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Microbial Metabolites of 3-In/I-butylphthalide as Monoamine Oxidase A Inhibitors

International journal of molecular sciences, 2023-06, Vol.24 (13) [Peer Reviewed Journal]

COPYRIGHT 2023 MDPI AG ;ISSN: 1422-0067 ;EISSN: 1422-0067 ;DOI: 10.3390/ijms241310605

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  • Title:
    Microbial Metabolites of 3-In/I-butylphthalide as Monoamine Oxidase A Inhibitors
  • Author: Gach, Joanna ; Grzelczyk, Joanna ; Strzała, Tomasz ; Boratyński, Filip ; Olejniczak, Teresa
  • Subjects: Metabolites
  • Is Part Of: International journal of molecular sciences, 2023-06, Vol.24 (13)
  • Description: Novel compounds with antidepressant activity via monoamine oxidase inhibition are being sought. Among these, derivatives of 3-n-butylphthalide, a neuroprotective lactone from Apiaceae plants, may be prominent candidates. This study aimed to obtain the oxidation products of 3-n-butylphthalide and screen them regarding their activity against the monoamine oxidase A (MAO-A) isoform. Such activity of these compounds has not been previously tested. To obtain the metabolites, we used fungi as biocatalysts because of their high oxidative capacity. Overall, 37 strains were used, among which Penicillium and Botrytis spp. were the most efficient, leading to the obtaining of three main products: 3-n-butyl-10-hydroxyphthalide, 3-n-butylphthalide-11-oic acid, and 3-n-butyl-11-hydroxyphthalide, with a total yield of 0.38–0.82 g per g of the substrate, depending on the biocatalyst used. The precursor–3-n-butylphthalide and abovementioned metabolites inhibited the MAO-A enzyme; the most active was the carboxylic acid derivative of the lactone with inhibitory constant (K[sub.i]) < 0.001 µmol/L. The in silico prediction of the drug-likeness of the metabolites matches the assumptions of Lipinski, Ghose, Veber, Egan, and Muegge. All the compounds are within the optimal range for the lipophilicity value, which is connected to adequate permeability and solubility.
  • Publisher: MDPI AG
  • Language: English
  • Identifier: ISSN: 1422-0067
    EISSN: 1422-0067
    DOI: 10.3390/ijms241310605
  • Source: PubMed Central
    ProQuest Central
    DOAJ Directory of Open Access Journals
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