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

A chemical investigation of a methanol extract of <i>Spongia</i> sp., a marine sponge collected from the Philippines, identified 12 unreported scalarane-type alkaloids—scalimides A–L (<b>1</b>–<b>12</b>)—together with two previously described scalarin derivatives....

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Bibliographic Details
Main Authors: A-Young Shin, Hyi-Seung Lee, Jihoon Lee
Format: Article
Language:English
Published: MDPI AG 2022-11-01
Series:Marine Drugs
Subjects:
Online Access:https://www.mdpi.com/1660-3397/20/11/726
Description
Summary:A chemical investigation of a methanol extract of <i>Spongia</i> sp., a marine sponge collected from the Philippines, identified 12 unreported scalarane-type alkaloids—scalimides A–L (<b>1</b>–<b>12</b>)—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 <b>1</b>–<b>12</b> featured a <i>β</i>-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 <b>1</b>–<b>12</b> against several Gram-positive and Gram-negative bacteria showed that <b>10</b> and <b>11</b> were active against <i>Micrococcus luteus</i> and <i>Bacillus subtilis,</i> respectively, with MIC values ranging from 4 to 16 μg/mL.
ISSN:1660-3397