Additional sesterterpenes and a nortriterpene saponin from the sponge Clathria gombawuiensis

J Nat Prod. 2015 Feb 27;78(2):218-24. doi: 10.1021/np500753q. Epub 2015 Jan 29.

Abstract

Three new terpene metabolites (1-3) were isolated from the marine sponge Clathria gombawuiensis collected from Korean waters. On the basis of the results of combined spectroscopic analyses, the structures of phorone B (1) and ansellone C (2) were determined to be the sesterterpenes of the phorone and ansellone classes, respectively, whereas the saponin gombaside A (3) was a nortriterpene sodium O-sulfonato-glucuronide of the rare 4,4,14-trimethylpregnane class. The absolute configuration of the glucuronate of 3 was assigned by an application of the phenylglycine methyl ester (PGME) method. The new compounds exhibited moderate cytotoxicity against A549 and K562 cell lines, and compound 3 showed antibacterial activity. The cytotoxicity of 1 may be related to the presence of a free phenolic -OH group, as the corresponding O-methoxy derivative 4 is inactive.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemistry
  • Antineoplastic Agents / chemistry
  • Drug Screening Assays, Antitumor
  • Humans
  • K562 Cells
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Porifera / chemistry*
  • Saponins / chemistry
  • Saponins / isolation & purification*
  • Saponins / pharmacology
  • Sesterterpenes / chemistry
  • Sesterterpenes / isolation & purification*
  • Sesterterpenes / pharmacology
  • Structure-Activity Relationship
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification*
  • Triterpenes / pharmacology

Substances

  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Saponins
  • Sesterterpenes
  • Triterpenes
  • phorone A