Engyodontochones, Antibiotic Polyketides from the Marine Fungus Engyodontium album Strain LF069.
Six new (2, 4-8) and two known polyketides with a basic structure of an anthraquinone-xanthone were isolated from mycelia and culture broth of the fungus Engyodontium album strain LF069. The structures and relative configurations of these compounds were established by spectroscopic means, and their absolute configurations were defined mainly by comparison of quantum chemical TDDFT calculated and experimental ECD spectra. Compounds 2 and 4-8 were given the trivial names engyodontochone A (2) and B-F (4-8). Compounds 5-8 represent the first example of a 23,28 seco-beticolin carbon skeleton. The relative and absolute configurations of two known substances JBIR-97/98 (1) and JBIR-99 (3) were determined for the first time. All isolated compounds were subjected to bioactivity assays. Compounds 1-4 exhibited inhibitory activity against methicillin-resistant Staphylococcus aureus (MRSA) that was 10-fold stronger than chloramphenicol.
Ocean College, Zhejiang University, Hangzhou, 310058, China.
Bin
B
Wu
Marine Microbiology, GEOMAR Helmholtz Center for Ocean Research Kiel, Düsternbrooker Weg 20, 24105, Kiel, Germany.
Jutta
J
Wiese
Marine Microbiology, GEOMAR Helmholtz Center for Ocean Research Kiel, Düsternbrooker Weg 20, 24105, Kiel, Germany.
Arlette
A
Wenzel-Storjohann
Marine Microbiology, GEOMAR Helmholtz Center for Ocean Research Kiel, Düsternbrooker Weg 20, 24105, Kiel, Germany.
Susan
S
Malien
Marine Microbiology, GEOMAR Helmholtz Center for Ocean Research Kiel, Düsternbrooker Weg 20, 24105, Kiel, Germany.
Rolf
R
Schmaljohann
Marine Microbiology, GEOMAR Helmholtz Center for Ocean Research Kiel, Düsternbrooker Weg 20, 24105, Kiel, Germany. jimhoff@geomar.de.
Johannes F
JF
Imhoff
D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000302:isolation & purification*; D002867:Chromones / Q000737:chemistry; D006999:Hypocreales / Q000737:chemistry*; D008386:Marine Biology; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D061065:Polyketides / Q000737:chemistry* / Q000302:isolation & purification*
D000900:Anti-Bacterial Agents; D002867:Chromones; C553368:JBIR-97; C553370:JBIR-99; D061065:Polyketides
antibiotics; drug discovery; natural products; polyketides; structure elucidation