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  1. Article ; Online: Alternative pathway for dopamine production by acetogenic gut bacteria that O-Demethylate 3-Methoxytyramine, a metabolite of catechol O-Methyltransferase.

    Rich, Barry E / Jackson, Jayme C / de Ora, Lizett Ortiz / Long, Zane G / Uyeda, Kylie S / Bess, Elizabeth N

    Journal of applied microbiology

    2022  Volume 133, Issue 3, Page(s) 1697–1708

    Abstract: Aims: The gut microbiota modulates dopamine levels in vivo, but the bacteria and biochemical processes responsible remain incompletely characterized. A potential precursor of bacterial dopamine production is 3-methoxytyramine (3MT); 3MT is produced when ...

    Abstract Aims: The gut microbiota modulates dopamine levels in vivo, but the bacteria and biochemical processes responsible remain incompletely characterized. A potential precursor of bacterial dopamine production is 3-methoxytyramine (3MT); 3MT is produced when dopamine is O-methylated by host catechol O-methyltransferase (COMT), thereby attenuating dopamine levels. This study aimed to identify whether gut bacteria are capable of reverting 3MT to dopamine.
    Methods and results: Human faecal bacterial communities O-demethylated 3MT and yielded dopamine. Gut bacteria that mediate this transformation were identified as acetogens Eubacterium limosum and Blautia producta. Upon exposing these acetogens to propyl iodide, a known inhibitor of cobalamin-dependent O-demethylases, 3MT O-demethylation was inhibited. Culturing E. limosum and B. producta with 3MT afforded increased acetate levels as compared with vehicle controls.
    Conclusions: Gut bacterial acetogens E. limosum and B. producta synthesized dopamine from 3MT. This O-demethylation of 3MT was likely performed by cobalamin-dependent O-demethylases implicated in reductive acetogenesis.
    Significance and impact of the study: This is the first report that gut bacteria can synthesize dopamine by O-demethylation of 3MT. Owing to 3MT being the product of host COMT attenuating dopamine levels, gut bacteria that reverse this transformation-converting 3MT to dopamine-may act as a counterbalance for dopamine regulation by COMT.
    MeSH term(s) Catechol O-Methyltransferase/genetics ; Catechol O-Methyltransferase/metabolism ; Dopamine/analogs & derivatives ; Dopamine/biosynthesis ; Gastrointestinal Microbiome ; Humans ; Oxidoreductases, O-Demethylating ; Vitamin B 12
    Chemical Substances Oxidoreductases, O-Demethylating (EC 1.-) ; Catechol O-Methyltransferase (EC 2.1.1.6) ; 3-methoxytyramine (JCH2767EDP) ; Vitamin B 12 (P6YC3EG204) ; Dopamine (VTD58H1Z2X)
    Language English
    Publishing date 2022-06-29
    Publishing country England
    Document type Journal Article
    ZDB-ID 1358023-1
    ISSN 1365-2672 ; 1364-5072
    ISSN (online) 1365-2672
    ISSN 1364-5072
    DOI 10.1111/jam.15682
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

    Zs.A 259: Show issues Location:
    Je nach Verfügbarkeit (siehe Angabe bei Bestand)
    bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular
    Jg. 1995 - 2021: Lesesall (1.OG)
    ab Jg. 2022: Lesesaal (EG)

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  2. Article: Alternative pathway for dopamine production by acetogenic gut bacteria that O‐Demethylate 3‐Methoxytyramine, a metabolite of catechol O‐Methyltransferase

    Rich, Barry E. / Jackson, Jayme C. / de Ora, Lizett Ortiz / Long, Zane G. / Uyeda, Kylie S. / Bess, Elizabeth N.

    Journal of applied microbiology. 2022 Sept., v. 133, no. 3

    2022  

    Abstract: AIMS: The gut microbiota modulates dopamine levels in vivo, but the bacteria and biochemical processes responsible remain incompletely characterized. A potential precursor of bacterial dopamine production is 3‐methoxytyramine (3MT); 3MT is produced when ... ...

    Abstract AIMS: The gut microbiota modulates dopamine levels in vivo, but the bacteria and biochemical processes responsible remain incompletely characterized. A potential precursor of bacterial dopamine production is 3‐methoxytyramine (3MT); 3MT is produced when dopamine is O‐methylated by host catechol O‐methyltransferase (COMT), thereby attenuating dopamine levels. This study aimed to identify whether gut bacteria are capable of reverting 3MT to dopamine. METHODS AND RESULTS: Human faecal bacterial communities O‐demethylated 3MT and yielded dopamine. Gut bacteria that mediate this transformation were identified as acetogens Eubacterium limosum and Blautia producta. Upon exposing these acetogens to propyl iodide, a known inhibitor of cobalamin‐dependent O‐demethylases, 3MT O‐demethylation was inhibited. Culturing E. limosum and B. producta with 3MT afforded increased acetate levels as compared with vehicle controls. CONCLUSIONS: Gut bacterial acetogens E. limosum and B. producta synthesized dopamine from 3MT. This O‐demethylation of 3MT was likely performed by cobalamin‐dependent O‐demethylases implicated in reductive acetogenesis. SIGNIFICANCE AND IMPACT OF THE STUDY: This is the first report that gut bacteria can synthesize dopamine by O‐demethylation of 3MT. Owing to 3MT being the product of host COMT attenuating dopamine levels, gut bacteria that reverse this transformation—converting 3MT to dopamine—may act as a counterbalance for dopamine regulation by COMT.
    Keywords Eubacterium limosum ; acetates ; acetogens ; catechol O-methyltransferase ; digestive system ; dopamine ; humans ; intestinal microorganisms ; iodides ; metabolites
    Language English
    Dates of publication 2022-09
    Size p. 1697-1708.
    Publishing place John Wiley & Sons, Ltd
    Document type Article
    Note JOURNAL ARTICLE
    ZDB-ID 1358023-1
    ISSN 1365-2672 ; 1364-5072
    ISSN (online) 1365-2672
    ISSN 1364-5072
    DOI 10.1111/jam.15682
    Database NAL-Catalogue (AGRICOLA)

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    In stock of ZB MED Cologne/Königswinter

    Zs.A 259: Show issues Location:
    Je nach Verfügbarkeit (siehe Angabe bei Bestand)
    bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular
    Jg. 1995 - 2021: Lesesall (1.OG)
    ab Jg. 2022: Lesesaal (EG)

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  3. Article: Spatially resolved detection of small molecules from press-dried plant tissue using MALDI imaging.

    Long, Zane G / Le, Jonathan V / Katz, Benjamin B / Lopez, Belen G / Tenenbaum, Emily D / Semmling, Bonnie / Schmidt, Ryan J / Grün, Felix / Butts, Carter T / Martin, Rachel W

    Applications in plant sciences

    2023  Volume 11, Issue 5, Page(s) e11539

    Abstract: Premise: Matrix-assisted laser desorption/ionization mass spectrometry imaging (MALDI-MSI) is a chemical imaging method that can visualize spatial distributions of particular molecules. Plant tissue imaging has so far mostly used cryosectioning, which ... ...

    Abstract Premise: Matrix-assisted laser desorption/ionization mass spectrometry imaging (MALDI-MSI) is a chemical imaging method that can visualize spatial distributions of particular molecules. Plant tissue imaging has so far mostly used cryosectioning, which can be impractical for the preparation of large-area imaging samples, such as full flower petals. Imaging unsectioned plant tissue presents its own difficulties in extracting metabolites to the surface due to the waxy cuticle.
    Methods: We address this by using established delipidation techniques combined with a solvent vapor extraction prior to applying the matrix with many low-concentration sprays.
    Results: Using this procedure, we imaged tissue from three different plant species (two flowers and one carnivorous plant leaf). Material factorization analysis of the resulting data reveals a wide range of plant-specific small molecules with varying degrees of localization to specific portions of the tissue samples, while facilitating detection and removal of signal from background sources.
    Conclusions: This work demonstrates applicability of MALDI-MSI to press-dried plant samples without freezing or cryosectioning, setting the stage for spatially resolved molecule identification. Increased mass resolution and inclusion of tandem mass spectrometry are necessary next steps to allow more specific and reliable compound identification.
    Language English
    Publishing date 2023-09-11
    Publishing country United States
    Document type Journal Article
    ZDB-ID 2699923-7
    ISSN 2168-0450
    ISSN 2168-0450
    DOI 10.1002/aps3.11539
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  4. Article ; Online: Butenolide Synthesis from Functionalized Cyclopropenones.

    Nguyen, Sean S / Ferreira, Andrew J / Long, Zane G / Heiss, Tyler K / Dorn, Robert S / Row, R David / Prescher, Jennifer A

    Organic letters

    2019  Volume 21, Issue 21, Page(s) 8695–8699

    Abstract: A general method to synthesize substituted butenolides from hydroxymethylcyclopropenones is reported. Functionalized cyclopropenones undergo ring-opening reactions with catalytic amounts of phosphine, forming reactive ketene ylides. These intermediates ... ...

    Abstract A general method to synthesize substituted butenolides from hydroxymethylcyclopropenones is reported. Functionalized cyclopropenones undergo ring-opening reactions with catalytic amounts of phosphine, forming reactive ketene ylides. These intermediates can be trapped by pendant hydroxy groups to afford target butenolide scaffolds. The reaction proceeds efficiently in diverse solvents and with low catalyst loadings. Importantly, the cyclization is tolerant of a broad range of functional groups, yielding a variety of α- and γ-substituted butenolides.
    Language English
    Publishing date 2019-10-17
    Publishing country United States
    Document type Journal Article
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.9b03298
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  5. Article: Butenolide Synthesis from Functionalized Cyclopropenones

    Nguyen, Sean S / Ferreira, Andrew J / Long, Zane G / Heiss, Tyler K / Dorn, Robert S / Row, R. David / Prescher, Jennifer A

    Organic letters. 2019 Oct. 17, v. 21, no. 21

    2019  

    Abstract: A general method to synthesize substituted butenolides from hydroxymethylcyclopropenones is reported. Functionalized cyclopropenones undergo ring-opening reactions with catalytic amounts of phosphine, forming reactive ketene ylides. These intermediates ... ...

    Abstract A general method to synthesize substituted butenolides from hydroxymethylcyclopropenones is reported. Functionalized cyclopropenones undergo ring-opening reactions with catalytic amounts of phosphine, forming reactive ketene ylides. These intermediates can be trapped by pendant hydroxy groups to afford target butenolide scaffolds. The reaction proceeds efficiently in diverse solvents and with low catalyst loadings. Importantly, the cyclization is tolerant of a broad range of functional groups, yielding a variety of α- and γ-substituted butenolides.
    Keywords catalysts ; catalytic activity ; chemical reactions ; moieties ; organic compounds ; phosphine ; solvents
    Language English
    Dates of publication 2019-1017
    Size p. 8695-8699.
    Publishing place American Chemical Society
    Document type Article
    ISSN 1523-7052
    DOI 10.1021/acs.orglett.9b03298
    Database NAL-Catalogue (AGRICOLA)

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  6. Article: Isomeric triazines exhibit unique profiles of bioorthogonal reactivity.

    Kamber, David N / Nguyen, Sean S / Liu, Fang / Briggs, Jeffrey S / Shih, Hui-Wen / Row, R David / Long, Zane G / Houk, K N / Liang, Yong / Prescher, Jennifer A

    Chemical science

    2019  Volume 10, Issue 39, Page(s) 9109–9114

    Abstract: Expanding the scope of bioorthogonal reactivity requires access to new and mutually compatible reagents. We report here that 1,2,4-triazines can be tuned to exhibit unique reaction profiles with biocompatible strained alkenes and alkynes. Computational ... ...

    Abstract Expanding the scope of bioorthogonal reactivity requires access to new and mutually compatible reagents. We report here that 1,2,4-triazines can be tuned to exhibit unique reaction profiles with biocompatible strained alkenes and alkynes. Computational analyses were used to identify candidate orthogonal reactions, and the predictions were experimentally verified. Notably, 5-substituted triazines, unlike their 6-substituted counterparts, undergo rapid [4 + 2] cycloadditions with a sterically encumbered strained alkyne. This unique, sterically controlled reactivity was exploited for dual bioorthogonal labeling. Mutually orthogonal triazines and cycloaddition chemistries will enable new multi-component imaging applications.
    Language English
    Publishing date 2019-08-21
    Publishing country England
    Document type Journal Article
    ZDB-ID 2559110-1
    ISSN 2041-6539 ; 2041-6520
    ISSN (online) 2041-6539
    ISSN 2041-6520
    DOI 10.1039/c9sc01427f
    Database MEDical Literature Analysis and Retrieval System OnLINE

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