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... Imbibed seeds of A. theophrasti were placed in Petri dishes and treated with 0-6 × 10-4 M benzyl isothiocyanate (BITC) extracted from mature papaya seeds. At 6 × 10-4 M BITC germination was completely inhibited and after exposure to 4 × 10-4 M BITC for 4 days germination was only 28% of that in the absence of BITC. When 4 × 10-4 M BITC was applied to 3-day-old etiolated seedlings all died within 2 ...
... The effect of ethylene on in vitro plant regeneration from frond and rhizome explants of Platycerium coronarium was investigated. Ethylene levels in the culture vessels increased with time, resulting in a decrease in the percentage of sporophytes produced. Addition of the ethylene action inhibitor silver thiosulfate resulted in an increase in the percentage of plants regenerated, indicating an inh ...
... The interaction of benzyl isothiocyanate (in concentrations of 2.5-250 mg benzyl-ITC g-1 protein) with myoglobin leads to the formation of derivatives which have been characterised in terms of their solubility, free epsilon amino groups, content of tryptophan and its quenching, as well as their molecular properties determined with electrophoretic and chromatographic methods. The reaction takes pla ...
Drypetes; essential oils; bark; benzyl isothiocyanate; cyanides; chemical constituents of plants; Central African Republic
Abstract:
... Essential oils obtained from bark samples of Drypetes gossweileri collected in Central African Republic and Gabon were analyzed by GC and GC/MS. Their chemical composition is particularly simple, with only three constituents: benzyl isothiocyanate (56-94%), accompanied by benzyl cyanide and benzaldehyde. ...
Capparis; essential oils; volatile compounds; benzyl isothiocyanate; methyl isothiocyanate; leaves; bark; pods; chemical constituents of plants; Brazil
Abstract:
... Essential oil analysis of Capparis flexuosa (Capparaceae) from Brazil allowed us to characterize 3-methyl-3-buteneisothiocyanate, 4-methyl-4-pentenenitrile and butyl isothiocyanate. Structure determinations were established by spectroscopic analysis (IR, MS, NMR) and chemical derivatization. ...
... The interactions of different isothiocyanates (ITCs, benzyl- and phenyl-ITC) with selected food proteins such as egg white proteins, myoglobin, and legumin have been investigated. The first aspect summarizes the changes in physicochemical properties of the derivatized proteins such as a decrease in solubility and in the amount of free epsilon-amino groups coupled with an increase in the hydrophobi ...
... Effects of benzyl isothiocyanate (BITC) on urinary bladder carcinogenesis were examined in rats simultaneously treated with N-butyl-N-(4-hydroxybutyl)nitrosamine (BBN). Groups of 20 6-wk-old Fischer 344 male rats were given 10, 100, or 1,000 ppm BITC in the diet or a basal diet with 50 ppm BBN in the drinking water for 40 wk and then killed for autopsy. Additional groups consisting of 10 or 9 rats ...
Salvadora persica; essential oils; roots; limonene; alpha-pinene; benzyl isothiocyanate; chemical constituents of plants; Jordan
Abstract:
... The composition of the essential oil from the roots of Salvadora persica L. (Salvadoraceae), collected in Jordan, was analyzed by GC and GC/MS. Seventeen compounds were detected, the main constituents being benzyl isothiocyanate (70%), limonene (9.4%) and alpha-pinene (8.7%). ...
... Rates of degradation of 2-propenyl isothiocyanate (PrITC), benzyl isothiocyanate (BeITC) and 2-phenylethyl isothiocyanate (2-PeITC) in a soil known to biodegrade methyl isothiocyanate (MITC) at an accelerated rate, but never previously exposed to the other ITCs, were higher (persistence in soil increased by 1150, 80 and 100%, respectively,) than in a similar non-degrading soil. The rate of degrada ...
... Glutathione (GSH) is an important antioxidant and cofactor of detoxifying metabolism. Therefore, elevation of GSH as achieved by inducing γ-glutamylcysteine synthetase (GCS), the limiting enzyme of GSH synthesis, may contribute to chemoprevention against cancer. In previous animal studies, increases in GCS were mainly found in liver and other organs that are not easily accessible in humans. Thus, ...
Lewis acids; benzyl isothiocyanate; biotechnology; cyclosporine; membrane permeability; mitochondria; thiols
Abstract:
... We found that both benzyl isothiocyanate (ITC) and phenyl ITC inhibited respiration in the mitochondria in an electrophilic reaction-dependent manner. ITC-induced mitochondrial swelling and cytochrome c release were prevented by cyclosporin A, indicating that they are mediated through the ITC moiety-dependent reaction to critical thiol groups for the opening of membrane permeability transition-dep ...
... Benzyl isothiocyanate (BITC) is known to be a strong antifungal compound in vitro against different fungi. The effectiveness of benzyl isothiocyanate to control Alternaria alternata growth in vitro and in vivo was tested. BITC in vitro activity was evaluated in A alternata growing on potato dextrose agar and exposed to 0.025, 0.05, 0.1, 0.2 or 0.4 mg ml(-1). In vivo activity was evaluated by expos ...
... Early effects (only 1 h of exposure) of three isothiocyanates (benzyl, phenylethyl, and sulforaphane) on nuclear accumulation of thioredoxin, APE/Ref-1, and transcription factors NF-kappaB and Nrf2, as well as production of reactive oxygen species (ROS) and reduced glutathione levels were examined in human adenocarcinoma Caco-2 cells. Nuclear increase of NF-kappaB, Nrf2, and thioredoxin contents w ...
... Volatile constituents of the seeds, roots and dried non-flowering aerial parts of Lepidium sativum L. collected after hydrolysis were analyzed by GC and GC/MS. The main volatile constituents of the seeds were phenylacetonitrile (52.9%), benzyl isothiocyanate (26.2%) and 1,8-cineole (12.3%), while the main volatile constituents of the roots and the non-flowering aerial parts were benzyl isothiocyan ...
... (−)-Epigallocatechin-3-gallate (EGCG), one of the main constituents of green tea, has been reported to function as an antioxidant with chemopreventive potential. In contrast, we have recently reported that EGCG enhanced pro-matrix metalloproteinase (MMP)-7 in HT-29 human colon cancer cells via spontaneous superoxide generation. In the present study, we examined the effects of dietary antioxidants ...
functional foods; chemical composition; papayas; seeds; anticarcinogenic activity; glucosinolates; benzyl isothiocyanate; fruit pulp; thioglucosidase; chemical constituents of plants; superoxide anion; antioxidant activity; apoptosis; Carica papaya
Abstract:
... In the present study, papaya (Carica papaya) seed and edible pulp were carefully separated and then the contents of benzyl isothiocyanate and the corresponding glucosinolate (benzyl glucosinolate, glucotropaeolin) quantified in each part. The papaya seed with myrosinase inactivation contained >1 mmol of benzyl glucosinolate in 100 g of fresh seed. This content is equivalent to that of Karami daiko ...
... A method was developed for collecting isothiocyanates (ITCs) from compost and their detection by gas chromatography-mass spectrometry. Identification of the compounds was based on retention time, molecular weight and previously published information (Wiley Database, Hewlett Packard ChemStation Library). The release of ITCs from freeze-dried plant material of Brassica carinata, Cleome spinosa and T ...
... (−)-Epigallocatechin-3-gallate (EGCG)-induced apoptosis was along both the extracellular signal-regulated protein kinase (ERK) and c-jun N-terminal kinase (JNK) pathways in Jurkat cells. Co-treatment with EGCG potentiated the cytotoxicity induced by benzyl isothiocyanate (BITC) and H₂O₂, both being inhibited by ERK and JNK inhibitors. These results suggest the significant role of mitogen-activated ...
Alliaria petiolata; Impatiens capensis; Pinus strobus; benzyl isothiocyanate; biogeochemical cycles; biomass; conifers; ectomycorrhizae; forest ecosystems; forests; fungal communities; greenhouse experimentation; herbaceous plants; indigenous species; invasive species; mycorrhizal fungi; seedlings; soil; trees; New England region; United States
Abstract:
... 1. Ectomycorrhizal (EM) fungi play key roles in forest ecosystems, but the potential effects of invasive plants on EM fungal communities have not been assessed. In this study, we tested whether the non-mycorrhizal herbaceous plant Alliaria petiolata (garlic mustard) can alter the abundance of EM fungal communities in North America. 2. In three forests in New England, USA, we compared EM root tip a ...
... The breakdown of brassicaceous plant material produces nematotoxic isothiocyanates (ITCs). However, after the incorporation of brassicaceous plant material into soil, many nematodes are likely to be exposed only to sublethal concentrations of these compounds. Although unknown, the effect of these low ITC concentrations on the behaviour of plant-parasitic nematodes could play a role in nematode sup ...
degradation; benzyl isothiocyanate; glucosinolates; pesticides; chemical constituents of plants; hydrolysis; soil organic matter; Brassica; A horizons; B horizons; sandy soils; loam soils
Abstract:
... Isothiocyanates of natural origin produced by the hydrolysis of plant-produced glucosinolates have the potential to control soil pests, but getting sufficiently high isothiocyanate concentrations in soil is difficult. Furthermore, the isothiocyanates have proven toxic to a wide range of organisms and hence may also harm nontarget organisms. Knowledge of the sorption and degradation of the isothioc ...
... Cancer prevention by dietary phytochemicals has been shown to involve decreased cell proliferation and cell cycle arrest. However, there is limited understanding of the mechanisms involved. Previously, we have shown that a common effect of phytochemicals investigated is to oxidize the intracellular glutathione (GSH) pool. Therefore, the objective of this study was to evaluate whether changes in th ...
... The aim of the study was to evaluate the in vitro antibacterial activity of glucosinolates and their enzymatic hydrolysis product against bacteria isolated from the human intestinal tract. Using a disc diffusion bioassay, different doses of intact glucosinolates and their corresponding hydrolysis products were tested. There were clear structure-activity and concentration differences with respect t ...
functional foods; vegetables; human cell lines; metalloproteinases; signal transduction; benzyl isothiocyanate; biochemical pathways; protein kinase C; plasminogen; colorectal neoplasms; u-plasminogen activator; mitogen-activated protein kinase; anticarcinogenic activity
Abstract:
... Benzyl isothiocyanate (BITC), a component of dietary cruciferous vegetables, has antioxidant and anticancer properties. In this study, we show for the first time the antimetastatic effects of BITC in human colon cancer HT29 cells. BITC had an inhibitory effect on cell migration and invasion. Protein levels of matrix metalloproteinase-2 (MMP-2), matrix metalloproteinase-9 (MMP-9), and urokinase-pla ...
... Reproduction of Meloidogyne incognita on either Capsicum annuum or Glycine max was suppressed when infective second-stage juveniles (J2) were exposed to 0.03 mM benzyl isothiocyanate (BITC) for 2 h prior to inoculation of the host. Infectivity as rated by a gall index was significantly reduced on both G. max and C. annuum. In C. annuum, nematode egg masses were recovered from 48% of the plants ino ...
... The changes in volatile compounds during papaya juice fermentation with three Williopsis saturnus yeasts were investigated in this study. Time-course papaya juice fermentations were carried out using three Williopsis saturnus yeasts: W. saturnus var. mrakii NCYC2251, W. saturnus var. saturnus NCYC22 and W. saturnus var. sargentensis NCYC2727. Changes in yeast cell population, Brix and pH were simi ...
... In a previous study we prepared monoclonal antibody against allyl isothiocyanate (AITC)-modified lysine (Lys), and found that AITC reacted with Lys under physiological conditions in vitro (T. Nakamura et al., Chem. Res. Toxicol., 22, 536–542 (2009)). In the present study, antibodies against benzyl isothiocyanate (ITC), 6-methylsulfinylhexyl ITC and phenethyl ITC modified protein were prepared, and ...
... Purpose – The purpose of this paper is to assess the potential of papaya juice fermentation and to evaluate the kinetic changes of volatile organic compounds (VOCs) produced during fermentation by three commercial wine yeasts. Design/methodology/approach – Laboratory-scale fermentations were carried out in papaya juice using three commercial wine yeasts Saccharomyces cerevisiae var. bayanus strain ...
... The ‘Pluk Mai Lie' papaya (Carica papaya L.) is a promising cultivated fruit for use in fresh and processed products due to its firm flesh, but the aroma it releases is flat. Changes in quality and volatile profiles were analyzed during on- and off-tree fruit ripening. Detached fruit ripened faster than attached fruit, accumulating high internal ethylene levels. Aside from peel color, which was re ...
... Transgenic papaya (Carica papaya L.) was produced with the introduction of replicase (rep) gene for resistance to papaya ringspot virus (PRSV). In order to investigate the potential unintended compositional changes in transgenic papaya, profiles of volatile organic compounds (VOCs), sugar/polyals, organic acids, carotenoids and alkaloids in transgenic and non-transgenic papaya were obtained respec ...
... Natural isothiocyanates (ITCs) are toxic to a range of pathogenic soil‐living species, including nematodes and fungi, and can thus be used as natural fumigants called biofumigants. Natural isothiocyanates are hydrolysis products of glucosinolates (GSLs) released from plants after cell rupture. The study investigated the toxic effects of benzyl‐GSL and its hydrolysis product benzyl‐ITC on the sprin ...
Dobrosława Gradecka-Meesters; Jadwiga Palus; Gabriela Prochazka; Dan Segerbäck; Elżbieta Dziubałtowska; Natalia Kotova; Dag Jenssen; Joanna Arkusz; Cecilia Lundin; Elisabet Vikström; Konrad Rydzyński; Robert Nilsson; Maciej Stępnik
DNA adducts; DNA damage; benzo(a)pyrene; benzyl isothiocyanate; bone marrow; cytogenetics; ellagic acid; erythrocytes; flow cytometry; leukocytes; liver; mice; oral administration; protective effect; toxicology
Abstract:
... The protective action in C57BL/6J mice from orally administered ellagic acid (EA), benzyl isothiocyanate (BITC), an extract of epigallocatechins (Tegreen®) as well as chlorophyllin (CHL) against benzo[a]pyrene (B[a]P)-induced DNA damage and cytogenetic effects was investigated. In pilot experiment the comet assay indicated protective effects for all compounds, while such activity was confined to E ...
... BACKGROUND: In general, about 300 g kg−1 of the weight of papaya fruits appears as waste materials during processing, including a considerable amount of papaya seeds. To make a more efficient use of papaya, it is worth investigating the utilization of the seeds. The aim of this study was to comprehensively assess the lipid characteristics of papaya seed oil obtained by expelling processes. RESULTS ...
... A headspace solid-phase microextraction (HS-SPME) procedure based on five commercialised fibres (85μm polyacrylate – PA, 100μm polydimethylsiloxane – PDMS, 65μm polydimethylsiloxane/divinylbenzene – PDMS/DVB, 70μm carbowax/divinylbenzene – CW/DVB and 85μm carboxen/polydimethylsiloxane – CAR/PDMS) is presented for the characterization of the volatile metabolite profile of four selected Madeira isla ...
... The substrate-binding H-site of human glutathione transferase (GST) M2-2 was subjected to iterative saturation mutagenesis in order to obtain an efficient enzyme with the novel epoxide substrate indene 1,2-oxide. Residues 10, 116, and 210 were targeted, and the activities with the alternative substrates, benzyl isothiocyanate and the prodrug azathioprine, undergoing divergent chemical reactions we ...
... Moringa oleifera Lamarck is commonly consumed for nutritional or medicinal properties. We recently reported the isolation and structure elucidation of novel bioactive phenolic glycosides, including 4-[(2′-O-acetyl-α-L-rhamnosyloxy)benzyl]isothiocyanate (RBITC), which was found to suppress inducible nitric oxide synthase (iNOS) expression and nitric oxide (NO) production in lipopolysaccharide-stimu ...
... Dietary isothiocyanates have been shown to possess anti-tumour activity, inhibiting several types of cultured human cancer cell growth. However, there are limited studies on their effects on cancer cell metastasis. Our previous study showed that benzyl isothiocyanate (BITC) and phenethyl isothiocyanate (PEITC) suppressed human lung cancer cell metastasis potential. In the present study, we found B ...
... Benzyl isothiocyanate (BITC), a compound found in cruciferous vegetables, is an effective chemopreventive agent. The objective of this study was to develop nanoemulsion formulations for the oral delivery of BITC. Optimized oil-in-water BITC nanoemulsions were prepared by a spontaneous self-nanoemulsification method and a homogenization-sonication method. Both nanoemulsions entrapped high amounts o ...
Savarni Tripathi; Jon Y. Suzuki; James B. Carr; Grant T. McQuate; Stephen A. Ferreira; Richard M. Manshardt; Karen Y. Pitz; Marisa M. Wall; Dennis Gonsalves
... Rainbow papaya (Carica papaya L.) is a genetically engineered (GE) cultivar with resistance to papaya ringspot virus (PRSV). This cultivar currently accounts for about 70% of Hawaii's papaya acreage. The nutritional composition of Rainbow papaya and a non-transgenic control were analyzed to address GE food safety concerns regarding the potential for altered nutritional composition and altered expr ...
apoptosis; benzyl isothiocyanate; breast neoplasms; cell growth; cisplatin; cytotoxicity; epithelial cells; humans; mitogen-activated protein kinase; synergism; uterine cervical neoplasms; watercress
Abstract:
... Scope: Naturally‐occurring chemopreventive agent phenethyl isothiocyanate (PEITC), derived primarily from watercress, has been shown to inhibit cell growth and induce apoptosis in cancer cells. In this study, we examined the potential of PEITC in enhancing cisplatin‐induced apoptosis in cervical cancer cells and its mechanisms. Methods and results: HeLa cells were exposed to PEITC, cisplatin or bo ...
... Sulforaphane, a major isothiocyanate derived from cruciferous vegetables, protects living systems against electrophile toxicity, oxidative stress, inflammation, and radiation. A major protective mechanism is the induction of a network of endogenous cytoprotective (phase 2) genes that are regulated by transcription factor Nrf2. To obtain a more detailed understanding of the anti-inflammatory and im ...
anticarcinogenic activity; benzyl isothiocyanate; biochemical pathways; chemical reactions; chemical structure; diet; foods; glucose; glucosinolates; inflammation; metabolites; oral administration; osteoarthritis
Abstract:
... Through a well-established enzymatic transformation glucosinolates release reactive isothiocyanates that can undergo further metabolic pathways affording a plethora of reactive metabolites. This study explores in detail the reaction of benzyl isothiocyanate, which possesses antitumor activity as alkylating agent, with d-glucosamine, commonly employed in oral treatments against osteoarthritis and i ...
... Plant samples of Hornungia petraea were analyzed for glucosinolate (GLS) autolysis metabolites for the first time. GC–MS analysis of the autolysate and the synthesis of a series (12 compounds) of possible glucosinolate breakdown products revealed/corroborated the presence of glucoaubrietin, glucolimnanthin, glucolepigramin and glucotropaeolin in this species as the most likely “mustard oil” precur ...
... Benzyl isothiocyanates (BITC), a member of the isothiocyanate (ITC) family, inhibits cell growth and induces apoptosis in many types of human cancer cell lines. The present study investigated mechanisms underlying BITC-induced apoptosis in A375.S2 human melanoma cancer cells. To observe cell morphological changes and viability, flow cytometric assays, cell counting, and a contrast-phase microscopi ...
... BACKGROUND: The toxicity to adult Dermatophagoides farinae of allyl isothiocyanate identified in horseradish, Armoracia rusticana, oil and another 27 organic isothiocyanates was evaluated using contact + fumigant and vapour‐phase mortality bioassays. Results were compared with those of two conventional acaricides, benzyl benzoate and dibutyl phthalate. RESULTS: Horseradish oil (24 h LC50, 1.54 µg ...
... In the present study, we examined the toxicity of benzyl ITC (BITC) and its urinary mercapturic acid metabolite (BITC-NAC), using a normal renal proximal tubular cell line, pig LLC-PK1. BITC increased cell death with an IC₅₀ value of about 7 μM, whereas the cytotoxic effect of BITC-NAC was five times weaker than that of BITC. We observed a significant necrosis of the compounds on LLC-PK1 cells wit ...
... A reversed phase-high performance liquid chromatography method was developed to quantify sinigrin, sinalbin, allyl isothiocyanate and benzyl isothiocyanate present in aqueous and freeze-dried yellow and Oriental (brown) mustard extract samples using two pre-treatment methods (autoclaving, boiling) to prevent degradation by myrosinase. The lowest detection limits for sinigrin and sinalbin were 0.05 ...