32,35-Anhydrobacteriohopanetetrol: an unusual bacteriohopanepolyol widespread in recent and past environments

A novel series of sedimentary C35 diol and triol hopanoids is reported in a wide range of sediments ranging in age from Recent to Jurassic. The predominant diol homologue has been isolated from a Jurassic sediment using reversed phase HPLC and the structure of the functionalised side chain has been elucidated by 1D and 2D 1H NMR spectroscopy. It corresponds to 32,35-anhydrobacteriohopanetetrol, a compound recently identified in the Caribbean sponge Plakortis simplex. Its widespread occurrence in the sediment record suggests that this novel family of hopanepolyols likely derives from microorganisms which remain to be identified in the bacterial community.