Isolation of Scalimides A-L: β-Alanine-Bearing Scalarane Analogs from the Marine Sponge Spongia sp

Mar Drugs. 2022 Nov 18;20(11):726. doi: 10.3390/md20110726.

Abstract

A chemical investigation of a methanol extract of Spongia sp., a marine sponge collected from the Philippines, identified 12 unreported scalarane-type alkaloids-scalimides A-L (1-12)-together with two previously described scalarin derivatives. The elucidation of the structure of the scalaranes based on the interpretation of their NMR and HRMS data revealed that 1-12 featured a β-alanine-substituted E-ring but differed from each other through variations in their oxidation states and substitutions occurring at C16, C24, and C25. Evaluation of the antimicrobial activity of 1-12 against several Gram-positive and Gram-negative bacteria showed that 10 and 11 were active against Micrococcus luteus and Bacillus subtilis, respectively, with MIC values ranging from 4 to 16 μg/mL.

Keywords: Spongia sp.; antimicrobial activity; marine sponge; scalarane sesterterpene; scalimide.

MeSH terms

  • Animals
  • Anti-Bacterial Agents* / pharmacology
  • Bacillus subtilis
  • Gram-Negative Bacteria
  • Methanol
  • Porifera*

Substances

  • Anti-Bacterial Agents
  • Methanol