Oligoprenyl-curcumanes and other new aromatic isoprenoids from the 1.64 billion year old Barney Creek Formation

Carbonaceous dolomites and shales of the 1.64 billion years (Ga) old Barney Creek Formation (BCF), McArthur Basin, northern Australia contain the oldest, clearly indigenous biomarkers. We describe three new series of regularly branched aryl isoprenoids with base ions at m/z 119, 161 and 175. The m/z 119 compounds were identified as a complete series of C15-C40 oligoprenyl-perhydro-ar-curcumenes (oligoprenyl-curcumanes). Their likely biogenic precursors are oligoprenyl-β-curcumenes that occur in a wide range of bacterial phyla.