Details

Autor(en) / Beteiligte

• Bringmann, Gerhard
• Lang, Gerhard
• Bruhn, Torsten
• Schäffler, Katrin
• Steffens, Stefan
• Schmaljohann, Rolf
• Wiese, Jutta
• Imhoff, Johannes F.

Titel

Sorbifuranones A-C, sorbicillinoid metabolites from Penicillium strains isolated from Mediterranean sponges

Ist Teil von

• Tetrahedron, 2010-12, Vol.66 (52), p.9894-9901

Ort / Verlag

Kidlington: Elsevier Ltd

Erscheinungsjahr

2010

Quelle

Access via ScienceDirect (Elsevier)

Beschreibungen/Notizen

• Three novel natural products, sorbifuranones A-C ( 4- 6), were isolated from a Penicillium chrysogenum fungus isolated from the marine sponge Ircinia fasciculata. Sorbifuranones B ( 5) and C ( 6) and 2',3'-dihydrosorbicillin, a putative precursor to sorbifuranone B, were also found in the culture of another Penicillium strain, which was isolated from the sponge Tethya aurantia. Their constitutions were elucidated mainly by 2D NMR. NOE correlations in combination with quantum chemical calculations and comparison of experimental and calculated electronic circular dichroism (CD) spectra permitted assignment of the absolute configuration of sorbifuranone C. The structures hint at a two-step cleavage-cyclization sequence of sorbifuranone A ( 4) leading to the spiro compound sorbifuranone C, while sorbifuranone B is likely to be the respective cleavage product of a putative 2',3'-dihydrosorbifuranone A, which cannot cyclize further. ▪