The first sorbicillinoid alkaloids, the antileucemic sorbillactones A and B, from a sponge derived Penicillium chrysogenum strain

Bringmann, G., Lang, G., Gulder, T.A.M., Tsurata, H., Mühlbacher, J., Maksimenka, K., Steffens, S., Schaumann, K., Stöhr, Rüdiger, Wiese, Jutta, Imhoff, Johannes F., Perovic-Ottstadt, S., Boreiko, O. and Müller, W.E.G. (2005) The first sorbicillinoid alkaloids, the antileucemic sorbillactones A and B, from a sponge derived Penicillium chrysogenum strain Tetrahedron (61). pp. 7252-7265. DOI 10.1016/j.tet.2005.05.026.

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Abstract

The saltwater culture of a Penicillium chrysogenum strain isolated from the Mediterranean sponge Ircinia fasciculata yielded three new sorbicillin-derived compounds (1-3), whose structures were elucidated mainly by 2D NMR and mass spectrometry. Among them, sorbicillactones A (1) and B (2) are the first sorbicillinoid natural products that contain nitrogen. Compound 1 is anti-HIV active and it exhibits a strong cytotoxic activity against L5178y leukemic cells, combined with a relatively low toxicity to cervical carcinoma HeLa S3 cells and pheochromocytoma PC 12 cells. The absolute configurations of I and 2 were elucidated by quantum chemical calculation of circular dichroism (CD) spectra. Another compound isolated, sorbivinetone (3), might be an artifact derived from sorbicillinol (4) by Diels-Alder reaction with ethyl vinyl ether. Furthermore, the known sorbicillinoid fungal metabolites oxosorbicillinol (5), sorbicillin (6), and bisvertinolone (7) were identified, as well as the alkaloids meleagrine and roquefortine C. The biosynthetic origin of sorbicillactone A (1) from acetate, alanine, and methionine was investigated by feeding experiments with C-13-labeled precursors

Document Type: Article
Additional Information: WOS:000230327300021
Keywords: marine natural products; Penicillium chrysogenum; sorbicillin; alkaloids; quantum chemical CD calculations; circular dichroism; biosynthetic feeding experiments; antileukemic activity; TRICHODERMA SP USF-2690; VERTICILLIUM-INTERTEXTUM; TNF-ALPHA; TRICHODIMEROL; BIOSYNTHESIS; FUNGUS; BISORBICILLINOL; METABOLITES; BISORBIBUTENOLIDE; LONGIBRACHIATUM
Research affiliation: OceanRep > GEOMAR > FB3 Marine Ecology > FB3-MI Marine Microbiology
Refereed: Yes
DOI etc.: 10.1016/j.tet.2005.05.026
ISSN: 0040-4020
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Date Deposited: 03 Dec 2008 16:51
Last Modified: 05 Dec 2017 12:05
URI: http://eprints.uni-kiel.de/id/eprint/4546

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