catechols

Summary

Summary: A group of 1,2-benzenediols that contain the general formula R-C6H5O2.

Top Publications

  1. ncbi Update on the chemopreventive effects of ginger and its phytochemicals
    Manjeshwar Shrinath Baliga
    Research and Development, Father Muller Medical College, Father Muller Hospital Road, Kankanady, Mangalore, 575002, Karnataka, India
    Crit Rev Food Sci Nutr 51:499-523. 2011
  2. ncbi Plasma levels of catechols and metanephrines in neurogenic orthostatic hypotension
    D S Goldstein
    Clinical Neurocardiology Section, National Institute of Neurological Disorders and Stroke, NIH, Bethesda, MD 20892 1620, USA
    Neurology 60:1327-32. 2003
  3. ncbi 6-Shogaol, an active constituent of dietary ginger, induces autophagy by inhibiting the AKT/mTOR pathway in human non-small cell lung cancer A549 cells
    Jen Yu Hung
    Graduate Institute of Medicine, College of Medicine, Kaohsiung Medical University, No 100, Shih Chuan 1st Road, Kaohsiung 807, Taiwan
    J Agric Food Chem 57:9809-16. 2009
  4. ncbi Inhibition of NADPH oxidase activation in endothelial cells by ortho-methoxy-substituted catechols
    David K Johnson
    Department of Chemistry, State University of New York College at Geneseo, USA
    Endothelium 9:191-203. 2002
  5. pmc 6-Shogaol, an active constituent of ginger, inhibits breast cancer cell invasion by reducing matrix metalloproteinase-9 expression via blockade of nuclear factor-κB activation
    H Ling
    Department of Pharmacy, National University of Singapore, Singapore, Singapore
    Br J Pharmacol 161:1763-77. 2010
  6. ncbi Molecular mechanisms of chemopreventive effects of selected dietary and medicinal phenolic substances
    Y Surh
    Laboratory of Biochemistry and Molecular Toxicology, College of Pharmacy, Seoul National University, Shinlim Dong, Kwanak gu, Seoul, South Korea
    Mutat Res 428:305-27. 1999
  7. ncbi Sources and significance of plasma levels of catechols and their metabolites in humans
    David S Goldstein
    Clinical Neurocardiology Section, National Institute of Neurological Disorders and Stroke, National Institutes of Health, Bethesda, MD 20892 1620
    J Pharmacol Exp Ther 305:800-11. 2003
  8. ncbi Anti-inflammatory effects of [6]-shogaol: potential roles of HDAC inhibition and HSP70 induction
    Sehwan Shim
    Department of Laboratory Animal Medicine, College of Veterinary Medicine, Chonbuk National University, Jeonju 561 756, Republic of Korea
    Food Chem Toxicol 49:2734-40. 2011
  9. pmc Pharmacokinetics of 6-gingerol, 8-gingerol, 10-gingerol, and 6-shogaol and conjugate metabolites in healthy human subjects
    Suzanna M Zick
    Deoartment of Family Medicine, University of Michigan Medical School, Ann Arbor, MI 48104, USA
    Cancer Epidemiol Biomarkers Prev 17:1930-6. 2008
  10. ncbi New antimalarial and cytotoxic 4-nerolidylcatechol derivatives
    Ana Cristina da Silva Pinto
    Universidade Federal do Amazonas, Campus Universitario, 69077 000 Manaus, AM, Brazil
    Eur J Med Chem 44:2731-5. 2009

Detail Information

Publications249 found, 100 shown here

  1. ncbi Update on the chemopreventive effects of ginger and its phytochemicals
    Manjeshwar Shrinath Baliga
    Research and Development, Father Muller Medical College, Father Muller Hospital Road, Kankanady, Mangalore, 575002, Karnataka, India
    Crit Rev Food Sci Nutr 51:499-523. 2011
    ..The above-mentioned mechanisms of ginger seem to be promising for cancer prevention; however, further clinical studies are warranted to assess the efficacy and safety of ginger...
  2. ncbi Plasma levels of catechols and metanephrines in neurogenic orthostatic hypotension
    D S Goldstein
    Clinical Neurocardiology Section, National Institute of Neurological Disorders and Stroke, NIH, Bethesda, MD 20892 1620, USA
    Neurology 60:1327-32. 2003
    ..From the concept of a unitary sympathoadrenomedullary system, one might predict parallel sympathoneural and adrenomedullary abnormalities in NOH...
  3. ncbi 6-Shogaol, an active constituent of dietary ginger, induces autophagy by inhibiting the AKT/mTOR pathway in human non-small cell lung cancer A549 cells
    Jen Yu Hung
    Graduate Institute of Medicine, College of Medicine, Kaohsiung Medical University, No 100, Shih Chuan 1st Road, Kaohsiung 807, Taiwan
    J Agric Food Chem 57:9809-16. 2009
    ..Taken together, these findings suggest that 6-shogaol may be a promising chemopreventive agent against human non-small cell lung cancer...
  4. ncbi Inhibition of NADPH oxidase activation in endothelial cells by ortho-methoxy-substituted catechols
    David K Johnson
    Department of Chemistry, State University of New York College at Geneseo, USA
    Endothelium 9:191-203. 2002
    ..A critical event is the reaction of ortho-methoxy-substituted catechols with reactive oxygen species (ROS) and peroxidase...
  5. pmc 6-Shogaol, an active constituent of ginger, inhibits breast cancer cell invasion by reducing matrix metalloproteinase-9 expression via blockade of nuclear factor-κB activation
    H Ling
    Department of Pharmacy, National University of Singapore, Singapore, Singapore
    Br J Pharmacol 161:1763-77. 2010
    ..However, the antimetastatic potential of shogaols remains unexplored. This study was performed to assess the effects of shogaols against breast cancer cell invasion and to investigate the underlying mechanisms...
  6. ncbi Molecular mechanisms of chemopreventive effects of selected dietary and medicinal phenolic substances
    Y Surh
    Laboratory of Biochemistry and Molecular Toxicology, College of Pharmacy, Seoul National University, Shinlim Dong, Kwanak gu, Seoul, South Korea
    Mutat Res 428:305-27. 1999
    ..In addition, these compounds have ability to suppress proliferation of human cancer cells via induction of apoptosis...
  7. ncbi Sources and significance of plasma levels of catechols and their metabolites in humans
    David S Goldstein
    Clinical Neurocardiology Section, National Institute of Neurological Disorders and Stroke, National Institutes of Health, Bethesda, MD 20892 1620
    J Pharmacol Exp Ther 305:800-11. 2003
    Human plasma contains several catechols, including the catecholamines norepinephrine, epinephrine, and dopamine, their precursor, L-3,4-dihydroxyphenylalanine (L-DOPA), and their deaminated metabolites, dihydroxyphenylglycol, the main ..
  8. ncbi Anti-inflammatory effects of [6]-shogaol: potential roles of HDAC inhibition and HSP70 induction
    Sehwan Shim
    Department of Laboratory Animal Medicine, College of Veterinary Medicine, Chonbuk National University, Jeonju 561 756, Republic of Korea
    Food Chem Toxicol 49:2734-40. 2011
    ..Taken together, our results suggest that [6]-shogaol can significantly attenuate a variety of neuroinflammatory responses by inducing HSP70, that is associated with HDAC inhibition in cortical astrocytes...
  9. pmc Pharmacokinetics of 6-gingerol, 8-gingerol, 10-gingerol, and 6-shogaol and conjugate metabolites in healthy human subjects
    Suzanna M Zick
    Deoartment of Family Medicine, University of Michigan Medical School, Ann Arbor, MI 48104, USA
    Cancer Epidemiol Biomarkers Prev 17:1930-6. 2008
    ..We conducted a clinical trial with 6-gingerol, 8-gingerol, 10-gingerol, and 6-shogaol, examining the pharmacokinetics and tolerability of these analytes and their conjugate metabolites...
  10. ncbi New antimalarial and cytotoxic 4-nerolidylcatechol derivatives
    Ana Cristina da Silva Pinto
    Universidade Federal do Amazonas, Campus Universitario, 69077 000 Manaus, AM, Brazil
    Eur J Med Chem 44:2731-5. 2009
    ..These derivatives provide leads for the development of a novel class of antimalarial drugs with enhanced chemical and pharmacological properties...
  11. pmc 6-Shogaol induces apoptosis in human hepatocellular carcinoma cells and exhibits anti-tumor activity in vivo through endoplasmic reticulum stress
    Rong Hu
    State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, China
    PLoS ONE 7:e39664. 2012
    ..Altogether our results indicate that the PERK/eIF2α pathway plays an important role in 6-shogaol-mediated ER stress and apoptosis in SMMC-7721 cells in vitro and in vivo...
  12. pmc Detoxication of structurally diverse polycyclic aromatic hydrocarbon (PAH) o-quinones by human recombinant catechol-O-methyltransferase (COMT) via O-methylation of PAH catechols
    Li Zhang
    Centers of Excellence in Environmental Toxicology and Cancer Pharmacology, Department of Pharmacology, Perelman School of Medicine, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA
    J Biol Chem 286:25644-54. 2011
    ..catechol-O-methyltransferase (S-COMT) is a feasible detoxication step for a panel of structurally diverse PAH-catechols produced during the redox-cycling process...
  13. ncbi Anti-inflammatory effects of catechols in lipopolysaccharide-stimulated microglia cells: inhibition of microglial neurotoxicity
    Long Tai Zheng
    Department of Pharmacology, Brain Science and Engineering Institute, CMRI, Kyungpook National University School of Medicine, 101 Dong In, Joong Gu, Daegu, 700 422, Republic of Korea
    Eur J Pharmacol 588:106-13. 2008
    ..The four catechol compounds showed anti-inflammatory effects with different potency. The catechols significantly decreased lipopolysaccharide (LPS)-induced NO and tumor necrosis factor (TNF)-alpha production in ..
  14. ncbi Shogaols at proapoptotic concentrations induce G(2)/M arrest and aberrant mitotic cell death associated with tubulin aggregation
    Fei Fei Gan
    Department of Pharmacy, Faculty of Science, National University of Singapore, Singapore 117543, Republic of Singapore
    Apoptosis 16:856-67. 2011
    ..In summary, our results conclude that shogaols cause apoptosis by inducing aberrant mitosis at least through the attenuation of cell cycle and spindle assembly checkpoint proteins...
  15. ncbi Crystal structure of 4-chlorocatechol 1,2-dioxygenase from the chlorophenol-utilizing gram-positive Rhodococcus opacus 1CP
    Marta Ferraroni
    Dipartimento di Chimica, Universita di Firenze, Via della Lastruccia 3, Sesto Fiorentino I 50019, Italy
    J Biol Chem 279:27646-55. 2004
    ..The present structure is the first of intradiol dioxygenases that specifically catalyze the cleavage of chlorocatechols, key intermediates in the aerobic catabolism of toxic chloroaromatics...
  16. ncbi Synthesis of the o-quinones and other oxidized metabolites of polycyclic aromatic hydrocarbons implicated in carcinogenesis
    Ronald G Harvey
    The Ben May Institute for Cancer Research, University of Chicago, Chicago, IL 60637, USA
    J Org Chem 69:2024-32. 2004
    ..The latter include the corresponding o-catechols, trans-dihydrodiols, and the corresponding anti- and syn-diol epoxides.
  17. ncbi [6]-Gingerol inhibits COX-2 expression by blocking the activation of p38 MAP kinase and NF-kappaB in phorbol ester-stimulated mouse skin
    Sue Ok Kim
    College of Pharmacy, Seoul National University, Seoul 151 742, South Korea
    Oncogene 24:2558-67. 2005
    ..Taken together, our data suggest that [6]-gingerol inhibits TPA-induced COX-2 expression in mouse skin in vivo by blocking the p38 MAP kinase-NF-kappaB signaling pathway...
  18. pmc Formation of catechols via removal of acid side chains from ibuprofen and related aromatic acids
    Robert W Murdoch
    Institute for Comparative and Environmental Toxicology, Cornell University, Ithaca, NY 14850, USA
    Appl Environ Microbiol 71:6121-5. 2005
    ..while 3- and 4-tolylacetic acids and 2-(4-tolyl)-propionic acid were metabolized to the corresponding methyl catechols before ring cleavage...
  19. ncbi Catechols in caffeic acid phenethyl ester are essential for inhibition of TNF-mediated IP-10 expression through NF-κB-dependent but HO-1- and p38-independent mechanisms in mouse intestinal epithelial cells
    Job O Mapesa
    ZIEL Research Center for Nutrition and Food Sciences, CDD Center for Diet and Disease, Technische Universitat Munchen, Freising Weihenstephan, Germany
    Mol Nutr Food Res 55:1850-61. 2011
    ....
  20. ncbi Hydroxyl radical formation via iron-mediated Fenton chemistry is inhibited by methylated catechols
    A J Nappi
    Department of Biology, Loyola University Chicago, IL 60626, USA
    Biochim Biophys Acta 1425:159-67. 1998
    ..These results highlight the importance of O-methylation in forming catechols that are less reactive than their dihydroxyphenyl precursors...
  21. ncbi Dietary ginger constituents, galanals A and B, are potent apoptosis inducers in Human T lymphoma Jurkat cells
    Noriyuki Miyoshi
    Laboratory of Food and Biodynamics, Nagoya University Graduate School of Bioagricultural Sciences, Nagoya 464 8601, Japan
    Cancer Lett 199:113-9. 2003
    ..In conclusion, the results from this study provide biological evidence that ginger-specific constituents other than curcuminoids are potential anticancer agents...
  22. ncbi Effects of [6]-shogaol on cholinergic signaling in HT22 cells following neuronal damage induced by hydrogen peroxide
    Sehwan Shim
    Department of Laboratory Animal Medicine, College of Veterinary Medicine, Chonbuk National University, Jeonju 561 756, Republic of Korea
    Food Chem Toxicol 50:1454-9. 2012
    ..These data suggest that [6]-shogaol protects neurons by increasing ChAT and ChTp expression through a BDNF increase and thus may be useful for treating neurodegenerative diseases...
  23. ncbi Hispolon induces apoptosis through JNK1/2-mediated activation of a caspase-8, -9, and -3-dependent pathway in acute myeloid leukemia (AML) cells and inhibits AML xenograft tumor growth in vivo
    Pei Ching Hsiao
    School of Medicine, Institute of Biochemistry and Biotechnology, and Institute of Medicine, Chung Shan Medical University, No 110, Section 1, Chien Kuo N Road, Taichung 40201, Taiwan
    J Agric Food Chem 61:10063-73. 2013
    ..In hispolon-treated tumors, activation of caspase-3 and a decrease in Ki67-positive cells were observed. Our results indicated that hispolon may have the potential to serve as a therapeutic tool to treat AML. ..
  24. ncbi An impression on current developments in the technology, chemistry, and biological activities of ginger (Zingiber officinale Roscoe)
    I Rahath Kubra
    Plantation Products, Spices, and Flavor Technology Department, Central Food Technological Research Institute, Mysore 570020, India
    Crit Rev Food Sci Nutr 52:651-88. 2012
    ..Further studies are required for the validation of the beneficial uses. Formulation for novel products and new usages may emerge in the years to come, based on the revealed results of various studies...
  25. ncbi 6-Shogaol, a ginger product, modulates neuroinflammation: a new approach to neuroprotection
    Sang Keun Ha
    Graduate School of East West Medical Science, Kyung Hee University Global Campus, 1732 Deogyeong daero, Giheung gu, Yongin, Gyeonggi Do 446 701, Republic of Korea
    Neuropharmacology 63:211-23. 2012
    ..These results suggest that 6-shogaol is an effective therapeutic agent for treating neurodegenerative diseases...
  26. ncbi In vitro and in vivo modulation of testosterone mediated alterations in apoptosis related proteins by [6]-gingerol
    Yogeshwer Shukla
    Proteomics Laboratory, Industrial Toxicology Research Centre, Mahatma Gandhi Marg, Lucknow, India
    Mol Nutr Food Res 51:1492-502. 2007
    ..Thus, [6]-gingerol shows its protective effects in both in vivo and in vitro prostate cancer models by modulation of proteins involved in apoptosis pathway...
  27. ncbi Biomimetic anchor for surface-initiated polymerization from metal substrates
    Xiaowu Fan
    Department of Biomedical Engineering, Robert R McCormick School of Engineering and Applied Sciences, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, USA
    J Am Chem Soc 127:15843-7. 2005
    ..Due to the ability of catechols to bind to a large variety of inorganic surfaces, this biomimetic anchoring strategy is expected to be a highly ..
  28. ncbi [6]-Gingerol attenuates β-amyloid-induced oxidative cell death via fortifying cellular antioxidant defense system
    Chan Lee
    College of Oriental Medicine, Daegu Haany University, Daegu 706 828, South Korea
    Food Chem Toxicol 49:1261-9. 2011
    ..These results suggest that [6]-gingerol exhibits preventive and/or therapeutic potential for the management of AD via augmentation of antioxidant capacity...
  29. pmc Multiple mechanisms are involved in 6-gingerol-induced cell growth arrest and apoptosis in human colorectal cancer cells
    Seong Ho Lee
    The Laboratory of Environmental Carcinogenesis, Department of Pathobiology, College of Veterinary Medicine, University of Tennessee, Knoxville, Tennessee 37996 4542, USA
    Mol Carcinog 47:197-208. 2008
    ..Multiple mechanisms appear to be involved in 6-gingerol action, including protein degradation as well as beta-catenin, PKCepsilon, and GSK-3beta pathways...
  30. ncbi [6]-Gingerol, a pungent ingredient of ginger, inhibits angiogenesis in vitro and in vivo
    Eok Cheon Kim
    Department of Biochemistry, College of Natural Sciences, Yonsei University, Seoul, Republic of Korea
    Biochem Biophys Res Commun 335:300-8. 2005
    ..Taken together, these results demonstrate that [6]-gingerol inhibits angiogenesis and may be useful in the treatment of tumors and other angiogenesis-dependent diseases...
  31. pmc [6]-Gingerol induces cell cycle arrest and cell death of mutant p53-expressing pancreatic cancer cells
    Yon Jung Park
    Department of Internal Medicine, Yonsei University College of Medicine, 134 Shinchon dong, Seodaemoon Gu, Seoul 120 752, Korea
    Yonsei Med J 47:688-97. 2006
    ....
  32. pmc Increased growth inhibitory effects on human cancer cells and anti-inflammatory potency of shogaols from Zingiber officinale relative to gingerols
    Shengmin Sang
    Department of Chemical Biology, Ernest Mario School of Pharmacy, Rutgers University, 164 Frelinghuysen Road, Piscataway, New Jersey 08854 8020, USA
    J Agric Food Chem 57:10645-50. 2009
    ..In addition, we found that [6]-shogaol had much stronger inhibitory effects on arachidonic acid release and nitric oxide (NO) synthesis than [6]-gingerol...
  33. ncbi Chemical properties of catechols and their molecular modes of toxic action in cells, from microorganisms to mammals
    N Schweigert
    Swiss Federal Institute for Environmental Science and Technology, Eawag,
    Environ Microbiol 3:81-91. 2001
    b>Catechols can undergo a variety of chemical reactions. In this review, we particularly focus on complex formations and the redox chemistry of catechols, which play an inportant role in the toxicity of catechols...
  34. pmc Mechanism of metabolic activation and DNA adduct formation by the human carcinogen diethylstilbestrol: the defining link to natural estrogens
    Muhammad Saeed
    Eppley Institute for Research in Cancer and Allied Diseases, University of Nebraska Medical Center, Omaha, NE 68198 6805, USA
    Int J Cancer 124:1276-84. 2009
    ....
  35. ncbi In vitro synthesis of curcuminoids by type III polyketide synthase from Oryza sativa
    Yohei Katsuyama
    Department of Biotechnology, Graduate School of Agriculture and Life Sciences, The University of Tokyo, Tokyo, Japan
    J Biol Chem 282:37702-9. 2007
    ....
  36. ncbi Anti-tumor promoting potential of selected spice ingredients with antioxidative and anti-inflammatory activities: a short review
    Young Joon Surh
    Laboratory of Biochemistry and Molecular Toxicology, College of Pharmacy, Seoul National University, 151 742, Seoul, South Korea
    Food Chem Toxicol 40:1091-7. 2002
    ....
  37. ncbi Induction of apoptosis by [6]-gingerol associated with the modulation of p53 and involvement of mitochondrial signaling pathway in B[a]P-induced mouse skin tumorigenesis
    Nidhi Nigam
    Proteomics Laboratory, Indian Institute of Toxicology Research CSIR, M G Marg, P O Box 80, Lucknow 226001, India
    Cancer Chemother Pharmacol 65:687-96. 2010
    ....
  38. ncbi Cerebrospinal fluid levels of catechols in patients with neurogenic orthostatic hypotension
    David S Goldstein
    Clinical Neurocardiology Section, National Institute of Neurological Disorders and Stroke, National Institutes of Health, Building 10, Room 6N252, 10 Center Drive, MSC 1620, Bethesda, MD 20892 1620, U S A
    Clin Sci (Lond) 104:649-54. 2003
    ..90+/-0.09 and 9.64+/-0.46 nmol/l respectively; P =0.0001). The MSA+OH group had higher plasma levels of both catechols (noradrenaline, 1.31+/-0.16 nmol/l; dihydroxyphenylglycol, 5.08+/-0...
  39. ncbi The molecular basis for adaptive evolution in novel extradiol dioxygenases retrieved from the metagenome
    Hikaru Suenaga
    Institute for Biological Resources and Functions, National Institute of Advanced Industrial Science and Technology AIST, Ibaraki 305 8566, Japan
    FEMS Microbiol Ecol 69:472-80. 2009
    ....
  40. ncbi Effect of [6]-shogaol on cytosolic Ca2+ levels and proliferation in human oral cancer cells (OC2)
    Chung Yi Chen
    Department of Medical Technology, School of Medical and Health Sciences, Fooyin University, Ta Liao, Kaohsiung County 83101, Taiwan, Republic of China
    J Nat Prod 73:1370-4. 2010
    ....
  41. ncbi Pharmacokinetics of [6]-shogaol, a pungent ingredient of Zingiber officinale Roscoe (Part I)
    Akitoshi Asami
    Department of Clinical Pharmacy, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma machi, Kanazawa, Ishikawa 920 1192, Japan
    J Nat Med 64:281-7. 2010
    ..When these results are combined with those obtained with the labeled compound, it would suggest that [6]-shogaol is mostly metabolized in the body and excreted as metabolites...
  42. pmc Biotransformation in double-phase systems: physiological responses of Pseudomonas putida DOT-T1E to a double phase made of aliphatic alcohols and biosynthesis of substituted catechols
    Antonia Rojas
    Department of Biochemistry and Molecular and Cellular Biology of Plants, CSIC Estacion Experimental del Zaidin, E 18008 Granada, Spain
    Appl Environ Microbiol 70:3637-43. 2004
    ..8). The amount of 3-methylcatechol produced in an aliphatic alcohol/water bioreactor was 10- to 20-fold higher than in an aqueous medium, demonstrating the usefulness of double-phase systems for this particular biotransformation...
  43. ncbi Dioxygenase- and monooxygenase-catalysed synthesis of cis-dihydrodiols, catechols, epoxides and other oxygenated products
    Louise C Nolan
    School of Biomolecular and Biomedical Science, Centre for Synthesis and Chemical Biology, Conway Institute for Biomolecular and Biomedical Research, University College Dublin, Belfield, Dublin 4, Ireland
    Biotechnol Lett 30:1879-91. 2008
    ..and oxidase enzymes that have been manipulated for the synthesis of products such as cis-dihydrodiols, catechols, epoxides and other oxygenated products...
  44. ncbi Ginger ingredients reduce viability of gastric cancer cells via distinct mechanisms
    Kazuhiro Ishiguro
    Molecular Biology and Pathogenesis of Gastroenterology, Nagoya University School of Medicine, 65 Tsurumai Cho, Showa Ku, Nagoya, Aichi 466 8550, Japan
    Biochem Biophys Res Commun 362:218-23. 2007
    ....
  45. ncbi Specific reaction of alpha,beta-unsaturated carbonyl compounds such as 6-shogaol with sulfhydryl groups in tubulin leading to microtubule damage
    Kazuhiro Ishiguro
    Molecular Biology and Pathogenesis of Gastroenterology, Nagoya University School of Medicine, 65 Tsurumai Cho, Showa Ku, Nagoya, Aichi 466 8550, Japan
    FEBS Lett 582:3531-6. 2008
    ..In addition, alpha,beta-unsaturated carbonyl compounds are more reactive with sulfhydryl groups in tubulin than in 2-mercaptoethanol, dithiothreitol, glutathione and papain, a cysteine protease...
  46. ncbi Protection by [6]-shogaol against lipopolysaccharide-induced toxicity in murine astrocytes is related to production of brain-derived neurotrophic factor
    Sehwan Shim
    Department of Laboratory Animal Medicine, College of Veterinary Medicine, Chonbuk National University, Jeonju 561 756, Republic of Korea
    Food Chem Toxicol 50:597-602. 2012
    ..Thus, the neuroprotective effects of [6]-shogaol is mediated by up-regulation of BDNF...
  47. ncbi Identification of catechols as histone-lysine demethylase inhibitors
    Anders L Nielsen
    Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, Copenhagen, Denmark
    FEBS Lett 586:1190-4. 2012
    ..In this subset, two inhibitors (2 and 10) had comparable affinities towards KDM4C and KDM6A but no effect on PHF8. One inhibitor restored H3K9me3 levels in KDM4C transfected U2-OS cells...
  48. ncbi Influence of dietary catechols on the growth of enteropathogenic bacteria
    Primrose P E Freestone
    Department of Infection, Immunology and Inflammation, University of Leicester School of Medicine, Leicester, UK
    Int J Food Microbiol 119:159-69. 2007
    ..The present report examines whether other, non-catecholamine, dietary catechols, which occur widely in plant foods, can also influence enteropathogen growth in an iron-restrictive environment ..
  49. ncbi Effects of ginger constituents on the gastrointestinal tract: role of cholinergic M3 and serotonergic 5-HT3 and 5-HT4 receptors
    Heinz H Pertz
    Institut fur Pharmazie, Freie Universitat Berlin, Berlin Dahlem, Germany
    Planta Med 77:973-8. 2011
    ..5-HT (4) receptors, which play a role in gastroduodenal motility, appear not to be involved in the action of these compounds...
  50. ncbi Diarylheptanoid hirsutenone enhances apoptotic effect of TRAIL on epithelial ovarian carcinoma cell lines via activation of death receptor and mitochondrial pathway
    Chung Soo Lee
    Department of Pharmacology, College of Medicine, Chung Ang University, Seoul 156 756, South Korea
    Invest New Drugs 30:548-57. 2012
    ..Hirsutenone may confer a benefit in the TRAIL treatment of epithelial ovarian adenocarcinoma...
  51. ncbi Invadopodia-associated proteins blockade as a novel mechanism for 6-shogaol and pterostilbene to reduce breast cancer cell motility and invasion
    Bo Han Hong
    Department of Food Science and Biotechnology, National Chung Hsing University, Taichung, Taiwan
    Mol Nutr Food Res 57:886-95. 2013
    ..The aim of this study was to investigate the modulatory effects of 6-shogaol and pterostilbene on invadopodia in aggressive breast cancer cells...
  52. ncbi Simultaneous determination of 6-gingerol, 8-gingerol, 10-gingerol and 6-shogaol in rat plasma by liquid chromatography-mass spectrometry: Application to pharmacokinetics
    Wei Wang
    Key Laboratory of Modern Chinese Medicines China Pharmaceutical University, Ministry of Education Nanjing, 210009, China
    J Chromatogr B Analyt Technol Biomed Life Sci 877:671-9. 2009
    ..Glucuronide of 6-gingerol was determined after beta-glucuronidase hydrolysis for more information, and the intestinal glucuronidation was further confirmed by comparison of plasma samples of hepatic portal vein and femoral vein...
  53. ncbi [Bibrocathol eye ointment is efficacious in blepharitis. Results from a randomized, double-blind, controlled clinical trial]
    W Behrens-Baumann
    Universitätsaugenklinik Magdeburg, Leipziger Strasse 44, Haus 60b, 39120 Magdeburg, Germany
    Ophthalmologe 103:960-5. 2006
    ..Bibrocathol treatment is well tolerated and safe...
  54. pmc Metabolism of [6]-shogaol in mice and in cancer cells
    Huadong Chen
    Center for Excellence in Post Harvest Technologies, North Carolina Agricultural and Technical State University, North Carolina Research Campus, 500 Laureate Way, Kannapolis, NC 28081, USA
    Drug Metab Dispos 40:742-53. 2012
    ..Our results suggest that 1) [6]-shogaol is extensively metabolized in these two models, 2) its metabolites are bioactive compounds, and 3) the mercapturic acid pathway is one of the major biotransformation pathways of [6]-shogaol...
  55. ncbi Instrument dependence of electrospray ionization and tandem mass spectrometric fragmentation of the gingerols
    Hongliang Jiang
    Department of Plant Sciences, University of Arizona, Tucson, AZ 85721, USA
    Rapid Commun Mass Spectrom 20:3089-100. 2006
    ....
  56. ncbi Design, synthesis, and biological evaluation of bromophenol derivatives as protein tyrosine phosphatase 1B inhibitors
    Bo Jiang
    Institute of Oceanology, Chinese Academy of Sciences, Qingdao, China
    Arch Pharm (Weinheim) 345:444-53. 2012
    ..Among these, compound 26 exhibited remarkable inhibitory activity against PTP1B with an IC(50) of 0.89 µmol/L, which was approximately two-fold more potent than the initial lead compound BDB...
  57. ncbi Cancer preventive properties of ginger: a brief review
    Yogeshwer Shukla
    Environmental Carcinogenesis Division, Industrial Toxicology Research Centre, P O Box 80, M G Marg, Lucknow 226 001, Uttar Pradesh, India
    Food Chem Toxicol 45:683-90. 2007
    ..A number of mechanisms that may be involved in the chemopreventive effects of ginger and its components have been reported from the laboratory studies in a wide range of experimental models...
  58. ncbi Conjugation of catechols by recombinant human sulfotransferases, UDP-glucuronosyltransferases, and soluble catechol O-methyltransferase: structure-conjugation relationships and predictive models
    Jyrki Taskinen
    Department of Pharmacy, University of Helsinki, Helsinki, Finland
    Drug Metab Dispos 31:1187-97. 2003
    ..endogenous compounds, such as catecholamines and catecholestrogens, drugs, natural plant constituents, and other catechols with diverse substituent properties and substitution patterns...
  59. ncbi Sex steroids, carcinogenesis, and cancer progression
    Luigi Castagnetta
    Department of Experimental Oncology and Clinical Application, University Medical School, Palermo, Italy
    Ann N Y Acad Sci 1028:233-46. 2004
    ....
  60. ncbi Gingerol content of diploid and tetraploid clones of ginger (Zingiber officinale Roscoe)
    Hans Wohlmuth
    School of Natural and Complementary Medicine, Southern Cross University, PO Box 157, Lismore, NSW 2480, Australia
    J Agric Food Chem 53:5772-8. 2005
    ..In contrast to previous findings, this study did not find significant differences in gingerol concentrations between the tetraploid clones and their parent diploid cultivar...
  61. ncbi Specificity of catechol ortho-cleavage during para-toluate degradation by Rhodococcus opacus 1cp
    M M Suvorova
    Pushchino State University, Pushchino, Moscow Region, 142290, Russia
    Biochemistry (Mosc) 71:1316-23. 2006
    ..This supports the hypothesis on the existence of multiple forms of dioxygenases as adaptive reactions of microorganisms in response to environmental stress...
  62. ncbi Simultaneous determination of 5-hydroxyindoles and catechols by high-performance liquid chromatography with fluorescence detection following derivatization with benzylamine and 1,2-diphenylethylenediamine
    Kaoru Fujino
    Chemicals Evaluation and Research Institute, 3 822 Ishii machi, Hita, Oita 877 0061, Japan
    J Chromatogr A 1012:169-77. 2003
    A highly selective and sensitive method for the simultaneous determination of 5-hydroxyindoles and catechols (serotonin, norepinephrine, dopamine and related compounds) by high-performance liquid chromatography with fluorescence ..
  63. ncbi 6-Shogaol, a natural product, reduces cell death and restores motor function in rat spinal cord injury
    Kang Soo Kyung
    Department of Physiology, School of Medicine, Pusan National University, 1 10 Ami dong, Seo Gu, Busan, South Korea
    Eur J Neurosci 24:1042-52. 2006
    ....
  64. ncbi Simultaneous determination and pharmacokinetic studies on (3,4-Dihydroxyphenyl)-lactic acid and protocatechuic aldehyde in rat serum after oral administration of Radix Salviae miltiorrhizae extract
    Guan Ye
    School of Pharmaceutical Sciences and Modern Research Center for Traditional Chinese Medicine, Peking University, Beijing 100083, China
    J Chromatogr Sci 41:327-30. 2003
    ..This validated assay is applied to the determination of Dhpl and Pal concentrations and used to take a limited view of the pharmacokinetic profile in rat serum after oral administration of Radix Salviae miltiorrhizae extract...
  65. ncbi 6-shogaol (alkanone from ginger) induces apoptotic cell death of human hepatoma p53 mutant Mahlavu subline via an oxidative stress-mediated caspase-dependent mechanism
    Chung Yi Chen
    Basic Medical Science Education Center and Department of Medical Technology, Fooyin University, Kaohsiung County 831, Taiwan
    J Agric Food Chem 55:948-54. 2007
    ..These data also provide evidence to reaffirm the notion that consumption of certain foodstuffs can be beneficial to health because some of the constituents contained in them may be anticarcinogenic...
  66. ncbi 6-Shogaol is more effective than 6-gingerol and curcumin in inhibiting 12-O-tetradecanoylphorbol 13-acetate-induced tumor promotion in mice
    Hou Wu
    Department of Food Science, Rutgers University, New Brunswick, NJ, USA
    Mol Nutr Food Res 54:1296-306. 2010
    ..It is suggested that 6-shogaol is a novel functional agent capable of preventing inflammation-associated tumorigenesis...
  67. pmc Induction of apoptosis by [8]-shogaol via reactive oxygen species generation, glutathione depletion, and caspase activation in human leukemia cells
    Po Chuen Shieh
    Department of Pharmacy and Graduate Institute of Pharmaceutical Technology, Tajen University, Pingtung, Taiwan
    J Agric Food Chem 58:3847-54. 2010
    ..Taken together, these results suggest for the first time that ROS production and depletion of glutathione that contributed to [8]-shogaol-induced apoptosis in HL-60 cells...
  68. ncbi Mechanism of cytotoxicity of catechols and a naphthalenediol in PC12-AC cells: the connection between extracellular autoxidation and molecular electronic structure
    Alexandru Chichirau
    Department of Chemistry, Carleton University, 1125 Colonel By Drive, Ottawa, ON, Canada K1S 5B6
    Free Radic Biol Med 38:344-55. 2005
    ortho-Hydroxyphenols (catechols) form a common structural unit in naturally occurring antioxidants such as polyphenols. They also show pro-oxidant characteristics which depend on their particular structure...
  69. ncbi Investigation of the larvicidal activity of Pothomorphe peltata and isolation of the active constituent
    E Mongelli
    Catedra de Farmacognosia, IQUIMEFA CONICET, Facultad de Farmacia y Bioquimica, Universidad de Buenos Aires, Junin 956 1113 Buenos Aires, Argentina
    Phytother Res 16:S71-2. 2002
    ..This compound was quite potent against Aedes aegypti larvae (LC(50) = 9.1 microg/mL)...
  70. ncbi Methylcatechol 1,2-dioxygenase of Rhodococcus opacus 6a is a new type of the catechol-cleaving enzyme
    I P Solyanikova
    Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, Pushchino, Moscow Region, 142290, Russia
    Biochemistry (Mosc) 74:994-1001. 2009
    ..One of these enzymes belongs to the type of enzymes cleaving the catechol ring and known as methylcatechol 1,2-dioxygenases. In bacteria of the Rhodococcus genus, such an enzyme is described here for the first time...
  71. ncbi Naphthalene diols: a new class of antioxidants intramolecular hydrogen bonding in catechols, naphthalene diols, and their aryloxyl radicals
    Mario C Foti
    Department of Chemistry, Carleton University, 1125 Colonel By Drive, Ottawa, Ontario, K1S 5B6 Canada
    J Org Chem 67:5190-6. 2002
    ..diols, and this effect contributes to the increased HAT activity of 5 and 6 compared to the activities of the catechols. For example, the increased stabilization due to the intramolecular H-bond of 5 radical over 5 parent of 8...
  72. ncbi Enzymatic and spectroscopic studies on the activation or inhibition effects by substituted phenolic compounds in the oxidation of aryldiamines and catechols catalyzed by Rhus vernicifera laccase
    Luigi Casella
    Dipartimento di Chimica Generale, Universita di Pavia, Via Taramelli 12, 27100 Pavia, Italy
    J Inorg Biochem 100:2127-39. 2006
    ..g. the peroxy intermediate, that causes the release of hydrogen peroxide and prevents the reaction of this intermediate with the substrate...
  73. ncbi Protocatechuic aldehyde suppresses TNF-alpha-induced ICAM-1 and VCAM-1 expression in human umbilical vein endothelial cells
    Zhe Zhou
    Beijing Institute of Radiation Medicine, Haidian District, Beijing, PR China
    Eur J Pharmacol 513:1-8. 2005
    ..Collectively, these results indicate that protocatechuic aldehyde inhibits TNF-alpha-stimulated VCAM-1 and ICAM-1expression in HUVECs through a mechanism that involves NF-kappaB and AP-1...
  74. ncbi Neuroprotective effects of insulin-like growth factor-binding protein ligand inhibitors in vitro and in vivo
    Kenneth B Mackay
    Neurocrine Biosciences Inc, San Diego, California 92121 1102, USA
    J Cereb Blood Flow Metab 23:1160-7. 2003
    ..These results further define the neuroprotective properties of IGFs and IGFBP ligand inhibitors in experimental models of cerebral ischemia...
  75. ncbi Cytosolic catechols inhibit alpha-synuclein aggregation and facilitate the formation of intracellular soluble oligomeric intermediates
    Joseph R Mazzulli
    The Joseph Stokes Jr Research Institute, The Children s Hospital of Philadelphia and the University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA
    J Neurosci 26:10068-78. 2006
    ..These data indicate that intraneuronal dopamine levels can be a major modulator of alpha-syn aggregation and inclusion formation, with important implications on the selective degeneration of these neurons in Parkinson's disease...
  76. ncbi The laccase-catalyzed domino reaction between catechols and heterocyclic 1,3-dicarbonyls and the unambiguous structure elucidation of the products by NMR spectroscopy and X-ray crystal structure analysis
    Szilvia Hajdok
    Bioorganische Chemie, Institut fur Chemie, Universitat Hohenheim, Garbenstrasse 30, D 70599 Stuttgart, Germany
    J Org Chem 74:7230-7. 2009
    The laccase-catalyzed reaction between catechols and heterocyclic 1,3-dicarbonyls (pyridinones, quinolinones, thiocoumarins) using aerial oxygen as the oxidant delivers benzofuropyridinones, benzofuroquinolinones, and thiocoumestans in a ..
  77. ncbi Iron complexes of deferiprone and dietary plant catechols as cytoprotective superoxide radical scavengers(1)
    M Y Moridani
    Faculty of Pharmacy, University of Toronto, M5S 2S2, Toronto, Ontario, Canada
    Biochem Pharmacol 62:1579-85. 2001
    ..the present work, we found that deferiprone (L1), an iron-chelating drug, and dietary dihydroxycinnamic acids (catechols) were much more effective at protecting isolated rat hepatocytes against hypoxia-reoxygenation injury if ..
  78. ncbi Catechols as membrane anion transporters
    Sofya Kostina Berezin
    Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA
    J Am Chem Soc 131:2458-9. 2009
    ..This assay reveals that anion transport selectivity for this amphiphilic bis-catechol follows a Hofmeister sequence wherein anions that are easier to dehydrate are made more permeable to the membrane by 3...
  79. ncbi The role of catechols and free radicals in benzene toxicity: an oxidative DNA damage pathway
    George Barreto
    Instituto Cajal, CSIC E 28002 Madrid, Spain
    Environ Mol Mutagen 50:771-80. 2009
    ..In this review, we have addressed the cytotoxic effects of benzene and its main metabolite, catechol, focusing on the oxidative pathway and further DNA damage...
  80. ncbi Development of a stable isotope dilution analysis with liquid chromatography-tandem mass spectrometry detection for the quantitative analysis of di- and trihydroxybenzenes in foods and model systems
    Roman Lang
    Institut fur Lebensmittelchemie, Universitat Munster, Germany
    J Agric Food Chem 54:5755-62. 2006
    ....
  81. ncbi Hirsutenone inhibits phorbol ester-induced upregulation of COX-2 and MMP-9 in cultured human mammary epithelial cells: NF-kappaB as a potential molecular target
    Jung Hwan Kim
    College of Pharmacy, Seoul National University, Shillim Dong, Kwanak gu, Seoul 151 742, Republic of Korea
    FEBS Lett 580:385-92. 2006
    ..In summary, hirsutenone inhibits the TPA-induced upregulation of COX-2 and MMP-9 in human breast epithelial cells, possibly by targeting NF-kappaB, which may contribute to its chemopreventive effects...
  82. pmc Isolation of Alcaligenes sp. strain L6 at low oxygen concentrations and degradation of 3-chlorobenzoate via a pathway not involving (chloro)catechols
    J Krooneman
    Department of Microbiology, University of Groningen, Haren, The Netherlands
    Appl Environ Microbiol 62:2427-34. 1996
    ..In continuous culture with 3CBA as the sole growth substrate, strain L6 demonstrated an increased oxygen affinity with decreasing steady-state oxygen concentrations...
  83. ncbi High-rate 3-methylcatechol production in Pseudomonas putida strains by means of a novel expression system
    L E Hüsken
    Department of Food and Technology and Nutritional Sciences, Wageningen University, The Netherlands
    Appl Microbiol Biotechnol 55:571-7. 2001
    ..of toluene into 3-methylcatechol was studied as a model system for the production of valuable 3-substituted catechols in general. For this purpose, an improved microbial system for the production of 3-methylcatechol was obtained...
  84. ncbi Enzymatic dehydrogenative polymerization of urushiols in fresh exudates from the lacquer tree, Rhus vernicifera DC
    Sayoko Harigaya
    Department of Applied Chemistry, Meiji University, Kawasaki 214 8571, Japan
    J Agric Food Chem 55:2201-8. 2007
    ..This is of primary importance because the use of the urushi exudates as coating materials does not involve organic solvents and is an environmentally friendly process...
  85. ncbi Catechol-O-Methyltransferase (COMT)-mediated methylation metabolism of endogenous bioactive catechols and modulation by endobiotics and xenobiotics: importance in pathophysiology and pathogenesis
    Bao Ting Zhu
    Department of Basic Pharmaceutical Sciences, College of Pharmacy, University of South Carolina, Columbia 29208, USA
    Curr Drug Metab 3:321-49. 2002
    The metabolic O-methylation of endogenous catecholamines and other catechols catalyzed by catechol-O-methyltransferase (COMT; EC 2.1.1.6) was first described by Dr. Julix Axelrod and his colleagues almost half a century ago...
  86. ncbi Diarylheptanoid hirsutenone prevents tumor necrosis factor-alpha-stimulated production of inflammatory mediators in human keratinocytes through NF-kappaB inhibition
    Chung Soo Lee
    Department of Pharmacology, Chung Ang University, Seoul, South Korea
    Int Immunopharmacol 9:1097-104. 2009
    ..The findings suggest that hirsutenone may exert an inhibitory effect against the pro-inflammatory mediator-induced skin disease...
  87. ncbi Inhibitory effects of catechol accumulation on benzene biodegradation in Pseudomonas putida F1 cultures
    R Munoz
    Department of Chemical Engineering and Environmental Technology, University of Valladolid, Paseo del Prado de la Magdalena s n, Valladolid, Spain
    Chemosphere 68:244-52. 2007
    ..Thus, due to its toxic and inhibitory nature and its tendency to accumulate at high benzene loading, catechol must be carefully monitored during process operation...
  88. ncbi Synthesis of the catechols of natural and synthetic estrogens by using 2-iodoxybenzoic acid (IBX) as the oxidizing agent
    Muhammad Saeed
    Eppley Institute for Research in Cancer and Allied Diseases, University of Nebraska Medical Center, 986805 Nebraska Medical Center, Omaha, NE 68198 6805, USA
    Steroids 70:173-8. 2005
    ..yielded a mixture of estrone/estradiol-2,3- and -3,4-quinones, which were reduced in situ to the corresponding catechols by treatment with a 1 M aqueous solution of ascorbic acid...
  89. ncbi Suppression of T cell activation by hirsutenone, isolated from the bark of Alnus japonica, and its therapeutic advantages for atopic dermatitis
    Seong Soo Joo
    Research Institute of Veterinary Medicine, Chungbuk National University, Republic of Korea
    Eur J Pharmacol 614:98-105. 2009
    ..Therefore, our results suggest that hirsutenone may be a new topical drug candidate, which probably acts by mimicking calcineurin inhibitor mechanisms...
  90. ncbi Production of 3-nitrocatechol by oxygenase-containing bacteria: optimization of the nitrobenzene biotransformation by Nocardia S3
    J Kieboom
    Department of Food Technology and Nutritional Sciences, Wageningen Agricultural University, The Netherlands
    Appl Microbiol Biotechnol 55:290-5. 2001
    ..The inhibition of nitrobenzene biotransformation by 3-nitrocatechol greatly impacts 3-nitrocatechol production processes...
  91. ncbi Differences in toxicity of the catechol-O-methyl transferase inhibitors, tolcapone and entacapone to cultured human neuroblastoma cells
    L V Prasad Korlipara
    University Department of Clinical Neuroscience, Royal Free and University College Medical School, Rowland Hill Street, London NW3 2PF, UK
    Neuropharmacology 46:562-9. 2004
    ..However its toxicity may also involve a mechanism independent of its effects upon oxidative phosphorylation...
  92. ncbi Inhibitory effects of [6]-gingerol on PMA-induced COX-2 expression and activation of NF-kappaB and p38 MAPK in mouse skin
    Sue Ok Kim
    College of Pharmacy, Seoul National University, Seoul 151 742, South Korea
    Biofactors 21:27-31. 2004
    ..In addition, [6]-gingerol inhibited the phoshorylation of p38 mitogen-activated protein kinase which may account for its inactivation of NF-kappaB and suppression of COX-2 expression...
  93. ncbi Lipoxygenase-catalyzed polymerization of phenolic lipids suggests a new mechanism for allergic contact dermatitis induced by urushiol and its analogs
    Zuyong Xia
    Division of Biological Sciences, Graduated School of Science, Hokkaido University, Sapporo 060 0180, Japan
    Biochem Biophys Res Commun 315:704-9. 2004
    ..This lipoxygenase-mediated reaction implies a new mechanism for contact allergy of urushiol and its analogs...
  94. ncbi A structure-activity relationship study of catechol-O-methyltransferase inhibitors combining molecular docking and 3D QSAR methods
    Anu J Tervo
    Department of Pharmaceutical Chemistry, University of Kuopio, P O Box 1627, 70211 Kuopio, Finland
    J Comput Aided Mol Des 17:797-810. 2003
    ..Our models propose that increasing steric volume of e.g. the diethylamine tail of entacapone is favourable for COMT inhibitory activity...
  95. pmc The Bordetella bfe system: growth and transcriptional response to siderophores, catechols, and neuroendocrine catecholamines
    Mark T Anderson
    Department of Microbiology, University of Minnesota, MMC 196, 420 Delaware Street S E, Minneapolis, MN 55455 0312, USA
    J Bacteriol 188:5731-40. 2006
    ..To determine whether other siderophores or nonsiderophore catechols could be utilized by the Bfe system, various compounds were tested for the abilities to promote the growth of ..
  96. ncbi Novel beta-lactam antibiotics synthesized by amination of catechols using fungal laccase
    Annett Mikolasch
    Institute of Microbiology, Ernst Moritz Arndt University Greifswald, Greifswald, Germany
    Chem Pharm Bull (Tokyo) 56:902-7. 2008
    Novel cephalosporins, penicillins, and carbacephems were synthesized by amination of catechols with amino-beta-lactams like cefadroxil, amoxicillin, ampicillin and the structurally related carbacephem loracarbef using laccase from ..
  97. ncbi Optimization of catechol production by membrane-immobilized polyphenol oxidase: a modeling approach
    A Boshoff
    Department of Biochemistry, Rhodes University, Grahamstown, South Africa
    Biotechnol Bioeng 83:1-7. 2003
    ..been little consideration of the use of polyphenol oxidase in a biotransformation system for the production of catechols. In this study, polyphenol oxidase was successfully immobilized on various synthetic membranes and used to ..
  98. ncbi Cellular oligomerization of alpha-synuclein is determined by the interaction of oxidized catechols with a C-terminal sequence
    Joseph R Mazzulli
    Joseph Stokes Jr Research Institute, Children s Hospital of Philadelphia and University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA
    J Biol Chem 282:31621-30. 2007
    ..A critically important modulator of alpha-syn aggregation in vitro is dopamine and other catechols, which can prevent the formation of alpha-syn aggregates in cell-free and cellular model systems...
  99. ncbi Isolation of novel glucosides related to gingerdiol from ginger and their antioxidative activities
    Y Sekiwa
    Graduate School of Humanities and Sciences, Laboratory of Food Chemistry, Department of Nutrition and Food Science, Ochanomizu University, 2 1 1 Ohtsuka, Bunkyo ku, Tokyo 112 8610, Japan
    J Agric Food Chem 48:373-7. 2000
    ..Although 1 did not indicate any activity, 2 had as strong activity as the aglycon in both measurements...
  100. ncbi Laccase-based biosensor for determination of polyphenols: determination of catechols in tea
    A L Ghindilis
    A N Bakh Institute of Biochemistry, Academy of Sciences of the USSR
    Biosens Bioelectron 7:127-31. 1992
    ..The practical validity of the method was demonstrated by tannin analysis in tea of different brands...
  101. pmc Cir and Fiu proteins in the outer membrane of Escherichia coli catalyze transport of monomeric catechols: study with beta-lactam antibiotics containing catechol and analogous groups
    H Nikaido
    Department of Molecular and Cell Biology, University of California, Berkeley 94720
    J Bacteriol 172:1361-7. 1990
    ..We postulate that the main function of Cir and Fiu may be to recapture the hydrolytic products of enterobactin, such as 2,3-dihydroxybenzoic acid and 2,3-dihydroxybenzoylserine...

Research Grants63

  1. NADPH P450 REDUCTASE--THYROID HORMONE REGULATION
    David Waxman; Fiscal Year: 2002
    ..alterations in cellular P450 reductase activity on the metabolism and redox cycling of quinones, catechols and related carcinogens, and to elucidate the impact on the cell's adaptive response to oxidative stress...
  2. Aldo-Keto Reductases and PAH Metabolism/Activation
    Trevor M Penning; Fiscal Year: 2013
    ..AKR1C1-AKR1C4) catalyze the activation of polycyclic aromatic hydrocarbon (PAH) trans-dihydrodiols to yield catechols which autooxidize to electrophilic and redox-active PAH o-quinones...
  3. Breast Cancer Chemoprevention Strategies
    Ramesh C Gupta; Fiscal Year: 2010
    ..and its catechol metabolites have been implicated in breast cancer development, and it is believed that estrogen catechols cause free radical mediated, direct and/or indirect DNA damage, which may lead to gene mutations and ultimately ..
  4. Analysis of NGAL Metabolism Identifies a Therapy for Iron Overload
    Jonathan M Barasch; Fiscal Year: 2012
    ..a high affinity iron carrier (Barasch, Molecular Cell, 2002) when binding a family of novel cofactors called the catechols or else the related bacterial siderophores constructed from catechol...
  5. Identification of Novel Small Molecules as Tau Protein Aggregation Inhibitors for
    ALAN D SNOW; Fiscal Year: 2011
    ..and synthesize a class of [new chemical entities consisting of small molecules (200-400 MW) containing bis-catechols,] some of them found to be potent inhibitors of protein/peptide aggregates that are of central importance for AD,..
  6. Computational Design of Unnatural Amino Acid Dependent Metalloproteins
    Jeremy Mills; Fiscal Year: 2013
    ..b>Catechols like dopamine have inherently high affinities for iron suggesting the engineered proteins could serve as sensors ..
  7. CATECHOLAMINES AND SEROTONIN IN BLOOD PRESSURE CONTROL
    Curt Freed; Fiscal Year: 1991
    ..We found that only in the C1 nucleus were the electrochemical peaks for catechols and indoles reciprocally related to blood pressure for both hypertension and hypotension...
  8. BIOTRANSFORMATION OF ESTROGEN TO CARCINOGENIC QUINOIDS
    JUDY BOLTON; Fiscal Year: 2000
    ..GSH levels in microsomal incubations, measuring reactive oxygen species, and examining autoxidation rates of the catechols. These data will determine the role of quinoids in the carcinogenic effects of estrogens and provide a basis for ..
  9. Catechol-functionalized Coatings for Medical Devices
    KRISTIN S TATON; Fiscal Year: 2013
    ..b>Catechols have been shown to be key components in the adhesive proteins that mussels secrete to attach to underwater ..
  10. CHLORINATED HYDROCARBONS EFFECTS ON MAMMALIAN SYSTEMS
    David Kupfer; Fiscal Year: 2003
    ..The mechanism of hydroxylation of phenolic M-metabolites in particular and of phenols in general (forming catechols) by CYP3A4, the major human P450, will be investigated...
  11. STEROID SECRETORY MIXTURES OF ADRENAL CORTEX
    EDWARD BIGLIERI; Fiscal Year: 1991
    ..We will study the interaction of ANH with other volume regulating factors such as aldosterone, angiotensin II (AII) catechols, contrived and disease states with expanded extracellular fluid (ECF).
  12. PHENOLS/CATECHOLS IN OCCUPATIONAL/CONTACT VITILIGO SKIN
    Raymond Boissy; Fiscal Year: 2002
    ....
  13. GLUTATHIONE CONJUGATION--MEDIATOR OF ORGAN TOXICITY
    Serrine Lau; Fiscal Year: 1992
    ..In contrast to the oxidation of hydroquinones, catechols (o-diphenols) are substrates for the enzyme tyrosinase...
  14. NONHEME IRON DIOXYGEN ACTIVATION IN ENZYMES AND MODELS
    Lawrence Que; Fiscal Year: 2009
    ..of amino acids, neurochemicals, and antibiotics and carry out reactions that range from oxidative cleavage of catechols, aliphatic and aromatic hydroxylation, to ring cyclizations involving heteroatoms and cis-dihydroxylation of ..
  15. HEPATIC FORMATION AND TOXICITY OF CATECHOLS
    RUTH BILLINGS; Fiscal Year: 1990
    ..for more complex aromatic compounds, and are sufficiently diverse so that general conclusions about the role of catechols can be drawn...
  16. BINUCLEAR MIXED-METAL DERIVATIVES OF TYROSINASE
    KENNETH STROTHKAMP; Fiscal Year: 1991
    ..steps in the biosynthesis of melanin: hydroxylation of phenols (a monooxygenase reaction) and the oxidation of catechols to quinones (an oxidase reaction)...
  17. Neuroplasticity, Caloric Restriction & Dopamine Function
    THOMAS MCNEILL; Fiscal Year: 2003
    ..mesostriatal dopamine neurons, leads to an increase in dopamine oxidation and the formation of protein cysteinyl-catechols that can damaqe dopamine neurons and disrupt dopamine modulation of neural plasticity after brain iniury...
  18. NON-HEME IRON OXYGEN ACTIVATION IN ENZYME AND MODELS
    Lawrence Que; Fiscal Year: 1999
    ..Modeling efforts will focus on: 1) extradiol cleavage of catechols, 2) the role the a- keto acid cofactor plays in oxygenase reactions, 3) the role of the Fe(III)-OH moiety in the ..
  19. ETHINYL ESTRADIOL AND HEPATOCARCINOGENESIS
    JAMES YAGER; Fiscal Year: 2003
    ..cultured rat hepatocytes and cultured precision-cut liver slices requires estrogen metabolism, most likely to catechols, and the estrogen receptor...
  20. Catechol-functionalized Coatings for Cardiovascular Medical Devices
    KRISTIN TATON; Fiscal Year: 2009
    ..b>Catechols have been shown to be key components in the adhesive proteins that mussels secrete to attach to underwater ..
  21. CHEMICAL BASIS FOR DRUG TOXICITY
    MARJORIE HORNING; Fiscal Year: 1980
    ..interest in this series with respect to potential toxicity are monoepoxides, diepoxides, dihydrodiol epoxides, catechols and quinones...
  22. NQ01, Oxidative Stress and Proteasomal Inhibition
    David Ross; Fiscal Year: 2006
    ..The catechols DOPA dopamine and DOPAC generated in these cells can undergo oxidation to produce aggressive oxygen species and ..
  23. CATECHOLS AND PROSTAGLANDINS-UTERINE VASCULAR FUNCTION
    JOHN ROZAZZA; Fiscal Year: 1991
    ..Since a Medicinal Chemist collaborates on this study, there is an opportunity to design and synthesize the drugs needed to restory uterine blood flow to normalcy...
  24. De novo design of type 3 copper proteins
    Michael Rosenblatt; Fiscal Year: 2003
    ..We also aim to produce models that bind and convert phenols to catechols, capable of also performing oxidations...
  25. Syntheses of Highly Substituted Pryocatechols
    WAYNE FRANCIS SCHNATTER; Fiscal Year: 2010
    DESCRIPTION (provided by applicant): Pyrocatechols (a.k.a. catechols) comprise an important class of pharmacologically active compounds...
  26. CATECHOLS AND ADENOSINE IN MYOCARDIAL PRECONDITIONING
    Michael Cohen; Fiscal Year: 2006
    ..Finally, I will see if NECA's salvage of myocardium at reperfusion translates into rapid functional benefits. It is hoped that the potential of this new pharmacologic approach can be defined. ..
  27. Novel Divalent-Metal Chelating HIV-1 Integrase Inhibitor
    Raghavan Rajagopalan; Fiscal Year: 2005
    ..All the integrase inhibitors studied thus far contain a metal binding motif such as catechols, 1,2-diols, beta-dicarbonyls (DKA), o-hydroxyacids, hydrazides, etc...
  28. SURFACE ENHANCED RAMAN SPECTROSCOPY OF NEUROTRANSMITTERS
    Michael Morris; Fiscal Year: 1991
    ..of 19a catecholamine adsorption at a silver electrode will be elucidated, using substituted phenols and catechols and dopamine and norepinephrine agonists of known structure. Rat brain homogenates will be used as test samples...
  29. DIFFERENTIAL CONTROL OF SINUS NODE AND AV JUNCTION
    Ferdinand Urthaler; Fiscal Year: 1991
    ..AV junction; (2) this inhibition increases with maturation; (3) it is modulated by catecholamines; the effect of catechols on automaticity increases during maturation but the AV junctional automaticity is more dependent and more ..
  30. MOLECULAR ORIGIN OF CANCER--CATECHOL/SEMIQUINOE/QUINONE
    Ercole Cavalieri; Fiscal Year: 2003
    ..These results form the basis to investigate initiation of cancer by the pathway of oxidative activation of catechols yields semiquinones yields quinones for CE in breast cancer, benzene in leukemia and dopamine in Parkinson's ..
  31. Molecular Orgin Cancer--Catechol Estrogen 3 4 Quinones
    Ercole Cavalieri; Fiscal Year: 2004
    ..The knowledge acquired from these studies will be essential for developing preventive strategies. ..
  32. The 17th Annual Conference of the International Society of Exposure of Analysis
    Clifford Weisel; Fiscal Year: 2007
    ..The primary outcome of the meeting will be the advancement of knowledge of human exposure science. [unreadable] [unreadable] [unreadable] [unreadable]..
  33. Conference on Emerging Research Technologies
    Gail Mahady; Fiscal Year: 2004
    ....
  34. MATRIX-ASSISTED LASER DESORPTION TOF MASS SPECTROMETER
    Richard van Breemen; Fiscal Year: 2001
    ..abstract_text> ..
  35. Polynuclear Clusters in Nitrogenase-Structure Reactivity
    Dimitri Coucouvanis; Fiscal Year: 2007
    ..abstract_text> ..
  36. Proteomic Discovery in Parkinson-Dementia Complex of Guam
    Thomas Montine; Fiscal Year: 2008
    ..unreadable] [unreadable] [unreadable]..
  37. Botanicals for Chlamydia pneumonia infections-Revision 1
    Gail Mahady; Fiscal Year: 2005
    ..Data and active standardized extracts developed during this work will be used as the basis for future clinical trials. ..
  38. CARCINOGENIC METABOLITES FORMED FROM ANTIESTROGENS
    JUDY BOLTON; Fiscal Year: 2008
    ..abstract_text> ..
  39. PANDAS and Strep Infection: Are they Linked?
    Roger Kurlan; Fiscal Year: 2004
    ..Disproving the PANDAS hypothesis would prevent the use of expensive and potentially dangerous therapies (e.g., plasma exchange, immune globulin, antibiotics) that have been proposed for PANDAS patients. ..
  40. SYNTHESIS OF ANTICANCER AGENTS
    K C Nicolaou; Fiscal Year: 2010
    ..abstract_text> ..
  41. The Bioavilaibility of Folate in Humans
    Richard van Breemen; Fiscal Year: 2004
    ..Our new LC-MS-MS assay and the use of 13C-labeled folate species will provide new and more detailed information on the uptake, metabolism, and bioavailability of folates than has been possible previously. ..
  42. Treating Agitation/Psychosis in Dementia/Parkinsonism
    Roger Kurlan; Fiscal Year: 2004
    ..This study will provide important information regarding the optimal treatment of psychosis and agitation for patients with the commonly encountered combination of primary dementia and parkinsonism. ..
  43. NEW ANIMAL MODEL FOR EHEC PATHOGENESIS AND PREVENTION
    Joan Butterton; Fiscal Year: 2004
    ..The new mouse challenge model will be compared to prior mouse models in evaluating protection from disease in response to immunization with V. cholerae strains expressing the EHEC antigens. ..
  44. LIPID PEROXIDATION AND APOE IN ALZHEIMERS DISEASE
    Thomas Montine; Fiscal Year: 2003
    ..This new information will aid in laying the foundation for designing rational therapeutic approaches to ameliorate brain oxidative damage in Alzheimer's disease. ..
  45. ON THE ROLE OF THE HPS GENE PRODUCT IN MELANOCYTES
    Raymond Boissy; Fiscal Year: 2002
    ..These studies will contribute to our knowledge of cellular trafficking in general and the pathophysiology of HPS in specific. ..
  46. Iron Uptake and Virulence of Burkholderia pseudomallei
    JORGE CROSA; Fiscal Year: 2005
    ..Knowledge gained from our investigation will contribute to the development of measures to control the diseases caused by these pathogens. ..
  47. MECHANISMS OF NEUROPATHIC PAIN
    James Campbell; Fiscal Year: 2008
    ..These studies will provide a biological rationale for the development of peripheral treatments for neuropathic pain. [unreadable] [unreadable] [unreadable]..
  48. Biotransformation of Estrogens to Carcinogenic Quinoids
    JUDY BOLTON; Fiscal Year: 2005
    ..These data will determine the role of quinoids in the carcinogenic effects of estrogens and provide a basis for the development of estrogen replacement drugs devoid of carcinogenic activity. ..
  49. 2005 Gordon Conference on Catecholamines
    David Sulzer; Fiscal Year: 2005
    ..abstract_text> ..
  50. Botanicals from Central America for Menopause
    Gail Mahady; Fiscal Year: 2005
    ..Successful validation and standardization of traditional plant-based medicines used to treat menopause has great significance not only for the women of Central America but the rest of the world as well. ..
  51. Polynuclear Clusters in Biology - Structure, Reactivity
    Dimitri Coucouvanis; Fiscal Year: 2005
    ..The function of the catecholate ligands in these compounds, as storage sites of oxidizing equivalents, will be determined. ..
  52. International Conference on Biological Inorganic Chemistry
    Dimitri Coucouvanis; Fiscal Year: 2005
    ..A major use of the support sought in this application will assist mainly the junior participants of the meeting and particularly women and minorities among them. ..
  53. Southeastern Michigan Parkinson's Disease Program
    Peter LeWitt; Fiscal Year: 2006
    ..This application also discusses concepts for three pharmacological agents that could be investigated in pilot studies and, if promising, in multicenter clinical trials for assessing neuroprotection. ..
  54. Role of Endogenous Opioid System in the Placebo Effect
    James Campbell; Fiscal Year: 2006
    ..3) Identify relationships between the magnitude of the placebo response and regional mu opioid receptor availability in a non-painful condition. ..
  55. MAMMARY ESTROGEN METABOLISM AND BREAST CANCER RISK
    Fritz Parl; Fiscal Year: 2004
    ..The applicants will measure catechol estrogens in tissues selected by genotype and matched by menopausal status and body mass index and compare the results to those in their in vitro and cell line experiments. ..
  56. PATHWAYS TO ROS INDUCED CELL DEATH
    TERRENCE MONKS; Fiscal Year: 2006
    ..Basic knowledge of the mechanisms by which ROS induce cell death may yield strategies for clinical interventions in pathologies in which ROS play a prominent role ..
  57. Characterization of Dementia with Lewy Bodies: A Collaborative Study
    Thomas Montine; Fiscal Year: 2007
    ..This resource will be made available for future investigations of DLB. ..
  58. Lipid Oxidation Products in Alzheimer's Disease
    Thomas Montine; Fiscal Year: 2007
    ..abstract_text> ..
  59. A screen for small molecule inhibitors of soluble Abeta oligomer assembly
    Harry LeVine; Fiscal Year: 2007
    ..Anti-oligomer compounds could potentially block the cognitive impairment symptoms that oligomers elicit in animal models and interfere with the progression of Alzheimer's disease. [unreadable] [unreadable] [unreadable]..
  60. Discovery of Novel Pharmacotherapies: Cocaine Dependence
    PETER MELTZER; Fiscal Year: 2008
    ..vi) analogues of pyrovalerone. ..