1-Isothiocyanato-2-phenylethane (BioDeep_00000018119)
human metabolite PANOMIX_OTCML-2023 Toxin Antitumor activity
代谢物信息卡片
(2-Isothiocyanatoethyl)benzene, 9ci
化学式: C9H9NS (163.0455674)
中文名称: 异硫氰酸-2-苯乙酯
谱图信息:
最多检出来源 Chinese Herbal Medicine(otcml) 58.33%
分子结构信息
SMILES: C1=CC=C(C=C1)CCN=C=S
InChI: InChI=1S/C9H9NS/c11-8-10-7-6-9-4-2-1-3-5-9/h1-5H,6-7H2
描述信息
1-Isothiocyanato-2-phenylethane, also known as 2-phenylethyl isothiocyanate (PEITC) or (2-isothiocyanatoethyl) benzene is an isothiocyanate having a phenethyl group attached to the nitrogen. It is a naturally occurring compound found in some cruciferous vegetables (e.g. watercress) and is known to possess anticancer properties. It has a role as an antineoplastic agent, a metabolite and an EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor. It belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. PEITC is found in high concentrations in kohlrabis. In terms of biosynthesis, PEITC is produced from gluconasturtiin by the action of the enzyme myrosinase. PEITC has been used in trials studying the prevention and treatment of leukemia, lung cancer, tobacco use disorder, and lymphoproliferative disorders.
Phenethyl isothiocyanate, also known as peitc or beta-phenylethyl isothiocyanic acid, belongs to benzene and substituted derivatives class of compounds. Those are aromatic compounds containing one monocyclic ring system consisting of benzene. Phenethyl isothiocyanate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Phenethyl isothiocyanate is a bitter, gooseberry, and green tasting compound and can be found in a number of food items such as herbs and spices, brassicas, horseradish, and cabbage, which makes phenethyl isothiocyanate a potential biomarker for the consumption of these food products. Phenethyl isothiocyanate (PEITC) is a naturally occurring isothiocyanate whose precursor, gluconasturtiin is found in some cruciferous vegetables, especially watercress .
C1892 - Chemopreventive Agent > C54630 - Phase II Enzymes Inducer
D020011 - Protective Agents > D016588 - Anticarcinogenic Agents
D009676 - Noxae > D002273 - Carcinogens
D000970 - Antineoplastic Agents
D004791 - Enzyme Inhibitors
2-Phenylethyl isothiocyanate is a potent antifungal agent. 2-Phenylethyl isothiocyanate significantly inhibited spore germination and mycelial growth of Alternaria alternata, with a MIC (minimum inhibitory concentration) of 1.22 mM. The antifungal effect of 2-Phenylethyl isothiocyanate against Alternaria alternata might be via reduction in toxin content and breakdown of cell membrane integrity[1][2].
同义名列表
28 个代谢物同义名
(2-Isothiocyanatoethyl)benzene, 9ci; beta-Phenylethyl isothiocyanic acid; beta-Phenethyl isothiocyanic acid; 2-Phenylethyl isothiocyanic acid; b-Phenylethyl isothiocyanic acid; Β-phenylethyl isothiocyanic acid; beta-Phenylethyl isothiocyanate; 1-Isothiocyanato-2-phenylethane; b-Phenethyl isothiocyanic acid; Β-phenethyl isothiocyanic acid; (2-Isothiocyanatoethyl)benzene; Phenylethyl isothiocyanic acid; beta-Phenethyl isothiocyanate; 2-Phenylethyl isothiocyanate; Phenethyl isothiocyanic acid; b-Phenylethyl isothiocyanate; Β-phenylethyl isothiocyanate; Β-phenethyl isothiocyanate; 2-Phenethyl isothiocyanate; b-Phenethyl isothiocyanate; Phenylethyl isothiocyanate; Phenethyl isothiocyanate; Phenethylisothiocyanate; Phenethyl mustard oil; Phenylaethylsenfoel; PEITC compound; PEITC; 2-PE ITC
数据库引用编号
12 个数据库交叉引用编号
- ChEBI: CHEBI:351346
- PubChem: 16741
- HMDB: HMDB0038445
- DrugBank: DB12695
- ChEMBL: CHEMBL151649
- Wikipedia: Phenethyl_isothiocyanate
- KNApSAcK: C00057265
- foodb: FDB004307
- chemspider: 15870
- CAS: 2257-09-2
- PMhub: MS000002604
- medchemexpress: HY-23155
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
9 个相关的物种来源信息
- 50458 - Barbarea verna: 10.1300/J133V03N03_03
- 52824 - Brassica carinata: 10.1016/0031-9422(88)83085-1
- 3708 - Brassica napus: 10.1016/0031-9422(88)83085-1
- 3712 - Brassica oleracea: 10.1021/JF60209A053
- 3711 - Brassica rapa: 10.1016/0031-9422(88)83085-1
- 89411 - Descurainia sophia: 10.1016/S0021-9673(00)91513-9
- 75806 - Eutrema japonicum: 10.3136/NSKKK1962.37.4_256
- 9606 - Homo sapiens: -
- 65948 - Nasturtium officinale: 10.1093/CARCIN/21.11.1983
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Sotiris Kyriakou, Louiza Potamiti, Nikoletta Demosthenous, Tom Amery, Kyle Stewart, Paul G Winyard, Rodrigo Franco, Aglaia Pappa, Mihalis I Panayiotidis. A Naturally Derived Watercress Flower-Based Phenethyl Isothiocyanate-Enriched Extract Induces the Activation of Intrinsic Apoptosis via Subcellular Ultrastructural and Ca2+ Efflux Alterations in an In Vitro Model of Human Malignant Melanoma.
Nutrients.
2023 Sep; 15(18):. doi:
10.3390/nu15184044. [PMID: 37764828] - Chenxiao Zhen, Jindou Li, Junyu Liu, Yi Lyu, Li Xie, Huanhuan Lv. Phenethyl isothiocyanate induces oxidative cell death in osteosarcoma cells with regulation on mitochondrial network, function and metabolism.
Biochimica et biophysica acta. Molecular basis of disease.
2023 May; ?(?):166740. doi:
10.1016/j.bbadis.2023.166740. [PMID: 37142133] - Jie Wang, Ke Shi, Ning An, Shuaifei Li, Mei Bai, Xudong Wu, Yan Shen, Ronghui Du, Jingcai Cheng, Xuefeng Wu, Qiang Xu. Direct Inhibition of GSDMD by PEITC Reduces Hepatocyte Pyroptosis and Alleviates Acute Liver Injury in Mice.
Frontiers in immunology.
2022; 13(?):825428. doi:
10.3389/fimmu.2022.825428. [PMID: 35173734] - Hui-Ju Kim, Ah-Hyeon Jeong, Ji-Hoon Lee, Jun-Hwan Park. Persistence Enhancement of a Promising Tick Repellent, Benzyl Isothiocyanate, by Yeast Microcarriers.
Molecules (Basel, Switzerland).
2021 Nov; 26(22):. doi:
10.3390/molecules26226817. [PMID: 34833912] - Nitipon Kaewsit, Thunnalin Winuprasith, Dunyaporn Trachootham. Detoxification of heterocyclic aromatic amines from grilled meat using a PEITC-rich vegetable sauce: a randomized crossover controlled trial.
Food & function.
2021 Nov; 12(21):10411-10422. doi:
10.1039/d1fo01733k. [PMID: 34585700] - Nada H Eisa, Ahmed E Khodir, Mohamed El-Sherbiny, Nehal M Elsherbiny, Eman Said. Phenethyl isothiocyanate attenuates diabetic nephropathy via modulation of glycative/oxidative/inflammatory signaling in diabetic rats.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie.
2021 Oct; 142(?):111666. doi:
10.1016/j.biopha.2021.111666. [PMID: 34215478] - Klaudyna Krause, Agnieszka Pyrczak-Felczykowska, Monika Karczewska, Magdalena Narajczyk, Anna Herman-Antosiewicz, Agnieszka Szalewska-Pałasz, Dariusz Nowicki. Dietary Isothiocyanates, Sulforaphane and 2-Phenethyl Isothiocyanate, Effectively Impair Vibrio cholerae Virulence.
International journal of molecular sciences.
2021 Sep; 22(19):. doi:
10.3390/ijms221910187. [PMID: 34638525] - Prabhakaran Soundararajan, Sin-Gi Park, So Youn Won, Mi-Sun Moon, Hyun Woo Park, Kang-Mo Ku, Jung Sun Kim. Influence of Genotype on High Glucosinolate Synthesis Lines of Brassica rapa.
International journal of molecular sciences.
2021 Jul; 22(14):. doi:
10.3390/ijms22147301. [PMID: 34298919] - Min-Hee Gwon, Jung-Mi Yun. Phenethyl Isothiocyanate Improves Lipid Metabolism and Inflammation via mTOR/PPARγ/AMPK Signaling in the Adipose Tissue of Obese Mice.
Journal of medicinal food.
2021 Jun; 24(6):666-669. doi:
10.1089/jmf.2020.4881. [PMID: 34077672] - Cuiwei Wang, Christoph Crocoll, Niels Agerbirk, Barbara Ann Halkier. Engineering and optimization of the 2-phenylethylglucosinolate production in Nicotiana benthamiana by combining biosynthetic genes from Barbarea vulgaris and Arabidopsis thaliana.
The Plant journal : for cell and molecular biology.
2021 05; 106(4):978-992. doi:
10.1111/tpj.15212. [PMID: 33624307] - Min-Hee Gwon, Young-Sun Im, A-Reum Seo, Kyoung Yun Kim, Ha-Rin Moon, Jung-Mi Yun. Phenethyl Isothiocyanate Protects against High Fat/Cholesterol Diet-Induced Obesity and Atherosclerosis in C57BL/6 Mice.
Nutrients.
2020 Nov; 12(12):. doi:
10.3390/nu12123657. [PMID: 33261070] - Yuanyuan Zhu, Shuiping Liu, Sisi Yan, Ji Wang, Linyu Zhang, Xin Li, Lixin Wen, Jing Wu. Phenylethyl isothiocyanate induces oxidative damage of porcine kidney cells mediated by reactive oxygen species.
Journal of biochemical and molecular toxicology.
2020 Feb; 34(2):e22428. doi:
10.1002/jbt.22428. [PMID: 31860765] - Huanhuan Lv, Chenxiao Zhen, Junyu Liu, Peng Shang. β-Phenethyl Isothiocyanate Induces Cell Death in Human Osteosarcoma through Altering Iron Metabolism, Disturbing the Redox Balance, and Activating the MAPK Signaling Pathway.
Oxidative medicine and cellular longevity.
2020; 2020(?):5021983. doi:
10.1155/2020/5021983. [PMID: 32322335] - Jianxiang Huang, Bihan Wu, Zhuxian Zhou, Shiqi Hu, Hongxia Xu, Ying Piao, Hao Zheng, Jianbin Tang, Xiangrui Liu, Youqing Shen. Drug-binding albumins forming stabilized nanoparticles for efficient anticancer therapy.
Nanomedicine : nanotechnology, biology, and medicine.
2019 10; 21(?):102058. doi:
10.1016/j.nano.2019.102058. [PMID: 31344500] - Natasa S Giallourou, Ian R Rowland, Steve D Rothwell, Graham Packham, Daniel M Commane, Jonathan R Swann. Metabolic targets of watercress and PEITC in MCF-7 and MCF-10A cells explain differential sensitisation responses to ionising radiation.
European journal of nutrition.
2019 Sep; 58(6):2377-2391. doi:
10.1007/s00394-018-1789-8. [PMID: 30066177] - Maiko Chiba, Yoshiaki Ito, Takashi Nagasawa. Phenethyl isothiocyanate stimulates glucose uptake through the Akt pathway in C2C12 myotubes.
Bioscience, biotechnology, and biochemistry.
2019 Jul; 83(7):1319-1328. doi:
10.1080/09168451.2019.1594675. [PMID: 30919745] - Wei-Ting Chuang, Yun-Ta Liu, Chin-Shiu Huang, Chia-Wen Lo, Hsien-Tsung Yao, Haw-Wen Chen, Chong-Kuei Lii. Benzyl Isothiocyanate and Phenethyl Isothiocyanate Inhibit Adipogenesis and Hepatosteatosis in Mice with Obesity Induced by a High-Fat Diet.
Journal of agricultural and food chemistry.
2019 Jun; 67(25):7136-7146. doi:
10.1021/acs.jafc.9b02668. [PMID: 31240929] - Mathieu Schwartz, Thomas Perrot, Mélanie Morel-Rouhier, Guillermo Mulliert, Eric Gelhaye, Claude Didierjean, Frédérique Favier. The structure of Trametes versicolor glutathione transferase Omega 3S bound to its conjugation product glutathionyl-phenethylthiocarbamate reveals plasticity of its active site.
Protein science : a publication of the Protein Society.
2019 06; 28(6):1143-1150. doi:
10.1002/pro.3620. [PMID: 30972861] - Swastika Paul, Chang-An Geng, Tong-Hua Yang, Yong-Ping Yang, Ji-Jun Chen. Phytochemical and Health-Beneficial Progress of Turnip (Brassica rapa).
Journal of food science.
2019 Jan; 84(1):19-30. doi:
10.1111/1750-3841.14417. [PMID: 30561035] - Krishna B Singh, Eun-Ryeong Hahm, Lora H Rigatti, Daniel P Normolle, Jian-Min Yuan, Shivendra V Singh. Inhibition of Glycolysis in Prostate Cancer Chemoprevention by Phenethyl Isothiocyanate.
Cancer prevention research (Philadelphia, Pa.).
2018 06; 11(6):337-346. doi:
10.1158/1940-6207.capr-17-0389. [PMID: 29545400] - Zsolt Szűcs, Tamás Plaszkó, Zoltán Cziáky, Attila Kiss-Szikszai, Tamás Emri, Regina Bertóti, László Tamás Sinka, Gábor Vasas, Sándor Gonda. Endophytic fungi from the roots of horseradish (Armoracia rusticana) and their interactions with the defensive metabolites of the glucosinolate - myrosinase - isothiocyanate system.
BMC plant biology.
2018 May; 18(1):85. doi:
10.1186/s12870-018-1295-4. [PMID: 29743024] - Imran Khamis, John J Heikkila. Effect of isothiocyanates, BITC and PEITC, on stress protein accumulation, protein aggregation and aggresome-like structure formation in Xenopus A6 kidney epithelial cells.
Comparative biochemistry and physiology. Toxicology & pharmacology : CBP.
2018 Jan; 204(?):1-13. doi:
10.1016/j.cbpc.2017.10.011. [PMID: 29100952] - János Urbancsok, Atle M Bones, Ralph Kissen. Glucosinolate-Derived Isothiocyanates Inhibit Arabidopsis Growth and the Potency Depends on Their Side Chain Structure.
International journal of molecular sciences.
2017 Nov; 18(11):. doi:
10.3390/ijms18112372. [PMID: 29117115] - Krishna B Singh, Shivendra V Singh. Fatty Acid Synthesis Intermediates Represent Novel Noninvasive Biomarkers of Prostate Cancer Chemoprevention by Phenethyl Isothiocyanate.
Cancer prevention research (Philadelphia, Pa.).
2017 May; 10(5):279-289. doi:
10.1158/1940-6207.capr-17-0001. [PMID: 28292742] - Lucília P Pereira, Patrícia Silva, Marlene Duarte, Liliana Rodrigues, Catarina M M Duarte, Cristina Albuquerque, Ana Teresa Serra. Targeting Colorectal Cancer Proliferation, Stemness and Metastatic Potential Using Brassicaceae Extracts Enriched in Isothiocyanates: A 3D Cell Model-Based Study.
Nutrients.
2017 Apr; 9(4):. doi:
10.3390/nu9040368. [PMID: 28394276] - Jae Kyeom Kim, Daniel D Gallaher, Chi Chen, Cynthia M Gallaher, Dan Yao, Sabrina P Trudo. Phenethyl isothiocyanate and indole-3-carbinol from cruciferous vegetables, but not furanocoumarins from apiaceous vegetables, reduced PhIP-induced DNA adducts in Wistar rats.
Molecular nutrition & food research.
2016 09; 60(9):1956-66. doi:
10.1002/mnfr.201500790. [PMID: 27133590] - Takashi Kasukabe, Yoshio Honma, Junko Okabe-Kado, Yusuke Higuchi, Nobuo Kato, Shunichi Kumakura. Combined treatment with cotylenin A and phenethyl isothiocyanate induces strong antitumor activity mainly through the induction of ferroptotic cell death in human pancreatic cancer cells.
Oncology reports.
2016 Aug; 36(2):968-76. doi:
10.3892/or.2016.4867. [PMID: 27375275] - Jian-Min Yuan, Irina Stepanov, Sharon E Murphy, Renwei Wang, Sharon Allen, Joni Jensen, Lori Strayer, Jennifer Adams-Haduch, Pramod Upadhyaya, Chap Le, Mindy S Kurzer, Heather H Nelson, Mimi C Yu, Dorothy Hatsukami, Stephen S Hecht. Clinical Trial of 2-Phenethyl Isothiocyanate as an Inhibitor of Metabolic Activation of a Tobacco-Specific Lung Carcinogen in Cigarette Smokers.
Cancer prevention research (Philadelphia, Pa.).
2016 05; 9(5):396-405. doi:
10.1158/1940-6207.capr-15-0380. [PMID: 26951845] - Cornelia U Welte, Rob M de Graaf, Tijs J M van den Bosch, Huub J M Op den Camp, Nicole M van Dam, Mike S M Jetten. Plasmids from the gut microbiome of cabbage root fly larvae encode SaxA that catalyses the conversion of the plant toxin 2-phenylethyl isothiocyanate.
Environmental microbiology.
2016 05; 18(5):1379-90. doi:
10.1111/1462-2920.12997. [PMID: 26234684] - Yuko Terada, Hideki Masuda, Tatsuo Watanabe. Structure-Activity Relationship Study on Isothiocyanates: Comparison of TRPA1-Activating Ability between Allyl Isothiocyanate and Specific Flavor Components of Wasabi, Horseradish, and White Mustard.
Journal of natural products.
2015 Aug; 78(8):1937-41. doi:
10.1021/acs.jnatprod.5b00272. [PMID: 26263397] - Costas Ioannides, Nattaya Konsue. A principal mechanism for the cancer chemopreventive activity of phenethyl isothiocyanate is modulation of carcinogen metabolism.
Drug metabolism reviews.
2015 08; 47(3):356-73. doi:
10.3109/03602532.2015.1058819. [PMID: 26119477] - Anika E Wagner, Christine Sturm, Stefanie Piegholdt, Insa M A Wolf, Tuba Esatbeyoglu, Gina Rosalinda De Nicola, Renato Iori, Gerald Rimbach. Myrosinase-treated glucoerucin is a potent inducer of the Nrf2 target gene heme oxygenase 1--studies in cultured HT-29 cells and mice.
The Journal of nutritional biochemistry.
2015 Jun; 26(6):661-6. doi:
10.1016/j.jnutbio.2015.01.004. [PMID: 25776458] - Jared D Hoffman, William M Ward, George Loo. Effect of antioxidants on the genotoxicity of phenethyl isothiocyanate.
Mutagenesis.
2015 May; 30(3):421-30. doi:
10.1093/mutage/gev003. [PMID: 25681790] - Li Zheng, Feng Zheng. Development and validation of an LC-APCI-MS/MS method for the determination of phenethyl isothiocyanate in human plasma.
Biomedical chromatography : BMC.
2015 Apr; 29(4):619-25. doi:
10.1002/bmc.3323. [PMID: 25209958] - Kang-Mo Ku, Elizabeth H Jeffery, John A Juvik, Mosbah M Kushad. Correlation of quinone reductase activity and allyl isothiocyanate formation among different genotypes and grades of horseradish roots.
Journal of agricultural and food chemistry.
2015 Mar; 63(11):2947-55. doi:
10.1021/jf505591z. [PMID: 25684599] - Alessandra Pulliero, Yun Wu, Daniela Fenoglio, Alessia Parodi, Massimo Romani, Christiane P Soares, Gilberto Filaci, James L Lee, Patrick N Sinkam, Alberto Izzotti. Nanoparticles increase the efficacy of cancer chemopreventive agents in cells exposed to cigarette smoke condensate.
Carcinogenesis.
2015 Mar; 36(3):368-77. doi:
10.1093/carcin/bgv008. [PMID: 25653234] - Dan Wang, Bijaya Upadhyaya, Yi Liu, David Knudsen, Moul Dey. Phenethyl isothiocyanate upregulates death receptors 4 and 5 and inhibits proliferation in human cancer stem-like cells.
BMC cancer.
2014 Aug; 14(?):591. doi:
10.1186/1471-2407-14-591. [PMID: 25127663] - Jae Kyeom Kim, Eui-Cheol Shin, Cho Rong Kim, Gwi Gun Park, Soo Jung Choi, Cheung-Seog Park, Dong-Hoon Shin. Effects of brussels sprouts and their phytochemical components on oxidative stress-induced neuronal damages in PC12 cells and ICR mice.
Journal of medicinal food.
2013 Nov; 16(11):1057-61. doi:
10.1089/jmf.2012.0280. [PMID: 24175656] - Kang Mo Ku, Elizabeth H Jeffery, John A Juvik. Influence of seasonal variation and methyl jasmonate mediated induction of glucosinolate biosynthesis on quinone reductase activity in broccoli florets.
Journal of agricultural and food chemistry.
2013 Oct; 61(40):9623-31. doi:
10.1021/jf4027734. [PMID: 24032372] - E Freitas, A Aires, E Augusto de Santos Rosa, M José Saavedra. Antibacterial activity and synergistic effect between watercress extracts, 2-phenylethyl isothiocyanate and antibiotics against 11 isolates of Escherichia coli from clinical and animal source.
Letters in applied microbiology.
2013 Oct; 57(4):266-73. doi:
10.1111/lam.12105. [PMID: 23682789] - I S Chen, K T Mok, C T Chou, S I Liu, C C Kuo, S S Hsu, H T Chang, J Y Tsai, W C Liao, C R Jan. Effect of phenethyl isothiocyanate on Ca2+ movement and viability in MDCK canine renal tubular cells.
Human & experimental toxicology.
2012 Dec; 31(12):1251-61. doi:
10.1177/0960327112446841. [PMID: 22653687] - Shivendra V Singh, Su-Hyeong Kim, Anuradha Sehrawat, Julie A Arlotti, Eun-Ryeong Hahm, Kozue Sakao, Jan H Beumer, Rachel C Jankowitz, Kumar Chandra-Kuntal, Joomin Lee, Anna A Powolny, Rajiv Dhir. Biomarkers of phenethyl isothiocyanate-mediated mammary cancer chemoprevention in a clinically relevant mouse model.
Journal of the National Cancer Institute.
2012 Aug; 104(16):1228-39. doi:
10.1093/jnci/djs321. [PMID: 22859850] - Hanna Szaefer, Violetta Krajka-Kuźniak, Agnieszka Bartoszek, Wanda Baer-Dubowska. Modulation of carcinogen metabolizing cytochromes P450 in rat liver and kidney by cabbage and sauerkraut juices: comparison with the effects of indole-3-carbinol and phenethyl isothiocyanate.
Phytotherapy research : PTR.
2012 Aug; 26(8):1148-55. doi:
10.1002/ptr.3692. [PMID: 22173777] - Zhen Xiao, Lixin Mi, Fung-Lung Chung, Timothy D Veenstra. Proteomic analysis of covalent modifications of tubulins by isothiocyanates.
The Journal of nutrition.
2012 Jul; 142(7):1377S-81S. doi:
10.3945/jn.111.152041. [PMID: 22649267] - Ahmad F Abdull Razis, Manuela Bagatta, Gina R De Nicola, Renato Iori, Nick Plant, Costas Ioannides. Characterization of the temporal induction of hepatic xenobiotic-metabolizing enzymes by glucosinolates and isothiocyanates: requirement for at least a 6 h exposure to elicit complete induction profile.
Journal of agricultural and food chemistry.
2012 Jun; 60(22):5556-64. doi:
10.1021/jf3011195. [PMID: 22594452] - Shinichi Takahashi, Yoshikane Izawa, Norihiro Suzuki. Astroglial pentose phosphate pathway rates in response to high-glucose environments.
ASN neuro.
2012 Mar; 4(2):. doi:
10.1042/an20120002. [PMID: 22300409] - Ahmad F Abdull Razis, Nattaya Konsue, Myrto Dervetzoglou, Kathryn E Plant, Nick Plant, Costas Ioannides. Phenethyl isothiocyanate, a naturally occurring phytochemical, is an antagonist of the aryl hydrocarbon receptor.
Molecular nutrition & food research.
2012 Mar; 56(3):425-34. doi:
10.1002/mnfr.201100548. [PMID: 22174033] - Einar J Stauber, Petrissa Kuczka, Maike van Ohlen, Birgit Vogt, Tim Janowitz, Markus Piotrowski, Till Beuerle, Ute Wittstock. Turning the 'mustard oil bomb' into a 'cyanide bomb': aromatic glucosinolate metabolism in a specialist insect herbivore.
PloS one.
2012; 7(4):e35545. doi:
10.1371/journal.pone.0035545. [PMID: 22536404] - Regina G Belz, Hans-Peter Piepho. Modeling effective dosages in hormetic dose-response studies.
PloS one.
2012; 7(3):e33432. doi:
10.1371/journal.pone.0033432. [PMID: 22438929] - Sabita N Saldanha, Trygve O Tollefsbol. The role of nutraceuticals in chemoprevention and chemotherapy and their clinical outcomes.
Journal of oncology.
2012; 2012(?):192464. doi:
10.1155/2012/192464. [PMID: 22187555] - Syed M Meeran, Shweta N Patel, Yuanyuan Li, Samriddhi Shukla, Trygve O Tollefsbol. Bioactive dietary supplements reactivate ER expression in ER-negative breast cancer cells by active chromatin modifications.
PloS one.
2012; 7(5):e37748. doi:
10.1371/journal.pone.0037748. [PMID: 22662208] - H-P Chang, M-L Wang, C-Y Hsu, M-E Liu, M-H Chan, Y-H Chen. Suppression of inflammation-associated factors by indole-3-carbinol in mice fed high-fat diets and in isolated, co-cultured macrophages and adipocytes.
International journal of obesity (2005).
2011 Dec; 35(12):1530-8. doi:
10.1038/ijo.2011.12. [PMID: 21343904] - Le Diem Huong, Jung-Hyung Shim, Kyeong-Hee Choi, Ji-Ae Shin, Eun-Sun Choi, Hyung-Seop Kim, Sook-Jeong Lee, Sun-Ju Kim, Nam-Pyo Cho, Sung-Dae Cho. Effect of β-phenylethyl isothiocyanate from cruciferous vegetables on growth inhibition and apoptosis of cervical cancer cells through the induction of death receptors 4 and 5.
Journal of agricultural and food chemistry.
2011 Aug; 59(15):8124-31. doi:
10.1021/jf2006358. [PMID: 21702500] - Jana Jakubikova, David Cervi, Melissa Ooi, Kihyun Kim, Sabikun Nahar, Steffen Klippel, Dana Cholujova, Merav Leiba, John F Daley, Jake Delmore, Joseph Negri, Simona Blotta, Douglas W McMillin, Teru Hideshima, Paul G Richardson, Jan Sedlak, Kenneth C Anderson, Constantine S Mitsiades. Anti-tumor activity and signaling events triggered by the isothiocyanates, sulforaphane and phenethyl isothiocyanate, in multiple myeloma.
Haematologica.
2011 Aug; 96(8):1170-9. doi:
10.3324/haematol.2010.029363. [PMID: 21712538] - Sener Kurt, Ufuk Güneş, Emine M Soylu. In vitro and in vivo antifungal activity of synthetic pure isothiocyanates against Sclerotinia sclerotiorum.
Pest management science.
2011 Jul; 67(7):869-75. doi:
10.1002/ps.2126. [PMID: 21370393] - Anna A Powolny, Ajay Bommareddy, Eun-Ryeong Hahm, Daniel P Normolle, Jan H Beumer, Joel B Nelson, Shivendra V Singh. Chemopreventative potential of the cruciferous vegetable constituent phenethyl isothiocyanate in a mouse model of prostate cancer.
Journal of the National Cancer Institute.
2011 Apr; 103(7):571-84. doi:
10.1093/jnci/djr029. [PMID: 21330634] - Violetta Krajka-Kuźniak, Hanna Szaefer, Agnieszka Bartoszek, Wanda Baer-Dubowska. Modulation of rat hepatic and kidney phase II enzymes by cabbage juices: comparison with the effects of indole-3-carbinol and phenethyl isothiocyanate.
The British journal of nutrition.
2011 Mar; 105(6):816-26. doi:
10.1017/s0007114510004526. [PMID: 21092375] - Natalya Hanlon, Nattaya Konsue, Nick Coldham, Maurice J Sauer, Costas Ioannides. Exposure to isothiocyanates suppresses urinary mutagenicity in rats treated with heterocyclic amine IQ: lack of association with CYP1 activity.
Nutrition and cancer.
2011; 63(2):300-5. doi:
10.1080/01635581.2011.530735. [PMID: 21298592] - Jin-Nyoung Ho, Eun-Ryung Kang, Ho-Geun Yoon, Hyelin Jeon, Woojin Jun, Ronald R Watson, Jeongmin Lee. Inhibition of premature death by isothiocyanates through immune restoration in LP-BM5 leukemia retrovirus-infected C57BL/6 mice.
Bioscience, biotechnology, and biochemistry.
2011; 75(7):1234-9. doi:
10.1271/bbb.100840. [PMID: 21737943] - Anoop Kumar, Paolo Vineis, Carlotta Sacerdote, Laura Fiorini, Gabriele Sabbioni. Determination of new biomarkers to monitor the dietary consumption of isothiocyanates.
Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals.
2010 Dec; 15(8):739-45. doi:
10.3109/1354750x.2010.517567. [PMID: 21039313] - Dennis J Templeton, Myo-Sabai Aye, Joshua Rady, Fang Xu, Janet V Cross. Purification of reversibly oxidized proteins (PROP) reveals a redox switch controlling p38 MAP kinase activity.
PloS one.
2010 Nov; 5(11):e15012. doi:
10.1371/journal.pone.0015012. [PMID: 21085594] - Sharifah S Syed Alwi, Breeze E Cavell, Urvi Telang, Marilyn E Morris, Barbara M Parry, Graham Packham. In vivo modulation of 4E binding protein 1 (4E-BP1) phosphorylation by watercress: a pilot study.
The British journal of nutrition.
2010 Nov; 104(9):1288-96. doi:
10.1017/s0007114510002217. [PMID: 20546646] - Kuang-Chi Lai, Shu-Chun Hsu, Chao-Lin Kuo, Siu-Wan Ip, Jai-Sing Yang, Yuan-Man Hsu, Hui-Ying Huang, Shin-Hwar Wu, Jing-Gung Chung. Phenethyl isothiocyanate inhibited tumor migration and invasion via suppressing multiple signal transduction pathways in human colon cancer HT29 cells.
Journal of agricultural and food chemistry.
2010 Oct; 58(20):11148-55. doi:
10.1021/jf102384n. [PMID: 20863062] - Nashi Widodo, Didik Priyandoko, Navjot Shah, Renu Wadhwa, Sunil C Kaul. Selective killing of cancer cells by Ashwagandha leaf extract and its component Withanone involves ROS signaling.
PloS one.
2010 Oct; 5(10):e13536. doi:
10.1371/journal.pone.0013536. [PMID: 20975835] - Nattaya Konsue, Costas Ioannides. Differential response of four human livers to modulation of phase II enzyme systems by the chemopreventive phytochemical phenethyl isothiocyanate.
Molecular nutrition & food research.
2010 Oct; 54(10):1477-85. doi:
10.1002/mnfr.200900598. [PMID: 20440691] - Miran Jang, Eunyoung Hong, Gun-Hee Kim. Evaluation of antibacterial activity of 3-butenyl, 4-pentenyl, 2-phenylethyl, and benzyl isothiocyanate in Brassica vegetables.
Journal of food science.
2010 Sep; 75(7):M412-6. doi:
10.1111/j.1750-3841.2010.01725.x. [PMID: 21535549] - Monika Okulicz. Multidirectional time-dependent effect of sinigrin and allyl isothiocyanate on metabolic parameters in rats.
Plant foods for human nutrition (Dordrecht, Netherlands).
2010 Sep; 65(3):217-24. doi:
10.1007/s11130-010-0183-3. [PMID: 20809411] - Toru Okubo, Kazuto Washida, Akira Murakami. Phenethyl isothiocyanate suppresses nitric oxide production via inhibition of phosphoinositide 3-kinase/Akt-induced IFN-gamma secretion in LPS-activated peritoneal macrophages.
Molecular nutrition & food research.
2010 Sep; 54(9):1351-60. doi:
10.1002/mnfr.200900318. [PMID: 20229527] - Nicole M van Dam, Bao-Li Qiu, Cornelis A Hordijk, Louise E M Vet, Jeroen J Jansen. Identification of biologically relevant compounds in aboveground and belowground induced volatile blends.
Journal of chemical ecology.
2010 Sep; 36(9):1006-16. doi:
10.1007/s10886-010-9844-9. [PMID: 20737198] - Xiang-Lin Tan, Miao Shi, Hui Tang, Weiguo Han, Simon D Spivack. Candidate dietary phytochemicals modulate expression of phase II enzymes GSTP1 and NQO1 in human lung cells.
The Journal of nutrition.
2010 Aug; 140(8):1404-10. doi:
10.3945/jn.110.121905. [PMID: 20554899] - Eun-Sun Hwang, Hyong Joo Lee. Effects of phenylethyl isothiocyanate and its metabolite on cell-cycle arrest and apoptosis in LNCaP human prostate cancer cells.
International journal of food sciences and nutrition.
2010 May; 61(3):324-36. doi:
10.3109/09637481003639092. [PMID: 20402549] - Anoop Kumar, Gabriele Sabbioni. New biomarkers for monitoring the levels of isothiocyanates in humans.
Chemical research in toxicology.
2010 Apr; 23(4):756-65. doi:
10.1021/tx900393t. [PMID: 20131755] - Xiaoli Wei, Wei Guo, Shuhong Wu, Li Wang, Peng Huang, Jinsong Liu, Bingliang Fang. Oxidative stress in NSC-741909-induced apoptosis of cancer cells.
Journal of translational medicine.
2010 Apr; 8(?):37. doi:
10.1186/1479-5876-8-37. [PMID: 20398386] - Nattaya Konsue, Jo Kirkpatrick, Nikolai Kuhnert, Laurie J King, Costas Ioannides. Repeated oral administration modulates the pharmacokinetic behavior of the chemopreventive agent phenethyl isothiocyanate in rats.
Molecular nutrition & food research.
2010 Mar; 54(3):426-32. doi:
10.1002/mnfr.200900090. [PMID: 19866468] - Marie-Hélène Teiten, Serge Eifes, Mario Dicato, Marc Diederich. Curcumin-the paradigm of a multi-target natural compound with applications in cancer prevention and treatment.
Toxins.
2010 01; 2(1):128-62. doi:
10.3390/toxins2010128. [PMID: 22069551] - Toshiyuki Nakamura, Noritoshi Kitamoto, Toshihiko Osawa, Yoji Kato. Immunochemical detection of food-derived isothiocyanate as a lysine conjugate.
Bioscience, biotechnology, and biochemistry.
2010; 74(3):536-40. doi:
10.1271/bbb.90728. [PMID: 20208364] - Thomas Hofmann, A Kuhnert, A Schubert, C Gill, I R Rowland, B L Pool-Zobel, M Glei. Modulation of detoxification enzymes by watercress: in vitro and in vivo investigations in human peripheral blood cells.
European journal of nutrition.
2009 Dec; 48(8):483-91. doi:
10.1007/s00394-009-0039-5. [PMID: 19636603] - Kristin K Brown, Frances H Blaikie, Robin A J Smith, Joel D A Tyndall, Hongqi Lue, Jürgen Bernhagen, Christine C Winterbourn, Mark B Hampton. Direct modification of the proinflammatory cytokine macrophage migration inhibitory factor by dietary isothiocyanates.
The Journal of biological chemistry.
2009 Nov; 284(47):32425-33. doi:
10.1074/jbc.m109.047092. [PMID: 19776019] - David J Williams, Christa Critchley, Sharon Pun, Mridusmita Chaliha, Timothy J O'Hare. Differing mechanisms of simple nitrile formation on glucosinolate degradation in Lepidium sativum and Nasturtium officinale seeds.
Phytochemistry.
2009 Jul; 70(11-12):1401-9. doi:
10.1016/j.phytochem.2009.07.035. [PMID: 19747700] - A Aires, V R Mota, M J Saavedra, A A Monteiro, M Simões, E A S Rosa, R N Bennett. Initial in vitro evaluations of the antibacterial activities of glucosinolate enzymatic hydrolysis products against plant pathogenic bacteria.
Journal of applied microbiology.
2009 Jun; 106(6):2096-105. doi:
10.1111/j.1365-2672.2009.04181.x. [PMID: 19291239] - Justyna Szumiło. [Natural compounds in chemoprevention of esophageal squamous cell tumors--experimental studies].
Polski merkuriusz lekarski : organ Polskiego Towarzystwa Lekarskiego.
2009 Feb; 26(152):156-61. doi:
. [PMID: 19388525] - Syed Sultan Beevi, Lakshmi Narasu Mangamoori, Vivek Dhand, Damaraju Siva Ramakrishna. Isothiocyanate profile and selective antibacterial activity of root, stem, and leaf extracts derived from Raphanus sativus L.
Foodborne pathogens and disease.
2009 Jan; 6(1):129-36. doi:
10.1089/fpd.2008.0166. [PMID: 19182965] - N Konsue, C Ioannides. Tissue differences in the modulation of rat cytochromes P450 and phase II conjugation systems by dietary doses of phenethyl isothiocyanate.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2008 Dec; 46(12):3677-83. doi:
10.1016/j.fct.2008.09.046. [PMID: 18929617] - Jeong-Hyeon Lim, Hyung-Wook Kim, Ju-Hyun Jeon, Hoi-Seon Lee. Acaricidal constituents isolated from Sinapis alba L. seeds and structure-activity relationships.
Journal of agricultural and food chemistry.
2008 Nov; 56(21):9962-6. doi:
10.1021/jf8022244. [PMID: 18844359] - Kiran Dharmala, Jin Wook Yoo, Chi H Lee. Development of chitosan-SLN microparticles for chemotherapy: in vitro approach through efflux-transporter modulation.
Journal of controlled release : official journal of the Controlled Release Society.
2008 Nov; 131(3):190-7. doi:
10.1016/j.jconrel.2008.07.034. [PMID: 18723057] - Adam M Wentzell, Ian Boeye, Zhiyong Zhang, Daniel J Kliebenstein. Genetic networks controlling structural outcome of glucosinolate activation across development.
PLoS genetics.
2008 Oct; 4(10):e1000234. doi:
10.1371/journal.pgen.1000234. [PMID: 18949035] - Preetha Anand, Ajaikumar B Kunnumakkara, Ajaikumar B Kunnumakara, Chitra Sundaram, Kuzhuvelil B Harikumar, Sheeja T Tharakan, Oiki S Lai, Bokyung Sung, Bharat B Aggarwal. Cancer is a preventable disease that requires major lifestyle changes.
Pharmaceutical research.
2008 Sep; 25(9):2097-116. doi:
10.1007/s11095-008-9661-9. [PMID: 18626751] - Maria Traka, Amy V Gasper, Antonietta Melchini, James R Bacon, Paul W Needs, Victoria Frost, Andrew Chantry, Alexandra M E Jones, Catharine A Ortori, David A Barrett, Richard Y Ball, Robert D Mills, Richard F Mithen. Broccoli consumption interacts with GSTM1 to perturb oncogenic signalling pathways in the prostate.
PloS one.
2008 Jul; 3(7):e2568. doi:
10.1371/journal.pone.0002568. [PMID: 18596959] - Evelyn Lamy, Julia Schröder, Stefanie Paulus, Peter Brenk, Thorsten Stahl, Volker Mersch-Sundermann. Antigenotoxic properties of Eruca sativa (rocket plant), erucin and erysolin in human hepatoma (HepG2) cells towards benzo(a)pyrene and their mode of action.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2008 Jul; 46(7):2415-21. doi:
10.1016/j.fct.2008.03.022. [PMID: 18479797] - Joris Vriens, Bernd Nilius, Rudi Vennekens. Herbal compounds and toxins modulating TRP channels.
Current neuropharmacology.
2008 Mar; 6(1):79-96. doi:
10.2174/157015908783769644. [PMID: 19305789] - Hanneke van Leur, Louise E M Vet, Wim H van der Putten, Nicole M van Dam. Barbarea vulgaris glucosinolate phenotypes differentially affect performance and preference of two different species of lepidopteran herbivores.
Journal of chemical ecology.
2008 Feb; 34(2):121-31. doi:
10.1007/s10886-007-9424-9. [PMID: 18213497] - Lixin Mi, Xiantao Wang, Sudha Govind, Brian L Hood, Timothy D Veenstra, Thomas P Conrads, Daniel T Saha, Radoslav Goldman, Fung-Lung Chung. The role of protein binding in induction of apoptosis by phenethyl isothiocyanate and sulforaphane in human non-small lung cancer cells.
Cancer research.
2007 Jul; 67(13):6409-16. doi:
10.1158/0008-5472.can-07-0340. [PMID: 17616701] - D Van Eylen, I Oey, M Hendrickx, A Van Loey. Kinetics of the stability of broccoli (Brassica oleracea Cv. Italica) myrosinase and isothiocyanates in broccoli juice during pressure/temperature treatments.
Journal of agricultural and food chemistry.
2007 Mar; 55(6):2163-70. doi:
10.1021/jf062630b. [PMID: 17305356] - Rong Hu, Changjiang Xu, Guoxiang Shen, Mohit R Jain, Tin Oo Khor, Avantika Gopalkrishnan, Wen Lin, Bandaru Reddy, Jefferson Y Chan, Ah-Ng Tony Kong. Identification of Nrf2-regulated genes induced by chemopreventive isothiocyanate PEITC by oligonucleotide microarray.
Life sciences.
2006 Oct; 79(20):1944-55. doi:
10.1016/j.lfs.2006.06.019. [PMID: 16828809] - Cheryl Lans, Nancy Turner, Gerhard Brauer, Grant Lourenco, Karla Georges. Ethnoveterinary medicines used for horses in Trinidad and in British Columbia, Canada.
Journal of ethnobiology and ethnomedicine.
2006 Aug; 2(?):31. doi:
10.1186/1746-4269-2-31. [PMID: 16893454] - Seok-Jong Suh, Sung-Kwon Moon, Cheorl-Ho Kim. Raphanus sativus and its isothiocyanates inhibit vascular smooth muscle cells proliferation and induce G(1) cell cycle arrest.
International immunopharmacology.
2006 May; 6(5):854-61. doi:
10.1016/j.intimp.2005.11.014. [PMID: 16546717] - Moul Dey, David Ribnicky, Anvar G Kurmukov, Ilya Raskin. In vitro and in vivo anti-inflammatory activity of a seed preparation containing phenethylisothiocyanate.
The Journal of pharmacology and experimental therapeutics.
2006 Apr; 317(1):326-33. doi:
10.1124/jpet.105.096511. [PMID: 16373530] - Sunita B Jones, James D Brooks. Modest induction of phase 2 enzyme activity in the F-344 rat prostate.
BMC cancer.
2006 Mar; 6(?):62. doi:
10.1186/1471-2407-6-62. [PMID: 16539699] - Li Tang, Guolin Li, Liguo Song, Yuesheng Zhang. The principal urinary metabolites of dietary isothiocyanates, N-acetylcysteine conjugates, elicit the same anti-proliferative response as their parent compounds in human bladder cancer cells.
Anti-cancer drugs.
2006 Mar; 17(3):297-305. doi:
10.1097/00001813-200603000-00008. [PMID: 16520658]