Isolation of Scalimides A–L: <i>β</i>-Alanine-Bearing Scalarane Analogs from the Marine Sponge <i>Spongia</i> sp.

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

• scalarane sesterterpene
• scalimide
• <i>Spongia</i> sp.
• marine sponge
• antimicrobial activity