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

• Published in: Marine drugs Vol. 15; no. 11; p. 356
• Main Authors: Mokhlesi, Amin, Hartmann, Rudolf, Kurtán, Tibor, Weber, Horst, Lin, Wenhan, Chaidir, Chaidir, Müller, Werner E G, Daletos, Georgios, Proksch, Peter
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 11.11.2017; MDPI
• Subjects: 2-methoxy acetylenic acid; Absolute configuration; Acids; Alkaloids; Analytical methods; Cinachyrella; Cinachyrella sp; Cytotoxicity; Lymphoma; Magnetic resonance spectroscopy; Marine invertebrates; marine sponge; Metabolites; natural products; NMR; NMR spectroscopy; Nuclear magnetic resonance; Pyrazole; pyrazole alkaloid; Spectrometry; Spectrum analysis; Toxicity; natural products; marine sponge; 2-methoxy acetylenic acid; pyrazole alkaloid; Cinachyrella sp
• ISSN: 1660-3397; 1660-3397
• DOI: 10.3390/md15110356

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.