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Ominoxanthone—The First Xanthone Linearly Fused to a γ-Lactone from ICortinarius ominosus/I Bidaud Basidiomata. CASE- and DFT-Based Structure Elucidation

Molecules (Basel, Switzerland), 2023-02, Vol.28 (4) [Peer Reviewed Journal]

COPYRIGHT 2023 MDPI AG ;ISSN: 1420-3049 ;EISSN: 1420-3049 ;DOI: 10.3390/molecules28041557

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  • Title:
    Ominoxanthone—The First Xanthone Linearly Fused to a γ-Lactone from ICortinarius ominosus/I Bidaud Basidiomata. CASE- and DFT-Based Structure Elucidation
  • Author: Trac, Alice ; Issaad, Célia ; Beniddir, Mehdi A ; Bellanger, Jean-Michel ; Gallard, Jean-François ; Buevich, Alexei V ; Elyashberg, Mikhail E ; Le Pogam, Pierre
  • Subjects: Computer software industry ; Rankings
  • Is Part Of: Molecules (Basel, Switzerland), 2023-02, Vol.28 (4)
  • Description: The UHPLC–HRMS analysis of Cortinarius ominosus basidiomata extract revealed that this mushroom accumulated elevated yields of an unreported specialized metabolite. The molecular formula of this unknown compound, C[sub.17]H[sub.10]O[sub.8], indicated that a challenging structure elucidation lay ahead, owing to its critically low H/C atom ratio. The structure of this new isolate, namely ominoxanthone (1), could not be solved from the interpretation of the usual set of 1D/2D NMR data that conveyed too limited information to afford a single, unambiguous structure. To remedy this, a Computer-Assisted Structure Elucidation (CASE) workflow was used to rank the different possible structure candidates consistent with our scarce spectroscopic data. DFT-based chemical shift calculations on a limited set of top-ranked structures further ascertained the determined structure for ominoxanthone. Although the determined scaffold of ominoxanthone is unprecedented as a natural product, a plausible biosynthetic scenario involving a precursor known from cortinariaceous sources and classical biogenetic reactions could be proposed.
  • Publisher: MDPI AG
  • Language: English
  • Identifier: ISSN: 1420-3049
    EISSN: 1420-3049
    DOI: 10.3390/molecules28041557
  • Source: GFMER Free Medical Journals
    PubMed Central
    Alma/SFX Local Collection
    ProQuest Central
    DOAJ Directory of Open Access Journals
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