Isothiocyanates from Cruciferous Vegetables
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Report of the Advisory Group to Recommend Priorities for the IARC Monographs During 2020–2024
IARC Monographs on the Identification of Carcinogenic Hazards to Humans Report of the Advisory Group to Recommend Priorities for the IARC Monographs during 2020–2024 Report of the Advisory Group to Recommend Priorities for the IARC Monographs during 2020–2024 CONTENTS Introduction ................................................................................................................................... 1 Acetaldehyde (CAS No. 75-07-0) ................................................................................................. 3 Acrolein (CAS No. 107-02-8) ....................................................................................................... 4 Acrylamide (CAS No. 79-06-1) .................................................................................................... 5 Acrylonitrile (CAS No. 107-13-1) ................................................................................................ 6 Aflatoxins (CAS No. 1402-68-2) .................................................................................................. 8 Air pollutants and underlying mechanisms for breast cancer ....................................................... 9 Airborne gram-negative bacterial endotoxins ............................................................................. 10 Alachlor (chloroacetanilide herbicide) (CAS No. 15972-60-8) .................................................. 10 Aluminium (CAS No. 7429-90-5) .............................................................................................. 11 -
Bioavailability of Sulforaphane from Two Broccoli Sprout Beverages: Results of a Short-Term, Cross-Over Clinical Trial in Qidong, China
Cancer Prevention Research Article Research Bioavailability of Sulforaphane from Two Broccoli Sprout Beverages: Results of a Short-term, Cross-over Clinical Trial in Qidong, China Patricia A. Egner1, Jian Guo Chen2, Jin Bing Wang2, Yan Wu2, Yan Sun2, Jian Hua Lu2, Jian Zhu2, Yong Hui Zhang2, Yong Sheng Chen2, Marlin D. Friesen1, Lisa P. Jacobson3, Alvaro Muñoz3, Derek Ng3, Geng Sun Qian2, Yuan Rong Zhu2, Tao Yang Chen2, Nigel P. Botting4, Qingzhi Zhang4, Jed W. Fahey5, Paul Talalay5, John D Groopman1, and Thomas W. Kensler1,5,6 Abstract One of several challenges in design of clinical chemoprevention trials is the selection of the dose, formulation, and dose schedule of the intervention agent. Therefore, a cross-over clinical trial was undertaken to compare the bioavailability and tolerability of sulforaphane from two of broccoli sprout–derived beverages: one glucoraphanin-rich (GRR) and the other sulforaphane-rich (SFR). Sulfor- aphane was generated from glucoraphanin contained in GRR by gut microflora or formed by treatment of GRR with myrosinase from daikon (Raphanus sativus) sprouts to provide SFR. Fifty healthy, eligible participants were requested to refrain from crucifer consumption and randomized into two treatment arms. The study design was as follows: 5-day run-in period, 7-day administration of beverages, 5-day washout period, and 7-day administration of the opposite intervention. Isotope dilution mass spectrometry was used to measure levels of glucoraphanin, sulforaphane, and sulforaphane thiol conjugates in urine samples collected daily throughout the study. Bioavailability, as measured by urinary excretion of sulforaphane and its metabolites (in approximately 12-hour collections after dosing), was substantially greater with the SFR (mean ¼ 70%) than with GRR (mean ¼ 5%) beverages. -
Download Product Insert (PDF)
PRODUCT INFORMATION Glucoraphanin (potassium salt) Item No. 10009445 Formal Name: 1-thio-1-[5-(methylsulfinyl)-N- O (sulfooxy)pentanimidate]-β-D- OH O- glucopyranose, potassium salt O S MF: C H NO S • XK O 12 22 10 3 OH FW: 436.5 O N Purity: ≥95% UV/Vis.: λmax: 225 nm OH S S Supplied as: A crystalline solid OH O Storage: -20°C • XK+ Stability: ≥2 years Information represents the product specifications. Batch specific analytical results are provided on each certificate of analysis. Laboratory Procedures Glucoraphanin (potassium salt) is supplied as a crystalline solid. A stock solution may be made by dissolving the glucoraphanin (potassium salt) in the solvent of choice. Glucoraphanin (potassium salt) is soluble in the organic solvent DMSO, which should be purged with an inert gas, at a concentration of approximately 1 mg/ml. Further dilutions of the stock solution into aqueous buffers or isotonic saline should be made prior to performing biological experiments. Ensure that the residual amount of organic solvent is insignificant, since organic solvents may have physiological effects at low concentrations. Organic solvent-free aqueous solutions of glucoraphanin (potassium salt) can be prepared by directly dissolving the crystalline solid in aqueous buffers. The solubility of glucoraphanin (potassium salt) in PBS, pH 7.2, is approximately 10 mg/ml. We do not recommend storing the aqueous solution for more than one day. Description Glucoraphanin is a natural glycoinsolate found in cruciferous vegetables, including broccoli.1 It is converted to the isothiocyanate sulforaphane by the enzyme myrosinase.1 Sulforaphane has powerful antioxidant, anti-inflammatory, and anti-carcinogenic effects.1,2 It acts by activating nuclear factor erythroid 2-related factor 2 (Nrf2), which induces the expression of phase II detoxification enzymes.3,4 References 1. -
List of Cruciferous Vegetables
LIST OF CRUCIFEROUS VEGETABLES Arugula Bok choy Broccoli Brussels sprouts Cabbage Cauliflower Chard Chinese cabbage Collard greens Daikon Kale Kohlrabi Mustard greens Radishes Rutabagas Turnips Watercress Research of this family of vegetables indicates that they may provide protection against certain cancers. Cruciferous vegetables contain antioxidants (particularly beta carotene and the compound sulforaphane). They are high in fiber, vitamins and minerals. Cruciferous vegetables also cantain indole-3-carbidol (I3C). This element changes the way estrogen is metabolized and may prevent estrogen driven cancers. Cruciferous vegetables also contain a kind of phytochemical known as isothiocyanates, which stimulate our bodies to break down potential carcinogens (cancer causing agents). People who have hypothyroid function should steam cruciferous vegetables. Raw cruciferous vegetables contain thyroid inhibitors known as goitrogens. Goitrogens like circumstances that cause goiter, cause difficulty for the thyroid in making its hormone. Isothiocyanates appear to reduce thyroid function by blocking thyroid peroxidase, and also by disrupting messages that are sent across the membranes of thyroid cells. The materials and content contained on this form are for general holistic nutrition information only to help support and enhance the body’s own healing properties and are not intended to be a substitute for professional medical advice, diagnosis or treatment for any medical condition. You should not rely exclusively on information provided on this or any other nutritional guidelines for your health needs. All specific medical questions should be presented to the appropriate medical health care provider Reference: http://www.marysherbs.com/Miscellaneous/CruciferousVegetablesP.htm . -
MINI-REVIEW Cruciferous Vegetables: Dietary Phytochemicals for Cancer Prevention
DOI:http://dx.doi.org/10.7314/APJCP.2013.14.3.1565 Glucosinolates from Cruciferous Vegetables for Cancer Chemoprevention MINI-REVIEW Cruciferous Vegetables: Dietary Phytochemicals for Cancer Prevention Ahmad Faizal Abdull Razis1*, Noramaliza Mohd Noor2 Abstract Relationships between diet and health have attracted attention for centuries; but links between diet and cancer have been a focus only in recent decades. The consumption of diet-containing carcinogens, including polycyclic aromatic hydrocarbons and heterocyclic amines is most closely correlated with increasing cancer risk. Epidemiological evidence strongly suggests that consumption of dietary phytochemicals found in vegetables and fruit can decrease cancer incidence. Among the various vegetables, broccoli and other cruciferous species appear most closely associated with reduced cancer risk in organs such as the colorectum, lung, prostate and breast. The protecting effects against cancer risk have been attributed, at least partly, due to their comparatively high amounts of glucosinolates, which differentiate them from other vegetables. Glucosinolates, a class of sulphur- containing glycosides, present at substantial amounts in cruciferous vegetables, and their breakdown products such as the isothiocyanates, are believed to be responsible for their health benefits. However, the underlying mechanisms responsible for the chemopreventive effect of these compounds are likely to be manifold, possibly concerning very complex interactions, and thus difficult to fully understand. Therefore, -
Volume 73 Some Chemicals That Cause Tumours of the Kidney Or Urinary Bladder in Rodents and Some Other Substances
WORLD HEALTH ORGANIZATION INTERNATIONAL AGENCY FOR RESEARCH ON CANCER IARC MONOGRAPHS ON THE EVALUATION OF CARCINOGENIC RISKS TO HUMANS VOLUME 73 SOME CHEMICALS THAT CAUSE TUMOURS OF THE KIDNEY OR URINARY BLADDER IN RODENTS AND SOME OTHER SUBSTANCES 1999 IARC LYON FRANCE WORLD HEALTH ORGANIZATION INTERNATIONAL AGENCY FOR RESEARCH ON CANCER IARC MONOGRAPHS ON THE EVALUATION OF CARCINOGENIC RISKS TO HUMANS Some Chemicals that Cause Tumours of the Kidney or Urinary Bladder in Rodents and Some Other Substances VOLUME 73 This publication represents the views and expert opinions of an IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, which met in Lyon, 13–20 October 1998 1999 IARC MONOGRAPHS In 1969, the International Agency for Research on Cancer (IARC) initiated a programme on the evaluation of the carcinogenic risk of chemicals to humans involving the production of critically evaluated monographs on individual chemicals. The programme was subsequently expanded to include evaluations of carcinogenic risks associated with exposures to complex mixtures, life-style factors and biological agents, as well as those in specific occupations. The objective of the programme is to elaborate and publish in the form of monographs critical reviews of data on carcinogenicity for agents to which humans are known to be exposed and on specific exposure situations; to evaluate these data in terms of human risk with the help of international working groups of experts in chemical carcinogenesis and related fields; and to indicate where additional research efforts are needed. The lists of IARC evaluations are regularly updated and are available on Internet: http://www.iarc.fr/. -
Anti-Carcinogenic Glucosinolates in Cruciferous Vegetables and Their Antagonistic Effects on Prevention of Cancers
molecules Review Anti-Carcinogenic Glucosinolates in Cruciferous Vegetables and Their Antagonistic Effects on Prevention of Cancers Prabhakaran Soundararajan and Jung Sun Kim * Genomics Division, Department of Agricultural Bio-Resources, National Institute of Agricultural Sciences, Rural Development Administration, Wansan-gu, Jeonju 54874, Korea; [email protected] * Correspondence: [email protected] Academic Editor: Gautam Sethi Received: 15 October 2018; Accepted: 13 November 2018; Published: 15 November 2018 Abstract: Glucosinolates (GSL) are naturally occurring β-D-thioglucosides found across the cruciferous vegetables. Core structure formation and side-chain modifications lead to the synthesis of more than 200 types of GSLs in Brassicaceae. Isothiocyanates (ITCs) are chemoprotectives produced as the hydrolyzed product of GSLs by enzyme myrosinase. Benzyl isothiocyanate (BITC), phenethyl isothiocyanate (PEITC) and sulforaphane ([1-isothioyanato-4-(methyl-sulfinyl) butane], SFN) are potential ITCs with efficient therapeutic properties. Beneficial role of BITC, PEITC and SFN was widely studied against various cancers such as breast, brain, blood, bone, colon, gastric, liver, lung, oral, pancreatic, prostate and so forth. Nuclear factor-erythroid 2-related factor-2 (Nrf2) is a key transcription factor limits the tumor progression. Induction of ARE (antioxidant responsive element) and ROS (reactive oxygen species) mediated pathway by Nrf2 controls the activity of nuclear factor-kappaB (NF-κB). NF-κB has a double edged role in the immune system. NF-κB induced during inflammatory is essential for an acute immune process. Meanwhile, hyper activation of NF-κB transcription factors was witnessed in the tumor cells. Antagonistic activity of BITC, PEITC and SFN against cancer was related with the direct/indirect interaction with Nrf2 and NF-κB protein. -
Synthesis of Isothiocyanates Using DMT/NMM/Tso− As a New Desulfurization Reagent
molecules Article Synthesis of Isothiocyanates Using DMT/NMM/TsO− as a New Desulfurization Reagent Łukasz Janczewski 1,* , Dorota Kr˛egiel 2 and Beata Kolesi ´nska 1 1 Faculty of Chemistry, Institute of Organic Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, Poland; [email protected] 2 Department of Environmental Biotechnology, Faculty of Biotechnology and Food Sciences, Lodz University of Technology, Wolczanska 171/173, 90-924 Lodz, Poland; [email protected] * Correspondence: [email protected] Abstract: Thirty-three alkyl and aryl isothiocyanates, as well as isothiocyanate derivatives from esters of coded amino acids and from esters of unnatural amino acids (6-aminocaproic, 4-(aminomethyl)benzoic, and tranexamic acids), were synthesized with satisfactory or very good yields (25–97%). Synthesis was performed in a “one-pot”, two-step procedure, in the presence of organic base (Et3N, DBU or NMM), and carbon disulfide via dithiocarbamates, with 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4- methylmorpholinium toluene-4-sulfonate (DMT/NMM/TsO−) as a desulfurization reagent. For the synthesis of aliphatic and aromatic isothiocyanates, reactions were carried out in a microwave reactor, and selected alkyl isothiocyanates were also synthesized in aqueous medium with high yields (72–96%). Isothiocyanate derivatives of L- and D-amino acid methyl esters were synthesized, under conditions without microwave radiation assistance, with low racemization (er 99 > 1), and their absolute configuration was confirmed by circular dichroism. Isothiocyanate derivatives of natural and unnatural amino acids were evaluated for antibacterial activity on E. coli and S. aureus bacterial strains, where the Citation: Janczewski, Ł.; Kr˛egiel,D.; most active was ITC 9e. -
Figure 1. Metabolism of Glucoraphanin and Glucobrassicin to Biologically Active Metabolites
Legend to Figures: Figure 1. Metabolism of glucoraphanin and glucobrassicin to biologically active metabolites. (A) Sulforaphane is released from glucoraphanin by the plant enzyme myrosinase. Red dashed arrow marks the reactive carbon atom subject to glutathione conjugation. (B) Sulforaphane is metabolized via the mercapturic acid pathway into active metabolites. Glutathione-S-transferase (GST) first conjugates a GSH molecule (Glu-Cys-Gly) to the reactive carbon on sulforaphane. Glutamate is then removed by γ- glutamyltranspeptidase (GTP), followed by removal of the glycine residue by cysteinylglycinase (CGase). Cysteine is then acetylated by an acetyltransferase (AT) to sulforaphane-N-acetylcysteine, which is excreted in the urine. (C) Indole-3-carbinol is released from the glucosinolate glucobrassicin by myrosinase and undergoes spontaneous condensation in the acidic environment of the gut. Diindolylmethane (DIM) is the most abundant post-absorption acid condensation product. Acid condensation products can be modified further post-absorption. LTr1: Linear trimer 1. LTr2: Linear trimer 2. Structures from PubChem at National Center for Biotechnology Information (NCBI). Figure 2. Selected non-epigenetic effects of sulforaphane and I3C/DIM on prostate cancer cells. Sulforaphane (SFN) and I3C/DIM inhibit the Akt signaling axis, a signaling pathway often hyperactive in prostate cancer. Inhibition of this pathway decreases pro-survival signaling by mTOR, Akt, and NFkB. Sulforaphane and I3C/DIM treatment also lead to changes in gene expression (blue arrow) that trigger growth arrest and apoptosis. The expression of proteins controlling the cell cycle (e.g. p21, p27, CDK6) are altered to effect growth arrest, and apoptosis is finally induced through the mitochondrial pathway. Abbreviations: AR – Androgen Receptor, CDK6 – cyclin dependant kinase 6, IAP – inhibitors of apoptosis. -
Effects of Cruciferous Vegetable Consumption on Urinary
Cancer Epidemiology, Biomarkers & Prevention 997 Effects of Cruciferous Vegetable Consumption on Urinary Metabolites of the Tobacco-Specific Lung Carcinogen 4-(Methylnitrosamino)-1-(3-Pyridyl)-1-Butanone in Singapore Chinese Stephen S. Hecht,1 Steven G. Carmella,1 Patrick M.J. Kenney,1 Siew-Hong Low,2 Kazuko Arakawa,3 and Mimi C. Yu3 1University of Minnesota Cancer Center, Minneapolis, Minnesota; 2Department of Community, Occupational, and Family Medicine, National University of Singapore, Singapore; and 3Norris Comprehensive Cancer Center, University of Southern California, Los Angeles, California Abstract Vegetable consumption, including cruciferous vegeta- major glucosinolates in seven of the nine cruciferous bles, is protective against lung cancer, but the mechan- vegetables, accounting for 70.0% to 93.2% of all glu- isms are poorly understood. The purpose of this study cosinolates in these vegetables. There was a significant was to investigate the effects of cruciferous vegetable correlation (P = 0.01) between increased consumption consumption on the metabolism of the tobacco-specific of glucobrassicins and decreased levels of NNAL in lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1- urine after adjustment for number of cigarettes smoked butanone (NNK) in smokers. The study was carried out per day; similar trends were observed for NNAL-Glucs in Singapore Chinese, whose mean daily intake of (P = 0.08) and NNAL plus NNAL-Glucs (P = 0.03). cruciferous vegetables is three times greater than that These results are consistent with those of previous of people in the United States. Eighty-four smokers studies, which demonstrate that indole-3-carbinol de- provided urine samples and were interviewed about creases levels of urinary NNAL probably by inducing dietary habits using a structured questionnaire, which hepatic metabolism of NNK. -
(Raphanus Sativus L.) Based on Comparative
www.nature.com/scientificreports OPEN Insights into the species-specifc metabolic engineering of glucosinolates in radish (Raphanus Received: 10 January 2017 Accepted: 9 November 2017 sativus L.) based on comparative Published: xx xx xxxx genomic analysis Jinglei Wang1, Yang Qiu1, Xiaowu Wang1, Zhen Yue2, Xinhua Yang2, Xiaohua Chen1, Xiaohui Zhang1, Di Shen1, Haiping Wang1, Jiangping Song1, Hongju He3 & Xixiang Li1 Glucosinolates (GSLs) and their hydrolysis products present in Brassicales play important roles in plants against herbivores and pathogens as well as in the protection of human health. To elucidate the molecular mechanisms underlying the formation of species-specifc GSLs and their hydrolysed products in Raphanus sativus L., we performed a comparative genomics analysis between R. sativus and Arabidopsis thaliana. In total, 144 GSL metabolism genes were identifed, and most of these GSL genes have expanded through whole-genome and tandem duplication in R. sativus. Crucially, the diferential expression of FMOGS-OX2 in the root and silique correlates with the diferential distribution of major aliphatic GSL components in these organs. Moreover, MYB118 expression specifcally in the silique suggests that aliphatic GSL accumulation occurs predominantly in seeds. Furthermore, the absence of the expression of a putative non-functional epithiospecifer (ESP) gene in any tissue and the nitrile- specifer (NSP) gene in roots facilitates the accumulation of distinctive benefcial isothiocyanates in R. sativus. Elucidating the evolution of the GSL metabolic pathway in R. sativus is important for fully understanding GSL metabolic engineering and the precise genetic improvement of GSL components and their catabolites in R. sativus and other Brassicaceae crops. Glucosinolates (GSLs), a large class of sulfur-rich secondary metabolites whose hydrolysis products display diverse bioactivities, function both in defence and as an attractant in plants, play a role in cancer prevention in humans and act as favour compounds1–4. -
Toxicity of Glucosinolates and Their Enzymatic Decomposition Products to Caenorhabditis Elegans
Journal of Nematology 27(3):258-262. 1995. © The Society of Nematologists 1995. Toxicity of Glucosinolates and Their Enzymatic Decomposition Products to Caenorhabditis elegans STEVEN G. DONKIN, 1 MARK A. EITEMAN, 2 AND PHILLIP L. WILLIAMS 1'3 Abstract: An aquatic 24-hour lethality test using Caenorhabditis elegans was used to assess toxicity of glucosinolates and their enzymatic breakdown products. In the absence of the enzyme thioglucosi- dase (myrosinase), allyl glucosinolate (sinigrin) was found to be nontoxic at all concentrations tested, while a freeze-dried, dialyzed water extract of Crambe abyssinica containing 26% 2-hydroxyl 3-butenyl glucosinolate (epi-progoitrin) had a 50% lethal concentration (LC50) of 18.5 g/liter. Addition of the enzyme increased the toxicity (LCs0 value) of sinigrin to 0.5 g/liter, but the enzyme had no effect on the toxicity of the C. abyssinica extract. Allyl isothiocyanate and allyl cyanide, two possible breakdown products of sinigrin, had an LC50 value of 0.04 g/liter and approximately 3 g/liter, respectively. Liquid chromatographic studies showed that a portion of the sinigrin decomposed into allyl isothio- cyanate. The resuhs indicated that allyl isothiocyanate is nearly three orders of magnitude more toxic to C. elegans than the corresponding glncosinolate, suggesting isothiocyanate formation would im- prove nematode control from application of glucosinolates. Key words: Caenorhabditis elegans, Crambe abyssinica, enzyme, epi-progoitrin, glucosinolate, myrosi- nase, physiology, sinigrin, thioglucosidase. Glucosinolates are naturally occurring position products or between decomposi- compounds found primarily in plants of tion products. the family Cruciferae, where they are An objective of this work was to quantify thought to serve as repellents to potential the toxicity to the free-living nematode pests (5,10).