Microbial Hydroxylations of Bicyclic and Tricyclic Sesquiterpenes

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Abstract
The use of Chaetomium cochlioides and Diplodia gossypina to perform biotransformations of bicyclic and tricyclic sesquiterpenoids was examined. Using humulene as a substrate, a strain of Chaetomium cochlioides was found to produce numerous epoxides and hydroxylated derivatives. Hydroxylation of humulene monoepoxide proceeded much more readily than hydroxylation of the hydrocarbon. A further strain of Chaetomium cochlioides was found to be enantioselective with respect to its products of biotransformation. Similar epoxidation and hydroxylation biotransformations were performed on caryophyllene with the same fungal strain. The use of a strain of Diplodia gossypina to oxidize calarene and globulol also was studied. Many of the biotransformations studied were found to produce reasonable yields. Also, oxygenated sesquiterpenes were found to be more readily biotransformable than hydrocarbons. This was thought to be because of their better solubility in water.