Ophiobolin Sesterterpenoids and Pyrrolidine Alkaloids from the Sponge-Derived Fungus Aspergillus ustus
Chemical examination of the fungus Aspergillus ustus isolated from the Mediterranean sponge Suberites domuncula yielded the five new ophiobolin‐type sesterterpenoids 1–5 and the two new pyrrolidine alkaloids 6 and 7, together with the known compound aurantiamine and cerebroside D. The structures of...
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| Published in | Helvetica chimica acta Vol. 94; no. 4; pp. 623 - 631 |
|---|---|
| Main Authors | , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Zürich
WILEY-VCH Verlag
01.04.2011
WILEY‐VCH Verlag Wiley |
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| Abstract | Chemical examination of the fungus Aspergillus ustus isolated from the Mediterranean sponge Suberites domuncula yielded the five new ophiobolin‐type sesterterpenoids 1–5 and the two new pyrrolidine alkaloids 6 and 7, together with the known compound aurantiamine and cerebroside D. The structures of the new compounds were unambiguously elucidated on the basis of extensive spectroscopic‐data analysis (1D‐ and 2D‐NMR, MS, and UV) and comparison with literature data. All compounds were evaluated for their cytotoxicity against murine lymphoma cell line L5178Y. |
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| AbstractList | Chemical examination of the fungus
Aspergillus ustus
isolated from the Mediterranean sponge
Suberites domuncula
yielded the five new ophiobolin‐type sesterterpenoids
1
–
5
and the two new pyrrolidine alkaloids
6
and
7
, together with the known compound aurantiamine and cerebroside D. The structures of the new compounds were unambiguously elucidated on the basis of extensive spectroscopic‐data analysis (1D‐ and 2D‐NMR, MS, and UV) and comparison with literature data. All compounds were evaluated for their cytotoxicity against murine lymphoma cell line L5178Y. Chemical examination of the fungus Aspergillus ustus isolated from the Mediterranean sponge Suberites domuncula yielded the five new ophiobolin-type sesterterpenoids 1-5 and the two new pyrrolidine alkaloids 6 and 7, together with the known compound aurantiamine and cerebroside D. The structures of the new compounds were unambiguously elucidated on the basis of extensive spectroscopic-data analysis (1D- and 2D-NMR, MS, and UV) and comparison with literature data. All compounds were evaluated for their cytotoxicity against murine lymphoma cell line L5178Y. |
| Author | Wang, Yao Proksch, Peter Draeger, Siegfried Wray, Victor Edrada-Ebel, RuAngelie Ebel, Rainer Müller, Werner E. G. Liu, Hong-Bing Schulz, Barbara Lin, Wen-Han |
| Author_xml | – sequence: 1 givenname: Hong-Bing surname: Liu fullname: Liu, Hong-Bing organization: Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. China – sequence: 2 givenname: RuAngelie surname: Edrada-Ebel fullname: Edrada-Ebel, RuAngelie organization: Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, The John Arbuthnott Building, 27 Taylor Street, Glasgow G4 0NR, U.K – sequence: 3 givenname: Rainer surname: Ebel fullname: Ebel, Rainer organization: Department of Chemistry, University of Aberdeen, Meston Building, Meston Walk, AB24 3UE, Aberdeen, U.K – sequence: 4 givenname: Yao surname: Wang fullname: Wang, Yao organization: Institut für Pharmazeutische Biologie und Biotechnologie, Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1, Geb. 26.23, D-40225 Düsseldorf, (phone: +49-211-8114163; fax: +49-211-8111923) – sequence: 5 givenname: Barbara surname: Schulz fullname: Schulz, Barbara organization: Institut für Mikrobiologie, Technische Universität Carolo-Wilhelmina zu Braunschweig, Spielmannstrasse 7, D-38106 Braunschweig – sequence: 6 givenname: Siegfried surname: Draeger fullname: Draeger, Siegfried organization: Institut für Mikrobiologie, Technische Universität Carolo-Wilhelmina zu Braunschweig, Spielmannstrasse 7, D-38106 Braunschweig – sequence: 7 givenname: Werner E. G. surname: Müller fullname: Müller, Werner E. G. organization: Institut für Physiologische Chemie und Pathobiochemie, Johannes-Gutenberg-Universität, Duesbergweg 6, D-55128 Mainz – sequence: 8 givenname: Victor surname: Wray fullname: Wray, Victor organization: Helmholtz Center for Infection Research, Inhoffenstrasse 7, D-38124 Braunschweig – sequence: 9 givenname: Wen-Han surname: Lin fullname: Lin, Wen-Han email: whlin@bjmu.edu.cn organization: State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100083, P. R. China (phone: +86-10-82806188; fax: +86-10-82806188) – sequence: 10 givenname: Peter surname: Proksch fullname: Proksch, Peter email: proksch@uni-duesseldorf.de organization: Institut für Pharmazeutische Biologie und Biotechnologie, Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1, Geb. 26.23, D-40225 Düsseldorf, (phone: +49-211-8114163; fax: +49-211-8111923) |
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| Cites_doi | 10.1021/np50051a011 10.7164/antibiotics.49.505 10.7164/antibiotics.41.1774 10.1016/0031-9422(92)83116-G 10.1515/BOT.2008.014 10.1021/np900268z 10.1021/np900220r 10.1016/j.tet.2004.05.021 10.7164/antibiotics.41.469 10.1021/jf00124a019 10.1017/S0953756203227775 10.1039/b301926h 10.1111/j.1432-1033.2004.04102.x 10.1002/cbic.200500087 |
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| Snippet | Chemical examination of the fungus Aspergillus ustus isolated from the Mediterranean sponge Suberites domuncula yielded the five new ophiobolin‐type... Chemical examination of the fungus Aspergillus ustus isolated from the Mediterranean sponge Suberites domuncula yielded the five new ophiobolin‐type... Chemical examination of the fungus Aspergillus ustus isolated from the Mediterranean sponge Suberites domuncula yielded the five new ophiobolin-type... |
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| SubjectTerms | Alkaloids Aspergillus ustus Chemistry Chemistry, Multidisciplinary Cytotoxic activity Fungi Physical Sciences Pyrrolidine alkaloids Science & Technology Sesterterpenoids Suberites domuncula |
| Title | Ophiobolin Sesterterpenoids and Pyrrolidine Alkaloids from the Sponge-Derived Fungus Aspergillus ustus |
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