New 2-Methoxy Acetylenic Acids and Pyrazole Alkaloids from the Marine Sponge Cinachyrella sp.

Three new 2-methoxy acetylenic acids (1–3) and a known derivative (4), in addition to three new natural pyrazole alkaloids (5–7) were isolated from an Indonesian marine sponge of the genus Cinachyrella. Compounds 5 and 6 have previously been reported as synthetic compounds. The structures of the new...

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Autores principales: Mokhlesi, Amin, Hartmann, Rudolf, Kurtán, Tibor, Weber, Horst, Lin, Wenhan, Chaidir, Chaidir, Müller, Werner E. G., Daletos, Georgios, Proksch, Peter
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
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Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5706045/
https://www.ncbi.nlm.nih.gov/pubmed/29137125
http://dx.doi.org/10.3390/md15110356
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author Mokhlesi, Amin
Hartmann, Rudolf
Kurtán, Tibor
Weber, Horst
Lin, Wenhan
Chaidir, Chaidir
Müller, Werner E. G.
Daletos, Georgios
Proksch, Peter
author_facet Mokhlesi, Amin
Hartmann, Rudolf
Kurtán, Tibor
Weber, Horst
Lin, Wenhan
Chaidir, Chaidir
Müller, Werner E. G.
Daletos, Georgios
Proksch, Peter
author_sort Mokhlesi, Amin
collection PubMed
description Three new 2-methoxy acetylenic acids (1–3) and a known derivative (4), in addition to three new natural pyrazole alkaloids (5–7) were isolated from an Indonesian marine sponge of the genus Cinachyrella. Compounds 5 and 6 have previously been reported as synthetic compounds. The structures of the new compounds were established on the basis of one- and two-dimensional NMR spectroscopy as well as by mass spectrometric data. The absolute configuration of the new acetylenic acid derivatives (1–3) was established by ECD spectroscopy. All isolated compounds were evaluated for their cytotoxicity against L5178Y mouse lymphoma cells. Compounds 1–4 exhibited strong activity with an IC(50) value of 0.3 µM. A plausible biosynthetic pathway for the pyrazole metabolites 5–7 is proposed.
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spelling pubmed-57060452017-12-04 New 2-Methoxy Acetylenic Acids and Pyrazole Alkaloids from the Marine Sponge Cinachyrella sp. Mokhlesi, Amin Hartmann, Rudolf Kurtán, Tibor Weber, Horst Lin, Wenhan Chaidir, Chaidir Müller, Werner E. G. Daletos, Georgios Proksch, Peter Mar Drugs Article Three new 2-methoxy acetylenic acids (1–3) and a known derivative (4), in addition to three new natural pyrazole alkaloids (5–7) were isolated from an Indonesian marine sponge of the genus Cinachyrella. Compounds 5 and 6 have previously been reported as synthetic compounds. The structures of the new compounds were established on the basis of one- and two-dimensional NMR spectroscopy as well as by mass spectrometric data. The absolute configuration of the new acetylenic acid derivatives (1–3) was established by ECD spectroscopy. All isolated compounds were evaluated for their cytotoxicity against L5178Y mouse lymphoma cells. Compounds 1–4 exhibited strong activity with an IC(50) value of 0.3 µM. A plausible biosynthetic pathway for the pyrazole metabolites 5–7 is proposed. MDPI 2017-11-11 /pmc/articles/PMC5706045/ /pubmed/29137125 http://dx.doi.org/10.3390/md15110356 Text en © 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Mokhlesi, Amin
Hartmann, Rudolf
Kurtán, Tibor
Weber, Horst
Lin, Wenhan
Chaidir, Chaidir
Müller, Werner E. G.
Daletos, Georgios
Proksch, Peter
New 2-Methoxy Acetylenic Acids and Pyrazole Alkaloids from the Marine Sponge Cinachyrella sp.
title New 2-Methoxy Acetylenic Acids and Pyrazole Alkaloids from the Marine Sponge Cinachyrella sp.
title_full New 2-Methoxy Acetylenic Acids and Pyrazole Alkaloids from the Marine Sponge Cinachyrella sp.
title_fullStr New 2-Methoxy Acetylenic Acids and Pyrazole Alkaloids from the Marine Sponge Cinachyrella sp.
title_full_unstemmed New 2-Methoxy Acetylenic Acids and Pyrazole Alkaloids from the Marine Sponge Cinachyrella sp.
title_short New 2-Methoxy Acetylenic Acids and Pyrazole Alkaloids from the Marine Sponge Cinachyrella sp.
title_sort new 2-methoxy acetylenic acids and pyrazole alkaloids from the marine sponge cinachyrella sp.
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5706045/
https://www.ncbi.nlm.nih.gov/pubmed/29137125
http://dx.doi.org/10.3390/md15110356
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