Penipyranicins A-C: Antibacterial Methylpyran Polyketides from a Hydrothermal Spring Sediment Penicillium sp.
Raha OrfaliShagufta PerveenAreej Al-TaweelAtallah F AhmedNajwa MajrashiKhulud AlluhayAfsar KhanPaolo LucianoTaglialatela-Scafati OrazioPublished in: Journal of natural products (2020)
Four new aromatic polyketides (1-4) were isolated from Penicillium sp. RO-11, obtained from the sediment of a hydrothermal spring in the southwestern region of Saudi Arabia. The new compounds are penipyranicins A-C (1-3), characterized by a 4-methyl-4H-pyran moiety, a structural motif unprecedented among fungal polyketides, and the naphthopyrone derivative isopyrenulin (4). The structures of the new compounds were elucidated on the basis of data from mass spectrometry, 1D and 2D NMR analysis, and comparison between experimental and time-dependent density functional theory-calculated electronic circular dichroism spectra. A plausible biosynthetic pathway connecting penipyranicins and isopyrenulin is proposed. The isolated compounds were active against Gram-positive and Gram-negative bacteria.
Keyphrases
- density functional theory
- saudi arabia
- high resolution
- mass spectrometry
- molecular dynamics
- heavy metals
- magnetic resonance
- polycyclic aromatic hydrocarbons
- anaerobic digestion
- gram negative
- electronic health record
- big data
- gas chromatography
- risk assessment
- high performance liquid chromatography
- multidrug resistant
- solid state
- artificial intelligence
- anti inflammatory
- organic matter
- deep learning
- tandem mass spectrometry
- simultaneous determination
- solid phase extraction