Novel hopanoids from Frankia spp. and related soil bacteria. Squalene cyclization and significance of geological biomarkers revisited.

Three series of hopanoids, differing by their configurations at C-17 and C-21, have been identified in several Frankia spp. and other related soil bacteria. The widespread bacterial hopanoids of the 17beta(H),21beta(H) series were accompanied by their isomers of the 17beta(H),21alpha(H) (moretane) and 17alpha(H), 21beta(H) series. The latter series has not previously been found in living organisms and is considered to be a result of the abiotic isomerization of the thermodynamically less stable 17beta(H),21beta(H) hopanoids. This simultaneous presence of three isomeric hopanoid series highlights intriguing problems in the biogenesis of the bacteriohopane skeleton and partly questions the significance of hopanic biomarkers in sediments.