New neoverrucosane diterpenoids produced by the marine gliding bacterium Saprospira grandis

Chemical examination of the culture broth extracts of the marine gliding bacterium Saprospira grandis (ATCC 23116) has resulted in the isolation of four new diterpenoids of the neoverrucosane class. The structures of the new diterpenoids, compounds 1-4, were assigned by combined spectroscopic methods emphasizing 2D NMR experiments. The relative stereochemistry of 1 was determined by 2D ROESY NMR methods, while the absolute stereochemistry was assigned by application of the modified Mosher method. This study adds to the rare observation of terpene production by prokaryotic microorganisms and suggests that marine gliding bacteria may be a significant source for new terpenoid secondary metabolites.