversed-phase high-performance liquid chromatography. The sinigrin content was not affected by steaming, regardless of heating time. Moreover, myrosinase was deactivated by steaming for 90 seconds or more. During the boiling of leaf mustard, dissolution into the water was deduced to be the main causal factor of the loss of water-soluble components, such as sinigrin, and the effect of decomposition by heat was relatively small. The GABA content was significantly decreased by both moist heat cooking methods. Steaming retained more of the GABA content than boiling for 60 seconds. We concluded that steaming for a sufficient amount of time for deactivating myrosinase is necessary to retain the sinigrin content. Furthermore, over a short heating time, steaming is a better cooking method than boiling to retain the GABA content. [ABSTRACT FROM AUTHOR]

Abstract \nHighlights In this work new isoquinazoline derivatives were synthesized in excellent yields using three component reactions of isoquinoline or its derivatives, isothiocyanates, and 1-(6-amino-2-(prop-1-en-2-yl)benzofuran-5-yl)ethan-1-one in the presence of triethylamine (Et3N) under solvent-free conditions at room temperature. Also, the antioxidant activity of some synthesized isoquinazoline was studied using trapping of radical by DPPH and ferric reduction activity potential (FRAP) experiment. The short time of reaction, high yields of products, easy separation of products are some benefits of this procedure. Green chemistry is the use of a set of principles to reduce or eliminate the use or generation of unsafe materials in the design, fabrication and applications of chemical products. Among solvents, water is a green solvents and very suitable for performing organic reaction. The present procedure avoids the use of toxic solvent. Some representatives of this class of N-heterocycles are known as antiviral agents, glycosidase inhibitors, anticancer agents or antidiabetics. Therefore, in view of their medicinal relevance, an increasing number of synthetic methods have been described in recent years for the construction of highly substituted isoquinazoline derivatives. Green chemistry is the use of a set of principles to reduce or eliminate the use or generation of unsafe materials in the design, fabrication and applications of chemical products. Among solvents, water is a green solvents and very suitable for performing organic reaction.The present procedure avoids the use of toxic solvent.Some representatives of this class of N-heterocycles are known as antiviral agents, glycosidase inhibitors, anticancer agents or antidiabetics. Therefore, in view of their medicinal relevance, an increasing number of synthetic methods have been described in recent years for the construction of highly substituted isoquinazoline derivatives. [ABSTRACT FROM AUTHOR]

Dysregulation of innate immune responses can result in chronic inflammatory conditions. Glucocorticoids, the current frontline therapy, are effective immunosuppressive drugs but come with a trade‐off of cumulative and serious side effects. Therefore, alternative drug options with improved safety profiles are urgently needed. Sulforaphane, a phytochemical derived from plants of the brassica family, is a potent inducer of phase II detoxification enzymes via nuclear factor‐erythroid factor 2–related factor 2 (NRF2) signaling. Moreover, a growing body of evidence suggests additional diverse anti‐inflammatory properties of sulforaphane through interactions with mediators of key signaling pathways and inflammatory cytokines. Multiple studies support a role for sulforaphane as a negative regulator of nuclear factor kappa‐light chain enhancer of activated B cells (NF‐κB) activation and subsequent cytokine release, inflammasome activation and direct regulation of the activity of macrophage migration inhibitory factor. Significantly, studies have also highlighted potential steroid‐sparing activity for sulforaphane, suggesting that it may have potential as an adjunctive therapy for some inflammatory conditions. This review discusses published research on sulforaphane, including proposed mechanisms of action, and poses questions for future studies that might help progress our understanding of the potential clinical applications of this intriguing molecule. [ABSTRACT FROM AUTHOR]

Based on ursolic acid, 3 compounds with isothiocyanate groups located at different distances from C-17 of the triterpenoid core have been synthesized through ursane-derived primary amines. To obtain terpene hybrids with thioureas and N,S-containing heterocycles, series of amines and ammonia were reacted with novel isothiocyanates. In the reactions with propargylamine, 3 triterpenoid hybrids with 4,5-dihydrothiazol-2-yl-amine have been selectively obtained in 81%–91% yields. Isothiocyanates containing several bonds between the -CNS group and the triterpenoid backbone reacted with (1-aryl-1H-1,2,3-triazole-4-yl)methanamines, as well as with ammonia, to form thiourea derivatives (78%–94%). The nor-compound with a -CNS group at C-17 of the triterpenoid was the least reactive due to deactivation by a donor terpene branched substituent and reacted readily only with sufficiently strong nucleophiles, such as primary and secondary aliphatic amines. The reaction of the nor-derivative of isothiocyanate 7 with ammonia at elevated temperature led to the unexpected formation of 3β-acetoxy-28-norurs-12-en-17-yl-amine, the precursor of isothiocyanate, as the main product (82%). [ABSTRACT FROM AUTHOR]

The diversity of herbivorous insects is attributed to their propensity to specialize on toxic plants. In an evolutionary twist, toxins betray the identity of their bearers when herbivores coopt them as cues for host-plant finding, but the evolutionary mechanisms underlying this phenomenon are poorly understood. We focused on Scaptomyza flava, an herbivorous drosophilid specialized on isothiocyanate (ITC)-producing (Brassicales) plants, and identified Or67b paralogs that were triplicated as mustard-specific herbivory evolved. Using in vivo heterologous systems for the expression of olfactory receptors, we found that S. flava Or67bs, but not the homologs from microbe-feeding relatives, responded selectively to ITCs, each paralog detecting different ITC subsets. Consistent with this, S. flava was attracted to ITCs, as was Drosophila melanogaster expressing S. flava Or67b3 in the homologous Or67b olfactory circuit. ITCs were likely coopted as olfactory attractants through gene duplication and functional specialization (neofunctionalization and subfunctionalization) in S. flava, a recently derived herbivore.

The structures of (S)-butan-2-yl N-(4-nitrophenyl)thiocarbamate, C11H14N2O3S, (I), (S)-butan-2-yl N-(4-methoxyphenyl)thiocarbamate, C12H17NO2S, (II), (S)-butan-2-yl N-(4-fluorophenyl)thiocarbamate, C11H14FNOS, (III), and (S)-butan-2-yl N-(4-chlorophenyl)thiocarbamate, C11H14ClNOS, (IV), all at 100 K, have monoclinic (P21) symmetry with two independent molecules in the asymmetric unit. The Flack absolute structure parameters in all cases confirm the absence of inversion symmetry. The structures display N—H...S hydrogen bonds, resulting in R22(8) hydrogen-bonded ring synthons connecting the two independent molecules. Despite the ring synthon, the packing follows two distinct patterns, with (I) and (IV) `pancaking' along the b-axis direction, while the other two `sandwich' in layers perpendicular to the b axis. Crystal morphologies were determined theoretically via the BFDH (Bravais, Friedel, Donnay–Harker) model and agree qualitatively with the experimentally indexed results. One of the butyl substituent of (II) exhibits structural disorder.

Brassica vegetables (Brassicaceae) produce a unique class of compounds known as glucosinolates. The breakdown products of glucosinolates, including isothiocyanates, are recognized as the primary sources of bioactivity and characteristic taste, flavor and aroma of these vegetables. An emerging market trend is to harvest leafy greens at the immature stage known as “baby greens”, however, much is still unknown about the phytochemistry at this earlier stage of development. Glucosinolates and their breakdown products were examined in three members of the Brassicaceae family: Eruca vesicaria subsp. sativa ‘Arugula’, Brassica juncea ‘Garnet Giant’ (mustard greens) and Brassica oleracea var. acephala ‘Red Kale’. A total of 16 glucosinolates were tentatively identified using UHPLC-QTOF/MS and seven volatile breakdown products were identified using GC/MS. Nine putative glucosinolates and one isothiocyanate are reported for the first time in these plant species and varieties. Glucobarbarin, glucocheirolin, glucoiberin, gluconapin and neoglucobrassicin were newly identified in Eruca vesicaria subsp. sativa. Glucoalyssin, glucobarbarin, glucobrassicanapin and glucotropaeolin were newly identified in B. oleracea var. acephala, and butane isothiocyanate was newly identified in B. oleracea. Future work will focus on correlating chemistry data with sensory analyses to determine the impact of these specific glucosinolates and breakdown products on taste, flavor and aroma.

The isothiocyanate's chemoprevention properties are reported to be present in cruciferous veggies through a variety of mechanisms. Sulforaphane, a phytochemical found in green leafy vegetables, has shown promise in the prevention and treatment of several cancers, including those of the prostate, breast, colon, skin, urinary bladder, and oral cavities. These malignancies include those that affect these organs. This substance is naturally present in broccoli sprouts, kale, cabbage, cauliflower, and garden cress. Broccoli should be a regular part of your diet because it contains a variety of bioactive substances such as vitamins, polyphenols, sulfides, glucosinolates, and antioxidants. Sulforaphane may be used as an inexpensive replacement or dietary supplement for chemo preventive therapy, according to the findings of epidemiological and experimental studies. Phase 2 detoxification enzymes like glutathione transferases, epoxide hydrolase, NAD(P)H: quinone reductase, and glucuronosyltransferases, as well as epoxide hydrolase and epoxide hydrolase, are produced when the body is stimulated. This is a useful tactic for preventing cancer and fending off the harm that electrophiles and reactive oxygen species can cause. Isothiocyanates are widely distributed in the Cruciferae family and Brassica genus of food plants, which include both broccoli and cauliflower. The most typical form of these substances is glucosinolate precursors. Sulforaphane and 4-methylsulfinylbutyl isothiocyanate, two of these isothiocyanates, are particularly powerful inducers of phase 2 enzymes. It is feasible to successfully extract glucosinolates and isothiocyanates from plants by homogenizing them at a temperature of around 50 degrees Celsius in a solution of equal parts dimethyl sulfoxide, dimethylformamide, and acetonitrile. This method avoids the hydrolysis of glucosinolates by myrosinase. It's interesting to note that glucoraphanin, the precursor to sulforaphane, is 10-100 times more abundant in 3-day-old sprouts of various cruciferous vegetables, including broccoli and cauliflower than it is in fully grown veggies. Dimethylbenz(a)anthracene-treated rats displayed notable reductions in mammary tumor occurrence, quantity, and rate of growth when fed extracts from 3-day-old broccoli sprouts. These extracts' primary enzyme-inducing components were either glucoraphanin or sulforaphane. As a result, crucifer sprouts might provide an equivalent amount of cancer prevention to eating far larger quantities of the same mature vegetable species. [ABSTRACT FROM AUTHOR]

Surface‐enhanced resonance Raman scattering (SERRS) is based on nanostructures supporting localized surface plasmon resonances as well as electronic resonances of the molecular adsorbate. Bright NIR‐SERRS nanotags require dyes with high Raman scattering cross‐sections upon NIR laser excitation in combination with functional groups for chemisorption. Here, we report on the role of isothiocyanate (ITC) and sulfonate (SO) groups in five cyanine dyes on sensitivity and performance of nanotags in SERRS‐based LFA. Dye concentration‐dependent SERRS and zeta potential measurements on bare gold nanostars (AuNS) revealed strong differences in their sensitivity and stability as a function of the number of ITC and SO groups. A positive correlation with the number of ITC groups due to stronger chemisorption and a negative correlation with the number of SO groups due to stronger desorption because of higher water solubility was observed. The application in SERRS‐based biosensing requires additional functionalization steps, for example, co‐adsorption of PEG with the NIR dye. The comparison of the Raman intensities before and after bioconjugation showed that the presence of at least one ITC group is necessary for minimizing Raman signal losses, irrespective of the additional presence of SO groups. In a SERRS‐based lateral flow assay (LFA) for sensing the pregnancy marker beta‐hCG, the two dyes NIR 4f and NIR 5e (both ITC = 2, SO = 0) showed the best performance. In contrast, we do not recommend to use IR‐783 (ITC = 0, SO = 2) for SERRS‐based biosensing. Overall, this study highlights the importance of surface‐seeking moieties such as the common ITC group for optimal performance in SERRS‐based biosensing platforms. [ABSTRACT FROM AUTHOR]

Light-emitting diode (LED) irradiation with different colors and densities was employed for investigating the effect of red light on glucosinolate metabolism in postharvest pakchoi (Brassica rapa L subsp. chinensis). The results showed that both chlorophyll degradation and pakchoi yellowing were inhibited by red LED irradiation at a density of 6.5 μmol/(m2·s). Subsequently, the changes in glucosinolate content and relative expression level of genes involved in the glucosinolate metabolism of pakchoi after red LED irradiation (6.5 μmol/m2·s) were analyzed to explore the underlying regulatory mechanism. The results indicated that the contents of total glucosinolate and isothiocyanate in pakchoi petiole were 2.72 and 1.32 times higher than those in leaves, respectively. Additionally, the expression of key aliphatic synthesis genes, including MYB28, CYP83A1, and GSTF11, was significantly upregulated by red LED irradiation, thus promoting the synthesis of glucosinolate such as 3-butenyl glucosinolate. Consequently, the total glucosinolate content in treated pakchoi petiole was 1.62~1.99 times higher than that in the control during 4~8 d of storage. The myrosinase activity was promoted, and consequently, the accumulation of total isothiocyanate was increased in pakchoi petiole following red LED irradiation. Notably, the total isothiocyanate content in the control group was 77.43%~91.98% lower than that in the irradiated group during 4~8 d. In conclusion, red LED light treatment delayed the loss of glucosinolates and isothiocyanates in pakchoi, as indicated by the upregulated relative gene expression levels involved in the synthesis of aliphatic glucosinolate and increased myrosinase activity. [ABSTRACT FROM AUTHOR]

The neutral N‐heterocyclic carbene stabilized bora‐alkene 1, conveniently prepared by a BH borenium/hydroboration route, forms stable copper, gold or palladium π‐complexes. The polar bora‐alkene B=C system undergoes regioselective hydroboration reactions with the (C6F5)2BH or C6F5BH2 ⋅ SMe2 boranes. The latter reaction involves a subsequent rearrangement that leads to internal hydride vs. isothiocyanate substituent exchange at the borane pair. [ABSTRACT FROM AUTHOR]

To identify the volatile flavor components in mustard paste (MP), the volatile compounds in seven MPs available on the market were isolated and analyzed by headspace solid-phase microextraction combined with gas chromatography–mass spectrometry. A total of 27 volatile constituents were found by mass spectra and retention index compared to the data obtained from reference compounds or the related literature and databases; these compounds included nine esters, three sulfur-containing compounds, two nitriles, three ketones, three alkenes, and seven other compounds. Of the 27 compounds, 6 compounds came from the turmeric added to MPs. Among the components detected, some compounds derived from AITC were allyl thiocyanate, carbon disulfide, allyl mercaptan, diallyl sulfide, and diallyl disulfide. The results obtained provide a better and comprehensive recognition of the volatile flavor compounds in MPs, and have some reference values for developing and applying isothiocyanate compounds. [ABSTRACT FROM AUTHOR]

In this work, we successfully prepared isothiocyanates in one‐pot manner from the corresponding amines using carbon tetrabromide as a desulfurizing agent. The in situ formation of dithiocarbamate salts from amines followed by desulfurization using carbon disulfide provided various isothiocyanates in good to excellent yields. Moreover, our method can be extended to prepare unsymmetrical thioureas in one‐pot process. Both methods are applicable to large scale synthesis. The benefits of this reaction include one‐pot synthesis, mild condition, simple operation, and metal‐free process. [ABSTRACT FROM AUTHOR]

The glucosinolates of Brassicaceae plants are converted into bioactive isothiocyanates and other volatiles during a challenge by pathogens and other biotic stressors. However, the role of alternative downstream products with weaker potency (e.g., nitriles) is far from being fully understood. This study tested the possible synergistic antifungal interaction between various glucosinolate-derived nitriles and 2-phenylethyl isothiocyanate (PEITC) on 45 fungal strains, including endophytes from horseradish roots (Brassicaceae) and soil fungi, using an airtight system enabling the accurate study of extremely volatile antifungal agents. The median minimal inhibitory concentrations (MICs) were 1.28, 6.10, 27.00 and 49.72 mM for 1H-indole-3-acetonitrile (IAN), 3-phenylpropanenitrile (PPN), 4-(methylsulfanyl)-butanenitrile (MSBN) and 3-butenenitrile (BN, = allyl cyanide), respectively. Thus, nitriles were considerably weaker antifungal agents compared to PEITC with a median MIC of 0.04 mM. For the same nitriles, the median fractional inhibitory concentration indices (FICIs) of the combinations were 0.562, 0.531, 0.562 and 0.625, respectively. Altogether, 47.7%, 56.8%, 50.0% and 27.3% of tested fungal strains showed a synergistic antifungal activity (FICI ≤ 0.5) for the nitrile–isothiocyanate combinations, respectively. Hypocreales strains showed the least sensitivity towards the GSL decomposition products and their combinations. The mean MIC values for PEITC showed 0.0679 ± 0.0358, 0.0400 ± 0.0214, 0.0319 ± 0.0087 and 0.0178 ± 0.0171 mM for Hypocreales, Eurotiales, Glomerellales and Pleosporales, respectively. In addition, nitriles, especially IAN, also showed significant differences. For the same fungi, the median FICI values fell in the ranges of 0.61–0.67, 0.52–0.61, 0.40–0.50 and 0.48–0.67, respectively, depending on the nitrile. Our results suggest that glucosinolate-derived nitriles may enhance isothiocyanate antifungal activity and that they may play an active role in shaping the plant microbiome and contribute to the filtering of microbes by plants. [ABSTRACT FROM AUTHOR]

Moringa oleifera Lam. is a tropical tree that has been traditionally used for food, medicine and industrial purposes. All parts of the tree have been utilized and have biological activities, including anti-inflammatory, antibacterial, antioxidant, antidiabetic, wound healing, cardiovascular, anti-asthmatic, hepatoprotective, protection of the central nervous system and more. The leaves and seeds of moringa are particularly rich in phytochemicals, including glucosinolates and isothiocyanates (ITCs). Glucosinolates are inactive precursors that are hydrolyzed into bioactive ITCs. Isothiocyanates, such as 4-(α-L-rhamnopyranosyloxy) benzyl isothiocyanate (moringa isothiocyanate 1, or MIC-1), are known for their diverse biological activities, including anti-inflammatory, antioxidant and anticancer properties. The unique sugar moiety in moringa's ITCs contributes to its stability and distinct properties compared to other cruciferous vegetables. In vitro models, such as the TIM-1 model and in vivo murine models demonstrate MIC-1's bioaccessibility and bioavailability, with no statistical difference in state. Inflammation, as a defense mechanism, is implicated in a wide range of diseases such as diabetes, cancer, obesity, cardiovascular disease, arthritis and multiple sclerosis. In vivo models were used to evaluate the efficacy of MIC-1 against acute skin inflammation, which inhibited the inflammatory pathway. Additional studies into Moringa oleifera seed extract effects on acute inflammation can contribute to future development of therapies managing chronic inflammatory conditions. [ABSTRACT FROM AUTHOR]

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.

This work represents an overview of the current investigations involving organosulfur compounds and colorectal cancer. The molecules discussed in this review have been investigated regarding their impact on colorectal cancer directly, at the in vitro, in vivo, and clinical stages. Organosulfur compounds may have indirect effects on colorectal cancer, such as due to their modulating effects on the intestinal microbiota or their positive effects on intestinal mucosal health. Here, we focus on their direct effects via the repression of multidrug resistance proteins, triggering of apoptosis (via the inhibition of histone deacetylases, increases in reactive oxygen species, p53 activation, β-catenin inhibition, damage in the mitochondrial membrane, etc.), activation of TGF-β, binding to tubulin, inhibition of angiogenesis and metastasis mechanisms, and inhibition of cancer stem cells, among others. In general, the interesting positive effects of these nutraceuticals in in vitro tests must be further analyzed with more in vivo models before conducting clinical trials.

Rau mầm là loại rau thu hoạch sau khi hạt nảy mầm được từ 5 - 10 ngày tùy thuộc vào từng loại rau để đảm bảo năng suất và thành phần dinh dưỡng chứa trong chúng. Trong nghiên cứu này, chúng tôi khảo sát vitamin, protein, tro, hợp chất sinh học và hợp chất kích thích sinh trưởng có trong cây rau cải mầm ở ngày thứ 5, 7 và 9. Kết quả cho thấy, năng suất, hàm lượng protein, tro, vitamin A, B3 và K tăng theo thời gian thu hoạch. Trong khi đó, vitamin B6 không có mặt trong cây rau mầm cải ngọt và vitamin B3 mới bắt đầu xuất hiện ở ngày thứ 7. Hai hợp chất Glucosinolate và Isothiocyanate giảm mạnh theo thời gian thu hoạch. Rau mầm cải ngọt ở tất cả các ngày thu hoạch đều không chứa chất kích thích sinh trưởng IAA và cytokinin 6-BA. Thu hoạch rau mầm cải ngọt vào ngày thứ 7 sau khi gieo trồng để đảm bảo trong cây chứa đầy đủ các chất cần thiết cho con người.

Sulforaphane (SFN) is an isothiocyanate with multiple biomedical applications. Sulforaphane can be extracted from the plants of the genus Brassica. However, broccoli sprouts are the chief source of sulforaphane and are 20 to 50 times richer than mature broccoli as they contain 1,153 mg/100 g. SFN is a secondary metabolite that is produced as a result of the hydrolysis of glucoraphanin (a glucosinolate) by the enzyme myrosinase. This review paper aims to summarize and understand the mechanisms behind the anticancer potential of sulforaphane. The data was collected by searching PubMed/MedLine, Scopus, Web of Science, and Google Scholar. This paper concludes that sulforaphane provides cancer protection through the alteration of various epigenetic and nonepigenetic pathways. It is a potent anticancer phytochemical that is safe to consume with minimal side effects. However, there is still a need for further research regarding SFN and the development of a standard dose. [ABSTRACT FROM AUTHOR]

Radish (Raphanus sativus) is one of the cruciferous vegetables containing high amounts of glucosinolates and phenolic compounds. The major glucosinolates in radish sprouts are glucoraphasatin and glucoraphenin. Glucoraphasatin can be converted to glucoraphenin and metabolized into sulforaphene, an isothiocyanate. This study aims to measure chemical compounds (total phenolics, flavonoids, glucoraphasatin, glucoraphenin, and sulforaphene) and bioactivities (antioxidant capacities and tyrosinase inhibitory effects) of extracts from radish sprouts exposed to red and blue LED during cultivation. On the fourth day of cultivation, total phenolic content (TPC), total flavonoid content (TFC), and glucoraphasatin content in radish sprout extracts (RSE) in the red LED group (TPC: 42.2 ± 2.01 mg gallic acid equivalent/g, dry weight) were significantly higher than those in the dark group (TFC: 1.71 ± 0.28 mg quercetin equivalent/g, dry weight; glucoraphasatin: 23.4 ± 7.76 mg/g, dry weight) (p < 0.05). ABTS free radical scavenging activities of the RSE in the red LED group were higher than those in the dark and blue LED groups on the fourth and seventh days of cultivation. On the seventh day of cultivation, in vitro tyrosinase inhibition rates of the RSE were the highest at concentrations of 0.5–1 mg/mL in the blue LED group. This study suggests that red LED exposure might promote the synthesis of glucoraphasatin during cultivation and contribute to high antioxidant capacities in radish sprouts. In addition, blue LED exposure might more efficiently promote the synthesis of substances possessing in vitro tyrosinase inhibitory effects of radish sprouts during cultivation. [ABSTRACT FROM AUTHOR]

Wasabi (Japanese horseradish, Eutrema japonicum) is the only cultivated species in the genus Eutrema with functional components that provide a strong pungent flavor. To evaluate genetic resources for wasabi breed‐ ing, we surveyed variations in the two most abundant isothiocyanate (ITC) components in wasabi, allyl iso‐ thiocyanate (AITC) and 6-methylsulfinyl (hexyl) isothiocyanate (6-MSITC, hexaraphane). We also examined the phylogenetic relationships among 36 accessions of wild and cultivated wasabi in Japan using chloroplast DNA analysis. Our results showed that (i) the 6-MSITC content in currently cultivated wasabi accessions was significantly higher than in escaped cultivars, whereas the AITC content was not significantly different. (ii) Additionally, the 6-MSITC content in cultivated wasabi was significantly lower in the spring than during other seasons. This result suggested that the 6-MSITC content responds to environmental conditions. (iii) The phylogenetic position and the 6-MSITC content of accessions from Rebun, Hokkaido Prefecture had different profiles compared with those from southern Honshu, Japan, indicating heterogeneity of the Rebun popula‐ tions from other Japanese wasabi accessions. (iv) The total content of AITC and 6-MSITC in cultivated wasabi was significantly higher than that of wild wasabi. In conclusion, old cultivars or landraces of wasabi, “zairai”, are the most suitable candidates for immediate use as genetic resources. [ABSTRACT FROM AUTHOR]