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Mar. Drugs 2017, 15(11), 356; doi:10.3390/md15110356

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

1
Institute of Pharmaceutical Biology and Biotechnology, Heinrich Heine University, Universitätsstraße 1, 40225 Düsseldorf, Germany
2
Department of Marine Biology, Faculty of Marine Sciences, Tarbiat Modares University, 46414-356 Noor, Iran
3
Institute of Complex Systems: Strukturbiochemie, Forschungszentrum Jülich GmbH, ICS-6, 52425 Jülich, Germany
4
Department of Organic Chemistry, University of Debrecen, 4002 Debrecen, Hungary
5
Institute of Pharmaceutical and Medicinal Chemistry, Heinrich Heine University, Universitätsstraße 1, 40225 Düsseldorf, Germany
6
State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Health Science Center, 100191 Beijing, China
7
Center for Pharmaceutical and Medical Technology, Agency for the Assessment and Application Technology, 10340 Jakarta, Indonesia
8
Institute of Physiological Chemistry, University Medical Center of the Johannes Gutenberg University Mainz, 55128 Mainz, Germany
*
Authors to whom correspondence should be addressed.
Received: 5 August 2017 / Revised: 1 November 2017 / Accepted: 6 November 2017 / Published: 11 November 2017
(This article belongs to the Collection Bioactive Compounds from Marine Invertebrates)
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Abstract

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 IC50 value of 0.3 µM. A plausible biosynthetic pathway for the pyrazole metabolites 5–7 is proposed. View Full-Text
Keywords: natural products; marine sponge; Cinachyrella sp.; 2-methoxy acetylenic acid; pyrazole alkaloid natural products; marine sponge; Cinachyrella sp.; 2-methoxy acetylenic acid; pyrazole alkaloid
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MDPI and ACS Style

Mokhlesi, A.; Hartmann, R.; Kurtán, T.; Weber, H.; Lin, W.; Chaidir, C.; Müller, W.E.G.; Daletos, G.; Proksch, P. New 2-Methoxy Acetylenic Acids and Pyrazole Alkaloids from the Marine Sponge Cinachyrella sp.. Mar. Drugs 2017, 15, 356.

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