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Ian A. Blair – 1st expert on this subject based on the ideXlab platform
Formation of a substituted 1,N(6)-etheno-2′-deoxyadenosine adduct by lipid hydroperoxide-mediated generation of 4-oxo-2-Nonenal.Chemical Research in Toxicology, 2000Co-Authors: Diane Rindgen, Masaharu Nakajima, Ian A. BlairAbstract:
: Analysis of the reaction between 2′-deoxyadenosine and 13-hydroperoxylinoleic acid by liquid chromatography/constant neutral loss mass spectrometry revealed the presence of two major products (adducts A and B). Adduct A was shown to be a mixture of two isomers (A(1) and A(2)) that each decomposed with the loss of water to form adduct B. The mass spectral characteristics of adduct B were consistent with the substituted 1, N(6)-etheno-2′-deoxyadensoine adduct 1′ ‘-[3-(2′-deoxy-beta-D-erythro-pentafuranosyl)-3H-imidazo[2, 1-i]purin-7-yl]heptan-2’ ‘-one. Adducts A(1), A(2), and B were formed when 2’-deoxyadenosine was treated with synthetic 4-oxo-2-Nonenal, which suggested that it was formed by the breakdown of 13-hydroperoxylinoleic acid. A substantial increase in the rate of formation of adducts A(1), A(2), and B was observed when 13-hydroperoxylinoleic acid and 2′-deoxyadenosine were incubated in the presence of Fe(II). Thus, 4-oxo-2-Nonenal was most likely formed by a homolytic process. Although adducts A(1), A(2), and B were formed in the reaction between 4-hydroxy-2-Nonenal and 2′-deoxyadenosine, a number of additional products were observed. This suggested that 4-hydroxy-2-Nonenal was not a precursor in the formation of 4-oxo-2-Nonenal from 13-hydroperoxylinoleic acid. This study has provided additional evidence which shows that 4-oxo-2-Nonenal is a major product of lipid peroxidation and that it reacts efficiently with DNA to form substituted etheno adducts.
Characterization of 4-oxo-2-Nonenal as a novel product of lipid peroxidation.Chemical Research in Toxicology, 2000Co-Authors: Ian A. BlairAbstract:
FeII-mediated decomposition of 13-[S-(Z,E)]-9,11-hydroperoxyoctadecadienoic (hydroperoxylinoleic) acid resulted in the formation of three α,β-unsaturated aldehydes. At low FeII concentrations or at early time points after the addition of FeII, two major products were observed. The least polar product had chromatographic properties that were identical with those of 4-oxo-2-Nonenal. Conversion of this product to its bis-oxime derivative with hydroxylamine hydrochloride resulted in two syn- and two anti-oxime isomers that had chromatographic and mass spectral properties identical with the properties of products derived from an authentic standard of 4-oxo-2-Nonenal. This confirmed for the first time that 4-oxo-2-Nonenal is a major product of the FeII-mediated breakdown of lipid hydroperoxides. The more polar product had chromatographic properties that were similar to those of 4-hydroperoxy-2-Nonenal. LC/MS analysis of its syn- and anti-oxime isomers confirmed this structural assignment. Thus, 4-hydroperoxy-2-…
characterization of 2 deoxyadenosine adducts derived from 4 oxo 2 nonenal a novel product of lipid peroxidationChemical Research in Toxicology, 2000Co-Authors: Diane Rindgen, Roy H Bible, Elisabeth Hajdu, Ian A. BlairAbstract:
Analysis of the reaction between 2‘-deoxyadenosine and 4-oxo-2-Nonenal by liquid chromatography/mass spectrometry revealed the presence of three major products (adducts A1, A2, and B). Adducts A1 a…
Peter Schieberle – 2nd expert on this subject based on the ideXlab platform
characterization of the key aroma compounds in yeast dumplings by means of the sensomics conceptJournal of Agricultural and Food Chemistry, 2019Co-Authors: Buket Sahin, Peter SchieberleAbstract:
The key odorants in the volatile fraction isolated from a steamed yeasted wheat dough (yeast dumpling) by solvent assisted flavor evaporation (SAFE) were characterized by an aroma extract dilution analysis (AEDA). The 29 aroma-active compounds were located within the flavor dilution (FD) factor range of 8–512. Among them, the highest FD factors were found for 2- and 3-methylbutanoic acid, 4-hydroxy-3-methoxybenzaldehyde, (E,E)-2,4-decadienal, 2-phenylethanol, 4-hydroxy-2,5-dimethyl-3(2H)-furanone, (E)-2-Nonenal, and butanoic acid. The 21 odorants were quantitated by stable isotope dilution assays (SIDA), and a subsequent calculation of odor activity values (OAV; ratio of concentration to odor threshold) revealed 3-methyl-1-butanol (malty), 2-phenylethanol (honey-like), trans-4,5-epoxy-(E)-2-decenal (metallic), 2,3-butanedione (buttery), 3-methylbutanoic acid (sweaty), (E)-2-Nonenal (cucumber-like), 1-octen-3-one (mushroom-like), and 3-(methylthio)-propanal (potato-like) as the most important contributors …
Potent odorants of rye bread crust-differences from the crumb and from wheat bread crustZeitschrift f??r Lebensmittel-Untersuchung und -Forschung, 1994Co-Authors: Peter Schieberle, Werner GroschAbstract:
Aroma extract dilution analyses revealed twenty-eight odorants in fresh rye bread crust and twenty in its crumb. On the basis of high flavour dilution factors, methional (boiled potato), 3-methylbutanal (malty), (E)-2-Nonenal (green, tallowy), (E,E)-2,4-decadienal (fatty) and acetic acid (sour, pungent) belonged to the potent odorants of the crust, and phenylacetaldehyde, (E)-2-Nonenal and (E,E)-2,4-decadienal to those of the crumb. Compared with the crust, especially the odour activities of methional, 3-methylbutanal, 2-ethyl-3,5-dimethyl-pyrazine and 4-hydroxy-2,5-dimethyl-3(2H)-furanone were significantly lower in the crumb
evaluation of potent odorants in cucumbers cucumis sativus and muskmelons cucumis melo by aroma extract dilution analysisJournal of Food Science, 1990Co-Authors: Peter Schieberle, S Ofner, Werner GroschAbstract:
The volatile components of cucumbers and muskmelons were analyzed by a technique which reveals the odorants having the highest odor units (ratio of the concentration to the odor threshold). (E/Z)-2,6-Nonadienal, followed by (Z)-2-Nonenal and (E)-2-Nonenal were the most significant odorants of cucumbers. The flavor of muskmelons was more complex. Methyl 2-methylbutanoate, (Z)-3-hexenal, (E)-2-hexenal, and ethyl 2-methylpropanoate were identified as the primary odorants.
Koji Uchida – 3rd expert on this subject based on the ideXlab platform
Immunochemical Detection of 4-Hydroxy-2-Nonenal-Specific Epitopes, 2020Co-Authors: Koji UchidaAbstract:
4-Hydroxy-2-Nonenal (HNE) is a major product of lipid peroxidation and is believed to be largely responsible for the cytopathological effects observed during oxidative stress. HNE exerts these effects because of its facile reactivity with biological materials, particularly proteins. Taking advantage of the fact that protein-bound HNE are excellent immunogens that are capable of stimulating adaptive immune response, a number of monoclonal antibodies against these epitopes have been developed. Moreover, using these antibodies, the HNE-specific epitopes have been detected as constituents in human patients with increased risk factors or clinical manifestations of lifestyle-related diseases, such as atherosclerosis.
Lipid Peroxidation Generates Body Odor Component trans-2-Nonenal Covalently Bound to Protein in VivoJournal of Biological Chemistry, 2010Co-Authors: Kousuke Ishino, Chika Wakita, Takahiro Shibata, Shinya Toyokuni, Sachiko Machida, Shun Matsuda, Tomonari Matsuda, Koji UchidaAbstract:
trans-2-Nonenal is an unsaturated aldehyde with an unpleasant greasy and grassy odor endogenously generated during the peroxidation of polyunsaturated fatty acids. 2-Nonenal covalently modified human serum albumin through a reaction in which the aldehyde preferentially reacted with the lysine residues. Modified proteins were immunogenic, and a specific monoclonal antibody (mAb) 27Q4 that cross-reacted with the protein covalently modified with 2-Nonenal was raised from mouse. To verify the presence of the protein-bound 2-Nonenal in vivo, the mAb 27Q4 against the 2-Nonenal-modified keyhole limpet hemocyanin was raised. It was found that a novel 2-Nonenal-lysine adduct, cis- and trans-Nϵ-3-[(hept-1-enyl)-4-hexylpyridinium]lysine (HHP-lysine), constitutes an epitope of the antibody. The immunoreactive materials with mAb 27Q4 were detected in the kidney of rats exposed to ferric nitrilotriacetate, an iron chelate that induces free radical-mediated oxidative tissue damage. Using high performance liquid chromatography with on-line electrospray ionization tandem mass spectrometry, we also established a highly sensitive method for detection of the cis- and trans-HHP-lysine and confirmed that the 2-Nonenal-lysine adducts were indeed formed during the lipid peroxidation-mediated modification of protein in vitro and in vivo. Furthermore, we examined the involvement of the scavenger receptor lectin-like oxidized low density lipoprotein receptor-1 in the recognition of 2-Nonenal-modified proteins and established that the receptor recognized the HHP-lysine adducts as a ligand.
Identification of Advanced Reaction Products Originating from the Initial 4-Oxo-2-Nonenal-cysteine Michael AdductsChemical Research in Toxicology, 2009Co-Authors: Yuuki Shimozu, Takahiro Shibata, Makoto Ojika, Koji UchidaAbstract:
4-Oxo-2-Nonenal (ONE), an aldehyde originating from the peroxidation of ω6 polyunsaturated fatty acids, preferentially reacts with the cysteine residues of protein. Despite the fact that there has …