The First 12-Methylhopanoid: 12-Methylbacteriohopanetetrol from the Marine Sponge Plakortis simplex

Large amounts of bacteriohopanoids have been isolated from the marine sponge Plakortis simplex. In addition to the common bacteriohopanetetrol, the new 12-methylbacteriohopanetetrol, with an unprecedented methylation at C-12, was isolated and characterized by an extensive NMR analysis. While bacteriohopanetetrol is most likely of dietary origin, the unusual methylation at C-12 could be carried out by the sponge.