Seed of Barbarea verna as a Rich Source of Phenethyl Isothiocyanate to Provide Natural Protection from Environmental and Dietary Toxins

ABSTRACT Cruciferous veg e ta bles have a long his tory as a healthy com po nent of a daily diet and con tain many com pounds that may pre vent can cer. Phenethyl isothiocyanate is a break down prod uct of glucosinolates and has many well-doc u mented anticancer ac tiv i ties. A method for maximizing the re lease of phenethyl isothiocyanate from up land cress (Barbarea verna) seed, the rich est source, is pre sented. Op ti mal re lease is de pend ent on time, tem per a ture and pH. This method, anal o gous to the mas ti ca tion of fresh plant ma te rial, en ables the prep a ra tion of an ef fi cacious di etary sup plement contain ing up to 2% of phenethyl isothio -cyanate.

[1]  G. Coetzee,et al.  Isothiocyanates, glutathione S-transferase M1 and T1 polymorphisms, and lung-cancer risk: a prospective study of men in Shanghai, China , 2000, The Lancet.

[2]  Paul J Thornalley,et al.  Studies on the mechanism of the inhibition of human leukaemia cell growth by dietary isothiocyanates and their cysteine adducts in vitro. , 2000, Biochemical pharmacology.

[3]  F. Kassie,et al.  Genotoxic effects of allyl isothiocyanate (AITC) and phenethyl isothiocyanate (PEITC). , 2000, Chemico-biological interactions.

[4]  H. Witschi,et al.  Chemoprevention of tobacco-smoke lung carcinogenesis in mice after cessation of smoke exposure. , 2000, Carcinogenesis.

[5]  S. Hecht,et al.  Effects of phenethyl isothiocyanate and benzyl isothiocyanate, individually and in combination, on lung tumorigenesis induced in A/J mice by benzo[a]pyrene and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. , 2000, Cancer letters.

[6]  L. Honig,et al.  Apoptosis and neurologic disease. , 2000, The American journal of medicine.

[7]  H. J. Kim,et al.  Effects of phenethylisothiocyanate on the expression of glutathione S-transferases and hepatotoxicity induced by acetaminophen , 2000, Xenobiotica; the fate of foreign compounds in biological systems.

[8]  J. Fahey,et al.  Antioxidant functions of sulforaphane: a potent inducer of Phase II detoxication enzymes. , 1999, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[9]  T. Imazawa,et al.  Failure of phenethyl isothiocyanate to inhibit hamster tumorigenesis induced by N-nitrosobis(2-oxopropyl)amine when given during the post-initiation phase. , 1999, Cancer letters.

[10]  B. P. Klein,et al.  Variation of glucosinolates in vegetable crops of Brassica oleracea. , 1999, Journal of agricultural and food chemistry.

[11]  S. French,et al.  Effects of chronic ethanol administration on rat liver proteasome activities: Relationship with oxidative stress , 1999, Hepatology.

[12]  S. Amin,et al.  Inhibition of N'-nitrosonornicotine-induced esophageal tumorigenesis by 3-phenylpropyl isothiocyanate. , 1998, Carcinogenesis.

[13]  W. Peters,et al.  Effects of dietary anticarcinogens on rat gastrointestinal glutathione S-transferase theta 1-1 levels. , 1998, Carcinogenesis.

[14]  W. Tatton,et al.  Mitochondria in neurodegenerative apoptosis: An opportunity for therapy? , 1998, Annals of neurology.

[15]  M. Hirose,et al.  Strong promoting activity of phenylethyl isothiocyanate and benzyl isothiocyanate on urinary bladder carcinogenesis in F344 male rats , 1998, International journal of cancer.

[16]  M. Hirose,et al.  Stage and organ dependent effects of 1‐ O‐hexyl‐2,3,5‐trimethylhydroquinone, ascorbic acid derivatives, N‐heptadecane‐8,10‐dione and phenylethyl isothiocyanate in a rat multiorgan carcinogenesis model , 1998, International journal of cancer.

[17]  M. Wallig,et al.  Induction of rat pancreatic glutathione S-transferase and quinone reductase activities by a mixture of glucosinolate breakdown derivatives found in Brussels sprouts. , 1998, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[18]  E. Jeffery,et al.  A comparison of the individual and collective effects of four glucosinolate breakdown products from brussels sprouts on induction of detoxification enzymes. , 1998, Toxicology and applied pharmacology.

[19]  A. Nishikawa,et al.  Mechanistic Insights into Chemopreventive Effects of Phenethyl Isothiocyanate in N‐Nitrosobis(2‐oxopropyl)amine‐treated Hamsters , 1997, Japanese journal of cancer research : Gann.

[20]  J. Fahey,et al.  Broccoli sprouts: an exceptionally rich source of inducers of enzymes that protect against chemical carcinogens. , 1997, Proceedings of the National Academy of Sciences of the United States of America.

[21]  S. Hecht,et al.  Effects of long term dietary phenethyl isothiocyanate on the microsomal metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in F344 rats. , 1997, Carcinogenesis.

[22]  G. Williamson,et al.  Mechanism of action of dietary chemoprotective agents in rat liver: induction of phase I and II drug metabolizing enzymes and aflatoxin B1 metabolism. , 1997, Carcinogenesis.

[23]  L. Anderson,et al.  Enzymes involved in the bioactivation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in patas monkey lung and liver microsomes. , 1997, Carcinogenesis.

[24]  V. Steele,et al.  Chemopreventive efficacy of anethole trithione, N‐acetyl‐L‐cysteine, miconazole and phenethylisothiocyanate in the DMBA‐induced rat mammary cancer model , 1997, International journal of cancer.

[25]  K. Reuhl,et al.  Effects of phenethyl isothiocyanate on acetaminophen metabolism and hepatotoxicity in mice. , 1997, Toxicology and applied pharmacology.

[26]  G. Stoner,et al.  Isothiocyanates and plant polyphenols as inhibitors of lung and esophageal cancer. , 1997, Cancer letters.

[27]  S. Hecht,et al.  Evidence for an important role of DNA pyridyloxobutylation in rat lung carcinogenesis by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone: effects of dose and phenethyl isothiocyanate. , 1997, Cancer research.

[28]  Hamilton Sm,et al.  Effects of isothiocyanates on cytochrome P-450 1A1 and 1A2 activity and on the mutagenicity of heterocyclic amines. , 1996 .

[29]  F. Chung,et al.  Inhibition of rat liver cytochrome P450 isozymes by isothiocyanates and their conjugates: a structure-activity relationship study. , 1996, Carcinogenesis.

[30]  S. Hecht,et al.  Complete inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced rat lung tumorigenesis and favorable modification of biomarkers by phenethyl isothiocyanate. , 1996, Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.

[31]  J. Jansen,et al.  MOLECULAR EPIDEMIOLOGY AND CANCER PREVENTION: Effect of oltipraz, α-tocopherol, β-carotene and phenethylisothiocyanate on rat oesophageal, gastric, colonic and hepatic glutathione, glutathione S-transferase and peroxidase , 1996 .

[32]  A. Nishikawa,et al.  SHORT COMMUNICATION: Chemopreventive effects of phenethy1 isothiocyanate on lung and pancreatic tumorigenesis inN-nitrosobis(2-oxopropyl)amine-treated hamsters , 1996 .

[33]  F. Guengerich,et al.  Metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) by human cytochrome P450 1A2 and its inhibition by phenethyl isothiocyanate. , 1996, Carcinogenesis.

[34]  V. Steele,et al.  Chemopreventive efficacy of arylalkyl isothiocyanates and N-acetylcysteine for lung tumorigenesis in Fischer rats. , 1996, Cancer research.

[35]  M. Ingelman-Sundberg,et al.  Role of cytochrome P4502E1‐dependent formation of hydroxyethyl free radical in the development of liver damage in rats intragastrically fed with ethanol , 1996, Hepatology.

[36]  M. Ingelman-Sundberg,et al.  Phenethyl isothiocyanate, a new dietary liver aldehyde dehydrogenase inhibitor. , 1995, The Journal of pharmacology and experimental therapeutics.

[37]  I. Johnson,et al.  On the cytotoxicity and genotoxicity of allyl and phenethyl isothiocyanates and their parent glucosinolates sinigrin and gluconasturtiin. , 1995, Mutation research.

[38]  G. Stoner,et al.  Effect of alkyl chain length on inhibition of N-nitrosomethylbenzylamine-induced esophageal tumorigenesis and DNA methylation by isothiocyanates. , 1995, Carcinogenesis.

[39]  B. Ketterer,et al.  Forward and reverse catalysis and product sequestration by human glutathione S-transferases in the reaction of GSH with dietary aralkyl isothiocyanates. , 1995, The Biochemical journal.

[40]  F. Guengerich,et al.  Cytochrome P450 enzymes involved in acetaminophen activation by rat and human liver microsomes and their kinetics. , 1993, Chemical research in toxicology.

[41]  S. Nelson,et al.  Oxidation of acetaminophen to N-acetyl-p-aminobenzoquinone imine by human CYP3A4. , 1993, Biochemical pharmacology.

[42]  C. Cho,et al.  A major inducer of anticarcinogenic protective enzymes from broccoli: isolation and elucidation of structure. , 1992, Proceedings of the National Academy of Sciences of the United States of America.

[43]  S. Amin,et al.  Effect of frequency of isothiocyanate administration on inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced pulmonary adenoma formation in A/J mice. , 1992, Cancer letters.

[44]  C. S. Yang,et al.  Effect of phenethyl isothiocyanate on microsomal N-nitrosodimethylamine metabolism and other monooxygenase activities. , 1990, Xenobiotica; the fate of foreign compounds in biological systems.

[45]  C. Lieber,et al.  Acetaminophen activation by human liver cytochromes P450IIE1 and P450IA2. , 1989, Archives of biochemistry and biophysics.

[46]  W. Kwolek,et al.  Glucosinolates in Crucifer Vegetables: Broccoli, Brussels Sprouts, Cauliflower, Collards, Kale, Mustard Greens, and Kohlrabi , 1987, Journal of the American Society for Horticultural Science.

[47]  S. Hecht,et al.  Effects of dietary indoles and isothiocyanates on N-nitrosodimethylamine and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone alpha-hydroxylation and DNA methylation in rat liver. , 1985, Carcinogenesis.

[48]  A. Y. Lu,et al.  N-acetyl-p-benzoquinone imine: a cytochrome P-450-mediated oxidation product of acetaminophen. , 1984, Proceedings of the National Academy of Sciences of the United States of America.

[49]  A. Macleod,et al.  Some glucosinolates of Farsetia aegyptia and Farsetia ramosissima , 1980 .

[50]  A. Macleod,et al.  Degradation of glucosinolates of Nasturtium officinale seeds , 1980 .

[51]  A. Macleod,et al.  Studies on glucosinolate degradation in Lepidium sativum seed extracts. , 1980 .

[52]  P. Williams,et al.  Glucosinolates and derived products in cruciferous vegetables. Analysis of the edible part from twenty-two varieties of cabbage. , 1976, Journal of agricultural and food chemistry.

[53]  A. Virtanen Studies on organic sulphur compounds and other labile substances in plants. , 1965, Bibliotheca nutritio et dieta.