Stemodin (1) is a biologically active natural product from Stemodia maritima. The compound possesses cytotoxic and antiviral properties and can be obtained in relatively large quantities from the plant. Stemodinone (2), also isolated from S. maritima (albeit in lower quantities), can be generated by simple oxidation of 1. In the presence of aqueous acid, 2 undergoes solvolytic rearrangement to form 15(13→12)abeo-13β-hydroxystemaran-2-one (3) and 15(8→9)abeo-8β(H)-12β-hydroxystachan-2-one (4). The skeleton of 3 is similar to that of the scopadulanes, which inhibit the porcine H+, K+-ATPase enzyme, and possess antitumour and antiviral activities against the Herpes simplex virus type 1. These natural products also interfere with the nutrient transport of the malarial parasite Plasmodium falciparum. The biological activity of compounds bearing the skeleton of 4 have not been explored. Diterpene 2 is readily chemically converted to analogues 5 and 6. The solvolyses of 1, 5 and 6 were carried out in order to generate similar products of rearrangement. These analogues served as substrates for transformation by the fungus Exophiala lecanii-corni. The aim is the production of a series of novel compounds for bioassay. E. lecanii-corni has previously been exploited as a catalyst for steroid biotransformation. However, its potential for microbial functionalization of terpenes is yet to be investigated.

Synthesis of novel rearranged stemodane diterpenoids and their biotransformation by Exophiala lecanii-corni

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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