Miniaturized Cultivation Profiling Returns Indolo-Sesquiterpene Michael Adducts from the Australian Soil-Derived Aspergillus terreus CMB-SWF012.

An integrated program of chemical profiling (GNPS) coupled with an expanded format 24-well-plate miniaturized cultivation profiling (MATRIX) utilizing traditional as well as grain/pulse and cereal media permitted rapid prioritization of Aspergillus terreus CMB-SWF012 as a source of unprecedented natural products. Scaled-up cultivation on rice and PDA yielded the rare tripeptides asterripeptides A-C ( 1 - 3 ), new indolo-sesquiterpene Michael adducts terreusides A and B ( 4 and 5 ), and known precursors asterresin A ( 6 ) and (+)-giluterrin ( 7 ). Structures for 1 - 7 were assigned by detailed spectroscopic and chemical analysis and biosynthetic considerations.