Diatoms as a source for 4-desmethyl-23,24-dimethyl steroids in sediments and petroleum

Analysis of the sterol composition of more than 100 diatom cultures, representing all major marine diatom orders, indicates that this group of algae may be an important source for 4-desmethyl-23,24-dimethyl steroids in sediments and petroleum, as their precursors, i.e. 4-desmethyl-23,24-dimethyl sterols, were present in 22 of the cultures. The phylogenetic positions of diatom species that produce 4-desmethyl-23,24-dimethyl sterols show that, within the centric diatoms, only a specific group of diatoms is able to produce these sterols, while within the pennate diatoms, a phylogenetic relationship between 4-desmethyl-23,24-dimethyl sterol-producing diatoms is less apparent. Based on the phylogenetic relationship, it is suggested that diatoms inherited the ability of producing these sterols from a single common ancestor, which originated between 150 and 100 Ma ago. Co-injection of an authentic 23R,24R-dimethyl-5 alpha-cholestane standard with extracts confirmed its presence in sediments. We also tentatively identified three other 4-desmethyl-23,24-dimethyl sterane isomers having different side-chain stereo-configurations and observed that some of the isomers co-clute with other steranes including 24-ethyl-5 alpha-cholestane. (C) 2008 Elsevier Ltd. All rights reserved.