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  1. Article: Quantitative Determination of Thiamine-Derived Taste Enhancers in Aqueous Model Systems, Natural Deep Eutectic Solvents, and Thermally Processed Foods

    Brehm, Laura / Frank, Oliver / Ranner, Josef / Hofmann, Thomas

    Journal of agricultural and food chemistry. 2020 May 01, v. 68, no. 22

    2020  

    Abstract: To obtain high-kokumi-active building blocks, which can be used to produce savory process flavors, it is essential to obtain a better understanding on the formation rate of kokumi-active compounds, such as 3-(((4-amino-2-methylpyrimidin-5-yl)methyl)thio)- ...

    Abstract To obtain high-kokumi-active building blocks, which can be used to produce savory process flavors, it is essential to obtain a better understanding on the formation rate of kokumi-active compounds, such as 3-(((4-amino-2-methylpyrimidin-5-yl)methyl)thio)-5-hydroxypentan-2-one or 2-methyl-5-(((2-methylfuran-3-yl)thio)methyl)pyrimidin-4-amine. The present work showed quantitative studies in several model reaction systems on the recently discovered kokumi-active thiamine derivates. It was possible to show that the thiamine conversion in aqueous model reactions could be directed toward the taste-modulating compounds by adjusting the pH value (6.5), the heating time (120 min), and the heating temperature (120 °C). With the development of a new natural deep eutectic solvents (NADES) system consisting of thiamine, cysteine, ribose, and sodium hydroxide, it was possible to obtain high yields of the targeted taste-modulating analytes, such as 3-(((4-amino-2-methylpyrimidin-5-yl)methyl)thio)-5-hydroxypentan-2-one and 2-methyl-5-(((2-methylfuran-3-yl)thio)methyl)pyrimidin-4-amine. Furthermore, the current study showed that kokumi-active thiamine derivates, such as S-((4-amino-2-methylpyrimidin-5-yl)methyl)-l-cysteine, 3-(((4-amino-2-methylpyrimidin-5-yl)methyl)thio)-5-hydroxypentan-2-one, 2-methyl-5-(((2-methylfuran-3-yl)thio)methyl)pyrimidin-4-amine, and 5-(((furan-2-ylmethyl)thio)methyl)-2-methylpyrimidin-4-amine, can be classified as natural “food-borne” taste enhancers and occur in thiamine-rich, thermally treated foodstuff.
    Keywords chemical species ; cysteine ; food chemistry ; pH ; quantitative analysis ; ribose ; savory ; sodium hydroxide ; taste ; temperature ; thiamin
    Language English
    Dates of publication 2020-0501
    Size p. 6181-6189.
    Publishing place American Chemical Society
    Document type Article
    Note NAL-AP-2-clean
    ZDB-ID 241619-0
    ISSN 1520-5118 ; 0021-8561
    ISSN (online) 1520-5118
    ISSN 0021-8561
    DOI 10.1021/acs.jafc.0c01849
    Database NAL-Catalogue (AGRICOLA)

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  2. Article ; Online: Quantitative Determination of Thiamine-Derived Taste Enhancers in Aqueous Model Systems, Natural Deep Eutectic Solvents, and Thermally Processed Foods.

    Brehm, Laura / Frank, Oliver / Ranner, Josef / Hofmann, Thomas

    Journal of agricultural and food chemistry

    2020  Volume 68, Issue 22, Page(s) 6181–6189

    Abstract: To obtain high-kokumi-active building blocks, which can be used to produce savory process flavors, it is essential to obtain a better understanding on the formation rate of kokumi-active compounds, such as 3-(((4-amino-2-methylpyrimidin-5-yl)methyl)thio)- ...

    Abstract To obtain high-kokumi-active building blocks, which can be used to produce savory process flavors, it is essential to obtain a better understanding on the formation rate of kokumi-active compounds, such as 3-(((4-amino-2-methylpyrimidin-5-yl)methyl)thio)-5-hydroxypentan-2-one or 2-methyl-5-(((2-methylfuran-3-yl)thio)methyl)pyrimidin-4-amine. The present work showed quantitative studies in several model reaction systems on the recently discovered kokumi-active thiamine derivates. It was possible to show that the thiamine conversion in aqueous model reactions could be directed toward the taste-modulating compounds by adjusting the pH value (6.5), the heating time (120 min), and the heating temperature (120 °C). With the development of a new natural deep eutectic solvents (NADES) system consisting of thiamine, cysteine, ribose, and sodium hydroxide, it was possible to obtain high yields of the targeted taste-modulating analytes, such as 3-(((4-amino-2-methylpyrimidin-5-yl)methyl)thio)-5-hydroxypentan-2-one and 2-methyl-5-(((2-methylfuran-3-yl)thio)methyl)pyrimidin-4-amine. Furthermore, the current study showed that kokumi-active thiamine derivates, such as
    MeSH term(s) Animals ; Cattle ; Cooking ; Fast Foods/analysis ; Flavoring Agents/chemistry ; Hot Temperature ; Meat/analysis ; Models, Biological ; Swine ; Taste ; Thiamine/chemistry
    Chemical Substances Flavoring Agents ; Thiamine (X66NSO3N35)
    Language English
    Publishing date 2020-05-20
    Publishing country United States
    Document type Journal Article
    ZDB-ID 241619-0
    ISSN 1520-5118 ; 0021-8561
    ISSN (online) 1520-5118
    ISSN 0021-8561
    DOI 10.1021/acs.jafc.0c01849
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article ; Online: Primary and Secondary Metabolites in

    Ranner, Josef L / Schalk, Sabrina / Martyniak, Cindy / Parniske, Martin / Gutjahr, Caroline / Stark, Timo D / Dawid, Corinna

    Journal of agricultural and food chemistry

    2023  Volume 71, Issue 30, Page(s) 11277–11303

    Abstract: ... Lotus ... ...

    Abstract Lotus japonicus
    MeSH term(s) Lotus/metabolism ; Tandem Mass Spectrometry ; Chromatography, Liquid ; Gas Chromatography-Mass Spectrometry/methods ; Mycorrhizae/physiology ; Symbiosis/physiology
    Language English
    Publishing date 2023-07-19
    Publishing country United States
    Document type Journal Article ; Review
    ZDB-ID 241619-0
    ISSN 1520-5118 ; 0021-8561
    ISSN (online) 1520-5118
    ISSN 0021-8561
    DOI 10.1021/acs.jafc.3c02709
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  4. Article: Novel Taste-Enhancing 4-Amino-2-methyl-5-heteroalkypyrimidines Formed from Thiamine by Maillard-Type Reactions

    Brehm, Laura / Frank, Oliver / Jünger, Manon / Wimmer, Miriam / Ranner, Josef / Hofmann, Thomas

    Journal of agricultural and food chemistry. 2019 Nov. 11, v. 67, no. 50

    2019  

    Abstract: Increasing the thiamine concentration in a respective process flavor yields a product with a significant higher kokumi activity. S-plot analysis of the mass spectrometric data revealed beside thiamine itself, 4-methyl-5-thiazoleethanol, (S)-((4-amino-2- ... ...

    Abstract Increasing the thiamine concentration in a respective process flavor yields a product with a significant higher kokumi activity. S-plot analysis of the mass spectrometric data revealed beside thiamine itself, 4-methyl-5-thiazoleethanol, (S)-((4-amino-2-methylpyrimidin-5-yl)methyl)-l-cysteine, N-((4-amino-2-methylpyrimidin-5-yl)methyl)formamide, 3-(((4-amino-2-methylpyrimidin-5-yl)methyl)thio)-5-hydroxypentan-2-one, and 2-methyl-5-(((2-methylfuran-3-yl)thio)methyl)pyrimidin-4-amine as marker molecules for a process flavor with higher thiamine concentration. Sensory-based targeted isolation revealed that (S)-((4-amino-2-methylpyrimidin-5-yl)methyl)-l-cysteine, 3-(((4-amino-2-methylpyrimidin-5-yl)methyl)thio)-5-hydroxypentan-2-one, and 2-methyl-5-(((2-methylfuran-3-yl)thio)methyl)pyrimidin-4-amine showed an influence on the kokumi taste activity with taste threshold concentrations between 35 and 120 μmol/L. An adapted mass spectrometric-based carbon module labeling experiment as well as quantitative studies clearly demonstrated thiamine as the only precursor and an intermolecular formation pathway for the compounds (S)-(((4-amino-2-methylpyrimidin-5-yl)methyl)thio)-5-hydroxypentan-2-one and 2-methyl-5-(((2-methylfuran-3-yl)thio)methyl)pyrimidin-4-amine. On the basis of the knowledge that several thiamine derivatives showed taste-modulating activity, selected thiamine-based binary model reactions and synthesis were carried out. This resulted in the isolation of further thiamine-derived taste modulators like (S)-((4-amino-2-methylpyrimidin-5-yl)methyl)-l-cysteinylglycine, (S)-3-((((4-amino-2-methylpyrimidin-5-yl)methyl)thio)methyl)piperazine-2,5-dione, 3-(((4-amino-2-methylpyrimidin-5-yl)methyl)thio)pentan-2-one, 5-(((furan-2-ylmethyl)thio)methyl)-2-methylpyrimidin-4-amine, and (4-amino-2-methylpyrimidin-5-yl)methanethiol, 2-methyl-5-((methylthio)methyl)pyrimidin-4-amine with taste thresholds ranging from 35 to 880 μmol/L.
    Keywords Maillard reaction ; carbon ; flavor ; mass spectrometry ; methanethiol ; taste sensitivity ; thiamin
    Language English
    Dates of publication 2019-1111
    Size p. 13986-13997.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 241619-0
    ISSN 1520-5118 ; 0021-8561
    ISSN (online) 1520-5118
    ISSN 0021-8561
    DOI 10.1021/acs.jafc.9b05896
    Database NAL-Catalogue (AGRICOLA)

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  5. Article ; Online: Novel Taste-Enhancing 4-Amino-2-methyl-5-heteroalkypyrimidines Formed from Thiamine by Maillard-Type Reactions.

    Brehm, Laura / Frank, Oliver / Jünger, Manon / Wimmer, Miriam / Ranner, Josef / Hofmann, Thomas

    Journal of agricultural and food chemistry

    2019  Volume 67, Issue 50, Page(s) 13986–13997

    Abstract: Increasing the thiamine concentration in a respective process flavor yields a product with a significant higher kokumi activity. S-plot analysis of the mass spectrometric data revealed beside thiamine itself, 4-methyl-5-thiazoleethanol, ( ...

    Abstract Increasing the thiamine concentration in a respective process flavor yields a product with a significant higher kokumi activity. S-plot analysis of the mass spectrometric data revealed beside thiamine itself, 4-methyl-5-thiazoleethanol, (
    MeSH term(s) Adult ; Female ; Flavoring Agents/chemistry ; Humans ; Maillard Reaction ; Male ; Mass Spectrometry ; Molecular Structure ; Pyrimidines/chemistry ; Taste ; Thiamine/chemistry ; Young Adult
    Chemical Substances Flavoring Agents ; Pyrimidines ; toxopyrimidine (G62V17J09J) ; Thiamine (X66NSO3N35)
    Language English
    Publishing date 2019-12-09
    Publishing country United States
    Document type Journal Article
    ZDB-ID 241619-0
    ISSN 1520-5118 ; 0021-8561
    ISSN (online) 1520-5118
    ISSN 0021-8561
    DOI 10.1021/acs.jafc.9b05896
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  6. Article: A High-Content Screen for the Identification of Plant Extracts with Insulin Secretion-Modulating Activity.

    Hager, Roland / Pitsch, Johannes / Kerbl-Knapp, Jakob / Neuhauser, Cathrina / Ollinger, Nicole / Iken, Marcus / Ranner, Josef / Mittermeier-Kleßinger, Verena / Dawid, Corinna / Lanzerstorfer, Peter / Weghuber, Julian

    Pharmaceuticals (Basel, Switzerland)

    2021  Volume 14, Issue 8

    Abstract: Bioactive plant compounds and extracts are of special interest for the development of pharmaceuticals. Here, we describe the screening of more than 1100 aqueous plant extracts and synthetic reference compounds for their ability to stimulate or inhibit ... ...

    Abstract Bioactive plant compounds and extracts are of special interest for the development of pharmaceuticals. Here, we describe the screening of more than 1100 aqueous plant extracts and synthetic reference compounds for their ability to stimulate or inhibit insulin secretion. To quantify insulin secretion in living MIN6 β cells, an insulin-
    Language English
    Publishing date 2021-08-17
    Publishing country Switzerland
    Document type Journal Article
    ZDB-ID 2193542-7
    ISSN 1424-8247
    ISSN 1424-8247
    DOI 10.3390/ph14080809
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  7. Article ; Online: Construction and Application of a Database for a Five-Dimensional Identification of Natural Compounds in Garcinia Species by Means of UPLC-ESI-TWIMS-TOF-MS: Introducing Gas Phase Polyphenol Conformer Drift Time Distribution Intensity Ratios.

    Stark, Timo D / Ranner, Josef / Stiglbauer, Benedikt / Weiss, Patrick / Stark, Sofie / Balemba, Onesmo B / Hofmann, Thomas

    Journal of agricultural and food chemistry

    2019  Volume 67, Issue 3, Page(s) 975–985

    Abstract: Thirty-four reference compounds from G. buchananii were analyzed by means of UPLC-ESI-IMS-TOF-MS to build a database consisting of retention time, accurate m/ z of precursors and fragment ions, and rotationally averaged collision cross-sectional area ( ... ...

    Abstract Thirty-four reference compounds from G. buchananii were analyzed by means of UPLC-ESI-IMS-TOF-MS to build a database consisting of retention time, accurate m/ z of precursors and fragment ions, and rotationally averaged collision cross-sectional area (CCS). The CCS value of six selected compounds analyzed in bark extract in different concentrations and solvent systems showed excellent intra- and interday precision (RSD ≤ 0.9%). The established database was applied on different organs of G. buchananii as well as G. kola, G. mangostana, and G. cambogia enabling a fast and reliable identification of these natural bioactives. For several compounds, more than one drift time species could be highlighted, which we propose to be hydrogen bond stabilized rotational isomers transferred from solution to gas phase. We used all CCS values of one compound, and we propose to add also the intensity ratio of the conformers as a new and additional characteristic compound parameter in compound identification/screening/database applications to reduce dereplication and false positives and to strengthen the identification.
    MeSH term(s) Databases, Chemical ; Garcinia/chemistry ; Garcinia/classification ; Plant Extracts/chemistry ; Polyphenols/chemistry ; Spectrometry, Mass, Electrospray Ionization
    Chemical Substances Plant Extracts ; Polyphenols
    Language English
    Publishing date 2019-01-09
    Publishing country United States
    Document type Journal Article
    ZDB-ID 241619-0
    ISSN 1520-5118 ; 0021-8561
    ISSN (online) 1520-5118
    ISSN 0021-8561
    DOI 10.1021/acs.jafc.8b06157
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  8. Article: Das Projekt 'Umsetzung eines Landschaftsplanes' in Stephankirchen

    Ranner, Josef

    1996  Volume 36, Page(s) 24–26

    Keywords Landschaftsplan ; Landschaftsplanung ; Laendlicher Raum ; Landwirtschaft ; Zusammenarbeit ; Extensivierung ; Flaechenstilllegung ; Naturschutz ; Marketing ; Oekologischer Landbau ; Dorferneuerung ; Kommunalebene ; Landschaftspflege ; Regionalplanung ; Beschaeftigungseffekt ; Wirtschaftsfoerderung
    Language German
    Document type Article
    Database OPAC and Environmental database (ULIDAT) of The Federal Environment Agency (UBA)

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