Hygrophorones A-G: fungicidal cyclopentenones from Hygrophorus species (Basidiomycetes).
Twenty new 5-(hydroxyalkyl)-2-cyclopentenone derivatives (hygrophorones) could be isolated from Hygrophorus latitabundus, H. olivaceoalbus, H. persoonii, and H. pustulatus. Their fungicidal activity was exemplarily tested. The hygrophorones have structural similarities to the antibiotic pentenomycin. Chemically, hygrophorones are 2-cyclopentenones with hydroxy or acetoxy substituents at C-4 and/or C-5. An odd-numbered 1' oxidized alkyl chain (C(11), C(13), C(15), or C(17)) is attached at C-5. In addition, from H. persoonii the new gamma-butyrolactone derivative [5-(E)-2-hydroxytetradexylidene-5H-furan-2-one] could be isolated. Some hygrophorones are responsible for the color reaction of the stipes of these fungi upon treatment with potassium hydroxide solution. Structural elucidations are based on 1D ((1)H, (13)C) and 2D (COSY, NOESY, HSQC, HMBC) NMR spectroscopic analyses as well as HR-FT-ICR-MS investigations.
Lübken
Tilo
T
Department of Bioorganic Chemistry, Leibniz-Institute of Plant Biochemistry, Weinberg 3, D-06120 Halle/Saale, Germany.
Schmidt
Jürgen
J
Porzel
Andrea
A
Arnold
Norbert
N
Wessjohann
Ludger
L
D000935:Antifungal Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D001487:Basidiomycota / Q000737:chemistry*; D002963:Cladosporium / Q000187:drug effects; D003517:Cyclopentanes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular
D000935:Antifungal Agents; D003517:Cyclopentanes; C013905:cyclopentenone