دورية أكاديمية
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Precursor-Directed Biosynthesis of Aminofulvenes: New Chalanilines from Endophytic Fungus Chalara sp.

التفاصيل البيبلوغرافية
العنوان: Precursor-Directed Biosynthesis of Aminofulvenes: New Chalanilines from Endophytic Fungus Chalara sp.
المؤلفون: Khoshbakht M; Department of Chemistry, Oregon State University, Corvallis, OR 97331, USA., Srey J; Department of Chemistry, Oregon State University, Corvallis, OR 97331, USA., Adpressa DA; Department of Chemistry, Oregon State University, Corvallis, OR 97331, USA., Jagels A; Whitney Laboratory for Marine Bioscience, Department of Chemistry, University of Florida, Gainesville, FL 32080, USA., Loesgen S; Department of Chemistry, Oregon State University, Corvallis, OR 97331, USA.; Whitney Laboratory for Marine Bioscience, Department of Chemistry, University of Florida, Gainesville, FL 32080, USA.
المصدر: Molecules (Basel, Switzerland) [Molecules] 2021 Jul 22; Vol. 26 (15). Date of Electronic Publication: 2021 Jul 22.
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: MDPI Country of Publication: Switzerland NLM ID: 100964009 Publication Model: Electronic Cited Medium: Internet ISSN: 1420-3049 (Electronic) Linking ISSN: 14203049 NLM ISO Abbreviation: Molecules Subsets: MEDLINE
أسماء مطبوعة: Original Publication: Basel, Switzerland : MDPI, c1995-
مواضيع طبية MeSH: Aniline Compounds*/chemistry , Aniline Compounds*/metabolism , Ascomycota*/chemistry , Ascomycota*/metabolism , Endophytes*/chemistry , Endophytes*/metabolism , Hydrocarbons, Fluorinated*/chemistry , Hydrocarbons, Fluorinated*/metabolism
مستخلص: The plant endophyte Chalara sp. is able to biotransform the epigenetic modifier vorinostat to form unique, aniline-containing polyketides named chalanilines. Here, we sought to expand the chemical diversity of chalaniline A-type molecules by changing the aniline moiety in the precursor vorinostat. In total, twenty-three different vorinostat analogs were prepared via two-step synthesis, and nineteen were incorporated by the fungus into polyketides. The highest yielding substrates were selected for large-scale precursor-directed biosynthesis and five novel compounds, including two fluorinated chalanilines, were isolated, purified, and structurally characterized. Structure elucidation relied on 1D and 2D NMR techniques and was supported by low- and high-resolution mass spectrometry. All compounds were tested for their bioactivity but were not active in antimicrobial or cell viability assays. Aminofulvene-containing natural products are rare, and this high-yielding, precursor-directed process allows for the diversification of this class of compounds.
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معلومات مُعتمدة: CHE 1808717/2020110 National Science Foundation; P41 GM122698 United States GM NIGMS NIH HHS; S10 OD018518 United States OD NIH HHS; S10 OD028753 United States OD NIH HHS; R01 EB009772 United States EB NIBIB NIH HHS
فهرسة مساهمة: Keywords: aminofulvenes; biotransformation; fungal metabolite; precursor-directed biosynthesis
المشرفين على المادة: 0 (Aniline Compounds)
0 (Hydrocarbons, Fluorinated)
تواريخ الأحداث: Date Created: 20210807 Date Completed: 20210916 Latest Revision: 20240626
رمز التحديث: 20240626
مُعرف محوري في PubMed: PMC8347292
DOI: 10.3390/molecules26154418
PMID: 34361574
قاعدة البيانات: MEDLINE
الوصف
تدمد:1420-3049
DOI:10.3390/molecules26154418