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

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

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.

Keywords: 2-methoxy acetylenic acid; Cinachyrella sp.; marine sponge; natural products; pyrazole alkaloid.

MeSH terms

  • Alkaloids / chemistry*
  • Alkaloids / pharmacology
  • Alkynes / chemistry*
  • Alkynes / pharmacology
  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Biosynthetic Pathways / drug effects
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor / methods
  • Fatty Acids, Unsaturated / chemistry*
  • Fatty Acids, Unsaturated / pharmacology
  • Indonesia
  • Lymphoma / drug therapy
  • Mice
  • Porifera / chemistry*
  • Pyrazoles / chemistry*
  • Pyrazoles / pharmacology

Substances

  • Alkaloids
  • Alkynes
  • Antineoplastic Agents
  • Fatty Acids, Unsaturated
  • Pyrazoles
  • 2-hexadecynoic acid
  • pyrazole