Differential reactivity of purified bioactive coffee furans, cafestol and kahweol, with acidic nitrite: product characterization and factors controlling nitrosation versus ring-opening pathways.

PubWeight™: 0.79‹?›

🔗 View Article (PMID 19894707)

Published in Chem Res Toxicol on December 01, 2009

Authors

Maria De Lucia1, Lucia Panzella, Dominique Melck, Italo Giudicianni, Andrea Motta, Alessandra Napolitano, Marco d'Ischia

Author Affiliations

1: Department of Organic Chemistry and Biochemistry and Centro Interdipartimentale di Metodologie Chimico-Fisiche, University of Naples Federico II, Via Cinthia 4, I-80126 Naples, Italy.

Articles by these authors

Nitro-fatty acid formation and signaling. J Biol Chem (2008) 1.95

Vitiligo puzzle: the pieces fall in place. Pigment Cell Res (2007) 1.39

Melanins and melanogenesis: methods, standards, protocols. Pigment Cell Melanoma Res (2013) 1.23

Citrantifidiene and citrantifidiol: bioactive metabolites produced by Trichoderma citrinoviride with potential antifeedant activity toward aphids. J Agric Food Chem (2008) 1.21

Chemical and structural diversity in eumelanins: unexplored bio-optoelectronic materials. Angew Chem Int Ed Engl (2009) 1.10

NMR spectroscopy metabolomic profiling of exhaled breath condensate in patients with stable and unstable cystic fibrosis. Thorax (2011) 1.07

Mitochondrial dysfunction in some oxidative stress-related genetic diseases: Ataxia-Telangiectasia, Down Syndrome, Fanconi Anaemia and Werner Syndrome. Biogerontology (2010) 1.07

Oxidative stress as a multiple effector in Fanconi anaemia clinical phenotype. Eur J Haematol (2005) 1.07

Cytochalasins Z1, Z2 and Z3, three 24-oxa[14]cytochalasans produced by Pyrenophora semeniperda. Phytochemistry (2002) 1.05

(-)-Amarbellisine, a lycorine-type alkaloid from Amaryllis belladonna L. growing in Egypt. Phytochemistry (2004) 1.01

SDS-resistant active and thermostable dimers are obtained from the dissociation of homotetrameric beta-glycosidase from hyperthermophilic Sulfolobus solfataricus in SDS. Stabilizing role of the A-C intermonomeric interface. J Biol Chem (2002) 1.00

Toxicity of melanin-free ink of Sepia officinalis to transformed cell lines: identification of the active factor as tyrosinase. Biochem Biophys Res Commun (2003) 1.00

Exercise improvement after pectus excavatum repair is not related to chest wall function. Eur J Cardiothorac Surg (2013) 0.97

A folding-dependent mechanism of antimicrobial peptide resistance to degradation unveiled by solution structure of distinctin. Proc Natl Acad Sci U S A (2005) 0.96

The cytoplasmic tail of invariant chain regulates endosome fusion and morphology. Mol Biol Cell (2002) 0.95

Trigoxazonane, a monosubstituted trioxazonane from Trigonella foenum-graecum root exudate, inhibits Orobanche crenata seed germination. Phytochemistry (2007) 0.94

Multiple evidence for an early age pro-oxidant state in Down Syndrome patients. Biogerontology (2006) 0.94

Separating smoking-related diseases using NMR-based metabolomics of exhaled breath condensate. J Proteome Res (2013) 0.94

Effect on cancer cell proliferation of palmitoylethanolamide, a fatty acid amide interacting with both the cannabinoid and vanilloid signalling systems. Fundam Clin Pharmacol (2002) 0.94

Polyphenols, including the new Peapolyphenols A-C, from pea root exudates stimulate Orobanche foetida seed germination. J Agric Food Chem (2010) 0.92

The "benzothiazine" chromophore of pheomelanins: a reassessment. Photochem Photobiol (2008) 0.92

Polydopamine and eumelanin: from structure-property relationships to a unified tailoring strategy. Acc Chem Res (2014) 0.92

Zinc-induced structural effects enhance oxygen consumption and superoxide generation in synthetic pheomelanins on UVA/visible light irradiation. Photochem Photobiol (2010) 0.90

In vivo prooxidant state in Werner syndrome (WS): results from three WS patients and two WS heterozygotes. Free Radic Res (2005) 0.90

Red human hair pheomelanin is a potent pro-oxidant mediating UV-independent contributory mechanisms of melanomagenesis. Pigment Cell Melanoma Res (2014) 0.90

Metabolomics using 1H-NMR of apoptosis and Necrosis in HL60 leukemia cells: differences between the two types of cell death and independence from the stimulus of apoptosis used. Radiat Res (2008) 0.89

Disentangling eumelanin "black chromophore": visible absorption changes as signatures of oxidation state- and aggregation-dependent dynamic interactions in a model water-soluble 5,6-dihydroxyindole polymer. J Am Chem Soc (2009) 0.89

Monitoring real-time metabolism of living cells by fast two-dimensional NMR spectroscopy. Anal Chem (2010) 0.88

Kinetic and chemical assessment of the UV/H2O2 treatment of antiepileptic drug carbamazepine. Chemosphere (2004) 0.88

Structural effects on the electronic absorption properties of 5,6-dihydroxyindole oligomers: the potential of an integrated experimental and DFT approach to model eumelanin optical properties. Photochem Photobiol (2008) 0.88

The eumelanin intermediate 5,6-dihydroxyindole-2-carboxylic acid is a messenger in the cross-talk among epidermal cells. J Invest Dermatol (2012) 0.88

Red hair benzothiazines and benzothiazoles: mutation-inspired chemistry in the quest for functionality. Acc Chem Res (2012) 0.88

From clinical description, to in vitro and animal studies, and backward to patients: oxidative stress and mitochondrial dysfunction in Fanconi anemia. Free Radic Biol Med (2013) 0.87

Electronic Nose and Exhaled Breath NMR-based Metabolomics Applications in Airways Disease. Curr Top Med Chem (2016) 0.87

Short-lived quinonoid species from 5,6-dihydroxyindole dimers en route to eumelanin polymers: integrated chemical, pulse radiolytic, and quantum mechanical investigation. J Am Chem Soc (2006) 0.87

Sphaeropsidins D and E, two other pimarane diterpenes, produced in vitro by the plant pathogenic fungus Sphaeropsis sapinea f. sp. cupressi. Phytochemistry (2002) 0.87

The first 5,6-dihydroxyindole tetramer by oxidation of 5,5',6,6'-tetrahydroxy- 2,4'-biindolyl and an unexpected issue of positional reactivity en route to eumelanin-related polymers. Org Lett (2007) 0.87

Viridenepoxydiol, a new pentasubstituted oxiranyldecene produced by Trichoderma viride. J Agric Food Chem (2006) 0.87

Atypical structural and π-electron features of a melanin polymer that lead to superior free-radical-scavenging properties. Angew Chem Int Ed Engl (2013) 0.87

Acid-induced structural modifications of unsaturated Fatty acids and phenolic olive oil constituents by nitrite ions: a chemical assessment. Chem Res Toxicol (2004) 0.86

Uncovering the structure of human red hair pheomelanin: benzothiazolylthiazinodihydroisoquinolines as key building blocks. J Nat Prod (2011) 0.86

Multiple involvement of oxidative stress in Werner syndrome phenotype. Biogerontology (2005) 0.86

Structural determinants of salmon calcitonin bioactivity: the role of the Leu-based amphipathic alpha-helix. J Biol Chem (2006) 0.86

Alternethanoxins A and B, polycyclic ethanones produced by Alternaria sonchi , potential mycoherbicides for Sonchus arvensis biocontrol. J Agric Food Chem (2009) 0.86

A reactive ortho-quinone generated by tyrosinase-catalyzed oxidation of the skin depigmenting agent monobenzone: self-coupling and thiol-conjugation reactions and possible implications for melanocyte toxicity. Chem Res Toxicol (2009) 0.86

The haptenation theory of vitiligo and melanoma rejection: a close-up. Exp Dermatol (2011) 0.85

Exploring airway diseases by NMR-based metabonomics: a review of application to exhaled breath condensate. J Biomed Biotechnol (2011) 0.85

Oxidation chemistry of norepinephrine: partitioning of the O-quinone between competing cyclization and chain breakdown pathways and their roles in melanin formation. Chem Res Toxicol (2007) 0.85

Soyasapogenol B and trans-22-dehydrocam- pesterol from common vetch (Vicia sativa L.) root exudates stimulate broomrape seed germination. Pest Manag Sci (2011) 0.85

Dopamine in the ink defence system of Sepia officinalis: biosynthesis, vesicular compartmentation in mature ink gland cells, nitric oxide (NO)/cGMP-induced depletion and fate in secreted ink. Biochem J (2004) 0.85

Regulatory roles of nitric oxide during larval development and metamorphosis in Ciona intestinalis. Dev Biol (2007) 0.85

Gender- and age-related distinctions for the in vivo prooxidant state in Fanconi anaemia patients. Carcinogenesis (2004) 0.84

Glyoxal formation by Fenton-induced degradation of carbohydrates and related compounds. Carbohydr Res (2006) 0.84

Superior photoprotective motifs and mechanisms in eumelanins uncovered. J Am Chem Soc (2014) 0.84

Eumelanin buildup on the nanoscale: aggregate growth/assembly and visible absorption development in biomimetic 5,6-dihydroxyindole polymerization. Biomacromolecules (2012) 0.84

Pheomelanin-induced oxidative stress: bright and dark chemistry bridging red hair phenotype and melanoma. Pigment Cell Melanoma Res (2014) 0.84

Tris buffer modulates polydopamine growth, aggregation, and paramagnetic properties. Langmuir (2014) 0.83

MG-63 human osteosarcoma cells grown in monolayer and as three-dimensional tumor spheroids present a different metabolic profile: a (1)H NMR study. FEBS Lett (2004) 0.83

Recent Advances on Nitric Oxide in the Upper Airways. Curr Med Chem (2016) 0.83

In vivo NMR metabolic profiling of Fabrea salina reveals sequential defense mechanisms against ultraviolet radiation. Biophys J (2011) 0.83

Bone marrow cell transcripts from Fanconi anaemia patients reveal in vivo alterations in mitochondrial, redox and DNA repair pathways. Eur J Haematol (2013) 0.82

Is DHICA the key to dopachrome tautomerase and melanocyte functions? Pigment Cell Melanoma Res (2010) 0.82

Aromatic cyclic peroxides and related keto-compounds from the Plakortis sp. component of a sponge consortium. J Nat Prod (2009) 0.82

Nuclear magnetic resonance-based metabolomics discriminates primary ciliary dyskinesia from cystic fibrosis. Am J Respir Crit Care Med (2014) 0.82

Chemo-ecological studies on hexactinellid sponges from the Southern Ocean. Naturwissenschaften (2012) 0.82

Converting the highly amyloidogenic human calcitonin into a powerful fibril inhibitor by three-dimensional structure homology with a non-amyloidogenic analogue. J Biol Chem (2010) 0.82