Scalalactams A⁻D, Scalarane Sesterterpenes with a γ-Lactam Moiety from a Korean Spongia Sp. Marine Sponge

Molecules. 2018 Dec 3;23(12):3187. doi: 10.3390/molecules23123187.

Abstract

Intensive study on the chemical components of a Korean marine sponge, Spongia sp., has led to the isolation of four new scalarane sesterterpenes, scalalactams A⁻D (14). Their chemical structures were elucidated from the analysis of spectroscopic data including 1D-and 2D-NMR as well as MS data. Scalalactams A⁻D (14) possess a scalarane carbon skeleton with a rare structural feature of a γ-lactam moiety within the molecules. Scalalactams A and B (1 and 2) have an extended isopropanyl chain at the lactam ring, and scalalactams C and D (3 and 4) possess a phenethyl group at the lactam ring moiety. Scalalactams A⁻D (14) did not show FXR antagonistic activity nor cytotoxicity up to 100 μM.

Keywords: Spongia sp; marine natural products; marine sponge; scalalactams; scalarane sesterterpenes.

MeSH terms

  • Animals
  • Aquatic Organisms / chemistry
  • Drug Evaluation, Preclinical / methods
  • Humans
  • Lactams / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Porifera / chemistry*
  • Receptors, Cytoplasmic and Nuclear / antagonists & inhibitors
  • Sesterterpenes / chemistry*
  • Sesterterpenes / pharmacology*

Substances

  • Lactams
  • Receptors, Cytoplasmic and Nuclear
  • Sesterterpenes
  • farnesoid X-activated receptor