Suvanine sesterterpenes and deacyl irciniasulfonic acids from a tropical Coscinoderma sp. sponge

J Nat Prod. 2014 Jun 27;77(6):1396-403. doi: 10.1021/np500156n. Epub 2014 May 14.

Abstract

The suvanines, a new suvanine salt, five new (2, 4-8) and two known sesterterpenes from the same structural class, and two new modified lipids (9 and 10) were isolated from a Coscinoderma sp. sponge collected from Chuuk Island, Micronesia. On the basis of the results of combined spectroscopic and chemical analyses, a new suvanine salt was determined to be the suvanine N,N-dimethyl-1,3-dimethylherbipoline salt (2) and suvanine-lactam derivatives (4-8) formed by condensations between an oxidized furan moiety and amino acids. The lipid metabolites were found to be new derivatives of the taurine-containing deacyl irciniasulfonic acid class. The suvanines exhibited moderate cytotoxicities against the K562 and A549 cell lines, while the new suvanine salt (2) had significant antibacterial activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Drug Screening Assays, Antitumor
  • Humans
  • K562 Cells
  • Microbial Sensitivity Tests
  • Micronesia
  • Nuclear Magnetic Resonance, Biomolecular
  • Porifera / chemistry*
  • Sesterterpenes / chemistry
  • Sesterterpenes / isolation & purification*
  • Sesterterpenes / pharmacology
  • Sulfonic Acids / chemistry
  • Sulfonic Acids / isolation & purification*
  • Sulfonic Acids / pharmacology

Substances

  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Sesterterpenes
  • Sulfonic Acids
  • suvanine