Structure elucidation of some highly unusual tricyclic cis-caryophyllane sesquiterpenes from Marasmiellus troyanus

Three new unusual sesquiterpenes (1–3) were isolated from the tropical rainforest basidiomycete, Marasmiellus troyanus and their structure elucidation was achieved by NMR spectroscopy, single-crystal X-ray structural analysis and a modified Mosher’s ester method to determine the absolute stereochemistry of compound 1. These unusual metabolites are probably derived from the caryophyllane class of sesquiterpenes and a possible biosynthetic route to these compounds is proposed. These small natural products represent the best possible features of chemical diversity, being chiral and exhibiting extensive functional group chemistry highlighting the value of natural products as a screening resource for therapeutics discovery programmes.

We report the isolation and structure elucidation of novel sesquiterpenes from Marasmiellus troyanus. Using NMR spectroscopy, single-crystal X-ray structural analysis and a modified Mosher’s ester method, the absolute stereochemistry of the unusual cis-caryophyllane sesquiterpene 1 was determined.Figure optionsDownload as PowerPoint slide