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.