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

Bringmann, Gerhard, Lang, Gerhard, Bruhn, Torsten, Schäffler, Katrin, Steffens, Stefan, Schmaljohann, Rolf, Wiese, Jutta and Imhoff, Johannes F. (2010) Sorbifuranones A–C, sorbicillinoid metabolites from Penicillium strains isolated from Mediterranean sponges. Tetrahedron, 66 (52). pp. 9894-9901. DOI 10.1016/j.tet.2010.10.057.

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Abstract

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 aurantium. 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.

Document Type: Article
Additional Information: WOS:000285727500016
Keywords: Microbiology; Quantum-chemical CD calculations; Isolation of marine natural products; Structure elucidation; Sorbicillinol derivatives; Attribution of absolute configuration; TRICHODERMA SP USF-2690; SEMIEMPIRICAL METHODS; BIOSYNTHESIS; FUNGUS; DENSITY; OXOSORBICILLINOL; BISORBICILLINOL; LONGIBRACHIATUM; BISVERTINOLONE; OPTIMIZATION
Research affiliation: OceanRep > GEOMAR > FB3 Marine Ecology > FB3-MI Marine Microbiology
Refereed: Yes
Open Access Journal?: No
DOI etc.: 10.1016/j.tet.2010.10.057
ISSN: 0040-4020
Projects: Future Ocean, BIOTECmarin
Date Deposited: 01 Dec 2010 11:41
Last Modified: 24 Jan 2019 09:55
URI: http://oceanrep.geomar.de/id/eprint/10276

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